Imagine yourself anchoring a sailboat near a pristine beach as the sun sets. As you step ashore, both locals and international sailors greet you with smiles. The sound of music fills the air while you sip on a refreshing cocktail. This is exactly what it’s like aboard Caribbean Sailing Charters.
Sailing in the Caribbean is an adventure like no other. With CKIM, every moment of your sailing vacation becomes a cherished chapter.
The Caribbean offers awe-inspiring vistas at every turn. Glide through gentle trade winds, past lush green hills, and over crystal-clear waters. Snorkeling and scuba diving are essential activities. Dive into serene waters to explore vibrant marine life, renowned shipwrecks, and intriguing underwater caves.
When you’re on a Caribbean sailing charter, your taste buds are in for a treat! Enjoy the freshest seafood right on the boat, whether grilled, blackened, or served with a Creole twist. Savor a rich tapestry of flavors, including sailors’ favorites like conch and lobster.
Many yachts also organize beach barbecues on secluded shores. It’s a feast with an unbeatable view.
With so many islands to explore, you can hop from one paradise to another. Each sailing destination has its own charm – be it the dazzling beaches of the British Virgin Islands, the lush landscapes of Grenada, or the pretty villages of Martinique.
Kitesurfing in the Caribbean combines warm waters, reliable winds, and stunning landscapes. offers warm waters, reliable winds, and stunning scenery. Head to Union Island in the Grenadines for top kitesurfing camps. This exciting water sport is ideal from November to July.
Caribbean sailing charters are more than just an adventure. They combine laid-back island experiences with visits to historical sites. Enjoy a journey through time and culture by exploring colonial towns in Curacao, ancient forts in the US Virgin Islands, and plantation houses in St. Kitts.
Dining under the stars, whether on a catamaran or a classic sailboat, creates unforgettable memories. The gentle sea breeze caresses your skin as you take in the mesmerizing panoramic views. Pairing your meal with a fine wine or tropical cocktail enhances the magic.
Rum tasting across the Caribbean Islands is a favorite activity for many sailors, offering endless delicious cocktail choices.
Whether you’re chasing the winter sun, seeking a romantic getaway, or planning a family vacation, the Caribbean provides ideal sailing charters.
Enjoy the Caribbean in comfort and luxury on crewed motor yacht charters, where you can easily hop between destinations of your choice. Ideal for special occasions or a romantic honeymoon, these vessels offer flexibility and action-packed adventures.
Power catamarans offer spacious living areas for both guests and crew, ensuring stability on the water during island-hopping adventures. On a crewed yacht, you can tailor your trip, whether for scuba diving in crystal-clear waters or exploring historical sites and wildlife.
Another option is a luxurious crewed sailing catamaran, providing more than two crew members to attend to your every need. It’s ideal for exploring the Caribbean at a leisurely pace, while enjoying fine cuisine and drinks onboard.
November 2022
Captain Sean was outstanding. Very accommodating but firm when necessary.
Chef Thomas Day
We were extremely surprised and pleased with the quality of Tom’s cuisine. He was a star.
Presentation, flavors, quality exceeded expectations, very thoughtful in terms of what we wanted and impressive variety.
We loved Stewardesses Becky and Jade. They were attentive even when we didn’t know it, we literally couldn’t touch a glass without them intervening and assisting. Also great personality fits for us.
The Deck Crew were very helpful with the toys and were outstanding in their own ways. . Impressive in the consistency and quality of service.
Yacht:
Interior & exterior condition was Like new, what else can I say?
Layout and ambiance was Superb.
Tenders & toys:
Really appreciated Susan’s assistance and guidance on this, the variety of toys made a huge difference.
Any room for improvements? No, my entire group was blown away, we will definitely do this again.
Will return to TAIL LIGHTS soon.
Early June, 2024
“Complete Happiness – because pf Capt. Gavin and this beautiful boat! We got to see several islands, taste wonderful cooking, and enjoy a relaxed sail.
Truly one of our happier trips. Thank you. We want more!” – The Morrisseys
And from the kids:
We ❤️ Captain Gavin, he is the best.
Love,
Olivia and Julianna
First Rate Vacation
Itinerary was so well thought out and executed. Crew was second to none. They were very proactive about safety, while making sure we were enjoying ourselves, not easy!
Not to mention, the food was top notch, lobsters and crème brûlée just to name a couple examples. The catamaran itself was very comfortable, plenty of space for 8 passengers and 3 crew.
I did not get seasick once for the 5 nights I spent on it. As for activities: snorkeling, island exploring, and just kicking back with a “few” painkiller cocktails at the bars was just the vacation I needed. Highly recommend! One tip, reapply sunscreen aggressively, BVI sun is very strong!
Why choose the Caribbean? Besides its perfect sailing weather, you’ll discover numerous white sand beaches, marinas, and anchorages ready for exploration.
Destinations in the Caribbean include:
First-time yacht charterers in the BVI have everything needed for a great sail—whether you prefer a laid-back vacation or staying active with watersports. Short sailing distances between islands offer easy exploration of beautiful places, with convenient access to marinas and anchorages ensuring yacht security.
The US Virgin Islands, a Caribbean paradise, allow U.S. citizens to travel between its islands without a passport. The territory includes three main islands—St. Thomas, St. John, and St. Croix—each offering distinct sailing experiences.
St. John caters to nature lovers with 60% of its area dedicated to national parks featuring coral reefs, lush forests, and turquoise waters. Visitors can explore scenic trails and snorkeling spots, or visit the historic Annaberg Sugar Plantation ruins to dive into the island’s past.
Explore the captivating Leeward Islands on a Caribbean sailing charter, located just a few nautical miles from the Virgin Islands. They offer a delightful mix of natural beauty, history, and relaxation.
Discover forts, rainforests, and volcanic peaks, such as the iconic Pitons in St. Lucia, offering breathtaking views from every angle. Here are other islands in the Windwards worth visiting:
The Caribbean enjoys sunny weather year-round, but it’s important to consider specific sailing seasons:
Relax on the islands with a professional crew, or sail around the Caribbean islands yourself on a bareboat charter.
In the Caribbean, there are many islands to explore. Consider these key factors when planning your dream vacation:
Depending on your preferences, CKIM Group will match you with the perfect yacht, destinations, and activities for your trip.
Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.
