The Best of the Secluded Caribbean

From $11,998 per person

11 days

Ship: SeaDream I

Map showcasing the secluded Caribbean route through islands like St. John, Anguilla, and Trinidad and Tobago.
SeaDream Yacht Club logo

The Caribbean’s incomparable sun, sand and sea come alive on your yachting journey through the U.S. and British Virgin Islands, French West Indies, and Grenadines. As you sail from San Juan, Puerto Rico, discover St. John’s delightful Cruz Bay, for snorkeling and diving spots off perfectly manicured beaches. Let time stand still in Prickly Pear, an uninhabited national-park island on the North Sound of Virgin Gorda, fringed by spectacular coral reefs. Appreciate the untouched beauty of Sandy Ground, Anguilla, before overnighting in chic St. Barths, the jetsetter’s Caribbean playground. Stroll Nevis Island’s historic Charlestown and explore Îles des Saintes, the small archipelago of islands off the southern coast of Guadeloupe, home to secluded beaches and coral-rich reefs brimming with marine life. Overnight in Bequia, just seven square miles of quiet lagoon and silvery stretches of beach, nestled in the heart of the Grenadines. Discover Tobago Cays, a respite for divers and snorkelers, boasting crystal-clear waters, coral reefs, and picture-perfect lagoons. Your journey concludes in Bridgetown, where you may choose to explore more of Barbados’ colonial capital.

Journey Summary

  • Day 1 - Jan. 10, 2026, Sat. - San Juan
  • Day 2 - Jan. 11, 2026, Sun. - Cruz Bay, St. John
  • Day 3 - Jan. 12, 2026, Mon. - Prickly Pear
  • Day 4 - Jan. 13, 2026, Tue. - Sandy Ground
  • Day 5 - Jan. 14, 2026, Wed. - Gustavia
  • Day 6 - Jan. 15, 2026, Thu. - Charlestown, Nevis
  • Day 7 - Jan. 16, 2026, Fri. - Terre De Haut, Îles des Saintes
  • Day 8 - Jan. 17, 2026, Sat. - Port Elizabeth, Bequia
  • Day 9 - Jan. 18, 2026, Sun. - Port Elizabeth, Bequia
  • Day 10 - Jan. 19, 2026, Mon. - Tobago Cays
  • Day 11 - Jan. 20, 2026, Tue. - Bridgetown, Barbados

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - January 10, 2026

San Juan

San Juan, founded in the 1520’s by Spanish settlers, is both the largest city and the capital city of Puerto Rico. A territory of the Unites States, Puerto Rico is comprised of the large main island as well as five smaller islands, including the popular islands of Vieques and Culebra (both ports of call on select SeaDream voyages).

SeaDream docks in Old San Juan, the oldest part of the city. Parts of this historic port city are still surrounded by stone walls dating back to the 1500’s. Narrow cobblestone streets, small shops, and points of interest like Cathedral of San Juan Bautista make this charming city a great place to stroll. Guests sailing into or departing from San Juan will enjoy views of Castillo de San Felipe del Morro, a mid- 1700’s Spanish fortress.

San Juan Luiz Munoz Marin Airport is approximately a 30-minute drive to the port in Old San Juan. Currency in Puerto Rico is USD.

Day 2 - January 11, 2026

Cruz Bay, St. John

Two-thirds of St. John Island has been dedicated as a national park and is the most virgin of the U.S. Virgin Islands. It is blessed with many beautiful beaches and bays, fine anchorages and verdant hills. Enjoy the day with snorkeling trip to Trunk Bay with its underwater guided trail, or join our kayaking land adventure. Ask your Club Director for a guided hike to Caneel Bay stopping at beautiful Honeymoon Beach for a quiet swim. Rental Cars are available should you want to explore on your own or you could borrow a SeaDream Mountain Bike for independent exploration.

Day 3 - January 12, 2026

Prickly Pear

A stunning island situated in the North Sound of Virgin Gorda and got its name because of the large flowering cactus all over the island. The island was declared a National Park in 1988 meaning the 180 acres will have no further development, just an island filled with natural beauty. Breathtaking hiking trails start from the main beach Vixen Point, winds around the island filled with salt ponds heading to the north shore which has two other amazing secluded beaches.

Day 4 - January 13, 2026

Sandy Ground

This British Overseas Territory is becoming more popular due to the incredible resort options as well as world recognized beaches and amazing golf. SeaDream offers an opportunity to tee off, snorkel, or, for the energetic, bike around the island with the Club Director. Naturally, we will also offer water sports while we are anchored off Sandy Ground.

