Island getaway with boats in the water | Sebastus Sailing Island getaway boating dock | Sebastus Sailing

Sailing Holidays in Caribbean

A nautical dream come true!

luxury motor yacht with deck lights on in the night


Up to 35% discounts and extra 5% on all bookings made until November 30th, 2023

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What makes Caribbean so attractive for sailing?

The Caribbean is a group of islands which is located on the Caribbean Sea to the East of North America, simply known to as “paradise on earth!”

Whether you’re planning a family vacation with the whole crew, a romantic getaway for two, searching for calm, preserved waters and short island hops or exhilarating blue water passages, the Caribbean is one of the most exciting sailing vacations you could ever experience.

Currency: East Caribbean Dollar, United States Dollar, Euro

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Antigua and Barbuda view of many boats anchored in the bay

Sailing season and climate

The climate in the Caribbean is tropical which means that the weather is hot and sunny all year long. Although most of the islands start their rainy season from May to October, the official hurricane season in the Caribbean begins from 1st of June until the 30th of November.

Caribbean yacht charter options

Tailored yacht vacation

Tell us everything you want to experience and explore and we will get started on working towards making your dream sailing trip come true

Family Sailing Holidays

All-Inclusive or self-catered, it’s your choice. These sailing trips are tailored to bring family close.

Romantic sailing holidays

Is there a better way to explore some of the world’s most romantic holiday destinations but island hopping with your private boat charter?

Bareboat Charter

Boat rental without any crew member. With a valid sailing license, you sail the boat by yourself.

Skippered Yacht Charter

Yacht charter holidays with a professional skipper and other crew members on request.

Luxury Sailing Yacht Charter

Embark on your next sailing trip with class! We strategically plan your luxury sailing holiday to suit all your wishes.

Cabin Yacht Charter

In case you are a solo traveler, couple or a smaller group, and want to have a wonderful sailing experience, but are not able to afford a whole boat charter, cabin charter is a great and accessible option for you!

Pick a route for your perfect sailing holiday

7-Days Sailing around BVI

This 7-day sailing itinerary promises a perfect blend of adventure and relaxation, offering a firsthand exploration of the BVI’s pristine beaches, vibrant coral reefs, and charming coastal villages.

7-Days Itinerary for Family Sailing Holidays in Bahamas

Embark on an unforgettable family sailing adventure in the Bahamas, where crystal-clear waters, white sandy beaches, and warm hospitality set the stage for a perfect nautical getaway.



Didn‘t find what you were looking for?

No problem! Reach out and let’s create your custom route together.


Top Caribbean Sailing Destinations

Street in Cuba | Sebastus Sailing


Cuba is located in the Northern Caribbean where the Caribbean Sea, the Gulf of Mexico and the Atlantic Ocean meet.

British Virgin Islands | Sebastus Sailing

BVI (United Kingdom)

You would definitely fancy a BVI sailing trip as it is known to be one of the top sailing destinations in the world.

Saint Martin sailing | Sebastus Sailing

Saint Martin

Saint Martin is an island in the Northeast Caribbean Sea, approximately 300 km East of Puerto Rico.

Antigua and Barbuda getaways | Sebastus Sailing

Antigua and Barbuda

Antigua and Barbuda is a country in the West Indies in the Americas, lying between the Caribbean Sea and the Atlantic Ocean

Saint Lucia beach | Sebastus Sailing

Saint Lucia

This part of the world offers some of the most vibrant and colourful snorkelling in the Caribbean and where you can relish a warm welcoming and sensational French Creole culture.

Martinique sailing | Sebastus Sailing


In Martinique, you could take joy in swimming and snorkelling among coral reefs or stay at the lovely fishing villages, hot springs, lush rainforests and rugged peaks.

Saint Vincent and the Grenadines | Sebastus Sailing

Saint Vincent and the Grenadines

This is a magical destination where the only limit is your time and how much you can pack into your itinerary.

Sint Maarten beach | Sebastus Sailing

Sint Maarten

The islands generally experience low humidity and recurrent droughts. The average temperature is 27 °C and the coolest period is between December and February.

The Bahamas | Sebastus Sailing

The Bahamas

A tropical paradise that has been a top family vacation destination for decades


Picking a boat type

Picking out the type of boat to go with will generally come down to your budget, the group size, and preferred method of sailing. Moreover, different sailboats available can be chartered independently or with a fully-staffed crew.

Sailboat on the water | Sebastus Sailing
2-12 people
Choose a Sailboat if you are an active traveler or you’re looking for a romantic getaway. Sailboat offer the classic sailing experience and tend to vary in size from 30 up to 64 feet
Starting from 160 EUR per day
luxury catamaran on the water aerial view
2-12 people
Catamaran is a top choice if you’re looking for a smoother sailing experience compared to sailboats. Since the size ranges from 38 to 70 feet, this is a right vessel for bigger groups or families
Starting from 500 EUR per day
Motor yacht on the water | Sebastus Sailing
Motor yacht
2 – 12 people
Depending on what you’re looking for, you may find motor yachts from one up to five cabins and their size tend to range from 30 to 100 ft. These beautiful vessels are perfect for a luxurious touch on sailing vacation
Starting from 500 EUR per day
Waves icon | Sebastus Sailing

Have a question?
We have the answer!

You ask yourself what kind of boat to choose? Which places to visit? We have answers to those questions and many more. So don’t hesitate to get in touch with our friendly team today!
Sailing certificate
Qualified skipper
Radio course
Waves icon | Sebastus Sailing

Requirements for bareboat charter

In order to be able to charter a bareboat in the Caribbean, the skipper is required to fill out a questionnaire and the sailing experience they had. No official sailing license is necessary to have on hand, however, before making any reservations, we advise you to check all the requirements with your agent. Otherwise, we can provide you with a local professional skipper and other crew members (such as hostess and a chef) to attend to you and make your sailing experience a holiday to remember!