The Best Caribbean Cruise!

Ready for a Caribbean Cruise? Rum punch? Pilates class? Breakfast in bed? Turn down service? Your favorite dessert? Dining under the stars at sea?

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best Caribbean cruise

“Anything you want, you got it,” is the mantra of the crew on Windstar Cruises.  After 7 days on the MV Star Legend, one of Windstar’s power yachts, and were treated like royalty and didn’t want to disembark.

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That’s why we keep cruising on Windstar Cruises.  This is our fourth cruise with Windstar Cruises.  We flew Jet Blue from Seattle to San Juan, Puerto Rico to cruise the Virgin Islands.

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Each day we arrived to a new island, excited to experience a new adventure. Here’s an overview on why we love Windstar, along with day-by-day highlights from our cruise to a Caribbean paradise.


There are many reasons we love Windstar Cruises.  High on our list is the fact that their small luxury ships are able to enter small ports and harbors that large vessels are unable to visit.

We also appreciate the wide array of excursions.  Some of the adventures offered are sailing, diving, snorkeling, zip lining, golfing, learning a local recipe, or joining expert-guided tours (eco, history, culinary, etc.).

Cruising on a small luxury ship is a great way to create long-lasting memories with your partner, friends and family.  It’s also fun getting to know other guests on board who share similar interests and are curious about the world.

Windstar cruising experiences are known for being 180° from ordinary.  It’s truly extraordinary.

The port talks, sunsets, deck BBQ, and signature sail-aways became our favorite evening routine.  Yoga, pilates, and morning stretch classes are complimentary.  Guests also have their own private photographer on the ship for complimentary photos. The Captain’s Reception, visiting the bridge, and getting pampered at WindSpa were highlights.  Ladies especially love the Ladies Night, and Ladies Pampering Party – complimentary as well!

Captain Richard Reville, Hotel Manager Savvas Marotos, the Officers and Crew extended a warm welcome and knew our name.  The crew raised the bar on delivering excellent service throughout our cruise.  With 212 guests and 153 crew, we received an uncompromising level of service.

Here’s the breakdown of our 7-day cruise from Puerto Rico to the Virgin Islands.



The 7-day cruise was filled with special moments and memories.  Below is our itinerary with day-to-day highlights for each destination.

best Caribbean cruise

Virgin Gorda:

We hiked through the obstacle course of gigantic boulders at two national parks, Devil’s Bay and the Virgin Gorda Baths, where around every bend is a natural wonder.  Find out more, click here (this post is from a previous Windstar Cruise).

best Caribbean cruise


Prickly Pear Windstar Beach Experience: 

An outstanding day on any Windstar Cruise is the private beach party, when a beach is reserved exclusively for the use of cruise guests. The crew rolled-out the sandy carpet, and greeted us with coconut drinks, and a party complete with a BBQ, music & entertainment. For more active guests, there are water sports activities to choose from.  For those seeking serenity, there are other options — beach yoga, a beach massage, or lounge chairs on a beautiful beach.

best Caribbean cruise

Jost Van Dyke:  

Not many cruise ships make it to this island, but Windstar’s ships are small enough, so we were able to anchor off the coast and tender to shore.  Jost Van Dyke is famous for some of the best beaches in the Caribbean, especially the beach at White Bay.

We anchored in the main bay, and stayed the night.  Some guests tendered to visit Foxy’s Bar.  Rumor has it that if you’re in the Caribbean on New Year’s Eve, this is THE place to celebrate.

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St. Maarten: 

This “two-flag” island offers so many activities on both the French side and Dutch side of the island.  One is to race on the America’s Cup sailing boat, and another is to take a cooking class in Marigot, on the French side of the island.

We had visited St. Maarten on a previous Windstar Cruises and decided to take a day trip to Anguilla. Find out about Anguilla, click here. Find out more about our previous Windstar Cruise visit to St. Maarten, click here.


Due to inclement weather, we weren’t able to visit Montserrat this cruise, so the Captain took us to St. Kitts where we visited the main park and square at Basseterre, then headed to a beach to relax.


Lots of British history and adventures to have on this island.  Don’t miss!  Nelson’s Dockyard & its Pillars, and the best lookout on the island – Shirley Heights overlooking Falmouth and English Harbors.

best Caribbean cruise

Spend a ½ day on a reef rider exploring the coastline, ride out to a reef and snorkel.  Find out more, click here.

St. Barts:

Called the “Little Provence” of the Caribbean.  This island is small with lots of hills and lookouts.   A wonderful way to see this island is to rent a car, and drive around it.  Along the way, there are many places to stop and visit, so plan on at least a half day to go around the island, if not a full day.

There are spectacular bays, beaches, boutiques and boulangeries.  Our day included stops at luxury boutique hotels, and checking out fashion boutiques throughout Gustavia and St. Jean.  Find a colorful straw hat, beach cover, sandals, a long necklace, and you’re St. Barts-ready.  Find out more, click here.

San Juan, Puerto Rico: 

It’s easy to spend a full day in Old San Juan – its quaint squares, churches, colorful Spanish buildings, and impressive forts.  Be sure to take a walking tour, and if you want to hike to a waterfall, visit the only tropical rain forest in the U.S. territory at El Yunque.  Find out more, click here.





Jet Blue:  Our airline of choice to fly from Seattle to San Juan, Puerto Rico is Jet Blue.  JetBlue offers flights to 90+ destinations with free inflight entertainment, free brand-name snacks and drinks, lots of legroom and award-winning service.

JetBlue Airways aims to provide superior service in every aspect of their customer’s air travel experience. They even offer a Bill of Rights for their customers.



Global Adventuress thanks Windstar Cruises for hosting our cruise, and Jet Blue for hosting our air flights.  All opinions above are our own.

Windstar Cruises offer boutique small ship cruising and deliver a casually elegant vacation with visits to smaller harbors, in-port overnights and immersive cultural experiences.  The Windstar fleet totals 6 luxury cruise ships — 3 sailing cruise ships & 3 luxury power yachts.

Book your reservation at, click here!

Raden:  Our favorite suitcase for this Caribbean trip is Raden!  Called the “Smart Suitcase” since Raden delivers a seamless travel experience by pairing the world’s best materials with technology – built-in charger, weight sensor, and location awareness, connecting seamlessly to the Raden mobile app. Raden cases are super light and incredibly strong, gliding smoothly across airport terminals and city sidewalks.  And there are several FUN colors to choose from.  We selected the checked bag A28, 28” in the Lavender – it stood out at the baggage carousel and was easy to find.  There’s also the A22, a 22” Carry On suitcase that is “smart” too.  Can’t wait to travel with the carry on soon.

Get your smart suitcase at

Gretchen Scott:  We are traveling this spring and summer in some of Gretchen Scott’s tunics, skorts, skirts and dresses!  Her designs are versatile and can be worn on vacation, and also when you return to home and work.

Gretchen’s mantra is, “Laugh More; Gripe Less; Ignore Critics; Say Yes; Order Dessert; Love Life ®.”  She has traveled the world, “looking and hoping always to see – really see.” She is convinced that is what makes for great design, “knowledge of what exists, along with a wide open view of it – coupled with the ability to interpret it cleverly.”

Find your vacation wardrobe at:

HATS!  Looking for some fun hats for your vacation or trips to the beach?  Here are some Etsy shops that sell fantastic hats with clever sayings:

Honeymoon Hats: OR email: based in Florida.

Panmilli: based in Toronto.

Bits and Pieces: based in London.

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