sailboats in annapolis md

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• Since our establishment in 1953 by Lawrence Hartge in Annapolis, MD, we have been proudly serving boating enthusiasts on the stunning Chesapeake Bay with exceptional service and unparalleled expertise.
• Lawrence Hartge, a visionary and passionate boater, laid the foundation of our company with a simple yet powerful mission: to offer a full-service boat buying experience that surpasses expectations.
• His dedication to the craft and his love for the Chesapeake Bay set the tone for our company's values, which we continue to uphold to this day.
• Over the years, we have become synonymous with excellence in the Mid-Atlantic region.
• Whether you're a seasoned sailor or a first-time buyer, we understand the unique needs and preferences of our customers, and we strive to match them with the perfect vessel.
• Our extensive selection of boats caters to all tastes and budgets. From sleek powerboats to classic sailboats, we offer a diverse range of options that will suit any boating enthusiast.
• Whether you're looking to buy, sell, or simply enhance your boating experience, we are here to make your dreams a reality.
• Come visit us and tour our boats at Pier 7 Marina in Edgewater, MD.

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• Annapolis: 410.263.8234
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A Grand Experience for All

Custom built for sailing, comfort and fun. Our cruising grounds are some of the most beautiful and historic in the country

Corporate Events

Special occasions, adventure & entertainment.

Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment.

USCG certified for 49 passengers. Music. Full bar. Every Sail is Unique.

One Great boat, two great locations

About the boat.

The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them.

The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser. Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design.

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SAIL LOFT ANNAPOLIS, MARYLAND, US

North Sails is the world's premier sailmaker for racing and cruising sailboats. Since opening our first sail loft in 1957, we have been the number one new sail choice for world-champion racers, superyachts, one-design sailboats , catamarans, trimarans, and casual cruisers. New sail options range to cater to any sailing adventure or budget. We look forward to welcoming you to our sail loft in Annapolis, Maryland. Contact our experts to learn more.

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Jeff is a dedicated salesman at North Sails, currently working with the One Design team in Annapolis. Starting as an Apprentice Sailmaker in 2021, he quickly rose through the ranks, gaining extensive experience. A 5th generation Lightning sailor, Jeff has excelled in various sailing championships. He studied Economics at Florida State University, where he was a captain of the sailing team.

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North Sails is the premier sailmaker for all  racing  and  cruising  sailboats. We are the number one new sail choice for world-champion racers, superyachts,  one-design sailboats , catamarans, trimarans, and casual cruisers. New sail options range to cater to any sailing adventure or budget. 

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Annapolis, Maryland

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About annapolis sail works, our mission.

As a veteran-owned and operated small business, we strive to serve the local sailors and performance water sports athletes of the Chesapeake Bay with the best boats, equipment, repairs, and expertise to make competitive sailing and other watersports accessible and sustainable for all.

Veteran-owned Small Business

 A veteran-owned and operated company, Jake Crespin and Jeff Daigle established Annapolis Sail Works in 2023 to serve the Chesapeake Bay waterfront community with high-quality sailboats, equipment, repair services, and expertise. Jake and Jeff are both avid lifelong sailors with extensive sailing and marine industry backgrounds and a passion for boats, performance, and recreational sailing. Jeff is a retired career Coast Guard Helicopter Pilot and a Texas Maritime Academy graduate, where he was captain of the varsity sailing team. Jake is a career Marine Corps Infantry Officer and graduate of the U.S. Merchant Marine Academy, where he sailed on the Kings Point varsity dinghy and offshore teams. Both owners race various classes of dinghies, keelboats, and offshore boats. They founded Annapolis Sail Works to make high-performance and recreational sailing on the Chesapeake Bay more accessible and sustainable by bringing a full-service dinghy shop back to Annapolis, MD. 

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Annapolis, Maryland

Bluewater yacht sales at south annapolis yacht centre.

Bluewater Yacht Sales - Annapolis, MD

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• Baltimore 410.342.6600
• Annapolis 443.716.7965
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Oxon Hill, MD

Beautiful Sailing Catamaran with Captain

Annapolis, MD

46' Catamaran Charter with Water Toys - Annapolis, MD

Edgewater, MD

Excellent Chesapeake sailing onboard Windsnap

Boston Whaler Harpoon 5.2 Sailboat

"Equinox" - Center of the Sun - Lippincott 30'

Sailing Charter - Sunset Cruises, Learn to Sail, and Family Fun Time!

Sailing Vessel (S/V) DreamCatcher

25' Coronado Clara B in Arnold, MD!

Stable, comfortable & fast - sleeps 8 w/4 baths!

Experience sailing in the heart of Annapolis md

Custom Sailing Charters - 44’ Catamaran

LANI - Leopard 42' Catamaran Sailboat

New Yacht Charter

Solomons, MD

"Hallelujah" Beneteau Oceanis 350 Sailboat

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Chestertown, MD

Catalina 30 II -1992

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Galesville, MD

Das Boot Custom Sailing Charters

How to rent a sailboat in annapolis, find the perfect boat.

