Cruise At-a-Glance: St. Maarten & The Virgin Islands
A 7-night boutique Caribbean voyage combining secluded anchorages, signature al fresco deck dining, and yacht-scale access to islands unreachable by mega-ships.
St. Maarten
St. Kitts
St. Barths
Antigua
Tortola
Jost Van Dyke
Virgin Gorda
$250M
Star Plus Initiative
“Travel may still have some obstacles to overcome, but cruising the Caribbean isn’t one of them. The moment you step aboard Windstar’s newly transformed Star Legend, the cares of the world vanish. Within a short period, our names and preferred beverages were known by the smiling crew.”
— Karen Lee Elder, Vincent Vacations
I was fortunate, and very excited, to sail roundtrip St. Maarten on the beautiful Star Legend. Along with sister ship Star Breeze and Star Pride, the Star Legend recently underwent a comprehensive $250 million transformation under Windstar Cruises’ ambitious Star Plus Initiative. In one of the most daring engineering feats in maritime history, Windstar literally cut the ship in half at Italy’s Fincantieri shipyard, inserted a new 84-foot midsection, installed cleaner eco-friendly engines, and redesigned the public spaces. The final result is a gorgeous yacht—intimate, spacious, and perfectly tailored for discerning travelers.
Yacht-Style Elegance: The transformed Star Legend boasts sleek yacht profiles, uncrowded decks, and an intimate guest capacity that allows entry into shallow Caribbean harbours.
Pre-Cruise Serenity: St. Maarten & Oyster Bay Beach Resort
Coming from the West Coast, we arrived in St. Maarten the day before embarkation. After completing pre-travel health registrations, securing testing within the embarkation window, finishing last-minute packing, and flying across time zones, our one-night pre-cruise stay at the Oyster Bay Beach Resort was refreshingly calm.
We spent a tranquil evening dining at the resort’s Infinity Restaurant, savoring exquisite fresh Caribbean seafood and listening to the rhythmic ocean waves. We purchased the pre-cruise hotel stay and ground transfers directly through Windstar Cruises, and their team made the entire arrival process remarkably seamless.
Balcony vistas overlooking the Atlantic coastline at Oyster Bay Beach Resort.
The calm oceanside infinity pool at Oyster Bay—the perfect pre-cruise decompression.
Effortless Embarkation & The Intimate All-Suite Experience
The next morning, our private shuttle delivered us to the pier in Philipsburg. Embarkation was calm, orderly, and rapid. Bags were tagged, rapid protocols were administered in comfortable cohorts of ten, and within minutes of receiving negative results, we were checked in and welcomed aboard. Notably, our sailing marked the joyous milestone when onboard mask mandates were officially lifted—allowing guests and crew to connect with genuine smiles and warmth.
Our accommodations were a Balcony Suite, and it proved wonderfully comfortable throughout the week. While it took a quick moment to master the French balcony door latch, we deeply appreciated the thoughtful residential touches: an expansive walk-in closet, a generous marble bathroom with double vanities, and an inviting sitting area where we happily hosted newly made friends for pre-dinner cocktails.
Because of the yacht’s boutique dimensions, getting from our suite to anywhere on the ship—from the Veranda breakfast terrace to the Spa or the outdoor pool deck—took no more than two or three minutes. Even on sea days when the ship sailed close to capacity, loungers on the open-air pool deck were readily available. There are never chair hogs, long queues, or crowded public spaces aboard Windstar.
Tranquil Open Decks: Sun loungers, whirlpools, and panoramic sea views on Star Legend’s pool deck make watching Caribbean horizons an unhurried delight.
Culinary Excellence: Candles, Cuadro 44 & The Onboard BBQ
Windstar Cruises is the Official Cruise Line of the James Beard Foundation, and the culinary program aboard Star Legend reflects this high gastronomic commitment. Evenings rotate between distinctive venues:
- Candles: The ship’s al fresco steakhouse and seafood grill set on the aft deck. (Advisor Insider Tip: Do not miss the Bang Bang Cauliflower appetizer—it is crispy, spicy, and utterly addictive!)
- Cuadro 44 by Anthony Sasso: An intimate Spanish tapas venue conceptualized by the Michelin-starred chef, highlighting Ibérico jamón, grilled octopus, paella croquetas, and churros with spiced chocolate.
- Amphora: The main dining room offering nightly rotating multi-course menus paired with regional vintages in a convivial, elegant setting where conversations with fellow travelers flow naturally.
The pinnacle evening of the cruise is the world-famous Windstar Onboard BBQ Night. The crew transforms the entire pool deck into a grand open-air banquet beneath the stars. Enormous carved suckling pigs, paella pans, grilled seafood, carved roasts, tropical fruits, and decadent desserts are accompanied by live music and dancing on deck as warm trade winds blow across the Caribbean Sea.
The culinary centerpiece: golden roast suckling pig prepared by the executive chefs.
An extravagant pool deck buffet spread of artisanal salads, seafood, and roasts.
Lively open-air dinner and convivial camaraderie among fellow yacht passengers.
Island Adventures: From St. Kitts Rum to Soggy Dollar Painkillers
On our very first afternoon, Casey from Windstar’s Destination Services desk sat down with us one-on-one to review our excursion options. His deep firsthand knowledge of every port helped us curate a flawless week tailored exactly to our preferences for wildlife, history, and beach relaxation:
Colonial architecture and sugarcane heritage during our private rum tasting in St. Kitts.
St. Kitts & St. Barths
In St. Kitts, we immersed ourselves in island history, touring lush colonial sugar plantations, historic botanical gardens, and savoring local handcrafted rums.
