Bridgetown to Bridgetown Caribbean Cruise - JWT Travel

Bridgetown to Bridgetown Caribbean Cruise

  • 20 November 2025
  • 17 Nights
  • From 8,450 Per Person
  • Crystal Serenity

Set sail from Bridgetown, Barbados, for a fun-filled island-hopping trip around the Caribbean aboard Cristal Serenity.

Sail through the Caribbean with Crystal Cruises. Your first port of call is St. Vincent, where you’ll explore its lush interior. Next, marvel at the dramatic landscapes of St. Lucia, and discover the palm trees and pain au chocolat of charming Guadeloupe.

Discover the black sand beaches of Montserrat, visit the beautiful port of Road Town on Tortola, and cruise the ocean to Fort Lauderdale. Next, you will encounter the turquoise waters around Georgetown in Grand Cayman, a popular spot for snorkeling and diving, the laid-back vibe of Montego Bay in Jamaica, and Santo Domingo, in the Dominican Republic, one of the Caribbean’s oldest cities.

Before returning to Bridgetown, there’s plenty more to see, including vibrant San Juan in Puerto Rico and French-style Marigot in St. Maarten.

Crystal Serenity offers a more comfortable and memorable journey, where you can enjoy world-class dining and wellness, and relax on board with the utmost in comfort, quality, personal service, and choice.

Talk to the JWT Cruises team to book your place on this Bridgetown to Bridgetown Caribbean Cruise with Crystal cruises.

_Crystal Cruises -Bridgetown to Bridgetown Caribbean Cruise - JWT CRUISES

Bridgetown to Bridgetown Caribbean Cruise

Set sail from Bridgetown, Barbados, for a fun-filled island-hopping trip around the Caribbean aboard Cristal Serenity.

Sail through the Caribbean with Crystal Cruises. Your first port of call is St. Vincent, where you’ll explore its lush interior. Next, marvel at the dramatic landscapes of St. Lucia, and discover the palm trees and pain au chocolat of charming Guadeloupe.

Discover the black sand beaches of Montserrat, visit the beautiful port of Road Town on Tortola, and cruise the ocean to Fort Lauderdale. Next, you will encounter the turquoise waters around Georgetown in Grand Cayman, a popular spot for snorkeling and diving, the laid-back vibe of Montego Bay in Jamaica, and Santo Domingo, in the Dominican Republic, one of the Caribbean’s oldest cities.

Before returning to Bridgetown, there’s plenty more to see, including vibrant San Juan in Puerto Rico and French-style Marigot in St. Maarten.

Crystal Serenity offers a more comfortable and memorable journey, where you can enjoy world-class dining and wellness, and relax on board with the utmost in comfort, quality, personal service, and choice.

Talk to the JWT Cruises team to book your place on this Bridgetown to Bridgetown Caribbean Cruise with Crystal cruises.

Itinerary

Bridgetown to Bridgetown Caribbean Cruise Itinerary

Day 1 – Bridgetown, Barbados

Barbados is sun-drenched beaches, clear blue-green waters and cool trade winds. Its capital is a UNESCO treasure and inland you’ll see lovingly preserved plantation houses, lush sugar cane fields and fragrant gardens. Reminders of former British rule abound, from cricket fields to Lord Nelson’s statue and the original Trafalgar Square. Don’t miss Bridgetown’s bustling Careenage and the shops on Broad Street, which offer deals on luxury imports from Britain.

Day 2 – Kingstown, St Vincent and Grenadines

A gem-like strand of 32 islands, of which only nine are inhabited, St. Vincent and the Grenadines is among the most idyllic and least touristy of all the Caribbean island nations. At 18 miles long, St. Vincent is the largest isle, regarded for its black-sand beaches and sky-blue waters – paradise for leisure sailors and a wonderland for scuba divers and snorkelers. The imposing, still-active La Soufriere volcano and its surrounding waterfalls and rainforest make St. Vincent a haven for eco-adventures with exceptional hiking trails and a spectacular Botanical Garden – the Caribbean’s oldest. In the capital city of Kingstown, cobblestone streets lined with arched stone doorways and magnificent churches recall both French and British colonization, as Fort Charlotte overlooks the city from its perch 600 feet above the sea.

Day 3 – Castries (St. Lucia), St Lucia, West Indies

Stunning and dramatic, the emerald green Pitons rise from azure waters on this magical isle of quaint bays and lush landscapes and delightful strains of Creole.

Day 4 – Les Saintes, French West Indies

This paradise archipelago of the French West Indies is the perfect place for those looking for perfect tropical weather, verdant landscapes and a serene atmosphere. Its small and charming coves feel like having your own private beach, although you can also visit the island’s only town of Le Bourg for a more active experience in this laid-back dream.

