Destination Area: Caribbean Ocean/Gulf Of Mexico
Length: 14 NIGHTS
Vessel: Star Flyer


Cienfuegos, Cuba * on January 27, 2018


Philipsburg, St. Maarten on February 10, 2018

Prices start at $3,150. per person, double occupancy. Port charge is $470 . per passenger. Single supplement is 150% for category 2 thru 6 (other categories 200%).

Call for clarification of the above as costs may change.

Call for air.

For more information call us toll free at 1-877-882-4395.

CROSSING THE CARIBBEAN FROM CUBA TO ST. MAARTEN WITH 8 PORT VISITS ALONG THE WAY: 14 Night Voyage From Cienfuegos, Cuba to Philipsburg, St. Maarten

Star Flyer and her sister ship Star Clipper are as fleet as the wind and as graceful as swans. These are 4-masted barkentines, and refle ...

Read more about the Star Flyer     

  • In Jamaica you will experience lush topography of mountains/ rainforests and reef lined beaches
  • Swim and snorkel
  • Note Spanish Colonial history in the Dominican Republic
  • Stroll some of the best beaches
  • Get pleasure in viewing many fabulous yachts sailing around BVI's four main islands

Sailing from Cuba to St. Maarten with many port stops along the way.

Cienfuegos, Cuba *
Cienfuegos is a city on the southern coast of Cuba. Near the entrance to Bahia de Cienfuegos is Castillo de Jagua, a fortress erected in the 1745 for protection against Caribbean pirates.

Cienfuegos, one of the chief seaports of Cuba, is a center of the sugar trade, as well as coffee and tobacco. While sugarcane is the chief crop, local farmers grow coffee.

There is no other place in the Caribbean which contains such a remarkable cluster of Neoclassical structures.

Attractions include parks, plazas, museums and castles used to guard against pirates. There is a dolphin and sea lion lagoon and a botanical garden.

Montego Bay, Jamaica
One of Jamaica's most fun-filled towns for travelers, beach goers and watersports the Montego Bay area is host to shops, restaurants and night clubs. Nature lovers take lazy raft rides down the Martha Brae River. There's even the possibility of a supernatural experience at 18th century Rose Hall, haunted by Annie Palmer, the famous "White Witch of Jamaica."

Port Antonio, Jamaica
Port Antonio is the capital of the town of Portland on the northeastern coast of Jamaica, about 60 miles from Kingston. The population is approximately 13,500.

Port Antonio is quiet and beautiful and very charming. However, if you have an eye for arts and crafts, and all the jewels Jamaica has to offer, you should spend time here. Visit the beautiful Blue Lagoon and the secluded Frenchman's Cove Beach, for example.

Santo Domingo, Dominican Republic
It is the oldest continuously inhabited European settlement in the Americas, and was the first seat of Spanish colonial rule in the New World. Santo Domingo came to be known as the "gateway to the Caribbean".

The city is the center of economic activity in the Dominican Republic. Many national and international firms have their headquarters or regional offices in Santo Domingo. The city attracts many international firms and franchises due to its geographic location, stability and vibrant economy.

Famous landmarks in Santo Domingo include the Calle El Conde, the Puerta de la Misericordia, the Catedral Santa María La Menor, and the Alcázar de Colón, all of which are located within the Zona Colonial district of the city. This part was declared a UNESCO World Heritage Site in 1990.

Other places of interest are Plaza de la Cultura, which houses the city's most important cultural venues such as the Teatro Nacional and the Museo de Arte Moderno; the Palacio de Bellas Artes , a neoclassical theatre that is the permanent home of the Orquesta Sinfónica Nacional; the Parque Mirador Sur, a six square kilometers park in the southwestern part of the city; the Faro a Colón, a cross-shaped lighthouse built in honor of Christopher Columbus; and the Boulevard 27 de Febrero, a pedestrian promenade located on the busy Avenida 27 de Febrero which displays many works of art from prominent Dominican artists and sculptors.

Jost van Dyke (Beach BBQ) & Soper's Hole, Tortola ,BVI (overnight)
JOST VAN DYKE, four miles long, is truly the "barefoot" island known by travelers around the world for its casual lifestyle, protected anchorages, fine beaches and beachfront restaurants and bars. Picture-postcard tropical isles, like Green Cay and Sandy Spit.

A sand bar and a very small bridge join Frenchman's Cay and Tortola at the West End of Tortola. Soper's Hole is a very picturesque harbor as well as an excellent overnight anchorage.

Blackbeard is said to have taken up residence in the BVI for a couple of years in the late 1700's at Soper's Hole. The area provided several excellent lookout points at which his men could spot ships laden with goods bound for far away lands.

A main street that's a beach, the Stress Free Bar, a harbor known for its Lobster feasts, a bypass road that's just a short-stroll, the Soggy Dollar bar named for a patron who swam ashore and home of the Painkiller drink--this is the life that defines laid back!

Sopers Hole, Tortola, Gorda Sound, Virgin Gorda

Road Bay, Anguilla
Road Bay is a commercial freight port in Anguilla, but it is also known for its calm, protected waters and water sports activities. The beach is long and features everything from bars to restaurants and shopping.

Seclusion and privacy are part of the draw to Anguilla's beaches, and you'll find a bit of that style of travel at Road Bay though you'll never be too far away, either. Neither too close nor too far from cities you'll have everything you need.

Falmouth Harbour, Antigua
Falmouth Harbour is the home of the Antigua Yacht Club, the host club for yachts sailing in Antigua Race Week and the Antigua Classic Yacht Regatta. It is situated on the south side of Antigua, at the opposite end of the island from St. John's the major cruise ship port on Antigua.

During the race & regatta weeks, Falmouth Harbour is filled with some of the most beautiful classic yachts, and the speediest of racing yachts. The races are held just outside the harbor entrance, ranging up to 8 miles offshore. These races are international events, attracting the best of the big yacht sailors from around the world.

Right next door to Falmouth Harbour is English Harbour, and the famous Nelson's Dockyard, Naval Base for the British Caribbean fleet during the great age of sail, from the late 1700's until it was abandoned in 1889. Nelson's Dockyard has since been restored. You can see the capstans used to warp ships into the sheltered anchorage, the remains of a sail loft, shore batteries for the protection of the ships in harbor, Clarence House built for soon-to-be crowned King William IV when he was captain of H.M.S Pegasus, one of the ships in Horatio Nelson's fleet. Around the harbor you can find Shirley Heights and the colonial observation post for the harbor, now a good vantage point to watch the racing yachts maneuver.

Philipsburg, St. Maarten
Philipsburg was founded in 1763 by John Philips, a Scottish captain in the Dutch navy, and soon became a bustling center of international trade. Two historic forts bear witness to Philipsburg's strategic importance in St. Martin's history: Fort Amsterdam and Fort Willem.

The main shopping district, Front Street, is in the heart of the city. Philipsburg has a port that is home to many cruise liners and tall ships.

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