sailboat charters san juan islands

• REQUEST A BROCHURE
• Privacy Policy
• Customer Reviews
• Google Reviews
• Trip Advisor

Sail the San Juans

Make a Reservation (800) 729-3207

Relaxing 6 and 12 day sailing adventures aboard Northwind!

Humpback whale encounter...

Afternoon nap...

Northwind's elegant salon.

Sailing with a pod of resident orcas.

Gourmet cuisine by Chef Jette.

San Juan Islands Sailing Charters and Cruises

We provide yacht and crew. you relax and enjoy., the art of slow travel.

Something special happens when we cast off the dock lines and head out into the San Juan Islands on a sailing charter. We become aware of the rhythm of the tides, the wind filling the sails, the salty sea air, and the porpoise following in our wake. The hidden coves and diverse marine life of the San Juans beckon us to make discoveries and submerge ourselves in its delightfully relaxed pace.

So much of the world passes by without our being able to see, touch, or feel it. A sailing charter through the San Juan islands allows us to take a moment to slow down and experience it for ourselves.

We have been perfecting the art of “slow travel” for over 25 years. Our new 55′ sailboat Northwind , offers a luxury yacht charter experience for up to six guests in private staterooms with ensuite baths. Each one of our San Juan Sailing Charters and Inside Passage cruises are one of a kind, designed for your group from the ground up. From your preferences on food and drink , to where we go and what we see and do, the result is a perfect blending of islands, yacht, crew, and cuisine. It’s your perfect vacation, Sailing the San Juan Islands in style.

 This is what a carefree sailing vacation is all about

Sailing the san juan islands.

Captains Jette & Jon Baker, with TailR

A fully crewed sailing charter with Sail the San Juans is a world away from any vacation experience you probably have ever had. A sailboat charter aboard Northwind  will open a door to see and experience the more remote islands and coves that are not easily accessible to most people.

At the same time, sailing yachts are in a unique position to be less intrusive to marine mammals which helps encourage encounters with Orca, seals and porpoise.

A sailboat charter with Sail the San Juans is a first class experience, from our impeccable yacht and crew to your private chef’s menu built around your preferences.

Join us to explore over 200 forested islands, help trim the sails on Northwind, or just relax while you savor gourmet fare , and great hiking and kayaking through protected bays and inlets.

This is the art of slow travel.

Request our 16 Page Full-Color Brochure

Two booking options

Private Charters: Groups of up to six people receive exclusive use of the sailboat for their group.

Join A Cruise: Reserve a stateroom for two, and let us take care of filling the other cabins.

Learn more about Booking Options and Rates

Two unique island cruises

San Juan Islands:  These six day sailing trips cruise through the San Juan Islands, an enchanting archipelago of hidden coves, abundant wildlife, and forested islands located in the sheltered inland waters of Washington State.

Learn more about San Juan Islands Sailing Charters

The Inside Passage: These twelve day wilderness sailing trips cruise through the southern portion of the Inside Passage, an area rich with native culture, mountain vistas, fjords and waterfalls located in British Columbia.

Learn more about Inside Passage Sailing Charters

Escape the ordinary with a San Juan Islands yacht charter vacation.

Adventure awaits

The San Juan Islands and Gulf Islands are some of the most popular cruising areas in the world.

What is it that draws people to these islands? A big reason is because the islands are remote but accessible at the same time. A short drive from Seattle or Vancouver puts you in Anacortes, Washington, the “Gateway to the San Juan Islands.” From there, the San Juan Islands start a mere 15 miles away.

Your Cruise. Your Choice.

Once in the islands, you’ll find quaint both communities and hidden hideaway, all surrounded by a calm inland sea. Seemingly endless miles of coastline and over 100 islands give you plenty of options for exploring and relaxing. Drop anchor in a quiet cove, or tie up at one of the island marinas – it’s your choice when you charter!

Anacortes Yacht Charters has provided San Juan Islands yacht charters for 45 years. We have the largest selection of motor yachts and sailboats in the Northwest. Our experience and fleet mean we can match you with the perfect boat for a trip of lifetime.

To book a bareboat or skippered San Juan Islands yacht charter contact us at:

800-233-3004 or [email protected]

Big Boat Charter Sale

We are offering our biggest savings on the biggest boats in the fleet.

Class/Charter Bundle

Save $1,900 and launch or build your bareboat charter resume.

Our Guarantee

Should you have a breakdown during your charter, we will complete repairs within four hours of notification for any vessel within 20 miles of our charter base. View Guarantee

Yacht Charter

A private yacht charter is your ticket to a Pacific Northwest vacation of a lifetime. Choose to bareboat charter a powerboat or sailboat for a hands-on adventure. Or, hire a skipper for a more guided experience. A few of our larger boats require a crew and are shown on the crewed yacht page.

Yacht Ownership

If you own a boat, or are pondering a purchase, consider placing your boat into charter service. This a great option to help offset the cost of ownership and earn real tax advantages, Use our in-house service department for year-round care of your boat. Arrange time on your boat for yourself as desired.

News and Announcements

We are proud to be celebrating our 45th Anniversary in 2024. Over the years providing San Juan Islands yacht charters, our crew has pioneered mini-fleet management. Along the way we have provided over 15,000 charter trips – illustrating our commitment to quality and customer service.

All of our charter vessels are clean, well-maintained, and include a breakdown guarantee. We take the risk out of chartering to better ensure the quality of your charter experience.

