Why Luxury Travelers Choose Windstar for the Caribbean
The Caribbean is filled with cruise choices. But if your idea of luxury is smaller ships, fewer crowds, exceptional destinations, and a personal connection to the sea, Windstar Caribbean cruises deserve a closer look.
Rather than building the experience around enormous onboard attractions found on mega-ships, Windstar focuses on intimate yacht-style cruising, destination immersion, relaxed service, and the romance of sailing under wind power or cruising on an all-suite motor yacht.
With a draft small enough to enter secluded bays like Jost Van Dyke and Tobago Cays, Windstar drops anchor where 5,000-guest liners cannot follow, dropping the stern watersports marina directly into turquoise waters.
Are Windstar Caribbean Cruises Worth It?
Yes. Windstar Caribbean cruises offer an exceptional value for travelers who prioritize small-ship intimacy, yacht-style cruising, destination access, and a relaxed luxury atmosphere. Carrying only 148 to 342 guests, Windstar avoids the crowds, long lines, and industrial container ports of mega-ships while providing James Beard Foundation culinary dining and open bridge access.
Windstar Caribbean Yacht Sailing & Island Hopping Showcase
Watch Windstar 4-masted sailing yachts and Star Class motor vessels navigate the turquoise bays of St. Lucia, Jost Van Dyke, and the Grenadines.
Who Should Choose Windstar Caribbean Cruises?
Couples & Romantic Travelers
Couples seeking intimate sail-aways, candlelit alfresco dining under white sails, and quiet anchorages off St. Barths and Jost Van Dyke.
You Enjoy:
- •Intimate small-ship atmosphere
- •Candlelight dining under canvas
- •Uncrowded open teak decks
Recommended For You:
Active Ocean & Watersports Enthusiasts
Active travelers eager to dive off the retractable stern watersports platform into marine reserves like Tobago Cays.
You Enjoy:
- •Direct stern marina swimming access
- •Complimentary kayaks & paddleboards
- •Snorkeling green sea turtle reefs
Recommended For You:
Culinary & Wine Connoisseurs
Foodies who appreciate James Beard Foundation culinary partnerships, fresh Caribbean spiny lobster, and Sommelier-curated French wine pairings.
You Enjoy:
- •James Beard Foundation regional dining
- •Chef-led local spice market tours
- •Zero specialty dining cover fees
Recommended For You:
Small-Ship Yachting Purists
Experienced travelers who prioritize small-ship access (148-342 guests max), open bridge policies, and relaxed luxury.
You Enjoy:
- •Open bridge policy with Captain
- •No formal dress code requirements
- •Unpack once across multiple islands
Recommended For You:
What Windstar Delivers in the Caribbean
FOUR PILLARS OF THE WINDSTAR CARIBBEAN EXPERIENCE
Stern Watersports Marina
Retractable stern platform deploys directly into protected marine parks - kayaks, paddleboards, and water skis included at no charge.
Secluded Beach BBQs
Windstar's legendary private beach parties on uninhabited Caribbean islands - steel drum bands, rum punch, and moonlit dancing.
Marine Reserve Snorkeling
Swim with green sea turtles inside Tobago Cays Marine Park and dive pristine coral gardens off Bonaire's Blue Bay.
Rainforest Immersion
Ready to Plan Your Windstar Caribbean Cruise?
Connect with Angela Hughes and the luxury travel advisors at Trips & Ships Luxury Travel to reserve your preferred suite and Caribbean itinerary.
Plan My Windstar Caribbean CruiseWindstar Caribbean Cruises at a Glance
Best For (Windstar Caribbean Yacht Experience)
- Cruising intimate Caribbean harbors (Jost Van Dyke, St. Barths, Tobago Cays, Virgin Gorda, Bequia, Dominica)
- Retractable stern watersports marina with complimentary kayaks, paddleboards, and water-skiing
- Authentic 4-masted sailing under wind power or spacious all-suite motor yacht accommodations
- Open-seating James Beard Foundation regional dining featuring local Caribbean catches and spices
- Casual luxury atmosphere with 148 to 342 guests max, open bridge policy, and zero formal dress code
May Not Be Best For (Consider Megaships)
- Travelers seeking massive 5,000-guest megaship casinos, waterslides, or Broadway production shows
- Families requiring extensive dedicated children's clubs, nurseries, and teenager video arcades
- Travelers who prefer large mega-resort swimming pool complexes and non-stop amplified pool deck parties
Windstar is designed for discerning travelers who want the destination, sailing romance, and ocean environment to be the centerpiece of their vacation.
