14-Day Yachtsman's Island Jewels Cruise

Day 1 - Philipsburg, St Maarten

Arrive: Sat 07 March 2026 / Depart: Sat 07 March 2026

Since 2010, Sint Maarten has been a constituent country within the kingdom of The Netherlands. It comprises the “Dutch Side” of the island of Saint-Martin, the other half being a French overseas territory. Philipsburg is its capital and a busy deep-water port city. It is a popular port for cruise ships, and consequently boasts a thriving duty-free shopping community, a range of resorts and villas, and numerous leisure and sightseeing activities, as well as a well-served airport.

Day 2 - Soper's Hole, Tortola, British

Arrive: Sun 08 March 2026 / Depart: Sun 08 March 2026

Day 3 - St. Kitts

Arrive: Mon 09 March 2026 / Depart: Mon 09 March 2026

A classic golden arc of sugary sand at South Friar’s Bay, Carambola is home to the island’s most luxurious beach clubs and restaurants. Umbrellas, loungers and optional water sports abound for those so inclined. Otherwise St. Kitts has other attractions, including a number of lovingly preserved plantation great houses, the UNESCO World Heritage Site of Brimstone Hill Fortress and a scenic narrow gauge sugarcane railway.

Day 4 - At Sea

Day 5 - Saint Pierre and Miquelon, Newfoundland, Canada

Arrive: Wed 11 March 2026 / Depart: Wed 11 March 2026

Saint Pierre and Miquelon is a French archipelago south of the Canadian island of Newfoundland. Sparsely populated Miquelon-­Langlade island contains the Grand Barachois lagoon, home to seabirds and seals. The busier Saint Pierre island has a distinct French atmosphere, with a cathedral and the Musée Heritage, which celebrates regional history. An island nearby, Île-aux-Marins, features an abandoned fishing village.

Day 6 - Port Elizabeth (Grenadines)

Arrive: Thu 12 March 2026 / Depart: Thu 12 March 2026

Bequia’s Admiralty Bay is a favorite yachtsman’s anchorage. They ferry ashore to join the friendly, low-key locals “under the almond tree,” the chosen meeting place. Stroll along the Belmont Walkway to the Gingerbread for homemade nutmeg ice cream, or Frangipani, run by the daughter of a former prime minister. Continue to lovely, golden Princess Margaret Beach, or round the bend to Lower Bay. Don’t miss the excellent craftsmanship at the Sargeant Brothers Model Boat Shop, it’s a Bequia specialty.

Day 7 - St Georges, Bermuda

Arrive: Fri 13 March 2026 / Depart: Fri 13 March 2026

The port facility known as Kings Wharf is actually the revitalized Royal Navy Dockyard of Bermuda in Sandy’s Parish. The facility was first developed in 1809, after the British lost their mainland docking rights in the American Revolution. After the two World Wars, with the British and Americans allied, there was no need for a Royal Navy base, and the facility was closed. Today it is the main cruise ship port for the island. It has many attractions for visitors, including the Bermuda National Museum and many galleries, shops, restaurants and etc. There are a number of beaches nearby, including the famous Sea Glass Beach. The port is also the start point for tours of other Bermuda highlights such as Hamilton, St. George’s and the beaches.

Day 8 - Barbados

Arrive: Sat 14 March 2026 / Depart: Sat 14 March 2026

Barbados has retained many of the trappings of its British colonial heritage. Judges and barristers wear proper robes and wigs, police don helmets styled after London bobbies and cricket remains a national passion. Barbados also has all the sporting appeal of the rest of the Caribbean, with pristine beaches, powerful surf and crystal clear waters. Brightly colored homes and hibiscus flowers mingle with mahogany trees and English churches dating back to the 17th century.

Day 9 - At Sea

Day 10 - St. Kitts

Arrive: Mon 16 March 2026 / Depart: Mon 16 March 2026

A classic golden arc of sugary sand at South Friar’s Bay, Carambola is home to the island’s most luxurious beach clubs and restaurants. Umbrellas, loungers and optional water sports abound for those so inclined. Otherwise St. Kitts has other attractions, including a number of lovingly preserved plantation great houses, the UNESCO World Heritage Site of Brimstone Hill Fortress and a scenic narrow gauge sugarcane railway.

Day 11 - Trois Ilets, Martinique

Arrive: Tue 17 March 2026 / Depart: Tue 17 March 2026

Les Trois-Îlets is a town on the Caribbean island of Martinique. It's known as the birthplace of Joséphine, Napoléon Bonaparte’s first wife. Her family’s sugar plantation is now the Pagerie Museum, with childhood mementos and a love letter from Napoléon. Nearby, exhibits at the Maison de la Canne detail how sugar cane shaped Martinique’s history. North, Pointe du Bout is a water-sports hub with boutiques and cafes.

Day 12 - Point-a-Pitre

Arrive: Wed 18 March 2026 / Depart: Wed 18 March 2026

Guadeloupe’s de facto capital is located near the narrow isthmus connecting the butterfly-shaped island’s two wings. Grand Terre is the larger wing, fringed with the sort of beaches that bring visitors to the Caribbean. The museum of Saint-John Perse is housed in an intact colonial-era mansion, and is dedicated to the Nobel Laureate Alexis Léger, whose nom de plume was St-John Perse. The house is a chance to see typical Creole domestic interiors of the period and find out more about his life and works. Recently opened to rave reviews is the Musée ACTe, a modern museum dedicated to the history and heritage of slavery in the Caribbean. It is the only museum of its kind in the world, explicating the effects of the institution in a clear-eyed and educational way.

Day 13 - Roseau

Arrive: Thu 19 March 2026 / Depart: Thu 19 March 2026

The Caribbean’s verdant “Nature Island” has resolved not to succumb to the high-rise hotels and casino culture that predominate on some other islands. The tiny nation is determined to thrive on its natural resources, which are many and attractive. Water is one, and the island does export delicious mineral water throughout the area. There are also thermal springs and a “boiling lake,” as well as lovely waterfalls. Citrus fruits such as grapefruit are another export. The island is the source of Rose’s Lime Juice, a requisite of the perfect gimlet cocktail. Fragrant bay rum, distilled from native trees, is a handmade commodity much prized on the global market. Visit the peaceful Botanical Gardens, or ascend Morne Bruce for a stunning view over the town, the harbor and the sea beyond.

Day 14 - Rodney Bay

Arrive: Fri 20 March 2026 / Depart: Fri 20 March 2026

This is the island’s yachting center, quieter and less crowded than the main port of Castries. You can visit the island’s “drive-in” volcano at Soufriere, view the iconic peaks of the Pitons or perhaps snorkel at Pigeon Island, one of Jacques Cousteau’s favorite dive spots.

Day 15 - Barbados

Arrive: Sat 21 March 2026 / Depart: Sat 21 March 2026

Barbados has retained many of the trappings of its British colonial heritage. Judges and barristers wear proper robes and wigs, police don helmets styled after London bobbies and cricket remains a national passion. Barbados also has all the sporting appeal of the rest of the Caribbean, with pristine beaches, powerful surf and crystal clear waters. Brightly colored homes and hibiscus flowers mingle with mahogany trees and English churches dating back to the 17th century.