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San Juan to Bridgetown

Embark on an unforgettable 10-day journey from San Juan to Bridgetown with Silversea. This luxurious voyage aboard the Silver Shadow promises an intimate exploration of the Caribbean's most enchanting islands, blending sophisticated comfort with breathtaking natural beauty.

Discover a vibrant tapestry of destinations including the serene beaches of Great Harbour, Jost Van Dyke, the chic allure of Gustavia, and the lush landscapes of Dominica and Grenada. Each port, from historic Basseterre to picturesque Îles des Saintes, offers unique cultural encounters and stunning scenic vistas.

Indulge in unparalleled service and gourmet dining as you sail through turquoise waters. This exceptional itinerary provides the perfect escape for discerning travelers seeking an immersive and opulent Caribbean adventure, creating memories that will last a lifetime.

  • Cruise Line: Silversea
  • Ship: Silver Shadow
  • Duration: 10 Nights
  • Departure: Jan - Feb
FROM
£3,400 pp
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San Juan to Bridgetown Prices

Price per person
Jan 10, 2027
£3,750 pp
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Feb 06, 2027
£3,400 pp
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San Juan to Bridgetown Itinerary

Day 1

San Juan (Puerto Rico)

The capital city of Puerto Rico, San Juan
is one of the busiest ports in the Caribbean and home to a third of
all Puerto Ricans. Nearly every visitor to the island arrives at
San Juan, many on cruise liners. It's one of the largest home-based
cruise ports in the world, hosting many vessels with more being
added each year.

San Juan is divided into three distinct
districts: Old San Juan, the historic walled city; the beach and
resort area; and the outlying suburbs. Tourists mainly visit Old
San Juan, the site of most restaurants, shops, entertainment venues
and some exquisite beaches.

The old city is linked to the new by the
largely residential barrio of Puerta de Tierra and a series of
modern highways leading to the Condado beachfront, which is
reminiscent of Florida's Miami Beach with its high-rise hotels and
apartment blocks.

It is not only tourism that keeps the
financial mills grinding in San Juan. The city is an important
centre for petroleum and sugar refining, brewing and distilling,
and the manufacturing of cement, pharmaceuticals, metal products
and tobacco products.

In the midst of all the hustle and bustle,
there are numerous attractions in San Juan to amuse, entertain and
interest many tourists, and the city is a perfect base for
exploring the rest of what this small Caribbean island has to
offer.

Day 2

Great Harbour, Jost Van Dyke

Great Harbour is a stunning and tranquil bay located on Jost Van Dyke, the smallest of the four main islands of the British Virgin Islands (BVI). Known for its picturesque scenery, crystal clear turquoise waters, and soft white sandy beaches, Great Harbour is an oasis for beach-goers, sailors, and adventure enthusiasts alike. Spanning just about three square miles, Jost Van Dyke hosts a small population, but it boasts an outsized reputation for its vibrant nightlife and welcoming community.

One of the most notable features of Great Harbour is its well-protected anchorage, which makes it a haven for yachts and boats throughout the year, especially during the peak sailing season. The harbour's natural geography provides shelter from the prevailing winds, creating a perfect natural marina. This has led to Great Harbour becoming a key stop on the Caribbean sailing circuit, with many sailors choosing to drop anchor and enjoy what the bay and its surroundings have to offer.

Upon arriving at Great Harbour, visitors are greeted with a laid-back vibe that is quintessential to the Caribbean way of life. The beachfront is lined with a selection of casual bars and restaurants that become hubs of activity as the sun sets. Among the most famous establishments is Foxy's Tamarind Bar & Restaurant, known for its beach barbecues, live music, and the legendary Old Year's Night (New Year's Eve) party that attracts party-goers from around the globe.

The village surrounding Great Harbour is charming and small-scale, allowing for an authentic island experience. The streets are often quiet, save for the bustle around the local businesses, which include quaint shops selling handcrafted goods, island apparel, and essential supplies for those continuing their sea voyage. The locals, known for their friendliness, are happy to share stories and offer recommendations to visitors, contributing to the harbour's reputation for warm hospitality.

For those looking to engage in watersports, Great Harbour does not disappoint. The clear waters are ideal for snorkeling and scuba diving, with vibrant coral reefs just a short swim away from the beach. Additionally, paddle-boarding, kayaking, and sailing are popular activities that allow visitors to explore the area at a leisurely pace. The nearby Sandy Cay and Sandy Spit offer additional opportunities for exploration and are excellent spots for a beach picnic or a day of seclusion and sunbathing.

