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8-Day Windstar Southern Caribbean Cruise

Windward Ways & Tobago Cays: Exotic Southern Caribbean Cruise

Dive, snorkel and swim with fish and sea turtles in Tobago’s newly established Speyside Marine Protected Area and Tobago Cays Marine Park. Swim in a picture-perfect waterfall pool surrounded by the oldest protected rainforest in the Western Hemisphere, the Main Ridge Forest Reserve. Take in the volcanic beauty of the Pitons on St. Lucia, where rainforest meets some of the healthiest coral reefs in the Caribbean. Those who are looking for the classic Caribbean will find it in Mayreau — fewer than 300 inhabitants, and just 1.5 square miles, making it a port exclusive to yachts. And those who love colonial harbors will enjoy British Bridgetown as well as the triple Dutch treat of Kralendijk, Willemstad and Oranjestad.
Cruise on the all-suite yacht Star Legend with just 312 guests. This intimate all-suite yacht features spacious ocean-view accommodations. On board, you’ll find a fully equipped fitness center, a spa with complimentary sauna, two full-service bars, on-deck hot tubs, a water-access marina, and much more.

“I sailed on Windstar’s Star Legend to Iceland and absolutely loved it. The ship was small and intimate, which made the experience feel personal and allowed us to visit smaller ports that larger ships couldn’t reach. The food was outstanding, and La Veranda on the top deck quickly became my favorite restaurant. It was casual during the day and transformed into fine dining at night. I dined there three times, and my favorite dish was the Seafood Skewers.

The staff was incredibly attentive and made us feel well cared for throughout the trip. I also loved the gelato, and we spent many evenings in the piano bar enjoying the great music. To top it all off, the crew put on a farewell show that was such a fun and memorable way to end the cruise.”

Lynne Cox, Cruise & Travel Experts

“The new Windstar Star Seeker is absolutely amazing in every way! We did the British Virgin Islands along with St. Barths and St. Maarten. There are only 224 passengers on board and plenty of space for all! They have a new specialty restaurant on the ship called Basil + Bamoo, absolutely a culinary delight and of course “Candles” the outdoor dining venue steakhouse is as good as any high-end steakhouse you’ll find anywhere, and the food in the main dining room is always outstanding.  They also have a new lounge on the ship (now two instead of just one) which is a super nice touch for a change of scenery.  I love Windstar and I highly recommend trying out this fabulous new ship!”

Tom Baumann, Cruise & Travel Experts

More Reasons to Say Yes – Receive complimentary All-inclusive Package per guest + Reduced deposit 0f $300 per stateroom/suite on select voyages through December 31, 2027*

All-inclusive Package includes

~Wi-Fi
~Unlimited beer, wine and cocktails
~All gratuities

 Plus receive our Exclusive Extras of Host Vickie and Brad Meeuwsen, cocktail party and $400 Onboard Credit per suite.

Ship: Star Legend | Cruise Line: Windstar| Sail Date: February 22, 2027 | From/To: Oranjestad, Aruba to Bridgetown, Barbados | Length: 8-Nights

Star Porthole Suite From

$5,220

Per person including all taxes, fees and port expenses

Star Ocean View Suite, Cat. 1 From

$7,260

Per person including all taxes, fees and port expenses

Star Balcony Suite From

$9,060

Per person including all taxes, fees and port expenses

Balcony Suite 1 From

$9,220

Per person including all taxes, fees and port expenses

All-Inclusive Package Includes:

~Wi-Fi

~Unlimited beer, wine and cocktails

~All gratuities

Popular Highlights:

  • Four magical colonial towns (including two that are UNESCO-listed) contrast with out-of-the-way ports and bays.
  • Snorkel the impressive coral reefs of Tobago Cays at the confluence of the Atlantic Ocean and Caribbean Sea.
  • The dramatic twin volcanic spires of the Pitons rise majestically from St. Lucia’s lush coastline, creating one of the Caribbean’s most breathtaking sailing backdrops.
  • Visit Mayreau, the smallest island of the Grenadines, and enjoy the exclusive Signature Beach Party.
  • Willemstad is a UNESCO site known for its brightly colored architecture

Jump in For Fun

A cruise to Tahiti, the Mediterranean or the Caribbean isn’t just about the land. It’s about the sea. That warm, turquoise water is more than willing to answer your question about what to do today, and the phenomenal Watersports Platform on the stern of your Windstar yacht is more than willing to provide the means — no beach required. It’s just one more way our yachts get you closer to your destination.

Complimentary Watersports Equipment and Activities Include*:

• Snorkeling gear (a personal custom-fit set for your use throughout your Tahiti cruise and in select Caribbean and Central • America destinations)
• Stand-up paddleboards
• Kayaks
• Foam flotation magic carpet
• Water trampoline.

World Class Dining Experience

We’ve upped the onboard dining game with our culinary program, featuring an array of fresh, seasonal ingredients sourced from each port along the journey. Each nightly menu is crafted to highlight the spectacular flavors of the regional cuisine.

