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Bridgetown – Santo Domingo · 22 December 2026 – 4 January 2027 – Main voyage image

Bridgetown – Santo Domingo · 22 December 2026 – 4 January 2027

22 December 2026 – 4 January 2027
13 nights
Bridgetown, Barbados – Santo Domingo, Dom. Republic
Sea Cloud II
from€8,990/ person
Places available
Visit operator's page

Route

Bridgetown, Barbados – Santo Domingo, Dom. Republic

Port

Bridgetown, BarbadosSanto Domingo, Dom. Republic

What's included

Raj pełen gwiazdNurkuj z maską, pływaj, wiosłujLuksus czasu wolnegoWeź głęboki oddechThe Baths

A tall ship cruise is more than a journey - it's an experience that stays with you for a long time

Why choose a Tall Ship cruise?

I want to set sail →

Authentic sailing experience

Feel the power of wind in the sails and take part in a real sea adventure – without commercial gimmicks and crowds of tourists.

Closeness to nature and peace

Immerse yourself in a world where time flows slower, and the only sound is the rush of waves and the crack of lines.

Cruises for everyone

Whether you have sailing experience or are taking your first steps on deck – you'll find a cruise tailored to your expectations and abilities.

Diversity of routes and ships

From short Baltic cruises to multi-week transatlantic voyages. Choose a cruise that fits your rhythm and dreams.

Check the voyage itinerary

Departure 22:00:00

More than 300 years of British rule have left their mark. The whole of Bridgetown, Barbados' historic center, with its colonial architecture surrounding Trafalgar Square, is a UNESCO World Heritage Site. A green hilly countryside and endless fields of sugar cane characterize the island's landscape. Old colonial houses are reminders of the high life of the plantation owners, while innumerable colorful chattel houses are evidence of their workers' moveable properties. The sweeping coastline is a picture postcard of fine sandy beaches and turquoise sea surrounded by vibrant coral reefs.

Arriving in Bridgetown, you come into a busy Caribbean harbour backed by low-rise city streets, palms, and the bright light of Barbados’ west coast. Nearby, visitors can explore the historic centre and waterfront areas, while the island’s easygoing, sun-washed atmosphere is never far from the quay.

Arrival 17:00:00Departure 13:30:00

Bequia is actually the largest island in the Grenadines, but still small and tranquil at just 87 square miles. Elegant sailing yachts sway in the natural shelter of Admiralty Bay, while in lovely Port Elizabeth, with its attractive beach bars, you are right in the heart of a lifestyle that likes to take things easy. You can find Princess Margaret Beach just nearby, named because it was once visited by the British royal. And on the eastern coast, you can find the Old Hegg Turtle Sanctuary focuses on rearing and caring for endangered turtles.

Photo: David Broad, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Admiralty_Bay,_Port_Elizabeth,_Bequia,_St_Vincent_and_the_Grenadines_-_panoramio.jpg)

Port Elizabeth opens onto a calm, yacht-filled bay backed by green hills and a waterfront lined with low, colorful Caribbean buildings. Arriving by ship, you get an easy sense of Bequia’s relaxed island rhythm, with beaches, small waterfront streets, and broad harbour views waiting nearby.

Photo: David Broad, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Admiralty_Bay,_Port_Elizabeth,_Bequia,_St_Vincent_and_the_Grenadines_-_panoramio.jpg)

Port Elizabeth opens onto a calm, yacht-filled bay backed by green hills and a waterfront lined with low, colorful Caribbean buildings. Arriving by ship, you get an easy sense of Bequia’s relaxed island rhythm, with beaches, small waterfront streets, and broad harbour views waiting nearby.

Arrival 08:00:00Departure 23:00:00

Beautiful beaches, aromatic spice plantations, dense rainforests, waterfalls, and a volcano that has long been extinct define this stunning island. For many people, Grenada is the incarnation of a tropical paradise and St. George's the most beautiful little port in the Grenadines. All around the horseshoe-shaped bay there are numerous houses reminiscent of colonial times. There is good reason why nutmeg is immortalized on the national flag. Alongside cloves, cinnamon and ginger, it is one of the island's biggest exports.

Photo: cwi.aida, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:St_Georges_Grenada_Fort_-_panoramio.jpg)

Arriving by ship, St. George’s unfolds around a deep, horseshoe-shaped harbour, with colorful hillside houses, church towers, and the green slopes beyond giving the waterfront a vivid Caribbean backdrop. Nearby, visitors can look out over the bay, wander into the compact historic streets, and enjoy the relaxed yet lively atmosphere of Grenada’s capital.