The island's lush, volcanic terrain provides opportunities beyond the beach as well. Hiking trails wind through the hills, offering breathtaking panoramic views of the surrounding islands and the expanse of the Caribbean Sea. Naturalists and bird watchers will delight in the diversity of flora and fauna found on the trails.

Great Harbour's appeal is not only in its natural beauty but also in its cultural events. Beyond Foxy's famous New Year's bash, the harbour hosts celebrations like the Jost Van Dyke Music Festival and the Halloween Party, which showcase local music talent and bring the community together in a lively and joyous atmosphere.

While Great Harbour has gained popularity as a tourist destination, it remains unspoiled and continues to offer an authentic island experience. The mix of relaxing beach life, friendly locals, delicious cuisine, and year-round sailing opportunities make Great Harbour a cherished spot in the British Virgin Islands, appealing to travelers of all stripes — from those seeking serenity to those eager for the next great beach party under the Caribbean stars.

Day 3

Gustavia

The beautiful beaches of St Barthelemy have captivated visitors from around the world for centuries. With its stunning white sand, crystal clear waters and lush tropical scenery, it’s easy to see why people fall in love with this charming island paradise. Whether you’re looking for a family vacation, romantic getaway or a place to party the night away, St Barthelemy has something for everyone.

Begin your beach vacation with a visit to Grand Cul-de-Sac, an area made up of stunning beaches that offer something for everyone. Whether you’re seeking adventure with snorkeling and jet skiing or just a place to relax with beautiful views and a gentle breeze, Grand Cul-de-Sac is sure to please. Take time to lounge on the beach with your feet in the sand and unwind with the sound of the waves crashing nearby.

Continue down the shoreline and experience the serenity of Anse du Gouverneur Beach. Here, you’ll have plenty of room to soak up the sun and lounge on the sand. Enjoy a nice picnic lunch by the sea and be sure to watch for dolphins swimming in the distance. Bring along your snorkeling gear if you’d like to explore the vibrant underwater world before continuing on your adventure.

For those who are looking for a bit of adventure and fun, head to Grand Fond Beach. Here, the surf is perfect for bodyboarding and surfing and there’s plenty of room to take part in beach games. After a long day at the beach, take a dip in the ocean and enjoy the cool water.

After a full day exploring St Barthelemy’s stunning beaches, be sure to check out the local culture and cuisine. The restaurants here offer a range of delicious dishes from international flavors to traditional Caribbean fare. Spend the evening exploring the area’s vibrant nightlife and enjoy some drinks with friends.

No matter what type of beach vacation you’re looking for, St Barthelemy will provide an unforgettable experience. From stunning views to exciting activities, this Caribbean paradise has it all. So, pack your bags and get ready for the trip of a lifetime to St Barthelemy’s stunning beaches!

Day 4

Basseterre, Saint Kitts

Basseterre is the capital city of Saint Kitts and Nevis, in the West Indies. It is also the main port and commercial center for the island nation. The city has a long and rich history, dating back to the early days of European colonization.

The city was named by the French after Christopher Columbus, who stopped here on his second voyage to the New World in 1493. The city was then known as Basseterre de Guadeloupe, or Basseterre of Guadeloupe. It was one of the first European settlements in the Caribbean and quickly became an important trading port.

In the 17th century, the British took control of the island and renamed it Basseterre. The city remained an important port and commercial center under British rule.

Today, Basseterre is a busy and vibrant city with a population of around 13,000. It is a popular tourist destination, with its beautiful beaches, historic buildings, and lively nightlife.

Day 5

Little Bay

The beautiful island of Montserrat has a distinctly explosive history that has drawn intrepid travellers to its awe-inspiring shores. It seems quite clear the earth is trying to rid itself of this small Caribbean island, as its recent history is a list of major natural disasters.

A hurricane swept over the island in 1989, damaging 90 percent of the buildings. Following a hurricane in 1989, Montserrat's volcano, the Soufriere Hills, erupted in 1995 after staying dormant for hundreds of years.

It erupted again two years later, covering the capital city, Plymouth, in ash and mud, while limiting the 39 square mile (101km) island to a much smaller, inhabitable safe zone in the north of Monserrat. Most of the 12,000 inhabitants got the message and emigrated.

