The Caribbean Sea is famous for its clear blue waters, sunny beaches and free sailing atmosphere.
If we have always dreamed of riding the wind and waves and exploring the hidden bays between the islands, then a Caribbean sailing trip will be an unforgettable adventure.
To help you plan a perfect itinerary, we have compiled a detailed guide.
Popular Sailing Routes Recommended
The Caribbean Sea is made up of countless islands. Here are a few classic sailing routes:
- British Caribbean Islands (BVI): Best for beginners, with calm seas and abundant anchorages. A 7-day round-the-island cruise will allow you to visit islands such as Tortola, Gorda, and Jost Town.
- St. Vincent and the Grenadines: Suitable for intermediate and advanced sailors, with dense islands, pure coral reefs and tranquil harbors.
- St. Martin to St. Barts: Combining French style and holiday luxury, it is suitable for sailors who like culture and food.
Price Information
The cost of sailboat rental varies greatly depending on the season, boat type and whether to hire a crew:
- Boat rental (bareboat): about $2,500-$6,000 per week (suitable for those with a sailing license)
- Charter (including captain and chef): about $8,000-$20,000+ per week
- Sailboat experience: 1-day tour about $100-$250, 3-7-day multi-island trip about $700-$2,000/person
- Recommended booking platform: Dream Yacht Charter, Moorings, Sunsail, Sailo
Opening hours and tourist season
- Best tourist season: December – April of the following year (dry season, sunny weather, stable wind direction)
- Avoid season: June – November (hurricane season, strong winds and waves, some companies suspend operations)
- Sailing companies operate all year round, but boats need to be booked in advance, and the peak season is usually fully booked 3 to 6 months in advance.
Transportation
Most sailing trips start from the port cities of the main islands and can be reached by international flights:
- Tortola (BVI): You can transfer via San Juan (Puerto Rico)
- St. Martin: Direct flights come from major cities in the United States, Canada and Europe
- Saint Vincent: Transfer via Barbados or Grenada
After arriving, you can take a taxi, shuttle bus or rent a car to the dock.
Sailing Travel Tips
1. Visa and customs clearance: The policies of each island country are different. It is recommended to confirm in advance whether the island you are passing through requires a visa and bring your passport.
2. Sailing experience requirements: Bareboat rental requires an international sailing certificate (such as ICC, RYA); if you have no experience, you can choose to charter a boat with a captain.
3. Sunscreen and windproof equipment: The Caribbean sun is strong, so be sure to bring sunscreen, windbreaker, sunglasses and hats.
4. Seasickness medicine is essential: Some seas are windy and rough, so prepare in advance just in case.
5. Drinking water and food: Some islands have limited resources, so it is recommended to purchase enough food and bottled water on the main island before boarding.
6. Environmental awareness: Avoid using disposable plastics, comply with marine ecological protection regulations, and do not anchor near coral reefs at will.
7. Limited WiFi on board: It is recommended to download offline maps and travel information to enjoy the tranquility of isolation from the world.
Recommended experience activities
- Snorkeling and diving: Explore The Baths (Gorda Island) and Tobago Cays coral reefs.
- Island hopping: Stop at different islands, each port has its own unique style.
- Sunset sailing party: Most shipping companies offer sunset sailing + light meal packages, priced at about $70–$120/person.
- Eat at the port market: There are many French restaurants and local handicraft markets in St. Martin and St. Barthelemy.
Let the wind go to the sails, let your heart go to the sea
A Caribbean sailing trip is not only a sightseeing trip, but also a way of life that slows down and embraces nature. Waking up in the sunshine and sea breeze, and falling asleep under the stars, we will rediscover the meaning of "freedom". Are you excited? Start planning our sailing vacation now!
Must-Know Tips: Sailing Liberty of the Seas
Video by OrlandoParksGuy