Arrival 08:00:00Departure 18:00:00

Right in the south of the Grenadines are the Tobago Cays – four small uninhabited islands, surrounded by a protective horseshoe-shaped coral reef. The Horseshoe Reef holds the Atlantic swell at bay and its unique animal and plant life make it an ideal place for snorkelling. The lagoon between the islets shimmers in all shades from turquoise through to emerald green and invites you to take a dip at the fantastic beaches.

Tobago Cays welcomes arriving ships with a dazzling lagoon of clear turquoise water, tiny islets, and bright coral shallows. The mood is peaceful and castaway-like, with nearby reefs, sandy beaches, and green cays creating one of the most idyllic seascapes in the Grenadines.

Arrival 08:00:00Departure 13:30:00

Two famous volcanic cones are indisputably the emblem of St. Lucia and have been designated as UNESCO World Heritage Sites. Gros and Petit Piton tower over the southern, windward side of the island and, in Soufrière, seem close enough to touch. The volcanoes have in fact long been extinct, but the sulphur springs demonstrate the power of the earth's core and still bubble up. In the Botanical Gardens, natural abundance is combined with artistic arrangements to create a colorful tropical paradise. Some people claim that Josephine, who later became Napoleon's wife, used to bathe in the little pool in the garden.

Photo: Caribbeandy, CC BY-SA 4.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Pitons-aerial.jpg)

Arriving off Soufrière, you are greeted by a dramatic green coastline where steep hills tumble toward a sheltered bay, giving this part of St. Lucia a lush, volcanic feel. Nearby, the famous Pitons rise over the coast, and the town itself has a relaxed Caribbean atmosphere with colorful buildings backed by dense tropical slopes.

Sea day

Few and far between are the occasions, on which one can experience two fascinating windjammers together and directly compare their maneuvers. When both yachts glide along side by side under full sail, they offer a truly breathtaking spectacle.

Arrival 13:30:00Departure 17:00:00

St. Barthélemy, affectionately known as St. Barths by most, already had many "owners" before the Lesser Antilles were acquired by France in 1877. When the first estate was acquired by the banker David Rockefeller in 1957, the island's future was finally sealed. It became a refuge for the international jet set and an elegant holiday paradise for many Hollywood stars. For over 40 years, St. Barths has cultivated a luxurious lifestyle with a Caribbean laissez-faire approach. You can stroll through the charming main town of Gustavia, whose beautifully restored houses and colonial facades look out over the sea with its elegant superyachts, browse in the shops for precious items, or enjoy a sundowner in the picturesque harbor surrounded by clusters of high class bars and restaurants.

Photo: digitalfilmphoto, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Gustaviaphare2.jpg)

Arriving in Gustavia, you are greeted by a compact Caribbean harbour framed by green hills, bright waterfront buildings, and a lively mix of yachts and ferries. Just beyond the port, the town’s boutiques, cafés, and hillside viewpoints give St. Barts its polished yet relaxed island atmosphere.

Photo: digitalfilmphoto, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Gustaviaphare2.jpg)

Arriving in Gustavia, you are greeted by a compact Caribbean harbour framed by green hills, bright waterfront buildings, and a lively mix of yachts and ferries. Just beyond the port, the town’s boutiques, cafés, and hillside viewpoints give St. Barts its polished yet relaxed island atmosphere.

Arrival 14:00:00Departure 18:00:00

The Sir Francis Drake Channel, where swords once crossed, is now one of the most beautiful sailing spots. Jost van Dyke, the smallest of the main islands in the British Virgin Islands, is a mountainous volcanic object of beauty with fewer than 300 inhabitants. One of them, Foxy, has been mixing his cocktails since 1968 and the bar of the same name enjoys a legendary reputation as perhaps the most famous beach bar in the Lesser Antilles. The island's past is less reputable – it was named by a Dutch pirate. The island gives its most beautiful treasures to all who visit – fine sand, green palm trees, colorful beach bars and the luminous blue of the sea.

White Bay welcomes ships with a brilliant curve of white sand, clear turquoise water, and low green hills that give this corner of Jost van Dyke its relaxed Caribbean feel. From the anchorage, the shoreline looks idyllic and unhurried, with beaches and coastal views nearby rather than a busy port scene.

Departure 06:00:00

The Sir Francis Drake Channel, where swords were once crossed, is now one of the most beautiful sailing spots. Jost van Dyke, the smallest of the main islands in the British Virgin Islands, is a mountainous volcanic object of beauty with fewer than 300 inhabitants. One of them, Foxy, has been mixing his cocktails since 1968 and the bar of the same name enjoys a legendary reputation as perhaps the most famous beach bar in the Lesser Antilles. The island's past is less reputable – it was named by a Dutch pirate. The island gives its most beautiful treasures to all who visit – fine sand, green palm trees, colorful beach bars and the luminous blue of the sea.

