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San Juan & The Virgin Islands - round trip from San Juan, Puerto Rico

Jan 22 - 30, 2026

$0.00

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Your Advisor

Jim and Judi Drennan

Cruisin' with the Drennans

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makememories@cwtdtravel.com

216-903-0701

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Overview


This cruise has it all. History and culture in San Juan, shopping and sightseeing in St. Maarten and St. Thomas, and relaxation on world-class beaches.

Trip Details


About Your Cruise Line - Windstar Cruises

Only Windstar brings you close enough so you can truly experience it. Each of Windstar Cruises yachts accommodates between 148 to 342 guests. This intimacy provides you with the luxuries of time, space, and freedom to immerse yourself in both the journey and the destination – in ways you may never have imagined possible. We scour the world for amazing places just this side of unreachable, then seek out the most authentic ways for guests to experience them – in small groups that are easily...

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About Your Ship - Star Seeker

Be one of the first to experience Star Seeker, Windstar’s newest yacht, during her first-ever sailing season beginning December 2025!

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Day 1 · Thu, Jan 22 · Travel Day


Flight to San Juan, Puerto Rico

Transfer to Hotel from Airport

Check In Hotel - TBD

Day 2 · Fri, Jan 23 · San Juan (Puerto Rico), Puerto Rico


San Juan (Puerto Rico)

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan. If you associate Puerto Ri...

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Day 3 · Sat, Jan 24 · Day at Sea


Day on the Water

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Day 4 · Sun, Jan 25 · Basseterre, Saint Kitts, Saint Kitts and Nevis


Basseterre, Saint Kitts

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill F...

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Day 5 · Mon, Jan 26 · Gustavia, Saint Barthélemy


Gustavia

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signa...

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Day 6 · Tue, Jan 27 · Philipsburg, Sint Maarten (Dutch part)


Philipsburg

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebr...

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Day 7 · Wed, Jan 28 · Great Harbour, Jost Van Dyke, British Virgin Islands


Great Harbour, Jost Van Dyke

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Si...

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Day 8 · Thu, Jan 29 · Day at Sea


Day on the Water

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Day 9 · Fri, Jan 30 · San Juan (Puerto Rico), Puerto Rico


San Juan (Puerto Rico)

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan. If you associate Puerto Ri...

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Transfer to Airport from Port

Return Flight Home

Cruisin' with the Drennans Travel Terms and Conditions

When you work Cruisin' with the Drennans to help plan your travel, you're hiring professional travel advisors. We bring our skills, experiences and training, our professional relationships and our industry connections. Our Professional Services in...

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Disclaimer

Pricing includes port fees and taxes. Pricing is dynamic and may change without notice. Gratuities are not included in pricing except where noted. Itineraries are subject to change without notice. Offers shown are subject to change without notice....

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