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BANANA BREEZE VACATIONS sailed on Windstar Cruises flagship Wind Surf sailing yacht. This is our day-to-day review and personal photos of the ship and the Classic Caribbean itinerary from our personal experience.


Windstar Cruises advertises casually elegant yacht-like ships with fewer than 300 guest that sail into Old World villages, hidden coves and harbors off the beaten path.  Well that sounds great for someone seeking a more exclusive sailing experience than what today's mega-lines deliver.

The idea of sailing on a Windstar yacht always intrigued me: Nice cabins, a level of elegance without over-the-top dress codes (resort-like, not stuffy), a water sports platform (complimentary) off the back of every yacht; actual sails furling (on three of their ships); and the ability to get into really cool, interesting ports larger ships simply cannot reach.  I've always been tempted. So sign me up

Before the Caribbean sailing season concluded I was determined to sail on a Windstar ship. So I booked myself and my wife on the flagship Wind Surf for the last sailing of the season - The Classic Caribbean itinerary, roundtrip out of lovely St Maarten. Here's my story - and I'm sticking' to it.

Traveling to the deep Caribbean requires a full day of airplane travels. We recommend arriving a day in advance for cruises to avoid unforeseen issues. "Do as we say, not as we do" - in this case. A busy schedule (and concert the night before) did not permit this luxury. So we arrived at the port to disembark in the late afternoon.

Follow our first day report as we learn the yacht layout, meet the crew, hear what lies ahead this week, and sample our first Windstar dinner. 

Good morning Barbuda. Our first view from the deck is of gorgeous blue skies, clear turquoise water and a long sliver of beach lined by trees behind it. After a few quick sunlight photos it is off to breakfast on Star Deck (top deck) at the Veranda. There are a few seats inside with air conditioning but why settle for that when you could have the Caribbean breeze and fabulous views from the deck.

Continue our Day 2 Review on the Wind Surf to learn about our day on tiny Barbuda and a nearly full afternoon and evening onboard. We will learn about the night time entertainment and what the Drink of the Day is.

Dominica is scenic, lush and mountainous. Today we will dock, and shuttles are available for anyone wanting to go into town center, about 10 minutes away. Dominica is the best port for excursions on our itinerary.

There are a plethora of cool excursions in Dominica, including visits to a terrifying site from Pirates in the Caribbean.  Continue reading to see our excursion choice - and of course the Drink of the Day. 

Windstar Cruises touts a private event on every sailing. In the Caribbean it is a private island experience in St. Lucia. Of course you are free to explore St. Lucia as you wish either independently or with a shore excursion offered through Windstar.

Continue reading to learn which new All-Inclusive resorts we inspected on St. Lucia, what the private beach party included, what the Beatles tribute was about, and what today's Drink of the Day is.

We woke up this morning offshore Iles des Saintes amidst anchored sailboats and catamarans, and surrounded by picturesque Guadeloupe with mountainous scenery in nearly all directions. Oh, and the Seabourn Odyssey is our neighbor once again. Can't get over the beauty of our surroundings. Every morning each new port seems to get more spectacular daily.

Continue reading to learn about our perfect Caribbean day, including the amazing Watersports Platform I took total advantage of, the talent displayed at the Crew Show and rum oriented Drink of the Day.

While St. Kitts does not present a new port for us, it is a return to one of our favorites. It is definitely an island to get out beyond the shops and explore the open spaces, great beaches and scenic vistas only St. Kitts can offer.

Continue reading to learn about our trip to the Reggae Bar & Grill, scenic St. Kitts, an absolutely mouthwatering Deck BBQ extravaganza, and the Drink of the Day.

What a way and location to spend the last full day of this Classic Caribbean Windstar Cruise: Fabulous St. Barts as we Americans refer to it. As I have described - each morning was a site to behold with our first glance of sail boats anchored in our vicinity and the occasional cruise ships nearby. But clearly the best was saved for last. I could not contain the smile I had when I witnessed all the neighboring yachts basking in the sparkling blue Caribbean waters. Truly St. Barts is the glamour capital of the Caribbean and this is the home of the rich and/or famous. If you want an example, Google Chopi Chopi yacht.

Please continue reading about our day independently exploring St. Barts by car including luxurious residential neighborhoods, Jimmy Buffett-made-famous Le-Select, Shell Beach and the amazing shopping and shore excursions in St. Barts. 


Our final thoughts on spending a week on the Windstar Wind Surf in the Caribbean.

To sail on a yacht of this magnitude and experience the furling of the sails, the service level only a smaller vessel can deliver, and essentially have all the amenities of a large cruise ship minus the crowds ... this experience fulfilled my every expectation. 

I loved the Wind Surf and the entire ambience. And while there are various Caribbean itineraries offered by Windstar, I can not complain about the diversity and authenticity of the Caribbean vibe we experienced on these islands big and small. I am grateful to have experienced each of these tropical paradises.

I can't wait to go on my next Windstar Cruise. Europe, Iceland, Alaska (new), Costa Rica? I do love the Caribbean, so we will have to see. 

VISIT OUR FULL PHOTO GALLERY. Be sure to click on a photo to see the captions.

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Why Choose Banana Breeze Vacations?

  • Experience: 17 Years planning Vacations, Honeymoons & Destination Weddings

  • Knowledge: We know Margaritaville Resorts intimately. Involved since Day 1

  • Backed by industry leaders like Funjet Vacations, Karisma Resorts and others

  • BEST RATES! No fees. Seriously!

  • Deposit for as little as $50 per person / Payment Plans available

  • Flexible Group Rates

  • We offer "Cancel for Any Reason" Insurance

  • The best Gift package: Koozies, Deluxe Parrot Head Transfers, Welcome kit. more!

  • Jimmy Buffett fans since 1978. Fins Up

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