Sailing trips Florida Keys

Plan your Sailing Trip in the Florida Keys now

Experience a sailing trip in the Florida Keys with family and friends. Cruise on a sailboat and feel the excitement of exploring the captivating coastlines. Or cruise on a catamaran and discover hidden sandbars and breathtaking beaches.

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Cruise on a sailboat in the Florida Keys

Discover our amazing collection of sailboats for a cruise with your family and friends

Sailboat Custom 19.12m

Key West
16

From $2,037 per day

Island Trader 41 (1990)

Key West
2

From $1,072 per day

Sailboat 40 (1990)

Key West
2

From $1,622 per day

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Cruise on a catamaran in the Florida Keys

Experience your dream vacation on a catamaran

Cruise catamaran and sailboat

Want to plan a sailing trip?

Our experts are here to help you organize the perfect sailing trip.

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Best time to visit the Florida Keys

The Florida Keys are warm all year round, with temperatures reaching over 90°F from June. The main tourist season in the Florida Keys stretches over the winter months, with temperatures starting from 65°F. If you want to avoid crowds and skip the heat, you should plan your trip from March to May.

Places to see in the Florida Keys

With 800 different keys, there is no shortage of exciting places to sail to in the Florida Keys. Also, don't miss out on exploring Western Sambo, the gorgeous coral reef in the Florida Keys National Marine Sanctuary. A sailing trip in the Florida Keys is the perfect way to spend your vacation.

Your guide to a dream sailing trip in the Florida Keys

Embark for a sailing trip in the Florida Keys. This island chain goes between the Atlantic Ocean and the Gulf of Mexico giving you plenty of things to do. The Florida Keys is home to a wide variety of plant and animal life with coral reefs, mangroves and seagrasses to explore. Cruise on a catamaran in the Florida Keys and visit as many keys as you can! Experience a new type of holiday unlike any other with the scenic ocean views.

Sailing trips in the Florida Keys with Family and Friends

The Florida Keys can be the perfect destination to visit for your sailing trip, whether you want to go with family, friends or both. You can explore the area, or add water sports equipment onto your charter to really create a unique experience. Adults can try things like water skiing or windsurfing, while the kids splash around in the water with the inflatables. There are also plenty of different areas for snorkeling and scuba diving that give you the chance to dive deep into the depths of the Atlantic Ocean and admire the rich marine life.

If you are going on a crewed cruise in a sailboat or catamaran with your partner, you can also have a romantic dinner on board, catered entirely by your own personal chef. What could be better than a sumptuous feast on board, underneath a sensational sunset in front of a breathtaking backdrop?

Sailing trips in the Florida Keys with captain and crew

Explore more with a sailing trip in the Florida Keys with a captain and crew. Click&Boat gives you the freedom to choose whether to cruise with a captain and crew, just a captain or bareboat charter.

Booking a cruise with a captain and crew is ideal so you can enjoy your vacation without worries. The captain will guide you through some of the most beautiful areas the Florida Keys has to offer. They will also take care of any sailing technicalities and problems you may have. The crew will also ensure the cooking, cleaning and drinks are taken care of so your group have more time to relax and have fun.

When you book your sailing trip in the Florida Keys with a captain and crew, the price of the boat rental is divided into the rental price of the boat, the additional services and the provision of funds. The provision of funds is the money clients give the captain so they pay for the extras of the trip such as gas, food, and drinks.

Your sailing trip in the Florida Keys can also be done only with a captain. The captain will take charge of navigating you and your group to your desired destination. Comfort, relaxation and safety in the palm of your hands. You can also choose to sail without a captain or crew if you have a valid boating license.

The best route for a sailing trip in the Florida Keys

The Florida Keys is a great place to visit with plenty of places to discover. Relax on the deck while listening to the sound of the waves and a drink in hand. During the day go snorkeling or deep diving through gorgeous caves and coral reefs. You may also choose to moor in the harbors and stroll through art galleries and local boutiques to spark your imagination. Then, find a great restaurant with fresh, local seafood and tropical cocktails while you watch the colorful sunset.

 Some of the best places to visit in the area include:

• Key Largo

• Islamorada

• Marathon

• Big Pine Key

• Key West

• Dry Tortugas

• Sunset Key

Your cruise on a catamaran or sailboat largely depends on what activities you are interested in doing while onboard. Do you like fishing? Are you a marine life fanatic? Do you want to go for a full adventure of kayaking and parasailing or would you rather find the most relaxing and remote beaches the Florida Keys has to offer? The choices are endless with Click&Boat. Decide in your group what activities you’d like to do and plan your itinerary around that!

Are you looking for a general week sailing itinerary in the Florida Keys? Look no further! Start in Biscayne Bay, one of Florida’s natural beauties with ecosystems not found anywhere else in the United States. The area is home to aquamarine waters and a wide variety of aquatic life. Get your snorkelling gear ready, you’ll want to dive into these waters and swim with the third-largest offshore reef in the world.

Then set sail to Key Largo. There is plenty to see during your time, from John Pennekamp Coral Reef State Park to Key Largo National Marine Sanctuary. Another great place to go snorkeling in the coral kingdom. Onto Islamorada, the ideal location if you want a more laid-back vacation with plenty of outdoor activities. Home to some of the best saltwater fishing in the world from trolling, deep-sea fishing, bottom fishing or fly fishing, there are year-round opportunities to cast off.

Cruise to Duck Key, and visit some of the most beautiful and famous beaches in the Florida Keys. Go swimming or snorkeling, play beach games, or lounge in the sun and relax with palm tree views. Then head to Hawks Cay and Newfound Harbor and paddleboard in the light blue waters before ending in Key West.

What should I choose: a cruise in a sailboat or a catamaran

Choose between a sailboat or catamaran for your sailing trip in the Florida Keys! Each boat type is special for certain occasions so check out which boat works best for you.

Cruise in a sailboat in the Florida Keys for an authentic sailing experience. If you are an experienced sailor, you may opt for a cruise in a sailboat in the Florida Keys so you can get a full adventure. Sailboats are also a more affordable option given their ability to travel large distances without consuming a lot of fuel. They are also suitable for both small and large groups however they are not very spacious.

A cruise on a catamaran in the Florida Keys is another great option if you’re looking for luxury. The double hull structure provides more space than monohull sailboats which make them perfect for larger groups and families. You also have access to shallow waters due to the double hull structure allowing you to cover more ground. However, this boat is more expensive compared to a sailboat. It will also most likely cost more when mooring at marinas due to the boat taking up more space.

What is the weekly cost for a sailing trip in the Florida Keys?

The price of a sailing trip in the Florida Keys can vary depending on the size and model of the boat as well as the type of boat you choose and the amenities the boat offers. Whether you decide to charter with a captain and crew or not can also affect the price. As a guide, a cruise in a catamaran in the Florida Keys is about $6.723 per week.


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