Leeward Islands Celebration

From $8,418 per person

8 days

Ship: SeaDream I

Map showcasing the Leeward Islands, featuring locations like San Juan, Anguilla, and St. Barths marked for exploration.
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The British Virgin Islands and French West Indies meld into the dreamiest of island journeys, complete with the most breathtakingly diverse spots in the Caribbean. Begin in Sint Maarten before sailing through the Caribbean islands—where you kick off your holiday journey on the secluded sand shores of Anguilla. Explore the verdant mountainous landscape of Nevis and venture into the island’s charming cobblestoned capital of Charlestown. Overnight in chic St. Barths, a jetsetter’s yachting paradise. Let time stand still in Prickly Pear, an uninhabited national-park island on the North Sound of Virgin Gorda fringed by spectacular coral reefs. Experience St. John’s Cruz Bay for snorkeling and diving spots off perfectly manicured beaches before disembarking in Old Town San Juan, where you may choose to explore more.

Journey Summary

  • Day 1 - Dec. 20, 2025, Sat. - Philipsburg
  • Day 2 - Dec. 21, 2025, Sun. - Sandy Ground
  • Day 3 - Dec. 22, 2025, Mon. - Charlestown, Nevis
  • Day 4 - Dec. 23, 2025, Tue. - Gustavia
  • Day 5 - Dec. 24, 2025, Wed. - Gustavia
  • Day 6 - Dec. 25, 2025, Thu. - Prickly Pear
  • Day 7 - Dec. 26, 2025, Fri. - Cruz Bay, St. John
  • Day 8 - Dec. 27, 2025, Sat. - San Juan

Detailed Itinerary

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

Day 1 - December 20, 2025

Philipsburg

Philipsburg is the main town on the Dutch side of St. Maarten. The town is situated on a narrow stretch of land between Great Bay and the Great Salt Pond. Philipsburg was founded in 1763 by John Philips, a Scottish captain in the Dutch navy. The settlement soon became a center for international trade. The main shopping district is located on Front Street and is in the heart of the city. Many consider Philipsburg to be the best shopping opportunity in the Caribbean. Depending on the traffic, SeaDream has the option to anchor or dock alongside. One of the highlight activities may be to participate in the America’s Cup 12 Metre Regatta.

Day 2 - December 21, 2025

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 3 - December 22, 2025

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 4 - December 23, 2025

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 5 - December 24, 2025

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 - December 25, 2025

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 7 - December 26, 2025

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 8 - December 27, 2025

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.

Dates and Prices

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Dec 20, 2025

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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