Which Windstar Caribbean Ship Style Is Best for You?
vs Star Class All-Suite Motor Yacht
- Authentic 4-masted motorized sailing experience under 21,000+ sq. ft. of white sails
- Intimate passenger scale carrying only 148 to 342 guests
- Classic teak deck nautical charm and romantic sail-away music ceremonies
- Access to tiny secluded anchorages where sails are hoisted daily
- Spacious all-suite accommodations starting at 277 sq. ft. with walk-in closets
- Marble double-sink vanities, French balconies, and infinity pools
- Expanded World Spa facilities and additional specialty dining venues
- Newer vessel design (Star Breeze, Star Legend, Star Seeker)
Who Is Each Brand Best For?
Best For Wind Class Sailing Yacht
- •Sailing purists, romantic couples, and travelers seeking classic maritime heritage
Best For Star Class All-Suite Motor Yacht
- •Travelers prioritizing suite space, newer ship design, and modern yacht amenities
The Caribbean Island & Watersports Marina Concierge
Select your preferred Caribbean travel style below to curate your ideal ship pairing, secret island anchorages, and watersports platform experiences.
Wind Class 4-Masted Sailing Yacht (Wind Star / Wind Spirit)
The Virgin Islands & BVI Sailing Haven
Experience authentic canvas-and-wind sailing through calm turquoise channels, anchoring steps from legendary beach bars and secret snorkel coves.
SIGNATURE CONCIERGE HIGHLIGHTS
- Overnight anchorage off Jost Van Dyke's White Bay & Soggy Dollar Bar
- Morning tender to the granite boulder grottoes of The Baths on Virgin Gorda
- Complimentary stern watersports swimming in sheltered Great Harbour
- Sunset champagne sailaway under 21,000 sq. ft. of towering white sails
"Romantics, sailing purists, and beach-bar enthusiasts seeking uncrowded island charm."
The Windstar Stern Watersports Marina Experience
Explore the retractable stern watersports platform offering complimentary paddleboarding, kayaking, water-skiing, and snorkeling directly off the ship.
Iconic Caribbean Ports & Islands
Explore secluded Virgin Island harbors, French chic harbors, and Grenadine coral coves
St. Barths (Gustavia)
Anchor in Gustavia's red-roofed harbor alongside private superyachts. Tender ashore for designer shopping, Shell Beach, and chic beach clubs.
Jost Van Dyke & Virgin Gorda
Overnight in White Bay off Soggy Dollar Bar and explore the iconic giant granite boulder grottoes at The Baths on Virgin Gorda.
St. Lucia (Rodney Bay & Pitons)
Sail past the dramatic 2,500-foot volcanic Pitons spires and anchor in Rodney Bay for catamaran sailing and rainforest ziplining.
Dominica (Roseau & Portsmouth)
Trek through lush tropical rainforests, soak in geothermal sulfur hot springs, and swim through the dramatic Titou Gorge.
Bonaire & Curaçao
Experience world-class coral reef scuba diving in Bonaire and explore Willemstad's colorful Dutch colonial UNESCO architecture.
Tobago Cays (Grenadines)
Drop anchor in an uninhabited turquoise lagoon inside the Marine Park horseshoe reef to swim alongside green sea turtles.
Caribbean Yachting & Watersports Gallery
Angela Hughes Authority & Credentials
CEO, Trips & Ships Luxury Travel | Founder, Luxury Travel University
Angela Hughes
Angela Hughes has explored over 121 countries and spent more than four decades designing luxury travel experiences. She is widely recognized across the travel industry as a leading river cruise authority and active travel advocate.
