The Caribbean is filled with sun-drenched islands, vibrant culture, and postcard-perfect beaches. But there’s a version of the Caribbean most travelers never get to see—the one accessible only by sea.
When you explore by private yacht charter, you don’t just visit the islands—you experience them differently. You drop anchor in secluded bays. You wake to new views each morning. And you escape the crowds with a level of luxury that resorts can’t match.
Here are 5 Caribbean destinations that come alive when explored by charter yacht—and why now is the time to start planning your winter escape.
1. The Tobago Cays, St. Vincent & the Grenadines
This protected marine park is a slice of untouched paradise. Five uninhabited islands surrounded by a horseshoe reef create calm, crystal-clear waters perfect for snorkeling, paddleboarding, or simply floating under the sun.
Why It’s Better by Yacht:
There are no hotels or ferry landings here—just quiet anchorages, gentle trade winds, and the magic of sleeping beneath the stars. You’ll have front-row access to sea turtles, vibrant coral reefs, and beach barbecues with local flair.
2. Anegada, British Virgin Islands
Unlike the volcanic peaks of its neighbors, Anegada is flat, wild, and fringed with pink-sand beaches. Famous for its fresh-caught lobster and low-key charm, this remote island feels like a well-kept secret.
Why It’s Better by Yacht:
Anegada’s shallow waters and limited ferry access make it hard to reach—unless you’re arriving by yacht. You’ll enjoy a peaceful sail up from Virgin Gorda, drop anchor just off the reef, and step ashore to a world without crowds.
3. Norman Island, BVI
Long rumored to be the real-life inspiration for Treasure Island, Norman offers stunning snorkeling caves, legendary beach bars, and calm waters for overnight anchoring.
Why It’s Better by Yacht:
You can snorkel The Caves early—before the day boats arrive—and toast the sunset from your aft deck while others scramble to catch the last ferry home. Norman is best enjoyed on your own schedule.
4. St. Barth’s
Glamorous, French-infused, and effortlessly chic, St. Barth’s offers world-class dining, boutique shopping, and beaches that are somehow both lively and serene.
Why It’s Better by Yacht:
Avoid ferry crowds and busy ports—sail in on your own time and tender ashore straight to the heart of Gustavia. Dine at Le Tamarin, shop in town, and return to your yacht for sunset champagne. It’s the ultimate blend of luxury and freedom.
5. The Exumas, Bahamas
A chain of 365 cays and islands stretching across the Bahamas, the Exumas are a playground of sandbars, lagoons, and turquoise water that looks unreal.
Why It’s Better by Yacht:
Island-hop with ease, visit the famous swimming pigs, dive into Thunderball Grotto, and anchor at deserted beaches that are otherwise unreachable. The Exumas are about total escapism—and your yacht makes it effortless.
Start Planning Your Winter Escape
Winter charter weeks are already starting to book up—especially for the most sought-after yachts and crews. If one of these destinations is calling your name, now’s the time to secure your spot.
Whether you’re dreaming of New Year’s in St. Barth’s or a secluded sail through the Tobago Cays, we’ll help you find the perfect yacht and itinerary for your group.
Reach out today and let’s start planning!
CLICK HERE to speak to a Regency Charter Specialist!