Our yacht charter fleet includes a variety of power yachts , sailing yachts and crewed yachts from 27’ to 70’.  Make your choice to host nearly any group of friends and family for a magical San Juan Islands yacht charter.

Toll Free: (800) 233-3004 | (360) 293-4555 | [email protected]

© 1979 - 2024 | All Rights Reserved, Anacortes Yacht Charters

• Power Yachts
• Sailing Yachts
• Catamaran Yachts
• Crewed Yachts
• 7-night San Juan Islands
• 7-night San Juan Islands and Taste of Gulf Islands
• 7-night San Juan Islands and Gulf Islands
• 7-night Perfect Sail or Trawler Cruise
• 14-night Desolation Sound and Princess Louisa Inlet
• 14-night Leisurely Sail or Trawler Cruise
• 14-night San Juan Islands to Desolation Sound
• How to Charter
• How to Book
• Boating Qualifications
• Charter Details
• Loyalty Programs
• Travel Protection Insurance
• AYC Power Cruising Classes
• ASA Sailing Classes
• Yacht Service
• Anacortes Yacht Brokers
• ROI Calculator
• Email Sign Up
• Owner Quarters

Sail In The San Juan Islands!

Relaxed. rejuvenated. awed by nature..

October 10, 2023

Carl Scandella

September 9, 2023

Michael Faulkner

Ed Janet Quinlivan

Collin Murch

August 8, 2023

Sakara Buyagawan

July 7, 2023

Sail the San Juan Islands with us!

Sit back, relax, and leave your cares behind when you join us for a life-changing journey on our comfortable 55' sailing yacht in the San Juan Islands. We'll show you the natural beauty of the Islands -  it is our home - and we look forward to sharing it with you. Our home port is in Deer Harbor Marina, Orcas Island. 

Our tours are a special way to experience the magic of these islands. We do group, private and custom charters and curate unique itineraries that include remote islands, wildlife viewing, gourmet meals, and activities. Once anchored you can go to shore, and we'll pack a gourmet lunch to take with you while you explore.  If your time is limited, you can take a day trip on one of our six-hour sailing tours from Deer Harbor Marina on Orcas Island.

Sailing with us in the San Juans, Gulf Islands, and the Inside Passage offers a chance to see bald eagles, humpback whales, sea lions, and our resident orca whales. Our multiple-day adventures include a naturalist captain and an experienced professional chef. You'll enjoy local Northwest gourmet cuisine made with fresh local ingredients. Bring us your special requests so we can make your private sailing memorable. We love customizing tours to exceed your expectations!

3-Day All Inclusive Sailing Tour of the San Juan Islands

Join us for an all-inclusive multi day sailing tour of the most beautiful marine environment in the world!

Prices start at $1999 USD per person. Early and late season discounts available. Gratuities are welcome, but not included in cost of trip.

2024 Dates for 3-Day Tour:

Please note: THE DATES BELOW DO NOT REFLECT CURRENT RESERVATIONS. Please use the "Check Availability" button on this page to see a real-time calendar.

May: 5/10-5/12 June: 6/7-6/9 September: 9/7-9/9, 9/13-9/15, 9/18-9/20

If the dates you want are not listed above, please contact us. We are very flexible, and can often adjust the sailing schedule, and can create tours of any duration.

Our multi-day, all-inclusive sailing tours are the best way to unwind, relax and immerse yourself in the Salish Sea's natural beauty. With each day aboard, you'll feel a deeper connection to the natural world as you let the stresses of everyday land-based life melt away. We follow the rhythms of the wind and tides to show you the true beauty of this magical archipelago.

Sailing from our home port of Deer Harbor, Orcas Island, we are quickly in one of the most scenic and wildlife-rich areas of the world. Our naturalist captain will hoist the sails and guide your small group in an intimate exploration of wildlife and nature by eco-friendly sail power.

Sailing aboard the S/V Nawalak is about escaping the crowds, relaxing, and connecting with nature and the sea while exploring the quiet beaches and pristine islands of the northwest. During our tours we share with you the gems and secrets we’ve discovered in our 30+ years of sailing these amazing waterways.

Sail & Paddle Tour

New this year!

Hey there, avid kayaker or paddle boarder! Think you've seen and conquered it all? We invite you to paddle the mystical waters of the San Juan Islands, while you return each evening to the safe, warm and cozy confines of our luxury 55' sailboat.

Aboard Sailing vessel Nawalak, you'll be treated to 3 luxury meals per day by our on-board chef to fuel your kayaking journeys, as well as a warm, dry berth aboard. No need to pitch a tent, or haul heavy gear - keep it all on the boat!

This tour blends the elegant simplicity of sailing with the intimacy of near shore kayaking, utilizing our vessel as a mother ship for your San Juan Islands kayaking adventures. This is a bring-your-own-kayak adventure where we board, our luxury 55' sail boat and sail deep into the majestic waters of the San Juan Islands. By sailing to these highly sought after kayaking destinations, we eliminate the hassle, and danger of paddling across large bodies of open sea to get to our coveted kayaking destinations. Tour durations are from 3-6 days, and are fully customizable for duration, skill levels and dates. Give us a call to learn more.

5-Day All Inclusive Sailing Tour of the San Juan Islands

Join us for an all-inclusive 5-Day sailing tour of the most beautiful marine environment in the world!

All inclusive prices start at $2499 USD per person. Early and late season discounts available. Gratuities are welcome, but not included in cost of trip.

