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Sail the Florida Keys
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Get Away to Key West and Explore the Florida Keys by Sailboat
Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.
Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks.
While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business.
Some of the highlights to experience on a Florida Keys Sailing Charter Vacation
Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.
Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable.
Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation.
A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife.
Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers.
From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place.
If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route.
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The Essential Guide to Sailing Holiday Charters
The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.
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Featured Yachts in Florida Keys
CAMILLE | From US$ 85,000/wk
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Florida Keys Yacht Charter
Often considered America 's Caribbean Islands the Florida Keys yacht charter offers spectacular locations to explore.
You will often read references to a 'jade necklace' or a 'string of pearls' in descriptions of the many (800+) islands that stretch off into the sea. The Keys have become increasingly busy over the last few years with an increase in cruise ship and other tourism. The keys feature plenty of energy ashore, but to get away into the quieter areas a charter yacht is the only way to go.
Photos: 1. A diver explores the coral reef in the Florida Keys National Marine Sanctuary off Key Largo - The reef system in the Keys is the only contiguous coral barrier reef in North America - Photo by Bob Care-Florida Keys News Bureau; 2. A Florida Keys fishing guide positions his angler to cast for a bonefish off Key Largo- Photo by Bob Krist-Florida Keys News Bureau; 3. Sunset in Key Largo- Florida Keys- paints a pretty picture at the Kona Kai Resort -Photo by Bob Krist-Florida Keys News Bureau
The first Key to come across on your cruise south will be Key Largo . Over the years Key Largo has become a busy weekender retreat from the mainland. As you sail further down though the Keys you will finally come to the last one, Key West .
The Florida Keys are sheltered by the only living coral reef in the United States. The Keys are well known to yacht charterers for the spectacular scuba diving and snorkelling, kayaking and eco-tours, dolphin watching, island hoping and fishing.
The types of yacht charter available in the Florida Keys are all the main types including motor, sailing, bareboat charter, skippered, crewed yachts, catamaran, power boat, sailboat, luxury yachts and super yacht charter.
The Florida Keys features a year round calendar of special events such as fishing tournaments, international yacht races, motor yacht races, Fantasy Fest, a lighted boat parade and Florida's own 10 day long Mardi Gras. We recommend charter yachts with a draft of under 4 or 5 ft (1.3 - 1.5m), as with a catamaran, so that you can get in to all the best areas within the Florida Keys.
Key West Yacht Charter
Key West has the ideal year round climate for yacht charter. Key West is a very unique town being the southernmost US city where history and tradition meets natural beauty and serenity. This city has real estate titles that date back to the King of Spain! Within walking distance from the historic Seaport District you will find palm-lined streets, tropical gardens, Ernest Hemingway's home, fine shops, art galleries, quaint restaurants and cafes. You can walk in the footsteps of Thomas Edison, Lou Gehrig, Harry Truman, and Tennessee Williams. You will also discover lively bars and pubs along with street musicians, jugglers, mimes and artists.
It is not unusual for charter guests to day sail their charter yachts using Key West as a base. They will sail and explore the keys during the day, utilising the restful anchorages, and then return to the first class marinas at night to experience Key West's nighttime entertainment. Remember to radio ahead to reserve marina space, as Key West is a busy part of the Florida Keys.
Below is a selection of fabulous Florida Keys charter yachts - please, contact us for additional vessels and more information here .
- Florida Keys Charter Itinerary
- Browse Florida Keys Charter Yachts
- Luxury Motor Yachts for Charter in Florida Keys
- Luxury Sailing Yachts for Charter in Florida Keys
- Luxury Catamarans for Charter in Florida Keys
- Florida Keys Yacht News
Florida Keys Yacht Charter Enquiry
"I have just emailed your post charter feedback to you. It doesn't say nearly enough about how well and hard you worked on this deal. I am a retired commercial real estate broker who understands the importance of the deal-maker in the deal. You are a deal maker of the first order." E. G - chartered in Florida Keys.
Yachting Destinations Near the Florida Keys
In close proximity to the Florida Keys are a number of exciting sailing destination.
New England
Napa Valley
Yachts for charter in the florida keys, queen miri | from eur€ 1,125,000/wk.
KENSHO | From EUR€ 850,000/wk
WAYFINDER | From EUR€ 375,000/wk
STARSHIP 185' | From US$ 275,000/wk
MARIA | From US$ 230,000/wk
LADY ELAINE | From US$ 225,000/wk
GIGI | From US$ 225,000/wk
TCB | From US$ 215,000/wk
MYSORAH | From US$ 200,000/wk
ASPEN ALTERNATIVE | From US$ 199,000/wk
FAM | From US$ 195,000/wk
GLORY | From US$ 179,000/wk
ZOOM ZOOM ZOOM | From US$ 175,000/wk
AVALON | From US$ 155,000/wk
FOCUS | From US$ 150,000/wk
AQUASITION | From US$ 150,000/wk
RELENTLESS | From US$ 150,000/wk
PERSISTENCE | From US$ 140,000/wk
ANTELOPE IV | From US$ 140,000/wk
CLAIRE | From US$ 139,500/wk
Florida Yacht News
Luxury yacht INVICTUS available for ...