For those that stayed, tourism on the island is slowly growing and curious visitors are now eager to take tours of the active volcano where an ominous dome over the volcano's crater rebuilds and periodically collapses sending great plumes of ash into the air. Much of the island is within the 'volcanic exclusion zone' which was previously inaccessible; however, Montserrat tourism now conducts guided tours into the ashen wasteland in the south.

Despite the destruction caused by the Soufriere Hills, the volcano has also made some fascinating changes to the natural environment. Divers can see unique coral formations that have grown healthier from the volcano's substrate; sun lovers can relax on soft, volcanic sand at a number of beaches; and the nature walks and hikes have lush vegetation from the fertilised soil. As a result, Montserrat is looking to establish itself as a major player in global ecotourism.

The country often refers to itself as the Emerald Isle, an homage to its Irish settlers escaping religious oppression. The Caribbean is an unlikely place to celebrate St. Patrick's Day, but the national holiday highlights Monserrat's unique charm. Unlike Columbus, who sailed right past the islands, visitors to the Caribbean should make this a place to explore. Flights from Antigua and some surrounding islands arrive daily.

Day 6

Îles des Saintes

This small group of islands lies opposite the western part of Guadeloupe. They were discovered in November 1493 by Columbus, who named them Los Santos. French settlers established themselves in 1648 and changed the name to Iles des Saintes, commonly known as Les Saintes. Since then the islands have been closely connected with Guadeloupe. Until a recent influx of tourism, Les Saintes were among the Caribbean’s most unspoiled destinations. Only two of the eight islands are inhabited: Terre-de-Bas and Terre-de-Haut. The latter is known for its impressive Fort Napoleon built in the early 19th century to replace an earlier 17th-century fort. From its vantage point there are fine views of the many tiny islets scattered in the bay and across to Guadeloupe. Terre-de-Haut is the main island of Les Saintes, with steeply scarped hills, scenic valleys, hidden coves and beautiful beaches. Its main settlement consists of a charming village of red-roofed houses situated along a curving bay. A number of small boutiques and gift shops invite browsing. Quaint cafés and restaurants offer food and drink. To the east of the village lies Grande Anse, a fine sand beach. Most of the attractions on this small island can be seen on foot. With just a few vehicles on the island, there are no organized tours possible. Time ashore here is at your leisure.

Day 7

Roseau

Roseau lies in a small area on Dominica's west coast, where
rugged green hills meet a deep blue sea. A mix of French and
British colonial structures run along its narrow streets,
punctuating the modern concrete buildings and recalling the
capital's history.

Most visitors gather along the Bayfront before browsing through
the Old Market. Historically speaking, the area hosted the slave
trade. These days, its craft and souvenir stalls are popular among
cruise-ship passengers. Tourists should also explore the compact
museum in the Old Post Office if time allows. Otherwise, seeing the
island's natural beauty should be the priority. The botanical
gardens are certainly a worthwhile stop in this regard. A hillside
enclave called Morne Bruce lies above them and offers a
breathtaking view of Roseau.

All in all, the destination appeals to travellers who want a
friendly, relaxed atmosphere, though the local hotel bars and clubs
can be lively. The World Creole Music Festival makes visiting in
late October a special treat.

Day 8

Trois-Ilets

Nestled in the heart of the Caribbean, Martinique is an overseas region of France and one of the many islands that make up the Lesser Antilles island group affectionately referred to as the 'Breezy Islands'.

The destination enjoys a rich and diverse history, as showcased through attractions such as the quaint little cottage of La Pagerie, which honours a family of the same name. Josephine, a daughter of that clan, became the Empress of Napoleon. The 600-foot (182m) pinnacle of Diamond Rock rises majestically from the sea and was once a strategic garrison during the Napoleonic wars. Today, the spectacular caves and coral reefs around the pinnacle attract scuba divers from all corners of the globe.

The majestic volcano, Mount Pelee, sits smoldering above the former capital Saint-Pierre, a once booming town destroyed by a volcanic eruption in 1902. The twin peaks of Carbet and Mount Pelee dominate the island, rising above Martinique's legendary tropical rainforest. Unlike so many exotic island locations, this area of unspoilt beauty has not yet been fully discovered by tourists.

