While far-off, exotic yacht charters might be intriguing, nothing beats a Caribbean bareboat charter destination right in our own backyard.
Tropical sandy beaches, steady trade winds, lazy beach bars, and convenient travel options characterize a visit to these many islands.
And if you’re limited to a week or 10 days, you’ll get to spend more time on your catamaran with a tropical beverage, and less stuffed into a crowded flight.
From Grenada to Puerto Rico, nearly every country in the leeward and windward islands has a Caribbean sailing vacation option for you.
So let's dive in. If you are still early in your chartering journey, these are the top Caribbean bareboat charter destinations you need to explore. You can visit each many times, and still find new fresh adventure on a return trip.
Yes, I know, it’s not technically the Caribbean, but it’s close enough.
I love the Exumas for the fishing, solitude, easy travel options from the USA, oh, and those dreamy blues...
This is also more of an advanced sailing destination and I would not recommend it until you have 2+ charters under your belt. You’ll need to anchor more frequently and pay close attention to weather, tides, currents, and depths. We first visited the Exumas on my third sailing trip.
The water in the Exumas is absolutely stunning, with some of the most vibrant turquoise blues I’ve ever seen.
Visit the stunning Tobago Cays, snorkel the coral reefs, swim with turtles, and arrange for a lobster beach barbeque
Anchor at idyllic Salt Whistle Bay and walk along the beautiful palm-lined beach
Explore the island where Captain Jack Sparrow was marooned - Petit Tabac
Head to Mustique and grab a cocktail at the legendary Basil’s Bar
Get your picture taken with the umbrella on the castaway island, Mopion
US Virgin Islands
During Covid, the US Virgin Islands made a resounding comeback due to travel restrictions elsewhere. Many long-time BVI visitors discovered the USVIs for the first time. Some were pleasantly surprised!
Why is the USVI appealing? Good provisioning options, cheaper prices, and direct flight options are a few reasons.
Consisting of St. Thomas, St. John, and St. Croix, most boaters spend the abundance of their time circumnavigating St. John and visiting the pristine National Park areas.
You can even use it as a jumping off point to explore the Spanish Virgin Islands. Read about how I did this in my recent USVI and SVI bareboat charter trip. Highlights of a US Virgin Islands yacht charter
Lounge on the beach at Maho Bay and take in the spectacular surroundings
Be adventurous and conduct an offshore passage to St. Croix to visit the pastel-colored town of Christiansted
Stroll the lovely town of Cruz Bay and grab a bite to eat or do some shopping
Sail the north shore of St. Thomas to the bight at Magens Bay. Simply enjoy the magical scenery or head ashore for a drink at the beach bar
Enjoy the solitude of the Salt Pond Bay anchorage - lime away the afternoon or hike for the views at Ram’s Head
Antigua & Barbuda
After spending a lot of time recently in the Virgin Islands and the Bahamas, we recently visited Antigua and Barbuda and absolutely loved it. You can read about the trip here.
Antigua and Barbuda is a single country, located in the southern Leeward Islands near Montserrat and Guadeloupe (potential offshore destinations for a longer yacht charter trip).
This destination has something for every type of crew. Gorgeous beaches (they attest to having 365 of them), offshore fishing, plenty of bars and restaurants, British naval history, reef snorkeling, and some adventure at offshore Barbuda.
Why else do I like this Caribbean bareboat charter destination? It has a great balance of the get-away-from-it-all anchorages that we enjoy, but it also has a great beach bar/nightlife scene. Highlights of a Antigua & Barbuda yacht charter
Sail offshore to Barbuda, one of the Caribbean’s hidden gems; anchor in solitude anywhere along the Caribbean’s longest pink sand beach (11 miles)
Relax amongst the reefs at peaceful Green Island
Drag some fishing lines and catch mahi, wahoo, or tuna in the deeper water offshore
Hike to Shirley Heights for commanding views and some nightlife at their famous Sunday evening bbq parties
Gaze at 200 foot mega yachts in Falmouth Harbour or rub elbows with the rich and famous at the establishments ashore near historic Nelson’s Dockyard
Arrange for a tour of the frigate bird sanctuary at Codrington Lagoon
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