2024 Dates for 5-Day Tour:

Please note: THE DATES BELOW DO NOT REFLECT CURRENT RESERVATIONS. Please use the "Check Availability" button on this page to see a real-time calendar. If the dates you want are not listed, please contact us. We are very flexible, and can often adjust the sailing schedule, and can create tours of any duration.

May: 5/3-5/7, 5/17-5/21, 5/31-6/4, June: 6/18-6/22, July: 7/2-7/6, 7/16-7/20, August: 8/1-8/5, 8/16-8/20, 8/31-9/4,

6-Day All Inclusive Sailing Tour of the San Juan Islands

Join us for an all-inclusive 6-Day sailing tour of the most beautiful marine environment in the world!

All inclusive prices start at $2699 USD per person. Early and late season discounts available. Gratuities are welcome, but not included in cost of trip.

2024 Dates for 6-Day Tour:

May: 5/24-5/29 June: 6/11-6/16, 6/25-6/30 July: 7/9-7/14, 7/24-7/29 August: 8/8-8/13, 8/23-8/28

Our multi-day, all inclusive sailing tours are the best way to unwind, relax and immerse yourself in the Salish Sea's natural beauty. With each day aboard, you'll feel a deeper connection to the natural world as you let the stresses of everyday land based life melt away. We follow the rhythms of the wind and tides to show you the true beauty of this magical archipelago.

San Juan Islands 6-hour Day Sail

Climb aboard and immerse yourself in the vibrant beauty of the San Juan Islands.

All inclusive prices start at $229 USD per person, check dates on the right. Please note: If the dates you want are not listed, or another tour is designated, please contact us. We can often adjust the sailing schedule.

INSIDE PASSAGE - Desolation Sound, Broughton Archipelago & Great Bear Rainforest

We will be offering this tour again in late August/early September 2025. Please use the contact form on this page to let us know you have interest, or have any questions. Prices are yet to be determined, but will probably be around $5999 per person all inclusive of food and beverages.

Sail with us to where civilization gradually fades astern. Northwest is where we're headed, underneath a golden sky as we begin to get a taste of the wilder side of the North American coast. Natural Hot Springs, 10,000 yr old protected First Nation villages, ancient totem poles, pods of leaping dolphins, Orcas, Humpbacks, Bears, Rain Wolves. These are just some of the highlights on our farthest north tour. This is a true adventure, but with all the creature comforts and safety we've developed from over 20 years of experience with this route.

We pass north through the Inside Passage roughly retracing the route that Captain George Vancouver did in 1792. Much of the area looks the same now as it did then. With each day aboard, you'll feel a deeper connection to the natural world as you let the stresses of everyday land based life melt away.

Why choose us?

Experience The Magic Of Sailing In The San Juan Islands

Emerald Isle sails on a beautiful 55' sailing vessel with the latest upgrades for private charter safety and comfort. Our naturalist captain is U.S. Coast Guard licensed. You'll enjoy a sailing charter with a quiet charging system using wind and solar power, and the only heated pilothouse charter sailboat in the area.

Our tours are led by Emerald Isle Sailing's owner/operator experienced naturalist USCG licensed captain.

Sit back and relax while our gourmet chef prepares another sumptuous meal! Our spacious, fully equipped 55’ custom pilot house sailboat will keep you warm and dry if we encounter a rain shower. After a day on the water or exploring the rainforest ashore, retire to one of 5 private staterooms with fresh linens, towels, and toiletries included. A luxury sailing package!

Feel yourself slipping into a deeper connection with nature as we sail to remote coves, harbors, and anchorages. The stresses of land-based life will quickly melt away. Read a book in the protected cockpit, or take the helm and feel the silent energy of the wind move the boat through tranquil waters.

On our 5, and 6-day tours, we venture farther north to where civilization fades astern. Bigger waters, bigger wildlife, and bigger adventures await - all from the comfort and safety of our USCG-documented vessel.

San Juan Islands, Washington

The San Juan Islands include 172 named islands and reefs off the coast of Washington State. Departing from Anacortes, the Washington State Ferries serve Orcas Island, Lopez Island, and San Juan Island. Each island offers a unique opportunity for adventure. Activities include sailing, hiking, biking, kayaking, and enjoying the simple rustic beauty of the San Juan Islands.

The San Juan Islands enjoy a moderate year-round climate. Winters experience an average temperature of 40 degrees F, while summers enjoy a glorious average of 70 degrees F. Sailing with us in the San Juan Islands offers a chance to spot humpback whales, orcas, and minke whales, and see flower-filled meadows, mountain-framed horizons, hidden coves, and emerald waters. The beauty of this area casts a spell hard to undo.

Frequently asked questions

What kinds of wildlife might i see.

The coastlines we sail are rich with life. Depending on the time of year, sea mammals you might see include Orca, Humpback and Minke Whales, Harbor Porpoise, Dahl’s Porpoise, White-sided Dolphins, Sea Otters, River Otters, Harbor Seals, and Sea Lions.

On land you have the opportunity to see Minks, Otters, Black-tailed Deer, Raccoons, and imported exotic wildlife. As we journey northward it becomes increasingly likely to find coastal Wolves, Mountain Goats, Black Bears, Grizzlies, and the White Kermode, or “Spirit” Bear.

There are too many feathered friends to list. The Bald Eagle is a daily visitor. Other favorites of ours include Oyster Catchers, Marbled Murrelettes, Scoters, and Great Blue Herons. For a truly world class natural experience the old-growth forests of northern B.C.’s Great Bear Rainforest house an especially rich and diverse community of creatures. Our unobtrusive electric powered dingy allows us the unique advantage of near silence while viewing and photographing wildlife.

