Group or Custom Journeys

Starting at $2,900 Per Person

An island-hopping cruise that combines relaxed glamour with intoxicating natural beauty, sunny skies and white sandy beaches. Explore volcanic mineral pools and hot sulphur springs at Ti Kwen Glo in Dominica or maybe observe the jewel-like aquatic wonderland in the clearest waters in the Caribbean by glass-bottomed boat while in Tortola.

Silversea’s small luxury ships are designed for those who delight in the thrill of discovery while indulging mind and body in the most lavish surroundings imaginable. All accommodations are spacious, ocean-view suites that include butler service, and most include private verandas. Our intimate, ultra-luxury ships can sail up narrow waterways into the heart of a city, or tie up right at the pier while others must anchor offshore.

Trip Highlights

  • Stop on the hidden gem that is the island of Dominica and its rivers, rainforests and wildlife.

  • Shop till you drop in fashionable St. Bart’s.

  • Wander through the historic streets of Old San Juan.



DAY 1: San Juan, Puerto Rico

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures. By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan.

DAY 2: Gustavia, St. Bart's

Hilly St. Barthélemy, popularly known as St. Barth (or St. Bart’s) is just 8 square miles (21 square km), but the island has at least 20 good beaches. What draws visitors is its sophisticated but unstudied approach to relaxation: the finest food, excellent wine, high-end shopping and lack of large-scale commercial development. A favorite among upscale cruise-ship passengers, who also appreciate the shopping opportunities and fine dining, St. Barth isn't really equipped for mega-ship visits, which is why most ships calling here are from smaller premium lines. This is one place where you don't need to take the ship's shore excursions to have a good time.

DAY 3: Roseau, Dominica

Although it's one of the smallest capitals in the Caribbean, Roseau has the highest concentration of inhabitants of any town in the eastern Caribbean. Caribbean vernacular architecture and a bustling marketplace transport visitors back in time. Although you can walk the entire town in about an hour, you'll get a much better feel for the place on a leisurely stroll. For some years now, the Society for Historical Architectural Preservation and Enhancement (SHAPE) has organized programs and projects to preserve the city's architectural heritage. Several interesting buildings have already been restored.

DAY 4: Bridgetown, Barbados

This bustling capital city is a major duty-free port with a compact shopping area. The principal thoroughfare is Broad Street, which leads west from National Heroes Square.

DAY 5: Castries, St. Lucia

With a lush interior featuring towering mountains, dense rain forest, fertile valleys and acres of banana plantations, St. Lucia is mostly distinguished by the Pitons: twin peaks that soar high above the ocean floor on the southwest coast. Whether you stay in Soufrière, in the north in or around Rodney Bay Village, or even farther north at Cap Estate, exploring the iconic natural sights and local history in Soufrière is a day well spent. Except for a small area in the extreme northeast, one main highway circles all of St. Lucia. The road snakes along the coast, cuts across mountains, makes hairpin turns and sheer drops, and reaches dizzying heights. It takes at least four hours to drive the whole loop.

DAY 6: St. John's, Antigua and Barbuda

Antigua's capital, with some 45,000 inhabitants (approximately half the island's population), lies at sea level at the inland end of a sheltered northwestern bay. Although it has seen better days, a couple of notable historic sights and some good waterfront shopping areas make it worth a visit. At the far south end of town, where Market Street forks into Valley and All Saints Roads, haggling goes on every Friday and Saturday, when locals jam the Public Market to buy and sell fruits, vegetables, fish and spices. Ask before you aim a camera; your subject may expect a tip. This is old-time Caribbean shopping, a jambalaya of sights, sounds and smells.

DAY 7: Road Town, Tortola, British Virgin Islands

The bustling capital of the BVI looks out over Road Harbour. It takes only an hour or so to stroll down Main Street and along the waterfront, checking out the traditional West Indian buildings painted in pastel colors and with corrugated-tin roofs, bright shutters and delicate fretwork trim. For sightseeing brochures and the latest information on everything from taxi rates to ferry schedules, stop in at the BVI Tourist Board office. Or just choose a seat on one of the benches in Sir Olva Georges Square on Waterfront Drive, and watch the people come and go from the ferry dock and customs office across the street.

DAY 8: San Juan, Puerto Rico


Pricing starts at $2,835 per person for double occupancy (cost will vary based on date and room category selected)

Ship capacity: 296 passengers


  • Spacious suite

  • Butler service

  • Free Wi-Fi

  • All meals – served in a variety of restaurants and including 24-hour dining service

  • Beverages in-suite and throughout the ship, including champagne, select wines and spirits

  • Onboard entertainment and lecturers

  • Transportation into town in most ports

  • Onboard gratuities

Solo Traveler

Accommodations are based on double occupancy. If you prefer single accommodations, and if such are available, you can pay a single supplement fee.

Caribbean: San Juan to San Juan

Silversea Cruises

Learn More