The following day in glamorous St. Barths, we indulged in pure French-Caribbean barefoot elegance, luxuriating along the pristine white sands of Grand Cul-de-Sac at the five-star Le Barthélemy Resort & Spa.
Snorkeling with gentle southern stingrays in the crystal shallows of Antigua.
Antigua & Tortola Safari
In Antigua, we had the exhilarating opportunity to swim and snorkel with gentle southern stingrays in warm, waist-deep turquoise waters.
In Tortola, our charismatic safari driver and guide, Colin, took us on an unforgettable scenic island journey in an open-air safari truck. We wound high along Tortola’s mountain ridges overlooking Sir Francis Drake Channel before descending to secluded powder-soft beaches.
Island Warmth: Our open-air safari truck tour through Tortola with local guide Colin, exploring panoramic mountain viewpoints and secluded bays.
The British Virgin Islands: Soggy Dollar Bar & The Baths
The crown jewel of sailing on a small yacht is entering the legendary British Virgin Islands. Mega-ships can only look on from afar, but Star Legend dropped anchor right in White Bay at Jost Van Dyke. We sailed catamaran tenders to shore, snorkeled colorful coral reefs, and swam right up to the famous Soggy Dollar Bar to enjoy their original handcrafted Painkiller cocktail with rum, pineapple, orange juice, cream of coconut, and freshly grated nutmeg.
On Virgin Gorda, we ventured into The Baths—a natural geological wonder of massive granite boulders rising from the shoreline, forming enchanted tidal grottos, hidden pools, and sun-dappled sea caves.
White Bay on Jost Van Dyke—home of the world-famous Soggy Dollar Bar.
The colossal granite boulders and secret tidal caverns of The Baths, Virgin Gorda.
The Grand Finale: Private Beach Barbecue on Prickly Pear Island
On the final day of the cruise, Windstar orchestrated an unforgettable private island experience for its guests on Prickly Pear Island in the North Sound of Virgin Gorda. The ship had the entire idyllic island reserved exclusively for us.
The crew shuttled ashore a lavish barbecue lunch, beach loungers, shaded umbrellas, stand-up paddleboards, and kayaks. We enjoyed freshly grilled meats, iced tropical cocktails, and the warm, translucent Caribbean waters with nothing but powdery sand between our toes. It was the quintessential Caribbean dream, and the most spectacular way to conclude an extraordinary voyage.
Island Paradise: Windstar’s exclusive private beach barbecue celebration on Prickly Pear Island, Virgin Gorda.
Why Book Your Windstar Cruise with Vincent Vacations
Small-ship yacht cruising offers an intimacy, flexibility, and service standard that simply cannot be replicated on mega-liners. However, maximizing the value and selecting the right suite, sailing season, and destination excursions requires firsthand knowledge.
As an elite member of the Signature Travel Network, Vincent Vacations delivers exclusive privileges when you book your Windstar yacht journey with our certified specialists:
- Exclusive Shipboard Credits: Complimentary on-board spending money usable for spa therapies, top-shelf vintages, or destination excursions.
- Preferred Suite Selection: Insider guidance on suite positioning across Star Plus Class yachts (Star Legend, Star Breeze, Star Pride) and masted sailing yachts (Wind Surf, Wind Star, Wind Spirit).
- Seamless End-to-End Logistical Care: Coordinated business class flights, pre- and post-cruise luxury hotel stays, private ground transfers, and curated shore excursions.
- Dedicated Advisor Advocacy: Direct phone and email access to advisors who have sailed the ships, sampled the menus, and explored the ports firsthand.
Ready to Sail the Caribbean Aboard Windstar’s Star Legend?
Let Karen Lee Elder and the luxury cruise team at Vincent Vacations tailor your yacht-style Caribbean voyage with exclusive Signature perks and personalized travel concierge care.
Frequently Asked Questions About Windstar Cruises Caribbean
With a maximum of just 312 guests and 204 crew members, Star Legend offers a relaxed, uncrowded yacht atmosphere. The small vessel size allows it to anchor directly in secluded harbours like Jost Van Dyke, St. Barths, and Virgin Gorda, where mega-ships cannot enter. There are no crowds, no lines for dining, and personalized service where crew members know your name and preferences.
The Star Plus Initiative cut the yacht in half to insert an 84-foot midsection. The renovation added 50 new comfortable suites, two brand-new specialty restaurants (Cuadro 44 by Anthony Sasso and Star Grill by Steven Raichlen), a completely redesigned luxury spa and fitness center, an elevated pool and whirlpool deck, and brand-new fuel-efficient, cleaner engines.
Yes, all specialty restaurants—including Candles steakhouse, Cuadro 44 Spanish tapas, Amphora main dining, and the iconic outdoor Deck BBQ—are fully included in your cruise fare with zero surcharge. The onboard ambiance is “casual elegance”; there are no formal nights, tuxedos, or evening gowns required, allowing for relaxed, sophisticated island style.
Star Legend features a fold-out Watersports Marina at the stern of the yacht that opens directly onto the sea when anchored in calm Caribbean bays. Guests can step right off the back of the ship to enjoy complimentary snorkeling equipment, stand-up paddleboarding, kayaking, water skiing, and a protected ocean pool.
Our advisors have personal firsthand sailing experience aboard Windstar yachts. Through our Signature Travel Network affiliation, we unlock exclusive onboard credits, special pricing promotions, customized pre- and post-cruise hotel arrangements, and seamless travel logistics at zero added cost compared to booking directly.
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