14-Day Exotic Caribbean Isles Cruise

Day 1 - Barbados

Arrive: Sat 24 January 2026 / Depart: Sat 24 January 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 2 - Castries, St. Lucia

Arrive: Sun 25 January 2026 / Depart: Sun 25 January 2026

St. Lucia is the sort of island that travelers to the Caribbean dream about--a small, lush tropical gem that is still relatively unknown. The Atlantic Ocean kisses its eastern shore, while the beaches of the west coast owe their beauty to the calm Caribbean Sea. St. Lucia seems like an island plucked from the South Pacific and set down in the Caribbean. Its dramatic twin coastal peaks, the Pitons, soar 2,500 feet up from the sea, sheltering magnificent rain forests where wild orchids, giant ferns, and birds of paradise flourish. Brilliantly-plumed tropical birds abound, including endangered species like the indigenous St. Lucia parrot.

Day 3 - At Sea

Day 4 - Little Bay, Montserrat

Arrive: Tue 27 January 2026 / Depart: Tue 27 January 2026

Day 5 - St John's, Antigua

Arrive: Wed 28 January 2026 / Depart: Wed 28 January 2026

Antigua is blessed with an abundance of shining white beaches, and many of these have sprouted top-end resort hotels that engender golf courses and other amenities counted among the best in the Caribbean. A pleasant drive up through farms and tiny villages leads to the commanding fortress on Shirley Heights, from which you can survey the town and the harbor of Nelson’s Dockyard across the island. Once a carenage for British frigates, today it is an enclave of shops and restaurants.

Day 6 - St. Kitts

Arrive: Thu 29 January 2026 / Depart: Thu 29 January 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 7 - Jost Van Dyke

Arrive: Fri 30 January 2026 / Depart: Fri 30 January 2026

There are approximately 40 British Virgin Islands (the exact number varies from authority to authority), many of which are uninhabited. Some have only a handful of residents. Jost Van Dyke has a small population of its own families: the Turners, Grants, Ringes and Callwoods to name the majority. The desire to continue in the old ways is strong here, and "Jost" looks much as it must have looked 100 or 200 years ago. This archipelago is pristine and traffic light free. Weather permitting, your captain will anchor in this idyllic location and deploy the Marina for a day of play in the sea and sun.

Day 8 - Philipsburg, St Maarten

Arrive: Sat 31 January 2026 / Depart: Sat 31 January 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 9 - Soper's Hole, Tortola, British

Arrive: Sun 01 February 2026 / Depart: Sun 01 February 2026

Day 10 - St. Kitts

Arrive: Mon 02 February 2026 / Depart: Mon 02 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 11 - At Sea

Day 12 - Saint Pierre and Miquelon, Newfoundland, Canada

Arrive: Wed 04 February 2026 / Depart: Wed 04 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 13 - Port Elizabeth (Grenadines)

Arrive: Thu 05 February 2026 / Depart: Thu 05 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 14 - St Georges, Bermuda

Arrive: Fri 06 February 2026 / Depart: Fri 06 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 15 - Barbados

Arrive: Sat 07 February 2026 / Depart: Sat 07 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.