What sort of clothes should I bring?

It’s best to be prepared for a temperature range of 55° to 80° F. When sailing, even on a warm summer day, the breeze experienced on deck when heading up wind can elicit the need for cozier clothing. The best dress for sailing is layers. For northern tours, close to the skin, wear a moisture wicking layer, then an insulative layer (fleece, wool...), and an outer wind/water resistant layer. Waterproof shoes or rubber boots are an advantage on deck and for getting to and exploring shorelines and estuaries. Shorts and a bathing suit are great for a summer swim or hot spring soak. For life below decks bring casual and comfortable clothing. Don’t forget your favorite pair of slippers! We’ll send you a detailed list of what to bring when you submit your reservation.

What is the weather like?

The San Juan and Gulf Islands are known for their sunny summer days. We receive about half the rain of Seattle due to the rainshadow of the Olympics and Vancouver Island mountain ranges. Temperatures range from 55°-80° F in the spring, summer, and fall, and average 40°-50° F in the winter months. The Great Bear Rainforest of northern B.C. produces more variable weather. It’s not called a rain forest for nothing! Temperatures are usually in the 60s throughout our sailing season there. You will likely encounter a mix of sunshine with occasional rain during your trip, but you will stay warm and dry in our roomy pilothouse.

What time of year should I sail with you?

It depends on what you are looking for. April and May display an incredible abundance of spring flowers. Some areas are particularly spectacular with color at this time. The sunniest and warmest months of the year are July, August, and September. This is the best time of year to see the Great Bear Rainforest. October through mid-June offers the best sailing wind and the most quiet privacy in anchorages. We have had incredible trips in January! With our heating systems and all-weather pilothouse this time of year can be a magically peaceful and comfortable experience.

What if I get seasick?

Nearly all of the waters we sail in are well protected. Most people who are concerned about seasickness are pleasantly surprised that its not an issue for them on our trips. However, some of our trips involve making brief passages that can occasionally get rough enough to elicit this unfortunate gastronomic state. We recommend you speak with your doctor or pharmacist regarding appropriate motion sickness medication. In our experience for mild queasiness, the acupressure wrist bands, ginger tea or crystallized ginger (which we have on board), and staying above decks can be of great help. The good news is that after we’ve finished a rough passage, the seasickness disappears!

Are children welcome on your charters?

Absolutely! We love having children on board. It can be a hugely educational experience for them. There are many activities to keep them occupied, and enough new and exiting experiences to keep them talking about their trip for a long time. We do, however, prefer that if your child is younger that 10 that the guest list is filled by your party alone.

What is a “crewed” charter?

It’s a cruise that includes a captain and crew/chef who take care of all shipboard duties including safe navigation, local knowledge of choice attractions, and meals and cleaning. You can do as much or as little as you like. We are at your service!

Do I need to be in good shape?

No. The level of activity varies depending on the trip. However, anyone who can get in and out of the dingy and go for short walks will do fine. We have had mobility-impaired guests having wonderful cruises with us without ever leaving the boat! There are many beautiful things to see right from the cabin and deck!

What do your trips include?

All onboard meals, including select wines with most dinners. On some trips you will cover one dinner ashore. Your heated cabin includes a bed made with sheets, pillows, comforters, and blankets. Towels, cloths, shampoo, and soap are also complimentary. You are welcome to use the inflatable, kayak, and all fishing, crabbing, and shrimping gear. If you prefer to overnight at a place with moorage fees, you are responsible for them, as well as any fishing licenses, and most off boat tours.

How often do we get off the boat?

Rainforest we typically take the dinghy up a pristine river and go for a short walk, or explore a remote beach, or abandoned native village. In the San Juans and Gulf Islands many forest trails, beaches, and country roads await the happy wanderer.

What can I expect to learn?

Opportunities for education abound. Your skipper is a trained naturalist, and enjoys pointing out a special plant, and its traditional uses, or identifying an animal and explaining its habits. Local history and native culture are other subjects you'll learn about. The captain also enjoys teaching sailing to anyone interested. Our trips in the Great Bear and the Inside Passage incorporate Native guides who will lead you through abandoned village sites, and enthrall with tales of battles, ancient customs, and the history of the once mighty Kwakwak’wakw. Or take part in a traditional open fire salmon bake and learn of the rich past of the Heiltsuk. The boat makes a great platform for seminars and workshops. We also offer instructor-led cruises in subjects such as meditation, photography, and whale observation. Please see charter options. If you are an instructor interested in leading an art cruise feel free to contact us.

What areas do you charter in?

Our scheduled tours focus in the San Juans April through July, with one trip up the Inside Passage/Southern Great Bear Rainforest in early August, mid August to mid September in the Northern Great Bear Rainforest of the northern B.C. coast, and one trip down the Inside Passage/Southern Great Bear Rainforest in mid September. Please see our schedule. Any time you don’t see a scheduled trip booked the boat is open and available, so don’t hesitate to inquire.

What if I'm a solo traveler who prefers my own stateroom?

All of our rooms are double occupancy (View ship schematic), and allow for a maximum of six guests. If you prefer a private stateroom we will try to accommodate you. There will be an additional 50% fee if the tour is otherwise full.

Can you take more than six passengers?

By Coast Guard regulation, we can take up to six guests. On our instructional cruises, and with workshops and seminars, we can bring an instructor in addition to the six guests.

Do I need to know how to sail?

No. The captain and crew are perfectly capable of taking care of all sailing. However, you are welcome to participate at any time for your own enjoyment. The captain is a lifetime sailor, and would love to help you with your sailing skills. By the end of the trip you may just be ready for the America’s Cup!

