Yacht Charter Vacation: Leeward Islands [Travel Itinerary]

Take a week long vacation and explore the Caribbean waters, from St. Barts to Antigua.

Located between Puerto Rico and Dominica on the northeastern rim of the Caribbean Sea, the Leeward Islands present a beguiling range of destinations. Each is markedly different, yet their close proximity and generally calm waters make for effortless cruising. The variety and accessibility of the islands mean this is one of the most popular cruising grounds in the world, no doubt helped that one of the prime Leeward ports of call is the super-stylish island of St. Barths, which is a charter mainstay. 

Those who want a spot quayside in Gustavia on New Year’s Eve – one of the best places in the world to ring in the New Year – or during the St. Barths Bucket superyacht regatta in March are advised to make their reservations well in advance. The Leeward Islands are made up of the US Virgin Islands, BVIs, Anguilla, St. Martin, super-chic St. Barths, historic Antigua and Barbuda, lush St. Kitts and Nevis, and volcanic Guadeloupe. This seven-day itinerary takes in the very best the islands have to offer. If you prefer a slower pace and would rather see fewer islands, that is always an option as well. It is the perfect mix of everything and nothing. Ideal for those wanting to sample what the Caribbean has to offer, from its flashy to its natural side. You’d be unlikely to find a better Caribbean primer if you tried. 

Day 1: St. Maarten/St. Martin

Divided by Dutch and French claimants, the island of St. Maarten/St. Martin has numerous superyacht marinas and inbound international flights, making it a good place to start your charter. After settling in on board, head over to Orient Bay, one of the best beaches in the Caribbean. At the aptly named Sunset Beach Bar, you can watch planes skim over the beach as they land nearby. When you’re hungry, make sure to stop at Grand Case beach, which is renowned for its myriad great restaurants, such as Le Cottage.

Day 2: Anguilla

After a leisurely breakfast, make a short hop north to Anguilla and be there in plenty of time for lunch. Drop the anchor in Sandy Ground and visit Scilly Cay, a restaurant on a tiny cay in the middle of Island Harbour Bay that specializes in lobster. Write off the rest of the afternoon as you drink rum cocktails and eat delicious barbecued lobster. Perhaps duck into the Four Seasons hotel for a spa treatment so you can fully unwind and settle into your vacation. That night, dine on board and admire the starry sky above. 

Day 3: Anguilla to St. Barths

St. Barths is a Caribbean staple, a luxurious, beautiful little island where the rich and famous have vacationed for eons. The main port of Gustavia has excellent shopping, from Cartier to Chanel, lining the quayside where the superyachts moor. Stroll, shop and relax in cafes, but don’t forget the island’s natural beauty – take a lap in the tender, stopping at any of the 32 gorgeous beaches. Book a table for lunch at the beachside Shellona, and for dinner don’t miss the elegant gardens and delicious fare at Tamarin.

Day 4: St. Barths to Antigua

From St. Barths, head for Antigua, settling in with a good book as the inky blue Caribbean Sea slips beneath your yacht. Arrive in time for lunch and spend the afternoon exploring Nelson’s Dockyard on foot or take a walk to Fort Berkeley, with its fantastic views. In the evening, sit out with a rum cocktail and dine on the aft deck.

Day 5: Antigua

Take the tender out to explore. Beach-hop along the south coast’s beautiful, white-sand beaches. With 365 beaches to choose from, it is still possible to find secluded anchorages. Have a car take you up to Shirley Heights, where you can enjoy the most spectacular views at sunset.  

Day 6: Antigua to St. Kitts and Nevis

After breakfast, the yacht will make its way to the lush islands of St. Kitts and Nevis. If you want to see the Caribbean as it used to be, this is where to look. There is no duty-free shopping center, just a sleepy Caribbean island that hasn’t changed much in 50 years, the one exception being the new Christophe Harbour marina, which is helping draw more superyachts. There’s plenty to do here though, from volcano hikes to zip lining. Have a sundowner at SALT Plage bar at Christophe Harbour, and dine on board your yacht. 

Day 7: St. Kitts to St. Martin

Cruise to St. Martin and before flying home, spend a few hours playing with the water toys and soaking up the sun, or do some serious duty-free shopping, taking gifts – and precious memories – home with you.