Great Harbour on Jost van Dyke welcomes you with a small Caribbean waterfront, clear turquoise water, and green hills rising just beyond the bay. From the anchorage or quay, the mood is relaxed and beachy, with quiet island scenery and a few nearby stretches of sand inviting an easy walk ashore.

Great Harbour on Jost van Dyke welcomes you with a small Caribbean waterfront, clear turquoise water, and green hills rising just beyond the bay. From the anchorage or quay, the mood is relaxed and beachy, with quiet island scenery and a few nearby stretches of sand inviting an easy walk ashore.

Approaching Norman Island by ship, you are greeted by steep green hills, rocky coves, and clear turquoise water that gives the anchorage a secluded, tropical feel. Nearby, the island’s sheltered bays and dramatic shoreline are the main sights, offering a relaxed atmosphere shaped more by sea and nature than by any town waterfront.

Arrival 08:00:00Departure 13:30:00

Explorers once used to cross swords in the Sir Francis Drake Channel. Nowadays the sea around the British Virgin Islands is one of the world's best sailing areas. Heavenly bays, gorgeous beaches, idyllic anchoring spots, smart yacht clubs and charming little beach bars make the island a popular haunt for sailors. On Virgin Gorda, once called "The Fat Virgin" by Columbus due to its shape, you can find "The Baths", one of nature's most beautiful oddities, in the National Park. Ground to a sphere and polished to a shine, the huge granite formations on the beach and in the water create a multi-branched labyrinth of giant boulders.

Photo: Gruepig, CC BY-SA 4.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Virgin_Gorda_North_Sound_2010.jpg)

North Sound welcomes ships with calm, bright-blue water, low green hills, and a scattered coastline of marinas, beaches, and small islands. From the anchorage, the atmosphere feels relaxed and upscale, with nearby shores offering easy views of Virgin Gorda’s sheltered bays and elegant Caribbean seascapes.

Sea day

Spend the day sunbathing, enjoy the fresh wind breeze, and relax into the day!

Arrival 06:00:00

On this island, which is part of Hispaniola, Columbus founded the first Spanish colony in America. Santo Domingo, the present capital of the Dominican Republic, is the first and oldest European-founded city in the New World. Old in the New World still means relatively young – it corresponds to Renaissance visions of the ideal and was the model for many cities in Latin America. A visit to the historic old city is like a journey through time. The splendid stone buildings are testament to the era of the colonial conquests and have been smartened up as World Heritage Sites under the protection of UNESCO.

Photo: Victor Ml Sanz, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Amanecer_Playa_Guibia_Santo_Domingo_(147620045).jpeg)

Arriving in Santo Domingo, you come to a busy Caribbean port backed by the broad city waterfront and the mouth of the Ozama River. Nearby, the historic Zona Colonial offers old stone streets, churches and plazas, while the seafront has an energetic urban feel with sea breezes, traffic and the pulse of the Dominican capital.

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Places you'll visit

Bridgetown

Arriving in Bridgetown, you come into a busy Caribbean harbour backed by low-rise city streets, palms, and the bright light of Barbados’ west coast. Nearby, visitors can explore the historic centre and waterfront areas, while the island’s easygoing, sun-washed atmosphere is never far from the quay.

Port Elizabeth, Bequia

Port Elizabeth opens onto a calm, yacht-filled bay backed by green hills and a waterfront lined with low, colorful Caribbean buildings. Arriving by ship, you get an easy sense of Bequia’s relaxed island rhythm, with beaches, small waterfront streets, and broad harbour views waiting nearby.

Photo: David Broad, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Admiralty_Bay,_Port_Elizabeth,_Bequia,_St_Vincent_and_the_Grenadines_-_panoramio.jpg)
Photo: David Broad, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Admiralty_Bay,_Port_Elizabeth,_Bequia,_St_Vincent_and_the_Grenadines_-_panoramio.jpg)

St. George’s

Arriving by ship, St. George’s unfolds around a deep, horseshoe-shaped harbour, with colorful hillside houses, church towers, and the green slopes beyond giving the waterfront a vivid Caribbean backdrop. Nearby, visitors can look out over the bay, wander into the compact historic streets, and enjoy the relaxed yet lively atmosphere of Grenada’s capital.

Photo: cwi.aida, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:St_Georges_Grenada_Fort_-_panoramio.jpg)
Photo: cwi.aida, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:St_Georges_Grenada_Fort_-_panoramio.jpg)

Tobago Cays

Tobago Cays welcomes arriving ships with a dazzling lagoon of clear turquoise water, tiny islets, and bright coral shallows. The mood is peaceful and castaway-like, with nearby reefs, sandy beaches, and green cays creating one of the most idyllic seascapes in the Grenadines.