There is something for just about everybody on Martinique. The active and adventurous can enjoy kitesurfing, yachting, diving, surfing and sailing as well as mountain biking, hiking, and cliff jumping. For the less adventurous, warm sunny days can be spent lazing on the sandy, white, palm-fringed beaches, many of which are truly magnificent.

Day 9

Castries

The main reason for the existence of the town of Castries capital of St Lucia is as a port of call for hundreds of cruise ships that dock in the deep harbour every year disgorging thousands of day-trippers who shop till they drop in the market and duty-free shopping malls. Visitors who linger find the town has a certain charm surrounded by hills although little to offer in the way of sightseeing or architectural heritage. Most of the buildings are fairly new with Castries having been destroyed several times by fire during its history most recently in 1948. There is a very vibrant and colourful market on the go every day except Sunday some good waterfront restaurants and a few remains of the defences of the island's various occupiers to claim the attention. Castries also serves as a good base for island exploration whether it is by road or water.

Day 10

Saint George's

Nutmeg, cinnamon, cloves, cocoa those heady aromas fill the air in Grenada (pronounced gruh-nay-da). Only 21 miles (33½ km) long and 12 miles (19½ km) wide, the Isle of Spice is a tropical gem of lush rain forests, white-sand beaches, secluded coves, exotic flowers, and enough locally grown spices to fill anyone's kitchen cabinet. St. George's is one of the most picturesque capital cities in the Caribbean, St. George's Harbour is one of the most picturesque harbors, and Grenada's Grand Anse Beach is one of the region's finest beaches. The island has friendly, hospitable people and enough good shopping, restaurants, historic sites, and natural wonders to make it a popular port of call. About one-third of Grenada's visitors arrive by cruise ship, and that number continues to grow each year. Grenada's capital is a bustling West Indian city, much of which remains unchanged from colonial days. Narrow streets lined with shops wind up, down, and across steep hills. Brick warehouses cling to the waterfront, and pastel-painted homes rise from the waterfront and disappear into steep green hills. The horseshoe-shaped St. George's Harbour, a submerged volcanic crater, is arguably the prettiest harbor in the Caribbean. Schooners, ferries, and tour boats tie up along the seawall or at the small dinghy dock. The Carenage (pronounced car-a-nahzh), which surrounds the harbor, is the capital's center. Warehouses, shops, and restaurants line the waterfront. The Christ of the Deep statue that sits on the pedestrian plaza at the center of The Carenage was presented to Grenada by Costa Cruise Line in remembrance of its ship, Bianca C, which burned and sank in the harbor in 1961 and is now a favorite dive site. An engineering feat for its time, the 340-foot-long Sendall Tunnel was built in 1895 and named for Walter Sendall, an early governor. The narrow tunnel, used by both pedestrians and vehicles, separates the harbor side of St. George's from the Esplanade on the bay side of town, where you can find the markets (produce, meat, and fish), the Cruise Ship Terminal, the Esplanade Mall, and the public bus station.

Day 11

Bridgetown

Bridgetown originally called 'Indian Bridge' is the capital and commercial centre of Barbados with about 80 000 inhabitants. It is a busy port with a natural harbour inlet known as the Careenage and is well utilised by pleasure craft and fishing boats.Bridgetown has a long and colourful history as a British settlement from the 17th century. A bustling city with many attractions for travellers its mix of modern and historic buildings are interspersed with markets monuments and a number of lush gardens.The main street Broad Street is where one finds banks department stores and duty-free shops. At the top of Broad Street is the Parliament Building (the Barbados Parliament is the third oldest in the Commonwealth dating from 1639) facing National Heroes Square. Bridgetown is home to a number of historical buildings that will interest visitors including the Garrison Historic Area which is a must-visit for military history buffs.Another attraction in Bridgetown is a massive Baobab tree (said to have been brought to the island from Guinea Africa around 1738). It takes 15 adults with outstretched arms to encircle the trunk.Tourists in Bridgetown will find much to see and do: cricket games at Kensington Oval which hosted the 2007 Cricket World Cup; the Barbados Derby at the racetrack in the Garrison area; and many other events and activities. A range of duty-free shops near the harbour sell staples like Mount Gay Rum while more colourful shopping options include the Cheapside Market and the Swan Street pedestrian mall. Local restaurants in the Careenage serve up fresh lobster and fish with Caribbean flair.

San Juan to Bridgetown Ships

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