"Cruising the Caribbean on a Windstar yacht is the difference between fighting crowds in commercial mega-ports and dropping anchor in a private turquoise cove as the sails rise above you. It is how the Caribbean was meant to be experienced."
— Angela Hughes, On Active River CruisingKEY QUALIFICATIONS & ACHIEVEMENTS
- Over 4 Decades Designing Luxury Travel Experiences
- Explored 121+ Countries Across Seven Continents
- Recognized Industry Leader & River Cruise Specialist
- CEO & Founder of Trips & Ships Luxury Travel
- Specialist in Active River Cruising & Multi-Generational Travel
- Personal Relationships with AmaWaterways Executives & Staff
Frequently Asked Questions About Windstar Caribbean Cruises
Yes. Windstar Caribbean cruises offer exceptional value for travelers who prioritize small-ship intimacy, yacht-style cruising, destination access, sailing, and a relaxed luxury atmosphere.
Yes. Windstar is positioned in the luxury small-ship segment, emphasizing personalized service, small ships, destination immersion, gourmet regional dining, and a relaxed yacht atmosphere.
Windstar's Wind Class vessels (Wind Star, Wind Spirit, Wind Surf) are motorized sailing yachts featuring sails, while Star Class vessels (Star Pride, Star Breeze, Star Legend, Star Seeker) are all-suite motor yachts with larger suites and expanded spa facilities.
There is no single best ship. Wind Class sailing yachts are best for sailing enthusiasts and romantic couples, while Star Class motor yachts are best for travelers prioritizing spacious suite accommodations and modern design.
Windstar Caribbean cruises generally range from $2,200 to $6,500+ per person for 7 to 14-night voyages depending on ship class, suite category, season, and promotions.
Standard fares include stateroom/suite accommodations, all gourmet dining, non-alcoholic beverages, watersports marina access, and port market tours. Windstar's All-In package adds unlimited fine wines, spirits, Wi-Fi, and gratuities for $99/day per guest.
January through April are peak winter months offering dry, warm weather and ideal sailing conditions. November and December are great shoulder-season months, while summer months feature lower rates and warmer waters.
Yes. Windstar specializes in smaller Caribbean ports that large ships cannot enter, such as Jost Van Dyke, Virgin Gorda, St. Barths, Tobago Cays, Bequia, Mayreau, and Montserrat.
Yes. Windstar's smaller scale, uncrowded decks, candlelit alfresco dining under canvas, and romantic sail-aways make it a top choice for honeymoons, anniversaries, and romantic getaways.
Yes. Windstar ships feature a retractable stern Watersports Marina offering complimentary paddleboards, kayaks, water-skiing, windsurfing, and snorkeling equipment directly off the back of the ship.
Yes. Arriving at the embarkation port (e.g. San Juan, St. Maarten, or Barbados) 1 to 2 nights before departure protects against flight delays and allows you to adjust to island time.
Pack lightweight resort wear, swimwear, sandals, sun protection, comfortable walking shoes for cobblestone or trail tours, and smart casual attire for evening dining. No tuxedos or formal gowns are required.
We recommend booking 8 to 12 months in advance, especially for popular winter holiday sailings, prime suite categories (like Owner's Suites), and specific sailing yacht itineraries.
Windstar is vastly superior for travelers seeking small ships, zero crowds, authentic destination access, and quiet elegance. Mega-ships are better suited for families needing waterparks and casinos.
Trips & Ships Luxury Travel, led by 40+ year luxury travel veteran Angela Hughes, provides expert suite selection, guidance on ship classes, exclusive promotional value, and personalized pre/post-cruise hotel and private transfer arrangements.
START PLANNING YOUR JOURNEY
Ready to Plan Your Windstar Caribbean Cruise?
Connect with Angela Hughes and the luxury travel advisors at Trips & Ships Luxury Travel to reserve your preferred suite and Caribbean itinerary.
Luxury Travel Services
- Custom Suite Selection
- Pre & Post Hotel Extensions
- Private Water Taxi Transfers
- Exclusive Shore Excursions
- Sommelier Wine Tastings
- VIP Concierge Service
