Written by Missy Johnston

St Barts harbor, Caribbean

St. Barts Harbor, Caribbean

There are many great reasons why vacationers go to the Leeward Islands during the winter. The lovely Caribbean weather and the ritzy lifestyles on St. Martin, St. Barts, and Anguilla draw yacht enthusiasts in particular, who feel right at home on their private yacht in the marinas and anchorages alongside other luxury yachts. And nothing can beat lounging on a pink sand beach in the sun when the alternative is staying at home especially if home in the winter is cold.

If a private luxury yacht charter to the Leeward Islands is beckoning, a wonderful treat awaits.

St. Martin

Overlook of Grand Case St Martin Caribbean

Overlook of Grand Case, St Martin, Caribbean

The Leeward Islands yacht charter begins and ends in St. Martin, so visitors have ample opportunities to acquaint themselves with the island.

History and Culture

Archaeological digs in St. Martin have unveiled remnants of indigenous settlements dating as early as 3,000 BC. More recently, the island’s inhabitants were conquered by Spanish forces and the subsequent arrivals of several new cultures. These different influences can still be seen in the island’s culture today.

Unfortunately, in 2017, Hurricane Irma destroyed many of the restaurants, hotels, and attractions that St. Martin was known for. But the locals were undeterred. They expended incredible effort to rebuild, and now St. Martin is home to an array of new and modern attractions.

An Island Divided

Scenic view of St. Maarten, Dutch-side, Caribbean

Scenic view of St. Maarten, Dutch-side, Caribbean

Both France and Holland sent settlers to St. Martin to exploit the island’s natural reserves, most specifically salt. In 1948, the French and Dutch signed the Treaty of Concordia, also known as the Partition Treaty and the island was officially split in two, half French and half Dutch, and so it has remained today with the French side to the north, and the Dutch side to the south. As legend tells it, two walkers, one a Frenchman and one a Dutchman, standing back-to-back in a spot forming one location of division, began to walk in opposite directions and where they met on the opposite side of the island created the other location of division. A line was drawn between the two locations of division on opposite sides of the island across the island and the island was divided between France and Holland.


Shopping street in St Maarten, Caribbean

Shopping Street in St.Maarten, Caribbean

Half of St. Martin is tax-free on the Dutch side, so its shopping opportunities are numerous and popular. Because of the island’s reputation as a haven for international shoppers, the Euro and the American dollar are accepted at most businesses alongside the local currency, the Antillean Guilder. Banks and local businesses are also happy to offer currency exchanges when needed.

In the city of Philipsburg, Front Street and Back Street offer so many shopping options that even experienced shoppers won’t have enough room to pack everything they purchase in their suitcases. Front Street is lined with luxury brands including Rolex, Dior, Ralph Lauren, and many others, along with jewelry stores, electronics stores, and duty-free alcohol and tobacco shops. Shoppers will find more affordable brands and backup vacation supplies on Back Street.

To truly experience the island’s shopping fare, be sure to check out all the small and local businesses in addition to the recognizable brands. Some of these shops offer unique souvenirs, gifts, artwork, and jewelry that can’t be found in chain stores. There are several local shopping strips to choose from, including Marigot Market, a collection of more than one hundred stalls.

Keep in mind that shops on the French side of the island typically only take Euros and are not duty free, so exchange some currency before venturing to the Marigot Market and the surrounding area.


Grand Case Beach Bar, St. Martin

Grand Case Beach Bar, St. Martin

Each of the more than 80 nationalities represented on St. Martin has its own recipes, cooking styles, and signature flavors. This means a nearly endless supply of local food prepared in any number of delicious ways is almost always within reach.

With so many options to choose from—including authentic Caribbean barbecue, Italian, Indian, French, and dozens of other cuisines—everyone in the yacht party can find something to enjoy.

Relax and savor dinner on the yacht deck or stroll along the beachfront to sample fare from the variety of restaurants near the water. Either way, one of the local rum punch drinks should top the list of things to try.

St. Barts

Gustavia Harbor with mega yachts at St Barts, Caribbean

Gustavia Harbor, St. Barts, Caribbean

The yacht can cruise from St. Martin and arrive in nearby St. Barthelemy, also known as St. Barts, or St. Barths, with plenty of time to explore this chic, exclusive island.

History and Culture

Arawak Indians were native to this island and originally named it “Ouanalao” for the once-prolific iguana population, but, in 1493, Christopher Columbus changed its name to St. Barthelemy. In time, the island became known simply as St. Barts.

St. Barts also faced numerous wars for territorial control. Over the centuries,St. Barts has changed hands several times. The island was ruled by the French, the knights of Malta, the Carib Indians, Britain, and Sweden at various points throughout its history, but France ultimately gained control.