Day 5 - January 14, 2026

Gustavia

Perhaps our most treasured destination in the Caribbean! This small island belonging to the French West Indies has so much to offer our SeaDream guests. Incredible shopping only steps away from the pier. Incredible beaches, resorts, restaurants and activities both day and night. SeaDream has created various land adventures for you to discover the island from sea or land. Ask one of the officers to take you on a hike or bike ride around the island. Another great activity here is to simply relax and watch all of the incredible yachts arriving and departing just off your SeaDream yacht.

Day 6 - January 15, 2026

Charlestown, Nevis

Nevis is one of our favorite islands, and we encourage you to explore Nevis beyond the small town to make the most of your visit! We offer several excellent and varied options for you to do so and still leave you with plenty of time on your own for the beach. Less commercial and laidback than its large neighbor St. Kitts, Nevis, at first glimpse, offers a stunning approach with dramatic views of the potentially active volcanic Nevis Peak (3,232 feet/985 meters). Your SeaDream tender will bring you within a few steps of the small town center. Charlestown does not offer too many sightseeing or shopping opportunities though the house where American statesman Alexander Hamilton was born is only a short walk away along the waterfront (now the Museum of Nevis History). To enjoy Nevis to its full potential, we recommend that you divide your day into Morning, Lunch/Afternoon and Evening activities.

Morning - Start your day by exploring the island, above or under water, on one of our fun optional Land Adventures. They are all enjoyable & exciting, and you will also support the local community. The Four Seasons Resort still offers incredible golf options as well as beautiful beach and dining facilities. Another option for lunch could be at Coconut Grove (less than ten minutes from Charlestown by taxi). Make sure to ask Gary, the owner, to show you his extensive wine & champagne cellar!

Evening - For a romantic sunset with cocktails and a snack or dinner, we like to take the short drive to see Gillian, the owner of the charming Bananas Restaurant, which offers lovely views surrounded by lush tropical gardens. Of course, there is also Sunshine's Beach Bar & Grill, home of the famous "Killer Bee" Caribbean rum drink. We hope that the above recommendations allow you to plan your special day on Nevis. Now, all you have to do is to decide which of the optional morning activities to join.

Day 7 - January 16, 2026

Terre De Haut, Îles des Saintes

If you’re looking for a small part of France in the heart of Guadeloupe, Terre de Haut is your go-to. Being the largest of the eight small islands that make up Les Saintes, Terre de Haut is a charming and scenic village rich with red-roofed houses and accompanying gardens of flourishing Hibiscus. Known for its robust reefs and great underwater visibility, Terre de Haut has also become a favorite among divers.

Day 8 - January 17, 2026

Port Elizabeth, Bequia

Bequia is the northernmost and largest of the Grenadines, just seven square miles of quiet lagoons, reefs, and long silvery stretches of beach. Among the first things you will notice are the colorful model boats set up on stands around the tiny harbor, representing the island's maritime history. If you are lucky enough to have a late call, don’t miss Mac’s Lobster Pizza.

Day 9 - January 18, 2026

Port Elizabeth, Bequia

Bequia is the northernmost and largest of the Grenadines, just seven square miles of quiet lagoons, reefs, and long silvery stretches of beach. Among the first things you will notice are the colorful model boats set up on stands around the tiny harbor, representing the island's maritime history. If you are lucky enough to have a late call, don’t miss Mac’s Lobster Pizza.

Day 10 - January 19, 2026

Tobago Cays

Imagine an intimate cluster of five uninhabited islands, heavenly lagoons full of green turtles, coral reefs, colorful fish and crystal clear waters. This is the setting when SeaDream anchors off the Tobago Cays. Zodiacs will whisk guests from the marina to the beautiful beach. There may be some locals selling crafts so remember to bring some dollars. This is an idyllic yachting anchorage, a dream for scuba divers, a paradise for beachcombers, and a film location for the Pirates of the Caribbean, the Tobago Cays and the Tobago Cays Marine Park is one of the world’s most awe inspiring island destinations.

Day 11 - January 20, 2026

Bridgetown, Barbados

SeaDream uses the port of Bridgetown as the hub for their Southern Caribbean voyages as well as some voyages that cross the Atlantic. The Island itself includes UNESCO Heritage Sites, excellent beaches and history dating back to 1628. The climate is tropical with constant warm temperatures during the year cooled by light trade winds.

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Jan 10, 2026

Ship

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SeaDream I anchored in vibrant blue waters, showcasing its luxurious design and elegant amenities for an exclusive cruise.
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