Recent News

2023 Great Bear Rainforest Trip Recap

In mid-August this past summer, after a long pause of four years, we once again set sail for a nearly month-long journey up the enchanting Inside Passage. Beyond the towering mountain lined fjords, winding channels, and secret, pristine anchorages, lay…

2024 SEASON SCHEDULE IS OUT!

Ahoy sailors! We've just finalized our 2024 sailing schedule! For details about our trips please click on the date. Our day-sails are bookable securely online from the "Day Sail" page. To book or inquire about the multi-day sails please complete…

7 Amazing Getaways & Weekend Trips from Seattle

Visitors come from around the world to check out the sights in Seattle. They love touring the Space Needle, seeing the workers toss fish at Pike Place Market, and grabbing a cup of coffee from one of the local shops.…

Join our email newsletter

Book your next sailing adventure with us ..

Orcas Island Sailing

  lessons and boat rental 360-310-0100 [email protected]  .

Boat rentals are available for a full day or half day.  In order to rent we ask that you have an intermediate level of boating experience.  We have 4 sailboats from 19 to 27 feet.

Prices vary based on boat.

BOAT RENTALS

Boat rentals are available for a full day or half day.  In order to rent we ask that you have a least an intermediate level of boating experience.  We have your choice of 3 sailboats, from 19 to 27 feet.

                Prices vary based on boat

SAILING LESSONS

Sailing lessons are private and personalized to you and your guests. They are available for a full day (6 to 7 hours) or half day (3 hours).  Rates include the boat, captain, and up to six passengers of your choosing.

half day rate..........................$475

full day rate...........................$950

ABOUT ORCAS SAILING

We began with a simple idea which continues to be our guide to business today:  Provide a fun sailing opportunity for visitors vacationing in the San Juan Islands.

Because we don't charge per person you will experience learning how to sail in the company of your traveling companions rather than with a group of strangers.  This way you get a private charter for you and yours only!  Every skippered charter is hands-on.  You will be sailing the boat and learning the ropes!

Where we are

We are located at 1945 Obstruction Pass Rd, Olga, WA  98279

From Eastsound, drive south through Moran State Park.  At the Artworks building in Olga turn left onto Point Lawrence Rd.  Two intersections later veer right onto Obstruction Pass Rd.  At the end of this road is the county boat ramp and parking lot.  My office shack is adjacent to the boat ramp just inside the property of Lieber Haven Resort. Please call ahead as I am not often there.

From Doe Bay, turn left onto Obstruction Pass Rd then follow the directions above.

NOTE:  We are located at Lieber Haven Resort, in Obstruction Pass, at the end of the Obstruction Pass Rd.  We are not at Obstruction Pass State Park which is at the end of Trails Rd.

Ground Transportation

All forms of ground transportation can be easily arranged by calling Orcas Island Shuttle and Rental Car.  We encourage you to walk on the ferry!  Click  here  to go directly to their website or call 360-376-7433 for info

"My husband arranged this sailing lesson for our recent visit to Orcas Island. This was the highlight of my trip. My husband has been sailing for a few years and I am brand new to the sport. Nat was awesome. He was so patient with my lack of knowledge and/or recall of the limited knowledge I have. The bay was quite choppy when we headed out but I immediately felt very confident with Nat at the helm. Nat is very personable and is a great teacher. I highly recommend Orcas Island sailing.'"

San Juan Islands

• Meet the Crew
• S/V Singawing
• The Interior
• Specifications
• Sample Menu
• The Bear Den
• Our Sailing Blog
• Guest Comments

San Juan Islands Sailing Adventures

NW Sailing Adventures of Bellingham, WA, offers an all-inclusive sailboat charter experience in the San Juan Islands. Our exciting sailing vacation packages are sure to fit almost any schedule, budget or occasion.

Private Sailing Yacht Charters in the San Juan Islands

Diminuendo is exclusively yours when you book a multi-day private yacht charter. This allows you the flexibility of creating your own customized charter schedule, itinerary, and menu.

Family or school reunion in the works? Your party will have the entire yacht at your disposal. Diminuendo’s three guest cabins can accommodate a maximum of six guests. We find that a party of four is ideal. Although a party of six can feel a bit close, they will be your friends and family! And unlike many charter companies, we gladly welcome kids aboard.

Planning a getaway for you and your special someone? Celebrate your special anniversary, honeymoon, or propose on bent knee in the most romantic of settings. Your Captain will gladly officiate your nuptials or renew your vows aboard your yacht or on a beautiful beach.

Take a look at a couple of sample itineraries.

This can help you understand what anchorages may be important to stop at or stay away from. Captain Scott and First Mate/Chef Todd are dedicated to creating a customized trip created around your personal desires.

• 5 or 6 Day Week Aweigh Sailing Tours  – San Juan Islands
• 3 or 4 Day Aweigh Sailing Tours  – San Juan Islands
• 2 day or 1 Day Sailing Adventures  – Bellingham and San Juans
• Wedding and Specialty Cruises

Looking for a San Juan Islands chartered sailboat vacation?

Look no further than Northwest Sailing Adventures!

• All Aboard Sailing Facebook
• All Aboard Sailing Foursquare
• All Aboard Sailing Mail

All Aboard Sailing

Whale watching sailing from friday harbor through the san juan islands – and beyond.

