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Caribbean Sailing Vacations

Caribbean Sailing Vacations

The best sailing vacation in the world awaits you in the Caribbean. My job as your charter broker is to assist you in finding the best well maintained, all-inclusive charter yachts that fits your needs and requirements. The yachts I recommend all include dedicated professional captains, gourmet chefs and crews to tend to your every wish.

Onboard a private charter yacht, guests set their own timetable and itinerary. Your yacht is equipped with a variety of exciting water sport toys to use, or you may want to just kick back and relax with a tropical drink in hand and let the world float by.

The warm climate and trade winds make your Caribbean sailing vacation the most relaxing and refreshing experience. You’ll encounter the breathtaking scenery of lush green islands rising out of the crystal clear blue water. You’ll also see the miles of beautiful white sand beaches, all from the deck of your own private yacht. The Caribbean, from this unique perspective, will appeal to your every sense.

The Caribbean has something for everyone. People new to chartering will appreciate the smooth and protected waters of both the Virgin Islands and the Grenadines. More experienced sailors may choose the open sea passages of all the islands in between those areas.

British Virgin Islands Map

Starting at the northern end of the Caribbean Archipelago is the popular cruising grounds of the U.S. Virgin Islands consisting of St. Thomas and St. John. .A short distance from the U.S. Virgin Islands is Tortola in the British Virgin Islands. This area is basically the home base to the majority of fully charter yachts in the Caribbean

St. Thomas and Tortola are home to more charter yachts than the rest of the Caribbean combined. Why is this?

The Virgin Islands are easy to reach by air. They offer well protected waters with ideal sailing conditions. These islands provide an amazing amount of safe comfortable anchorages that are never more than an hour away.

The Virgin Islands extend approximately 45 miles east to west with approximately 50 islands in that span. All offering hundreds of wonderful places to drop an anchor.

The next major cruising grounds heading south are the Leeward Islands, made up of such islands as Sint Maarten/St. Martin and Antigua. Numerous large sailing yachts, catamarans and motor yachts and mega yachts call these islands home. They cruise the open waters to such places as St. Barthelemy (St. Barts), St. Kitts, Nevis, Guadeloupe, and Barbuda.

Heading still further south you enter the Windward Islands, the base for many crewed charter yachts.. These islands are Martinique, St. Lucia to the north, and St. Vincent and Grenada to the south. Canouan, Union Island, in the Grenadines are popular departure points since both now offer luxury resorts and airports with connecting flights to major airports in the Virgin Islands. You can also find a few crewed charter yachts in Grenada offering the option to depart from the island of  Carriacou.

There are charter yachts to match every taste and budget. The typical cost of chartering a luxurious fully crewed all-inclusive private yacht in the Caribbean starts at around $10,000 a week. This includes all gourmet meals and in most cases, even the ship’s bar is included. Naturally this is dependent on the size of the yacht and the number guests in the charter party.

I’d like to suggest when book a charter yacht vacation in the Caribbean you purchase, Trip Insurance because of the rapidly changing weather patterns in these cruising areas to protect your investment should the possibility of bad weather arise and affect your sailing vacation.

Frequently Asked Questions

How much does a Caribbean sailing vacation cost?

On average for yachts between the sizes of 45 ft. to 70 ft. an average charter rate for a one week charter can be between $2,500 per person to over $5,000 per person. Rates will vary depending on the number of people in the charter party, the size & type of yacht, and the duration of the charter. BTW, as a rule you will find Motor Yachts charter rates are higher than Sailing Vessel charter rates.

What is the best time of year for a sailing vacation in the Caribbean?

The best months for a Caribbean sailing vacation in the Leeward Islands* are Mid-November through Mid-December, and Mid-January through June, when the weather is typically dry, sunny, and clear, providing the perfect cruising conditions, with mild temperatures and calm waves.

In the Windward Islands* the ideal months for a sailing vacation are June through Mid-December through June.

The period of Mid-December through Mid-January is known for the Christmas Winds. Generally, in both the Leeward and Windward islands, the wind speeds are higher, with possibly strong gusts, making sea conditions a bit rougher.

In regard to rain, as a rule the warmer months produce more rain. On the other hand, during the ideal months to sail you will experience an occasional rain squall. These rain squalls will be accompanied with a momentary blast of high wind. Rain squall last only a few minutes and before you know it the sun is back out. A full day of rainy conditions is rare, although you may have days when rain squalls appear more than once a day.

*Leeward Islands: From the Virgin Islands down to Dominica.
*Windward Islands: From Martinque down to Trinidad

Is the Caribbean good for sailing?

Yes! The Caribbean is a secure and enjoyable place to sail. The Caribbean sailing vacation can be a fantastic and stress-free way to experience this stunning region with the right planning.

Sailing in the Caribbean is a great opportunity for new sailors to get their feet wet and for seasoned sailors to put their knowledge to the test. Sailing in the Caribbean can be simply enjoyable with the proper yacht.

The Captain and Chef/1st Mate aboard your yacht are there to guide you throughout your journey by providing comfort, entertainment along with world class cuisine.

On your sailing vacation, you can unwind completely, and take in the finest scenery the Caribbean has to offer.

For more information, go to our Information Request page or contact Dennis at Charter the Caribbean at 321-233-2097 or email:

New To Yachting?

If you’re new to yachting, our First Time Yacht Charter Guide is the perfect resource to help you navigate the world of luxury yacht charters.

Caribbean Yacht Charter

Whether you’re a seasoned charterer or new to luxury yacht charters, our comprehensive First Time Yacht Charter Guide is designed to assist you every step of the way.

Filled with frequently asked questions, a detailed boat comparison guide, real-life experiences, and visually engaging infographics, this resource is the perfect tool to educate yourself on the world of yacht chartering.

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Contact us to start a conversation about your dream vacation, and let us show you how we can help bring your vision to life through our exceptional yacht charter services.

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