Destination Area: Caribbean Ocean/Gulf Of Mexico
Length: 12 NIGHTS
Vessel: Sea Cloud


Montego Bay, Jamaica on February 10, 2018


Bridgetown, Barbados on February 22, 2018

Call for flight arrangements, fares and specific shore excursions which may be available.

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

SAILING EAST IN THE CARIBBEAN FROM JAMAICA TO BARBADOS WITH 7 STOPS ALONG THE WAY: 12 Night Voyage From Montego Bay, Jamaica to Bridgetown, Barbados

Sea Cloud is a unique and romantic sailing vessel, with a fascinating history. She is a four-masted barque, spreading some 32,000 square feet ...

Read more about the Sea Cloud     

  • Relax in luxury aboard the magnificent Sea Cloud
  • Experience the glamor and night life of St. Bart's
  • Enjoy swimming & snorkeling at White's Beach
  • Take an excursion to the botanical gardens and hot springs in Soufriere
  • Explore the Maravillas caves with a shore excursion in La Romana
  • All shore excursions are included in your fare

Sail from Jamaica's Montego Bay to Barbados, for 11 nights on the luxurious Sea Cloud. In addition to the stops along the way (detailed below), you'll have three days of simply sailing. You'll enjoy watching Sea Cloud's crew as they brace the yard arms to trim sails to the wind, go aloft to set & furl sails, and exhibit all the traditional skills of square-rigged ship sailors. And you'll have an overnight in Gustavia along the way.

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.

At Sea

At Sea

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.

La Romana. Dominican Republic
La Romana, a city built and maintained by the sugar mills that proliferated in this region, is a burgeoning resort area. Nearby attractions include the artists village of Altos de Chavon, a re-creation of a 16th century Italian village with artisan workshops, an archeological museum, cobblestone streets and quaint architecture. Bayahibe--Near La Romana, the pristine beaches at laid-back Bayahibe are sites of splendid hotels. Visitors will find easy access to the off-shore wildlife preserves of Catalina and Saona, virgin islets embraced by the National Park of the East. The Park is the focus of international interest as anthropologists continue to unearth traces of the Taino civilization. Trendy La Romana lies east of Santo Domingo and is home to international polo matches and world-class championship golf. Enjoy an unbelievable variety of sports and recreational activities unmatched in the Caribbean including golf, polo, horseback riding, tennis, swimming and all other non-motorized water sports, with some of the finest snorkeling and scuba destinations in the region. The area also boasts some of the most unique shops and boutiques on the island.

At Sea

North Sound, Virgin Gorda
The North Sound has a rich history. Sir Francis Drake's vessel, the Golden Hind, carried a prize captured on his famous voyage, then weighted below its waterline with gold, and on whose deck he was knighted. Drake spent a few days collecting his fleet in the North Sound before joining the legendary Sir John Hawkins to attack Puerto Rico--back in the days when the Sir Francis Drake Channel was called "Freebooters Gangway."

The North Sound is like another world on Virgin Gorda--a boater's dreamworld. Here are vast anchorages for charterers and other activities in these well protected waters. Fairly frequently you may see tall ships at anchor.

Leave your ship on a dingy and go to Saba Rock or Bitter End for a lovely meal.

Great Harbor, Jost Van Dyke
Great Harbor is a fascinating melting pot of British Virgin Islanders & visiting sailors who land on this perfect BVI beach and stay a while! Great Harbor is the center of activity for Jost Van Dyke, one of the most popular anchorages for yachts in the BVI, with a variety of beach bars, including the famous Foxy's.

Gustavia, St. Barthelemy, France (overnight)
There was never any hope of lucrative sugar plantations in St.Barths. It was too dry, too steep, too rocky, and, finally, too small. Unsuitable for agriculture, the island was never coveted as a prize during the colonial wars of the 18th century.

The island did, however, have a serviceable harbor, and this allowed the town that grew around it, Gustavia, to play a key role in that intermittent conflict, a role that was to presage much of its future.

As a free port under Swedish rule, Gustavia provided a trade and supply center for the various warring factions. When a sea captain captured a prize or raided a settlement, he could sell the booty in St. Barths, and at the same time resupply his ship. Overflowing warehouses surrounded a harbor packed with ships from many nations, and a mercantile and architectural tradition was established that has lingered to the present day.

Today, the town has adjusted itself to satisfy the increasing number of visiting tourists. Restaurants, boutiques, and gift shops now line streets once busy with merchants, merchant seamen, and adventurers.

Gustavia, St. Barthelemy (France)
Discovered by Columbus in 1493, and named for his brother Bartolomeo, St. Barths was first settled in 1648 by French colonists from the nearby island of St. Kitts.

This original settlement was not a successful. In 1651 the island was sold to the Knights of Malta.

France repurchased the island in 1878. The free port status remained, and does to this day, along with such Swedish mementos as bits of architecture, a cemetery, a few street signs and, of course, the name of the harbor and capital, Gustavia.

In 1957, American millionaire David Rockefeller bought a property: the notoriety of the island quickly grew and its transformation as an upscale tourist destination was underway. In 1967, Britain cut loose most of their Caribbean dependencies because they had become a losing proposition.

During the last twenty years the resident population of St. Barths has more than doubled. Fewer natives are leaving, and growing number of outsiders are arriving to make an island home for themselves, especially from Metropolitan France.

Cabrits & Roseau, Dominica

Soufriere, St. Lucia
Soufriere is a fishing town on St. Lucia's southwest coast. Surrounded by lush tropical rainforest, Soufriere sits below the Pitons, St. Lucia's landmark volcanic peaks. The town is small and simple, with a central square on which is located the Church of the Assumption, and narrow streets lined with bright-painted houses. You can wander with your camera, stop at a local seafood restaurant, or buy some treats to eat from a street vendor, or perhaps linger at a bar for a rum drink. The people are friendly and fun-loving. There are spas for massage, and hot, volcanic spring-fed mineral baths for soaking. Visit an old sugar plantation. Rent a trail bike to ride along the French Wall Trail, an old hand-built stone wall, or any of several other trails. Go diving among the coral formations on the reef in the Soufriere Marine Management Area. Or try snorkeling if you prefer. Take a walk through the rainforest, visit a botanical gardens, or use binoculars to seek the elusive St. Lucia parrot. You'll not lack for things to do on this laid-back island.

Bridgetown, Barbados
On the wild and rugged east coast of Barbados, the isolated beaches are the colour of sunrise, the red sands having blown all the way across the Atlantic from the Sahara. The eastern most island of the Windwards, and indeed, of the entire Caribbean, reaches out to Africa and the Old World, as if not quite part of the New. Bridgetown, Barbados is an interesting town full of contrasts. George Washington actually slept here! Trafalgar Square reminds you that the laid back, rum-and-fun-loving island’s British-influenced heritage includes revered traditions like cricket and high tea.

Find a Voyage
Vessel Preference:
Voyage Duration:
Departing Between:
Date selection widget
Date selection widget


We are available Monday thru Friday 9am to 5pm (Eastern Time) to answer any questions you might have, to help you plan your vacation or to assist you in choosing the perfect voyage under sail.



Join Our Newsletter

Receive our complimentary monthly newsletter filled with in-depth tall ship profiles, news of tall ship events around the world, as well as special offers for unique or promotional voyages. Enter your email address and click to sign-up.

Privacy Statement