7-Day Yachtsman's Caribbean Cruise

Day 1 - Philipsburg, St Maarten

Arrive: Sat 21 February 2026 / Depart: Sat 21 February 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 22 February 2026 / Depart: Sun 22 February 2026

Day 3 - St. Kitts

Arrive: Mon 23 February 2026 / Depart: Mon 23 February 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 25 February 2026 / Depart: Wed 25 February 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 26 February 2026 / Depart: Thu 26 February 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 27 February 2026 / Depart: Fri 27 February 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 28 February 2026 / Depart: Sat 28 February 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.