Soufrière, St. Lucia

Arriving off Soufrière, you are greeted by a dramatic green coastline where steep hills tumble toward a sheltered bay, giving this part of St. Lucia a lush, volcanic feel. Nearby, the famous Pitons rise over the coast, and the town itself has a relaxed Caribbean atmosphere with colorful buildings backed by dense tropical slopes.

Photo: Caribbeandy, CC BY-SA 4.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Pitons-aerial.jpg)
Photo: Caribbeandy, CC BY-SA 4.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Pitons-aerial.jpg)

Gustavia, St. Barts

Arriving in Gustavia, you are greeted by a compact Caribbean harbour framed by green hills, bright waterfront buildings, and a lively mix of yachts and ferries. Just beyond the port, the town’s boutiques, cafés, and hillside viewpoints give St. Barts its polished yet relaxed island atmosphere.

Photo: digitalfilmphoto, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Gustaviaphare2.jpg)
Photo: digitalfilmphoto, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Gustaviaphare2.jpg)

White Bay, Jost van Dyke

White Bay welcomes ships with a brilliant curve of white sand, clear turquoise water, and low green hills that give this corner of Jost van Dyke its relaxed Caribbean feel. From the anchorage, the shoreline looks idyllic and unhurried, with beaches and coastal views nearby rather than a busy port scene.

Great Harbour, Jost van Dyke

Great Harbour on Jost van Dyke welcomes you with a small Caribbean waterfront, clear turquoise water, and green hills rising just beyond the bay. From the anchorage or quay, the mood is relaxed and beachy, with quiet island scenery and a few nearby stretches of sand inviting an easy walk ashore.

Norman Island

Approaching Norman Island by ship, you are greeted by steep green hills, rocky coves, and clear turquoise water that gives the anchorage a secluded, tropical feel. Nearby, the island’s sheltered bays and dramatic shoreline are the main sights, offering a relaxed atmosphere shaped more by sea and nature than by any town waterfront.

North Sound, Virgin Gorda

North Sound welcomes ships with calm, bright-blue water, low green hills, and a scattered coastline of marinas, beaches, and small islands. From the anchorage, the atmosphere feels relaxed and upscale, with nearby shores offering easy views of Virgin Gorda’s sheltered bays and elegant Caribbean seascapes.

Photo: Gruepig, CC BY-SA 4.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Virgin_Gorda_North_Sound_2010.jpg)
Photo: Gruepig, CC BY-SA 4.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Virgin_Gorda_North_Sound_2010.jpg)

Santo Domingo

Arriving in Santo Domingo, you come to a busy Caribbean port backed by the broad city waterfront and the mouth of the Ozama River. Nearby, the historic Zona Colonial offers old stone streets, churches and plazas, while the seafront has an energetic urban feel with sea breezes, traffic and the pulse of the Dominican capital.

Photo: Victor Ml Sanz, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Amanecer_Playa_Guibia_Santo_Domingo_(147620045).jpeg)
Photo: Victor Ml Sanz, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Amanecer_Playa_Guibia_Santo_Domingo_(147620045).jpeg)

Frequently asked questions about tall ship cruises and sailing ships

Many leisure and introductory voyages accept guests without sailing experience. Training and expedition voyages may require active participation, minimum ages or a particular level of mobility. Check the operator's conditions for the exact voyage before booking.
Start with the operator's joining instructions because space, dress rules and required equipment vary by ship. Soft luggage, layered clothing, a waterproof outer layer, sun protection and operator-approved non-slip footwear are common recommendations. Ask a medical professional about suitable seasickness precautions if needed.
Choose a cruise on the Cruise Tall Ships site, click the offer and go to the operator's booking page. We do not charge fees – we connect you directly with the cruise organizer.
Choosing a tall ship cruise is more than just booking a vacation; it is an invitation to experience the timeless romance of the sea. Unlike modern, crowded cruise liners, a traditional sailing vessel offers an intimate atmosphere where the sound of the wind in the canvas replaces the hum of engines. Taking part in such a unique voyage allows you to connect with maritime heritage while enjoying the comforts of a modern leisure cruise. Whether it’s the thrill of seeing the horizon from a wooden deck, the spectacular sight of a full press of sail, or the chance to visit hidden coastal gems inaccessible to larger ships, a tall ship voyage offers a sense of freedom that is simply unmatched. It is the perfect choice for travelers seeking authenticity, tranquility, and a truly luxury sailing experience that stays with them long after they return to shore.
Tall ships cruises take place on many waters: Baltic, North Sea, Atlantic, Caribbean, Mediterranean and others. Each offer indicates the region and route.
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