148–342 Guests · Iconic Sailing Yachts · Small Ship Luxury

Windstar Cruises

Discover the romance of sailing on intimate ships that take you closer to every destination — from secluded coves to the heart of charming villages most cruise ships can never reach.

Amazon Pink Dolphin

Small Ship, Big Adventure

Have you ever imagined sailing on a luxury yacht to far-off destinations and exotic locales? With Windstar Cruises, that dream becomes reality. Their 148- to 342-guest small ships and personalised approach bring you closer to each destination and every port, so you can see the world from new perspectives. Share intimate moments away from the crowds, and immerse yourself in local, exotic cultures — all on a small ship where surprise and delight are constant companions. Windstar is so exclusive that they currently have just six yachts in their fleet, of which half are classic wind-class yachts featuring majestic masts and sails.

At a Glance

Cruise Line: Windstar Cruises – Small Ship, Yacht-Style Cruising

Fleet: 6 intimate ships — 3 iconic sailing yachts and 3 all-suite Star Plus Class motor yachts

Capacity: 148–342 guests per ship

Destinations: Caribbean, Mediterranean, Greek Islands, Northern Europe, Alaska, Tahiti, Central America, and more

Atmosphere: Yacht casual — no formal nights, sophisticated yet refreshingly relaxed

Signature Feature: Retractable Watersports Platform, iconic Sail Away ceremony, and James Beard Foundation culinary partnership

  • Ship accommodations with ocean views
  • A variety of gourmet dining options across multiple venues
  • Unlimited beverages — wine, beer, spirits, and specialty coffees
  • Gratuities included
  • Complimentary Wi-Fi
  • Onboard entertainment and enrichment programs
  • Use of all onboard facilities including the Watersports Platform
  • Complimentary kayaking, paddleboarding, water skiing, and windsurfing

Shore excursions are available as an add-on or through excursion packages.

  • Intimate ships access small ports and hidden harbours larger ships simply cannot reach
  • Iconic sailing yachts with majestic sails — a truly unique cruising experience
  • James Beard Foundation culinary partnership for exceptional onboard dining
  • Complimentary Watersports Platform with kayaks, paddleboards, and more
  • Yacht casual atmosphere — no formal nights, no pretension
  • Guest lecturers sharing local knowledge to deepen your cultural immersion

AmphorA: Elegant main dining with open seating and destination-inspired menus

Candles: Intimate steakhouse and grill (Star Plus Class)

Cuadro 44 by Anthony Sasso: Celebrated Spanish cuisine on Star Plus Class ships

Star Grill: Casual poolside dining and deck barbecues

Stella Bistro: Casual café serving light bites and craft beverages

All dining is open seating — dine when and with whom you choose. Menus feature fresh, seasonal ingredients sourced from each port along the way, showcasing the distinctive flavours of local cuisine.

Sailing Yachts:

  • Wind Surf: 342 guests — the world’s largest sailing cruise ship
  • Wind Star: 148 guests — classic four-masted sailing yacht
  • Wind Spirit: 148 guests — classic four-masted sailing yacht

Star Plus Class Motor Yachts:

  • Star Pride: 312 guests — all-suite luxury
  • Star Legend: 312 guests — all-suite luxury
  • Star Breeze: 312 guests — all-suite luxury

Both ship types offer intimate yacht-style experiences with the Watersports Platform, open-seating dining, and personalised service.

At a Glance

All-Inclusive Yacht Experience

6 Intimate Ships

148–342 guests per voyage

  • Unlimited beverages included
  • Gratuities included
  • Complimentary Wi-Fi
  • James Beard Foundation dining
  • Watersports Platform access
  • Open-seating gourmet dining
  • No formal nights — yacht casual

Shore excursions available as add-on

Explore

Discover Windstar

A sleek and modern retail space within a cruise ship, featuring merchandise displays with blue and white branding, branded clothing, and souvenirs in glass cabinets with mood lighting.

The Signature Sail Away

Windstar’s sailing yachts feature a magical Signature Sail Away ceremony as the ship departs select ports. The sails are unfurled to the stirring sounds of Vangelis’s “1492: Conquest of Paradise,” creating an unforgettable moment that captures the pure romance of sailing. Watching the massive sails deploy while enjoying cocktails on deck is a quintessential Windstar experience — one that truly sets this cruise line apart from anything else at sea. It’s the kind of moment our advisors love hearing clients describe after they return home.

