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 - Saint Pierre and Miquelon, Newfoundland, Canada

Arrive: Tue 24 February 2026 at 08:00 / Depart: Tue 24 February 2026 at 18:00

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 5 - At Sea

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, Grenada

Arrive: Fri 27 February 2026 / Depart: Fri 27 February 2026

The island of Grenada rises up from the Caribbean in steep, green, volcanic mountains. Sheer cliffs and sandy beaches alternate as you proceed along the coast, and the rainforest interior boasts of crater lakes, natural springs and waterfalls. St. George's, Grenada's capital has long enjoyed the reputation of being the most picturesque harbor in the Caribbean. Founded by the French in 1732, the town retains many elements of its Gaelic heritage, particularly in the architecture along Market Square and the Esplanade. Since wooden structures were outlawed long ago because of repeated fires, many buildings were constructed out of the brick brought over as ballast in trading ships of old. Quaint buildings line the waterfront, tiny pastel houses stand between lush jungle and sandy beach, and multicolor-roofed bungalows climb up the hillsides. The island's fame is derived from the spices it produces and exports all over the world.

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.