Enter your desired location and date to explore our fleet of sailboats.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

Book with ease

Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

Top destinations for sailboat rentals

Top sailboat rentals reviews in Annapolis, MD

46' Catamaran...

We rented this boat for my sister's bachelorette party and had the BEST time! Seriously it was the highlight of the...

My group had the best time with Windsong Charters. Everything was exactly as described and we had a wonderful day....

Beautiful Sailing...

I just went on James’ boat with my family today and we had a fabulous time! James was fun to be around and we all got...

ESCAPE--Leopard...

We had a group of 8 to celebrate a birthday and Captain Jack was great! We had an amazing time and the catamaran was...

The boat was super spacious and filled with an array of water toys that were a crowd favorite at my sister’s...

We had an amazing sunset cruise with James! He was so responsive and went above and beyond to ensure we enjoyed our...

Wind on the Chesapeake picked up each day we were out, with mid-afternoon giving a good 10kn of wind which allowed us...

Sailing Charter -...

Audrey and Garrett were fun, friendly, knowledgable, and accommodating. Perfect first sailing experience. Highly...

Experience...

"Equinox" -...

Great time on the water, appreciate your facilitating

Birthday well spent! I couldn't ask for anything better. Best captain ever, fast response and great people all...

Excellent...

Another great day on the water! This is our second time out on Windsnap, sailing un-captained this time. Everything...

Sailboat Rentals in Annapolis, MD

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Sailing Season is Here. Join Us for a Sail!

2 Hour Public Sailing Cruises

“My husband and I sailed with you on last Saturday evening’s sunset cruise…we were with our dear friends who were celebrating their 25th anniversary. We all had such a wonderful time! Candidly, I was a bit apprehensive, having never sailed before and not knowing what to expect, but I will definitely be back! We all will. Thanks again, so much, for a wonderful adventure.”

Marieanne H.

“We love sailing on the Woodwind and Woodwind II; It is part of our summer plans every year, especially when family comes from out of town. The crew is always fun and professional and each sailing is a new adventure!”

The Paulsons Urbana, Maryland

Woodwind sails up to four times daily throughout our summer season from the Annapolis Waterfront Hotel. Each trip is unique. Let our captains and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel.

On our cruises you will see:

• United States Naval Academy
• Annapolis Harbor
• Chesapeake Bay
• Scenic views of Annapolis skyline
• Severn River

Depending on the wind direction and speed, you may see:

• Chesapeake Bay Bridge (we may even go underneath)
• Thomas Point Lighthouse
• Kent Island
• Regattas competing in the Bay
• Ospreys and other local birds
• Watermen checking their catch

The 74-foot schooner Woodwind and Woodwind II were custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as yachts in the early 1900s. Her handsome mahogany brightwork, gleaming chrome, and roomy cockpit distinguish her from cargo-carrying work vessels. Our bar is stocked with wine and beer, including a nice selection of local craft beer.

Have a group of up to 16 passengers?

You can get your tickets further in advance and be welcomed aboard first. Click here to learn about our group sailing packages on public cruises.

Weekday sunset sails include the following events or entertainment:

History Mondays

A guided tour exploring the history of the area, the Chesapeake, and the sights you see while on a sail. Each week we will focus on a specific interesting topic with a guest speaker aboard. Early May – September.

Beer Tasting Tuesdays

Sample while you sail! Each month we feature a different brewery from the Mid-Atlantic Region, and their representative comes aboard and teaches you about beer. 3 samples of beer come with the cruise, and then order full beers from the brews that you enjoyed the most.  Schedule of Breweries.

Wednesday Night Races

Join the crew and race Woodwind vs. Woodwind II every Wednesday night from April 27 through August 31. 100 other sailboats also race in the Wednesday Night Regatta. Wednesday’s are the nights to Party Like A Sailor.

Thursday, Friday, Saturday, and Sunday

There is no specific entertainment on these days of the week. There is so much to see as we sail by the United States Naval Academy and into the Chesapeake Bay. Let the crew serve up your favorite beverage as you relax watching the sunset over the city skyline.

4 thoughts on “2 Hour Public Sailing Cruises”

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2003 Marlow 65

Annapolis, MD, US

• Length 65 ft
• Price $1,299,000

2015 Sabre 48 Salon Express

• Length 48 ft
• Price $799,900

2004 Beneteau 473

• Length 47 ft
• Price $220,000

1997 Mainship 47 Motor Yacht

• Price $139,900

1998 Hylas H46

• Length 46 ft
• Price $324,900

2008 Beneteau 43

Galesville, MD, US

• Length 43 ft
• Price $169,000

1986 Hatteras 43 MY

Solomons, MD, US

• Price $119,900

2023 Ranger Tugs R-43 CB

• Price $999,987

2022 Ranger Tugs R-43 CB

Jensen Beach, FL, US

2003 Sea Ray 420 Sundancer

Baltimore, MD, US

• Length 42 ft
• Price $189,900

2003 Beneteau 423

Tracys Landing, MD, US

• Price $130,000

2016 Celtic Yachts 40

• Length 40 ft
• Price $375,000

2001 Carver 396 Motor Yacht

1985 morgan 384.