Local Immersion

Immerse Yourself in Local Flavor with Culinary Shore Excursions

Tantalize your taste buds with a variety of flavorful shore excursions. Choose from wine, brewery, and distillery tours as well as hands-on cooking classes with seasoned chefs practiced in the art of perfecting traditional and modern recipes. Ship to shore, we’ll intoxicate your senses.

Introducing Windstar’s Market Tours

Accompany your chef to a local market (where available) to select the local ingredients, seasonal produce, herbs and spices that will be included in your special evening meal. The essence of the culture you explored on shore miraculously appears as a delicious masterpiece on your plate.

Date Day Port Arrive Depart
Feb. 22, 2027 Mon. Oranjestad, Aruba 6:00pm
Feb. 23, 2027 Tues. Willemstad, Curacao 8:00am 10:00pm
Feb. 24, 2027 Wed. Kralendijk, Bonaire 7:00am 9:00pm
Feb. 25, 2027 Thurs. At Sea 8:00am 6:00pm
Feb. 26, 2027 Fri. St. Georges 8:00am 8:00pm
Feb. 27, 2027 Sat. Rodney Bay 8:00am 3:00pm
Feb. 27, 2027 Sat. The Pitons 5:30pm 6:30pm
Feb. 28, 2027 Sun. Mayreau 8:00am 6:00pm
March 1, 2027 Mon. Bequia 7:00am 5:00pm
March 2, 2027 Tues. Bridgetown 6:00am

Star Legend: All Suite Ship

Serving just 312 guests, Star Legend is the perfect size — small enough to offer the unique experiences that set Windstar apart (think crossing the Corinth Canal), yet large enough for you to make plenty of new connections on board — all without ever feeling crowded.

This intimate all-suite yacht features spacious ocean-view accommodations. On board, you’ll find a fully equipped fitness center, a spa with complimentary sauna, two full-service bars, on-deck hot tubs, a water-access marina, and much more.

And did we mention all dining is included? From gourmet bites at our Yacht Club Café to specialty restaurants like Basil + Bamboo, our award-winning cuisine is always complimentary so you can indulge freely.

All the Comforts of Home, All Around the World

You’re jet-setting all over the world, but the best part is coming back to the comfort of a well-appointed private space. A place to unwind and rest, to reflect on the day’s adventures. From the plush leather headboard to the fine Egyptian linens and marble bathroom. Enjoy the thoughtfully designed spaces, with more room for storage than you’ve ever imagined finding on a yacht, and the luxurious touches just for your pleasure, like L’Occitane bath products.

Everything is made to order for your enjoyment. Soft lighting. Beautiful artwork. Soothing, seascape color schemes. Every stateroom, every suite has been redesigned to Windstar’s exacting standards and matchless style. Go ahead and slip into your cozy robe and comfy slippers and surrender to the mesmerizing ocean view. There’s so much more awaiting you tomorrow.

All Accommodations Feature

• Queen-size bed with luxurious linens
• Waffle-weave robe and slippers
• L’Occitane bath amenities
• Granite vanity with magnifying mirror and chair
• Fully stocked minibar and fridge
• Walk-in closet
• TV with complimentary on-demand entertainment
• Safe
• Wi-Fi (available for purchase)
• 110/220-volt outlets
• In-room filtered water

Yacht Facts

    CAPACITY: 312 guests
OWNER’S SUITES: 4, with private verandas
CLASSIC SUITES: 2, with private verandas
DELUXE SUITES: 3, 2 with French-style balconies
STAR BALCONY SUITES: 22, with French-style balconies
BALCONY SUITES: 36, with French-style balconies
STAR OCEAN VIEW SUITES: 21, with picture windows
OCEAN VIEW SUITES: 58, with picture windows
STAR PORTHOLE SUITES: 10
DECKS: 6 guest decks
CREW: 200 international staff
SHIP’S REGISTRY: Bahamas
LENGTH: 522 ft (159 meters)
DRAFT: 18 ft (5.4 meters)
BEAM: 63 ft (19 meters)
TONNAGE: 12,995 gross registered tons (grt)
PROPULSION: Twin propeller, driven by two Wartsila diesel engines
SPEED: Cruising speed 16 knots

*Prices are in USD, per person based on double occupancy, availability and subject to change without notice. All taxes, fees and port expenses are included in the pricing. All promotions are capacity controlled by Winstar Cruises and can be eliminated at any time without notice. All pricing was confirmed on September 8, 2026; however, not guaranteed to be available. Certain sailings are excluded from this offer including Grand Prix voyages, Eclipse voyages, Mystery Cruises or other specialty cruises; these exclusions include: Explorer: 12/28/26; Legend 11/4/26 & 6/1/27; Prive: 4/15/27; Seeker: 9/14/26; Spirit: 6/2/27; Star: 2/1/27 and Surf: 7/27/27. Other restrictions may apply. Ships’ registry: Bahamas