Destination-Inspired Cuisine

Windstar Cruises has raised the bar for onboard dining through their partnership with the James Beard Foundation. Every night’s menu is designed to showcase the distinctive flavours of the local cuisine, featuring fresh, seasonal ingredients sourced from each port along the way. On the Star Plus Class ships, Cuadro 44 by Anthony Sasso brings celebrated Spanish cuisine to sea, while Candles offers an intimate steakhouse experience. Back on the sailing yachts, deck barbecues under the stars and open-seating dining create the feeling of a private dinner party on the water. It’s dining the way it should be — unhurried, exquisite, and always with a view.

An elegant cafe interior on a cruise ship featuring a curved bar, warm lighting, and yellow and brown color scheme. The 'Caffe Italia' sign highlights the Italian-themed dining area.
A picturesque historic street in Skagway, Alaska, featuring preserved gold rush-era buildings with snow-capped mountain peaks in the background. A small stream runs through the foreground, lined with purple lupine flowers.

The Watersports Platform

When conditions permit, Windstar’s ships deploy a retractable Watersports Platform from the stern, inviting guests to enjoy complimentary kayaking, paddleboarding, water skiing, windsurfing, and swimming directly from the ship. This unique amenity allows active water experiences in calm harbours and secluded bays — an experience larger ships simply cannot offer. Picture yourself diving into crystal-clear waters right from the back of a sailing yacht anchored in a hidden cove. That’s the kind of adventure that makes Windstar truly special, and it’s one of the reasons our expert advisors love recommending this cruise line.

Experience

The Windstar Difference

Intimate Small Ships

With just 148 to 342 guests, Windstar’s yachts access small ports and hidden harbours that larger ships cannot visit. Dock in the heart of charming villages, explore secluded coves, and experience destinations the way they were meant to be discovered.

True Sailing Experience

Windstar’s iconic sailing yachts are among the last true sailing cruise ships in the world. Feel the romance of wind-powered travel, experience the legendary Sail Away ceremony, and enjoy a connection to the sea that no motor ship can replicate.

Immersive Destinations

From the Greek Islands and the Caribbean to Alaska and Tahiti, Windstar sails to destinations ideally suited for small ship cruising. Guest lecturers share local knowledge before you ever step foot in port, deepening your appreciation of each culture.

Beyond the Ship — Windstar Cruise Tours

Windstar Cruise Tours fuse the finest of land and sea to help you cross experiences off your bucket list. To complement your ports of call, venture inland to discover more of the local culture and natural beauty. Windstar handles all ground arrangements including hotel accommodations and attraction tickets, giving you a seamless pre- or post-cruise extension that awakens your sense of adventure and awe. From exploring ancient ruins to tasting wines in the countryside, these tours transform your cruise into a complete journey of discovery. Our advisors can help you choose the perfect Cruise Tour to extend your Windstar voyage.

A picturesque Alaskan coastal scene featuring a traditional Orthodox church, totem pole, marina, and the Alaska Raptor Center wooden building in the foreground. Misty mountains and forested landscape provide a dramatic backdrop.

Your Windstar Cruise

What’s Included in Your Cruise Package?

Your Windstar adventure comes with many included amenities from the cruise line. When you book through Cruise Help, you also benefit from our exclusive group rates, weekly price monitoring, and personalised expert guidance — with no fees, ever.

Included in Every Windstar Cruise

  • Ship accommodations
  • A variety of gourmet dining options
  • Onboard entertainment and enrichment
  • Use of onboard facilities and Watersports Platform
  • Unlimited beverages
  • Gratuities
  • Wi-Fi

Your Cruise Help Booking Also Includes

  • Expert guidance choosing your itinerary, ship, and stateroom
  • Exclusive group rates — savings up to 50% off
  • Weekly price monitoring with automatic adjustments
  • Recommendations on shore excursions
  • Advice on cruise and travel policies
  • 365-day support from 23+ expert advisors
  • No booking fees — ever

Popular Upgrades Available

  • Pre- and post-cruise hotel arrangements
  • Airport transfers and car service
  • Flight bookings
  • Travel insurance guidance
  • Windstar Cruise Tours extensions
Images

Gallery

Questions

Frequently Asked Questions

Windstar operates small ships — both iconic sailing yachts and all-suite Star Plus Class vessels — carrying just 148 to 342 guests. Their intimate size allows access to small ports and hidden harbours that larger ships cannot visit. The experience combines yacht-style cruising with personal service, gourmet dining, and a casual elegance that appeals to experienced travellers seeking authentic destinations. If you enjoy boutique hotels over large resorts and appreciate fine dining, Windstar delivers an experience unlike any other at sea.