San Juan Island Wildlife & Whale Watching Sailing

Full Day Sails with whales around the San Juan Islands and Beyond

Aboard the six passenger 1956 classic 42′ pilot house sloop ‘Peniel’. Departing from Friday Harbor.

 Every trip is different

With an experienced Captain and Wildlife Guide 

A family adventure to remember

Photography Cruise

You can click the links below to:

Learn about Our Sails – what to bring and what to expect

See our Captains Blog – every sail is documented

Read about our Vessel and Crew

Sail with us – Contact Us

Share this:

Comments from our guest crew.

Boating, Sailing Tours, & Rentals

As a world-renowned boating destination, the San Juan Islands have an adventure for everyone. From day and overnight charters and rentals, to fuel and long-term moorage, you'll likely find what you're looking for. The San Juans are equally renowned for wildlife, especially whales. While out on the water, please follow the Be Whale Wise guidelines and help protect our spectacular marine wildlife. 

Tips & Resources for Boaters: If you want to maximize your enjoyment and boating safety in visiting the islands, you can find nearly 20 live-recorded educational webinars from the non-profit, America’s Boating Club of the San Juans . Review the  Green Boating Guide  from Friends of the San Juan Islands and explore the Maritime National Heritage Areas throughout the Islands!

Let us acknowledge that we reside on the ancestral lands and waters of the Coast Salish people who have called this place home since time immemorial and let us honor inherent, aboriginal, and treaty rights that have been passed down from generation to generation.  

Charters, Rentals & Tours

The shorter your stay in the islands the more important it is to plan ahead. Booking activities in advance will make your trip run smoothly and you'll be more likely to get your first picks! Most tour operators have generous cancellation policies in case you need to make changes. (Check with individual companies to be sure of their policies.)

Sponsored Links From Our Partners

• 360-378-3587

Cruise the San Juans with these Breathtaking Charters

If you’ve visited the scenic San Juan archipelago, you know about the endless coastline just waiting to be explored. Instead of a powerboat or kayaking adventure this time, why not try a sailing charter? There’s truly nothing like making your way by sail, exploring new island coves in a traditional and invigorating fashion. Here are some of the best sailboat charters around for your next trip to the San Juan Islands:

  All Aboard Sailing, San Juan Island

Join Captains David & Barbara aboard the Peniel, a 1956 wooden pilothouse sloop.

If you’re looking for a more intimate sailing experience, All Aboard Sailing may be the choice for you! Board the Peniel, a 42 foot Bill Garden design and embark a journey through the islands with your co-captains, naturalists, and Chef/Owners David and Barbara. The sailing tours offered are: Full day (8-9 hours), half-day (5 hours) and short sails (3 hours). Full day sails are the most popular as it allows ample time and range to circumnavigate the islands and has a significantly higher chance of seeing whales along the way. There are options available for drop off/pick up at the nearby islands. For more information and availability, contact All Aboard Sailing at:

Phone: 1-360-298-1918

Email: [email protected]

Website: allaboardsailing.com

  Griffin Bay Adventures, San Juan Island

Griffin Bay Adventures is a sailing and general boat handling school located in Friday Harbor, also providing skippered charters.

For those who want a private charter as well as a captain to explore the beautiful Pacific Northwest waters, this is a great way to experience the Salish Sea. Sit back and relax, or plan an exotic adventure tailored to you and your crews’ interests. Also, no sailing experience is necessary! For more information and availability, contact Griffin Bay Adventures at:

Phone: 1-503-995-3943

Email: [email protected]

Website: griffinbayadventures.com

Northwest Classic Day Sailing, Orcas Island

Sail with Captain Ward on “Aura”, a beautiful 1948 wooden sloop. 

If you want to expand your San Juan excursion to a nearby island, this might be just the perfect way! Hop on the inter-island ferry to Orcas Island for your sailing trip with Northwest Classic Day Sailing. Book either a group or a private tour with their crew. With a group tour, you may be sailing with other passengers on the boat. In a private tour, your party will be the only passengers — plus, the trip will be more customizable! For more information and availability, contact Northwest Classic Day Sailing at:

Phone: 1-360-376-5581

Email: [email protected]

Website: classicdaysails.com

  Emerald Isle Sailing Charters, Orcas Island

There are four ways to cruise with Captain Dave on S/V Na’Walak: Scheduled tours, custom itineraries, day charters, and Cruise & Learn trips.

If you’re looking for a day trip, Emerald Isle day charters are 6-hour sails that begin in Deer Harbor and embark on a journey to some of the most wildlife-rich and scenic areas of the islands. You can also book a custom itinerary trip, or plan the trip yourself. For more information and availability, contact Emerald Isle Sailing at:

Phone: 1-360-376-3472

Email: [email protected]

Website: www.emeraldislesailing.com

Hopefully this gives you a good start in your quest to sail the San Juan Islands!  Don’t hesitate to ask your innkeepers at the Harrison House Suites or Tucker House Inn for help finding more information or booking a tour. They can also make you a hearty homemade boxed lunch to take along on your wind-powered excursion.

We’ll see you at check-in!

Recent Posts

Lunch at westcott bay shellfish this summer.

The culinary scene on San Juan Island is as vibrant and fresh as the bounty of seafood pulled from the Salish Sea and produce grown by our local farmers in fertile soils. It’s this farm and boat-to-table approach that diners crave on a visit to the San Juans; one place,

Event Planning: The Best Catering on San Juan Island

If you have a destination wedding, special event, or milestone celebration coming up in the islands, you may be starting the process of searching for catering on San Juan Island. For those looking to impress your guests with farm-focused cuisine, Coho Restaurant in Friday Harbor is a great place to

Insider’s Guide: How to Get to the San Juan Islands

The San Juan Islands, north of Seattle in the top western corner of Washington State, is one of the best destinations for your summer getaways. This area is quiet and safe and feels a world away from the hustle and bustle. It’s truly a place to unwind and relax. Before

Join our email newsletter to get the lastest promotions & new package deals.