Sparrows Point, MD, US

• Length 38 ft
• Price $69,900

2006 Admiral 38

Pasadena, MD, US

• Price $249,900

2010 Regal 3760 Sportyacht

Saint Michaels, MD, US

• Price $169,900

1996 Sabre 362

• Length 36.17 ft
• Price $124,900

2017 Monterey 355 Sport Yacht

Mantoloking, NJ, US

• Length 35 ft
• Price $229,900

1981 Bristol 35.5 CB

Severna Park, MD, US

• Price $29,500

2007 Meridian 341 Sedan

Deale, MD, US

• Price $134,900

2011 Cruisers Yachts 330 Express

Traceys Landing, MD, US

• Price $174,900

2005 Beneteau Oceanis Clipper 343

• Length 34.75 ft
• Price $79,900

2023 Jeanneau Sun Odyssey 349

• Length 34 ft
• Price $249,990

2005 Pro-Line 34 walkaround

Chesapeake Beach, MD, US

• Price $74,900

2021 Sea Ray 320 Sundancer

Edgewater, MD, US

• Length 32 ft
• Price $299,900

2002 Hunter 326

• Price $49,900

2020 Cutwater C-32 CB

New Bern, NC, US

• Price $329,987

2019 Beneteau Swift Trawler 30

1988 trojan f32 sedan.

Gingerville, MD, US

• Price $19,900

2006 Beneteau 323 Centerboard

• Price $64,900

1980 Jarvis Newman 32

• Price $99,000

1994 Tiara Yachts 3100 Open

Colonial Beach, VA, US

• Length 31 ft

2016 Ranger Tugs R-31S

Grasonville, MD, US

• Price $239,987

2000 Catalina 310

• Price $59,900

2009 Pursuit 310 Sport

• Price $122,700

2002 Sea Ray 310 Sundancer

• Price $34,900

2023 Ranger Tugs R-31 CB

• Price $473,987

2007 Catalina 310

• Price $74,500

2020 Grady-White Canyon 306

• Length 30 ft
• Price $224,900

2016 Sailfish 290 CC

• Length 29 ft
• Price $159,987

2014 Regal 30 Express

• Price $99,900

2022 Ranger Tugs R-29 CB

• Price $359,987

2022 Cutwater C-288 Coupe

• Length 28 ft
• Price $339,987

2002 Albin 28 Tournament Express

Crownsville, MD, US

• Price $94,900

1994 Tartan 28 Piper

• Price $49,000

2018 Cutwater C-28

• Price $169,987

2006 Cruisers Yachts 280 Express

• Price $39,900

2002 Albemarle 280

Rock Hall, MD, US

• Price $53,900

2016 Crownline 270 SS

Pasadina, MD, US

• Length 27 ft
• Price $65,000

2001 Sea Ray 270 Sundancer

Middle River, MD, US

• Price $26,900

2023 Ranger Tugs R-27

• Price $249,987

2013 Pursuit DC 265 Dual Console

• Length 26 ft
• Price $99,987

2020 Crownline 264 CR

2007 edgewater 268cc, 2007 four winns 258 vista.

• Price $30,000

2013 Cutwater 26 Coupe

Woodbridge, VA, US

• Price $119,999

2003 Four Winns 268 Vista

• Price $24,500

1999 Parker 2520

• Length 25 ft
• Price $54,900

2010 Bayliner 255

2012 monterey m5 sport boat.

• Price $43,900

2005 Trophy 2503 Center Console

2014 vanquish 24 cc.

• Length 24 ft

2021 Ranger Tugs 23

• Length 23 ft

2023 Key West 219 FS

• Length 22 ft

2008 Boston Whaler 200 Dauntless

• Length 20 ft

Brokers You Can Trust

Experienced.

We’ve lived aboard, cruised, and owned both power and sail. Our expertise and passion for boating in the Annapolis area and beyond allows us to enhance your buying or selling experience. As recipients of industry awards and members of maritime clubs, we are truly immersed in the boating community.

We hold our customer’s satisfaction in the highest regard. We know the waters and can help lead you through the buying or selling process. Our knowledgeable team is here for you before, during, and after the sale.

We’ve been local residents for decades and are experts in Annapolis.  We leverage our knowledge of boating in Annapolis to help buyers find the perfect boat for their wants and needs.  From personally enjoying time on the water all across Maryland, we can share local insight into making the most of your new boat.

Ready to make a decision?

Yacht Brokers of Annapolis can help you get started today

Port Annapolis Marina 7080 Bembe Beach Rd #211, Annapolis, MD 21403

(410) 206-2755

[email protected]

Providing excellent yacht brokerage service to Annapolis as well as Kent Island, Washington D.C., Baltimore, and the surrounding areas.