Windstar’s All-Inclusive package includes all onboard meals, unlimited beverages (wine, beer, spirits, specialty coffees), gratuities, Wi-Fi, and use of the Watersports Platform. Shore excursions are additional unless you’ve purchased a package. The All-Inclusive approach means you won’t need to sign for drinks or worry about added costs throughout your voyage. When you book through Cruise Help, you also benefit from our exclusive group rates, weekly price monitoring, and no booking fees — ever.

Windstar operates two distinct ship types. The sailing yachts (Wind Surf, Wind Star, and Wind Spirit) feature majestic sails and carry 148–342 guests. The Star Plus Class vessels (Star Pride, Star Legend, and Star Breeze) are all-suite motor yachts carrying 312 guests with every stateroom featuring ocean views. Both offer intimate yacht-style experiences with exceptional service, the Watersports Platform, and open-seating gourmet dining.

When conditions permit, Windstar’s ships deploy a retractable Watersports Platform from the stern. Guests enjoy complimentary kayaking, paddleboarding, water skiing, windsurfing, and swimming directly from the ship. This unique amenity allows active water experiences in calm harbours and secluded bays — an experience larger ships simply cannot offer. It’s one of the features our advisors hear clients rave about most.

Windstar partners with the James Beard Foundation to create exceptional culinary experiences. The Star Plus Class ships feature four dining venues including Cuadro 44 by Anthony Sasso, celebrating Spanish cuisine, and Candles, an intimate steakhouse. All ships offer open seating, allowing you to dine when and with whom you choose. Special experiences include deck barbecues and destination-inspired menus featuring locally sourced ingredients from each port of call.

Windstar sails worldwide to destinations ideally suited for small ship cruising. Regions include the Caribbean, Mediterranean, Greek Islands, Northern Europe, Alaska, Tahiti and the South Pacific, Central America, and more. Itineraries emphasise small ports, overnight stays, and destinations where their intimate ships can dock in town centres that larger vessels cannot access.

Windstar’s sailing yachts feature a magical Signature Sail Away ceremony as the ship departs select ports. The sails are unfurled to the stirring sounds of Vangelis’s “1492: Conquest of Paradise,” creating an unforgettable moment. Watching the massive sails deploy while enjoying cocktails on deck is a quintessential Windstar experience that captures the romance of sailing.

Windstar maintains a relaxed “yacht casual” atmosphere throughout the voyage. During the day, resort casual attire including shorts and polo shirts is appropriate. Evenings are elegant casual — nice jeans, slacks, sundresses, or dress pants. There are no formal nights, and ties and jackets are never required. The atmosphere is sophisticated yet refreshingly unpretentious.

Windstar’s intimate ships carry between 148 and 342 guests — a fraction of typical cruise ship capacity. Wind Star and Wind Spirit accommodate 148 guests, Wind Surf carries 342, and the Star Plus Class vessels host 312 guests each. This small capacity ensures personalised service, uncrowded spaces, and authentic connection with destinations and fellow travellers.

Absolutely. Windstar is excellent for first-time cruisers who are hesitant about large ship experiences. The intimate atmosphere, small ports of call, and yacht-style service appeal to travellers who prefer authentic exploration over mega-ship entertainment. If you enjoy boutique hotels over large resorts, appreciate fine dining, and want to visit places larger ships cannot go, Windstar is an ideal introduction to cruising. Our expert advisors can help you choose the perfect ship and itinerary for your first voyage.

When you book Windstar through Cruise Help, you get access to exclusive group rates with savings up to 50% off published fares — with just one room. Our team of 23+ expert advisors, many with real cruise ship experience, provides personalised cabin selection advice, itinerary planning, and destination guidance. We perform weekly price monitoring on every booking and automatically adjust your rate if the price drops. Plus, we never charge booking, consultation, or change fees — ever. With 365-day support, you’re never on your own from the moment you enquire to the moment you disembark.

Get Started

Ready for a Yacht-Style Adventure?

You need a small ship for a big adventure, and with Windstar Cruises, that’s exactly what you’ll get. When you’re ready to explore the world from a truly unique perspective, speak with our expert advisors at Cruise Help. With exclusive group rates, weekly price monitoring, and no fees — ever — your Windstar voyage begins with us!

Not sure which specialty cruise is right for you?

Take our short quiz to discover the perfect specialty cruise for your travel style and bucket list.

We Know the Perfect Destinations for You

Alaska

Antarctica

Caribbean

Europe

Greece

Greenland

Iceland

Italy

Mediterranean

Start Your Extraordinary Family Adventure Now!

If you’re looking for a cruise agency that hoists the extra sail for your family, you’re looking for Extraordinary Adventures. We’re here to answer any questions and help you craft your next extraordinary family cruise adventure. Contact us now!