Get in touch.

• Check-In Address
• 275 C Street Friday Harbor, WA 98250
• Mailing Address
• 235 C Street Friday Harbor, WA 98250

Our Weather

Awards & social.

Site Navigation

• Accommodations
• Food & Wine
• Weddings & Groups
• Specials & Packages
• Best Place To Stay
• San Juan Islands
• Gift Certificates
• Ferry Schedule
• Privacy Policy
• Website Accessibility

Copyright 2024 - The San Juan Island Inn Collection

Website & marketing - logan marketing.

Recognized by Travel + Leisure Magazine

We have been recognized by Travel + Leisure Magazine as the best place to stay when visiting Friday Harbor and San Juan Island.

Give The Gift of Tucker & Harrison House This Holiday Season

Give your loved one a very special gift of a stay at our inns.  We offer gift certificates in many amounts.

RESERVATIONS

San Juan Island Yacht Charters

Cruise the san juan islands with jamal charters.

The San Juan Islands are located within the Washington’s Puget Sound and are a destination for fishing, boating, sea kayaking, scuba diving, golf, and snow sports, with proximity to Seattle. Home to some of America’s most well-known corporations, Seattle is a growing city that is still a popular vacation destination.

SAMPLE ITINERARY: SAN JUAN ISLANDS

The San Juan Islands are made up of many islands of which 172 have names. There are 17 state parks within the islands. All of the islands are within two to three hours of cruising. The four main islands are Orcas, San Juan, Lopez and Shaw. It is a day’s cruise from the Seattle area to the San Juans. From Bellingham it is two to three hours. There are so many bays, harbors and anchorages that you could spend several summers cruising the entire area.

A typical ten-day cruise in the San Juan Islands would be as follows:

• Day 1: Leave Bellingham Harbor and cruise to Sucia Islands. Drop anchor in Echo Bay. Sucia Islands are a cluster of 11 islands and inlets. Fossils can be found in one of the bays as well as oysters, clams & crabs. Hiking trails are abundant throughout the Islands. Sucia was known in the early days as the base for smuggling and rum running.
• Day 2: Cruise to Stuart Island. There are two main anchorages on this island: Reid and Prevost Harbors. Anchor in one of these areas to explore the island on one of the hiking trails. There are picnic sites, docks and floats. A typical hike would be to Turn Point lighthouse, which has a sweeping view of the Canadian Gulf Islands and Vancouver Island. Both harbors are good places to practice your kayaking.
• Day 3: Cruise to San Juan Island and Roche Harbor Resort, which is the famous home of the Roche Harbor Lime & Cement Company. This historical island provides many fun and interesting places to explore. The formal garden in front of the Hotel de Haro is quite beautiful. Besides a restaurant, bar, and shops, there is also an Olympic size swimming pool and tennis courts. The hike to the mausoleum is not to be missed. At sunset each night, we enjoy the traditional flag ceremony.
• Day 4: Cruise to Westcott and Garrison Bays. Here we will crab, tour an oyster farm and visit the British Camp, which was established in the 1860s and remained active until 1872 after the Pig War. The blockhouse, commissary and barracks are still standing.
• Day 5: Cruise to the town of Friday Harbor, the largest in the islands, which also serves as the county seat. There are all types of shopping available only a short walk from where the boat is anchored. Visit the Whale Museum or the University of Washington Marine Laboratories, located right in the harbor.
• Day 6: Cruise to Spencer Spit State Park on Lopez Island. This beautiful sandy finger of land is perfect for picnics and hiking. Also, it is a great place to catch crab.
• Day 7: Cruise the islands, looking for pods of Orca Whales (also known as killer whales) and do some exciting whale watching. Spend the evening in one of the dozens of lovely bays.
• Day 8: Cruise to the beautiful and charming city of Victoria, British Columbia. Clear customs, sightsee, shop, enjoy high tea at the Empress Hotel and visit the Maritime Museum. Victoria is not to be missed.
• Day 9: Cruise to Sidney Harbor and visit the famed and internationally known Butchart Gardens. Cruise to Sidney Spit Marine Park and enjoy a barbeque picnic on the beach. Hike around the island and see wild sheep, deer, pheasants and peacocks.
• Day 10: Return to Bellingham.

Book Your Amazing

360-821-9366

SeaWulff Sailing Charters

Port townsend sailing adventures, san juan islands.

Photograph the birds, orca, and whales native to these waters. The captain is familiar with many ports in the San Juans and can suggest a trip itinerary made to order for your interests.  Two resorts, Rosario on Orcas Island or Poet’s Cove Day Spa on Pender Island B.C.,  have hot tubs and swimming pools included with overnight moorage.  Hike isolated beaches to see harbor seals and sea otters basking in the warm sun or feeding on the kelp beds.

There are many quiet bays to anchor in, visit State Marine parks like Matia, Sucia, Stuart Island, and Jones Island, and many more.  See link below for the complete list.

State Marine parks map

An Escape to the San Juan Islands is Closer Than You Think

The San Juan Islands of NW Washington are among the most beautiful places in the Lower 48 States, and one of the least “discovered.” Few people know that the San Juans average 247 days a year of beautiful sunshine! Other surprises to visitors are the pristine beaches and abundant wildlife (orca whales, bald eagles, sea birds, seals, sea lions, and porpoises) of the San Juan Islands.

