Wind Surf Cruises & Sailings | CruiseHuddle - CruiseHuddle

Wind Surf Cruises: Sail the Seas in Elegant Style

Experience the romance of sailing aboard Windstar's luxurious 5-masted motor sailing ship, carrying just 376 guests to stunning destinations.

CruiseHuddle Snapshot

70

Upcoming Sailings

$2,658

From

Wind Surf

The Story

The Wind Surf stands apart as one of the most distinctive vessels sailing the world's oceans today. Built in 1990, this elegant 5-masted motor sailing ship combines the romance of traditional sailing with modern luxury amenities. With a gross tonnage of 14,745 and capacity for just 376 passengers, the Wind Surf offers an intimate cruising experience that larger ships simply can't match.

The ship's unique design allows guests to enjoy the thrill of sailing under billowing sails while exploring some of the world's most captivating destinations. The Wind Surf regularly sails the sparkling waters of the Mediterranean and Caribbean, with departures from sought-after ports including Philipsburg in St Maarten, Civitavecchia near Rome, and Piraeus for Athens. The smaller size means access to harbors and ports that mega-ships can't reach, opening up possibilities for more authentic and less crowded experiences ashore.

Windstar's approach aboard the Wind Surf appeals to travelers seeking something different from conventional cruising. The atmosphere is relaxed and unpretentious, with open-seating dining, casual dress codes, and a focus on destination immersion rather than onboard glitz. The ship attracts well-traveled guests who appreciate the blend of adventure and comfort, along with the unique sensation of sailing on a vessel where you can actually feel the wind and watch the sails unfurl. Whether you're drawn to exploring ancient Mediterranean ports or relaxing on Caribbean beaches, the Wind Surf delivers a refreshingly different way to experience ocean cruising.

Ready to discover what makes sailing aboard the Wind Surf so special? Browse the 84 upcoming sailings and connect with fellow cruisers who've experienced this remarkable ship firsthand.

Onboard Highlights

Five Towering Sails

Windstar's signature masts unfurl for a rare, near-silent sailing experience under wind power.

🌊

Watersports Marina

A fold-out platform at the stern launches kayaks, paddleboards, and windsurfers straight into the sea.

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Candles Open-Air Grill

Steaks and seafood sizzle tableside at this deck-top dinner venue under open skies.

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Compass Rose Lounge

The main bar buzzes nightly with live music and casual conversation near the atrium.

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Serenity Spa Retreat

An intimate spa offers massages and treatments suited to the ship's boutique scale.

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Pool & Sun Decks

Two small pools and whirlpools give sunbathers a relaxed, yacht-like deck atmosphere.

Departures

Upcoming Sailings

By the Numbers

Ship Specifications

📅 Year Built

1990

👥 Passengers

376

👨‍✈️ Crew

178

🏢 Decks

6

🛏️ Cabins

171

⚖️ Gross Tonnage

14745 gt

📏 Length

187 m / 614 ft

↔️ Beam

20 m / 66 ft

⚡ Speed

15 kn / 28 km/h / 17 mph

🏳️ Flag

Bahamas

🔧 Builder

Ateliers et chantiers du Havre (Le Havre, France)

🏷️ Ship Class

5-masted motor sailing ship

Questions

Wind Surf is a 5-masted motor sailing ship, meaning it uses both sails and engines. This creates a unique sailing experience on a vessel much smaller than conventional cruise ships, carrying only 376 passengers. The intimate size allows access to smaller ports and creates a more relaxed, yacht-like atmosphere.
Wind Surf primarily operates in the Mediterranean and Caribbean regions. Popular departure ports include Philipsburg in St Maarten, Civitavecchia near Rome, and Piraeus for Athens. The ship's itineraries focus on these warm-weather destinations throughout the year.
Wind Surf was built in 1990, making it over 30 years old. Windstar has invested in regular maintenance and upgrades to keep the ship current. The vessel's classic sailing ship design means its age contributes to its character rather than detracting from the experience.
The atmosphere is casual and relaxed, more like a private yacht than a traditional cruise ship. With just 376 passengers, the experience is intimate and unhurried. Expect open-seating dining, no formal nights, and a focus on destinations rather than elaborate onboard entertainment.
Wind Surf sailings start from around $1,507, though prices vary significantly based on itinerary, cabin type, season, and length of voyage. The smaller ship size and upscale experience typically position these cruises in the premium category compared to mass-market cruise lines.
Beyond the fare

What Windstar actually costs

These rates apply fleetwide across Windstar.

Verified July 2026
Gratuities are included in the fare

Unlike most mainstream lines, Windstar folds crew gratuities into the ticket price — so a fare that looks expensive next to a budget line may not be.

Published rates, not a quote. Cruise pricing changes frequently — confirm with the cruise line before booking.

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