Day 5 – Plymouth, Montserrat

Plymouth, once the capital of Montserrat, offers stunning natural beauty, including lush landscapes and scenic coastlines. This is one of the Caribbean’s lesser visited islands, and as an uncommon island, visitors can expect a warm welcome. However, the Soufrière Hills volcano’s eruptions in the 1990s and ongoing volcanic activity have significantly impacted the island’s infrastructure and specific areas, and today, Plymouth stands as a haunting testament to the volcanic eruptions that rocked the island. In the 1990s, the Soufrière Hills volcano’s activity led to the city’s abandonment and destruction, and the capital was relocated to Brades, leaving Plymouth an exclusion zone. Don’t let that put you off; however, the island has been open to tourism since 2021 and offers one of the most authentic Caribbean experiences in the archipelago.

Day 6 – Road Town, British Virgin Islands

Welcome to the capital city of the British Virgin Islands… its Main Street lined with colonial-era buildings painted in shades of pastel with colorful shutters and delicate wood trim. Trek through the rain-forested Mount Sage National Park for sweeping views, or play on spectacular white sand beaches with names like Smuggler’s Cove and Cane Garden Bay (immortalized in Jimmy Buffet’s “Mañana”).

Day 7 – Day at sea

Day 8 – Day at sea

Day 9 – Fort Lauderdale, United States of America

Known as the `Venice of America,` Fort Lauderdale is to Miami, what poetry is to prose. Despite the two cities being only 30 miles apart, there is a world of difference between them. With its stunning beaches, thriving arts, and culture scene, and picturesque waterways, Fort Lauderdale offers a perfect blend of relaxation and excitement. Visitors can soak up the sun on the pristine white sands of Fort Lauderdale Beach, explore the arty, independent boutiques and restaurants along Las Olas Boulevard, or take a scenic boat tour through the city’s intricate network of canals. The city also boasts a diverse range of attractions, including world-class museums, lush parks, and bustling nightlife.

Day 10 – Day at sea

Day 11 – George Town, Grand Cayman, Cayman Islands

Nestled along the Caribbean’s azure embrace, George Town beckons with its tropical charm. Crystal clear waters hide vibrant coral reefs, promising psychadelic underwater life for snorklers. Long ribbons of white sandy beaches are flanked by palm trees and promise hours of endless, enviable relaxation. Gran Cayman is Caribbean is truly a Caribbean ideal, pastel buildings dot the waterfront, hosting a fusion of Caribbean delights and international flavors, so find a cafe or bar, order a local rum punch and imbibe in a bit of Cayman culture. But it is not all fun in the sun, George Town is the hub of the island’s thriving financial district, which give this island an edge over its neighbours. George Town weaves a tapestry of sun-soaked days, reggae-infused memories, and the timeless allure of island life.

Day 12 – Montego Bay, Jamaica

This lively and picturesque town is a famous tourist destination on the island of Jamaica. Montego Bay has all you need for an idyllic experience, from sparkling blue waters, sandy beaches and diverse outdoor activities to great restaurants that showcase the best homemade Jamaican cuisine.

Day 13 – Day at sea

Day 14 – Santo Domingo, Dominican Republic

Capital of the Dominican Republic, Santo Domingo is a place full of color, history and culture. Learn about its rich colonial heritage by visiting the university, the cathedral and the historic Hospital San Nicolas de Bari in the UNESCO-listed neighborhood of Colonial City, but also save time to relax on its incredible beaches.

Day15 – San Juan, Puerto Rico

Rich in history, La Fortaleza is the oldest governor’s mansion in the western hemisphere; be sure to see the mahogany clock which stopped in time when the last Spanish governor of Puerto Rico struck it with his sword on his way out, heralding the last moment of Spanish rule in the New World.

Day 16 – Marigot, St. Martin, Saint Martin (French Part)

Marigot, a charming town on the French side of the dual-nation island of St. Martin, is a delightful fusion of Caribbean and European influences. Nestled along a picturesque bay, Marigot boasts colorful Creole-style buildings, bustling local life, and a relaxed, take-it-easy ambiance. Visitors can explore the quaint streets, indulge in French pastries, and shop for local crafts at the vibrant markets. Fort Louis offers a panoramic view of the town and the surrounding turquoise waters, and is an unmissable view for visitors whether it is your first or fiftieth time on the island! With its unique blend of cultures and stunning coastal beauty, Marigot remains a captivating destination for travelers seeking an authentic Caribbean experience with a touch of French sophistication.

Day 17 – Fort-de France, Martinique

Day 18 – Bridgetown, Barbados

Volcanic in origin, this overseas region of France is a tropical paradise of stunning beaches and rain-forested mountains. Known as the “isle of flowers” to the indigenous Arawak, it is today renowned for its culinary offerings and remains ever-enchanting with colonial architecture and glorious gardens. Adding to its mystic allure is the still-smoldering Mount Pelée that erupted in 1902, wiping out the capital of St. Pierre (today in Fort-de-France), often called the Pompeii of the Caribbean.

  • 16 nights Cruise aboard Crystal Serenity
  • Subject to availability
  • T&C’s apply

Request a Quote


JWT Travel logo icon