On the David B, we know where to find the most beautiful spots and the best wildlife. We know where the crowds are – and especially – where they aren’t.

Come with us on a trip to the San Juans and let the islands amaze you. We offer three different types of trip in the San Juan Islands.

• Weekend Getaway Cruises (3-days)
• San Juan Islands Escapes (4-days) and
• Guided Kayak Mothership Cruises

Each of these cruises offers you a chance to unwind in one of the most beautiful archipelagos anywhere.

3-day Weekend Getaway Cruises to the San Juan Islands

These trips leave Friday morning and return on Sunday evening. We leave Bellingham around 9am and can be in the San Juan Islands in time for a beach walk or short kayak paddle before dinner. We anchor in a different location each night. Enjoy hiking, wildlife viewing, and kayaking, as well as a good night’s rest in one of our cabins with comfortable queen-sized beds and private heads. You will be treated to gourmet meals prepared on board, while you explore the San Juan Islands. Visit our schedule page for dates and prices or  Email Reservations  for more information.

4-day San Juan Island Escapes

These cruises are longer and give you more time to explore the San Juan Islands. They leave out of Bellingham at 9am on Thursday morning and return on Sunday around 5pm. We offer 4-day cruises on our schedule, but we also welcome custom and private cruises that are for as long as you like.

We take our time cruising at about 7 knots to each night’s destination. Along the way we will make stops for hiking, tide pooling or shopping at one of the many small towns that make up the charming character of the San Juans. As with all of our cruises, your vacation includes all meals cooked by Christine on her wood cook-stove. Enjoy hand made croissants still warm from the oven for breakfast, or for dinner savory halibut tacos with just made corn tortillas and salsa prepared that afternoon. Contact us at 877-670-7863  or Email Reservations for more information.

Guided Kayak Mothership Cruises (By Special Arrangement)

Let the David B be your base camp. On our guided kayak tours you’ll explore a new area each day. In the mornings, you’ll be guided on an easy paddle of 1 1/2 to 2 hours before coming back to the boat for lunch and a change of location.  In the mid-afternoon, we’ll re-launch the kayaks for a comfortable paddle before a filling dinner with wine and conversation.

All of the sea kayak equipment, meals and, of course, guides are included. No kayaking experience necessary, the trips are open to adventurous people of all abilities, and because of the small group size (8 passengers max.) we can easily guide guests with different paddling abilities.

To Book Your San Juan Islands Getaway Call 360-474-7218 or Email .

"10 Days of Charter for the Price of 7 Days" Special! A 43% added value!

Available on select charter start dates: 3/20, 3/30, 4/10, 4/20, 5/1, 5/11, 5/22, 6/1, 6/12, 10/5. click here for details..

* NOTE: $20/day provides you and each member of your crew with a total of $1,000,000 personal liability coverage during your charter.

Discounts available for multi-week (2+) and for multiboat (3+) charters. For details and off-pattern rates please visit our charter FAQs.

Special Opportunities

T. 360-671-8089 (charter) | T. 360-671-8339 (school) | T. 360-671-0829 (brokerage)

2615 South Harbor Loop, Suite 1, Bellingham, Washington 98225

HOME       INSTRUCTION       CHARTERS       BROKERAGE       ABOUT US       CONTACT

©Copyright 2022 San Juan Yachting | All Rights Reserved | This Website was Handcrafted by the Staff at San Juan Yachting

View Our Sitemap

When you charter with San Juan Yachting, you experience...

• Professional maintenance – each off-season, all of our powerboats undergo a 105-task preventive maintenance checklist, the most comprehensive and exacting preventive maintenance program in the charter industry worldwide! (See this checklist under “Charter Planning/Preventive Maintenance” on our website.)
• 40 years of experience – Founded in 1982, we are among the region’s senior charter managers.
• Complimentary personalized service by boating specialists. We know the islands and love cruising them!
• Complimentary yacht cleaning service on your return from your charter.
• Free parking with 24 hour surveillance.
• Personal cruise planning assistance.
• Chase boat – available 24 hours should you encounter any difficulties.
• Discounts for multi-week and multi-boat cruises.
• Handy guides to our personal favorite spots in the islands.

Special Rates

• Multi-Week: 10% off the charter rate and 25% off the daily damage waiver for your second consecutive week of charter. 15% off the charter rate and 50% off the daily damage waiver for your 3rd consecutive week of charter and beyond.
• Multi-Boat Charters: 10% discounts for multi-boat charters (flotillas of 3 or more boats).
• Preferred Charter Guest Discount: As a repeat charter guest in good standing we give you 5% off the charter rate on your week-long charter.
• Veterans & First Responders: As a member or veteran of the US Armed Forces we offer you $150 off your week-long (or longer) sail or power charter. This discount is also extended to police, fire and EMT first responders. (Cannot be combined with the Preferred Charter Guest Discount.)

Special Opportunities

T. 360-671-8089 (charter) | T. 360-671-8339 (school) | T. 360-671-0829 (brokerage)

2615 South Harbor Loop, Suite 1, Bellingham, Washington 98225

HOME       INSTRUCTION       CHARTERS       BROKERAGE       ABOUT US       CONTACT

©Copyright 2023 San Juan Yachting | All Rights Reserved | This Website was Handcrafted by the Staff at San Juan Yachting

View Our Sitemap