14-Day Caribbean Yacht Harbors In Depth Cruise

Day 1 - Philipsburg, St Maarten

Arrive: Sat 05 February 2028 / Depart: Sat 05 February 2028 at 21:00

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 06 February 2028 at 08:00 / Depart: Sun 06 February 2028 at 17:00

Day 3 - St. Kitts

Arrive: Mon 07 February 2028 at 08:00 / Depart: Mon 07 February 2028 at 17:00

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 - Trois Ilets, Martinique

Arrive: Wed 09 February 2028 at 08:00 / Depart: Wed 09 February 2028 at 18:00

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 6 - Port Elizabeth (Grenadines)

Arrive: Thu 10 February 2028 at 08:00 / Depart: Thu 10 February 2028 at 17:00

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, Grenade

Arrive: Fri 11 February 2028 at 08:00 / Depart: Fri 11 February 2028 at 18:00

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 12 February 2028 at 07:00 / Depart: Sat 12 February 2028 at 21:00

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 - Castries, St. Lucia

Arrive: Sun 13 February 2028 at 08:00 / Depart: Sun 13 February 2028 at 18:00

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 10 - At Sea

Day 11 - Little Bay, Montserrat

Arrive: Tue 15 February 2028 at 08:00 / Depart: Tue 15 February 2028 at 18:00

Day 12 - St John's, Antigua

Arrive: Wed 16 February 2028 at 08:00 / Depart: Wed 16 February 2028 at 21:00

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 13 - St. Kitts

Arrive: Thu 17 February 2028 at 08:00 / Depart: Thu 17 February 2028 at 17:00

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 14 - Jost Van Dyke

Arrive: Fri 18 February 2028 at 08:00 / Depart: Fri 18 February 2028 at 18:00

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 15 - Philipsburg, St Maarten

Arrive: Sat 19 February 2028 at 07:00 / Depart: Sat 19 February 2028

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.