Today, visitors enjoy a primarily French Caribbean cultural experience although other cultural influences are present on the island.


St. Barths Shopping Streets Gustavia

St. Barths Shopping Streets

Those who enjoyed duty-free shopping on St. Martin will be pleased to discover that St. Barts is also duty-free. Gustavia and St-Jean both feature a plethora of shopping opportunities.

Fashions trend toward high-end chic, with luxurious European clothing, jewelry, and accessories offered in many stores. Other popular items in St. Barts that may be purchased at tax-free prices include perfumes, liquor, tobacco, china, watches, and silver. Expect shops to close for a couple of hours in the middle of the day, similar to stores in France.

For authentic souvenirs, frequent local small businesses. Native-made clothing, sandals, jewelry, art, lotions, oils, and other beauty products are great to bring home as gifts and memorabilia.


gustavia, st.barts Caribbean

Gustavia, St.Barts,Caribbean

Similar to St. Martin, St. Barts was made for food lovers.

When the gourmet festival is in town, it attracts famous chefs from around the world, so it’s an excellent opportunity to taste some of the best food on the planet. Even if the festival isn’t in town, there are many top Chefs and great restaurants on the island. Try L’isola for Italian food, Le Toiny for a romantic date night, Riviera for spectacular Mediterranean fare, GypSea Beach for wood-fired seafood, or L’Atelier de Joel Robuchon for fine dining with a rooftop view.

If desired, an exclusive visit to the chef’s table at Zion restaurant can be arranged by the yacht captain.

Other wonderful restaurants in Gustavia include Orega, Shellona, Bonito, and Fish Corner.


Caribbean beach on Anguilla

Caribbean Beach on Anguilla

Leave St. Barts for Anguilla, home to an interesting blend of cultures and a number of beautiful reefs perfect for diving.

History and Culture

Anguilla is just a quick yacht journey of five miles from St. Martin, but the population demographics are strikingly different. Anguilla was originally home to native Carib people from South America, but it came under English control in the 1600s. Similar to the other Leeward Islands, Anguilla has experienced its share of wars for control.

Today, most of the population is African, with a minority British population. Visitors will notice an intriguing blend of English and Creole spoken on the island, as well as other interesting cultural blends.

Meads Bay beach, Caribbean, Anguilla

Meads Bay beach, Anguilla

Shopping and Activities

Anguilla is far less of a shopping hub than St. Martin or St. Barts. Instead of high-end luxury items, shoppers in Anguilla will find native arts and crafts, fresh seafood and vegetable markets, and other local fare.

Anguilla is well-known for its devotion to the arts. The island has several art galleries, offers performances by an active theatrical group, and hosts the Anguilla Arts Festival every other year. Additionally, the Anguilla museum features prehistoric local artifacts and numerous other interesting historical exhibits.


Despite the island’s small size, Anguilla shines with the culinary arts. Expect the same ritzy and romantic options you’d expect from St. Martin or St. Barts, but set against a peaceful, quiet backdrop.

Try Veya Restaurant for a romantic evening out enjoying authentic Caribbean food, or the Straw Hat Restaurant for its dazzling oceanside view and delicious seafood. Ken’s BBQ is everything one might hope for in an outdoor Caribbean barbecue grill, including livestock raised on-site for the freshest meat possible.

Jacala is an open-air restaurant on the sand that serves a small—and therefore exclusive—list of guests each night. Diners enjoy a menu by French Chef Alain Laurent that includes fresh snapper, conch chowder, and on-demand steak tartare at the tableside.

Don’t mistake Aguilla’s relative tranquility for an absence of nightlife. Beach bars and hotel bars fill up at night, and they offer a good opportunity to enjoy local culture.

For an energetic night of dancing, try Elvis’s Beach Bar. It’s a fun way to spend an evening listening to music, watching sports on the outdoor big-screen television, or kicking back with a beer and a fresh fish taco.

Last, but not least, Bankie Banx’s Dune Preserve is an island institution that provides authentic reggae music. Local reggae star Bankie Banx owns and performs at this rustic little shack, offering guests the opportunity to relax by the sea and listen to wonderful live music.

Aerial view from Meads Bay in Anguilla Beach, Caribbean

Aerial view from Meads Bay in Anguilla Beach, Caribbean

A private crewed yacht charter visiting St. Martin, St. Barts and Anguilla is a mixture of chic, culture and history while being surrounded by beautiful crystal clear water, underwater coral gardens, and sparkling beaches, being cooled by balmy breezes under the warm Caribbean sun.