Florida charter yacht REAL SUMMERTIME ...
38m superyacht GLORY offering charters ...
Remodelled superyacht PERSISTENCE ...
Charter yacht disclaimer.
This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.
Key West & Marathon, Florida
We specialize in private luxury yacht & sailing charters at affordable prices. we offer day charters as well as multi-day charters., why blue ocean yacht charters.
Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing. We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys. Just looking for a day charter? Look no further. We offer four hour, eight hour, and 24 hour charters as well multi-day charters.
All our yachts come fully equipped to make your private boat charter experience what you’re looking for. We offer motor and sailing yachts that provide the best boat rental experience.
Florida Keys Yacht Charter
Embark on a unique yacht charter adventure in Key West and the Dry Tortugas. Discover history, pristine natural beauty, and thrilling offshore passages.
Discover the Florida Keys
Florida Keys & Key West: A charterers' delight with vibrant city life, the remote Dry Tortugas National Park, and underwater treasures waiting to be explored.
Key West offers more than just a lively city - it's a gateway to secluded Dry Tortugas, rich marine sanctuaries, and unforgettable offshore adventures.
Chart your course with confidence
Explore our handcrafted Florida Keys sailing itinerary.
Sail from bustling Key West to serene Dry Tortugas. Dive into history at Fort Jefferson, snorkel at Windjammer Wreck, and savor the majestic sunsets over Marquesas Keys
Florida Keys: explore what awaits you
Uncover the cruising conditions you can expect out there on the water and the various sailing seasons for this stunning destination.
Unlock in-depth Florida Keys yacht charter insights
Explore our latest Florida Keys blog posts to get a deeper understanding of its hidden gems.
Summer reads: nautical adventures & high-seas thrills
To help build your summer reading list for those relaxing moments on the beach, I’d like to share some books I highly recommend that I’ve read in the past.
What is the Distance from Key West to the Dry Tortugas?
Discover the distance from Key West to the Dry Tortugas in our guide including essential sailing insights for a successful yacht charter.
Key West Bareboat Charter | Sailing Adventure to the Dry Tortgas
Our 2021 Key West bareboat charter and sailing adventure to the Dry Tortugas. Great fishing, long passages, and plenty of history.
Florida Keys frequently asked questions
Have more questions? Visit our comprehensive FAQ page for detailed answers to common Florida Keys charter questions.
Key West offers a variety of provisioning options, from supermarkets to specialty stores. Visitors should plan to stock up on necessities since there are no provisioning options in the Dry Tortugas.
Sailors can enjoy steady trade winds and warm, comfortable temperatures year-round in Key West, with the best sailing conditions from December to May, avoiding the peak of hurricane season from June to November.
During the hurricane season, it's crucial to monitor weather forecasts closely and have flexible plans, as tropical systems can develop rapidly, potentially affecting sailing itineraries.
The sail to the Dry Tortugas is about 60 nautical miles west of Key West, offering a rewarding journey filled with potential wildlife sightings and the allure of visiting a remote national park. Read more here .
The offshore passage to the Dry Tortugas National Park is a unique opportunity to experience history, seclusion, and pristine natural beauty, which are not accessible to most visitors. Learn more about this here .
Explore pristine shores and hidden gems
Unveil the best of Florida Keys, from secluded beaches to enchanting islands and serene anchorages.
Florida Keys charter planning?
Consider booking with the Yacht Warriors.
Introducing Vivo Per Lei 58 Leopard Catamaran flagship model Learn More
Creating unforgettable journeys on custom designed luxury catamarans learn more, luxury catamaran sailing charters tailored in every way to suit your needs learn more, key west and key largo locations sailing the beautiful florida keys, bahamas and beyond learn more, catamaran sailing charters half day, full day & overnight learn more, welcome to calypso sailing.
Calypso Sailing was established in 1988 in the beautiful Florida Keys. With locations in both Key Largo and Key West we specialize in luxury sailing vacations on a range of Leopard Catamarans, both bareboat and Captained. Our monohull sailing charters can take groups of 6 to 38 on day, sunset and overnight trips whilst not forgetting the iconic African Queen steamboat from the 1951 movie starring Humphrey Bogart and Katharine Hepburn which operates daily in Key Largo.
Our aim is taking care of all your cruising needs
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