Windstar Cruises

A luxurious small cruise ship with four tall masts and white sails fully deployed, sailing on calm blue ocean waters under clear skies. The vessel combines classic sailing ship aesthetics with modern cruise ship amenities, representing expedition and luxury travel.
Vector graphic: windstar-logo.svg

Two Distinct Ship Classes, One Extraordinary Spirit

Windstar Cruises offers something truly rare in the world of cruise travel – the romance and intimacy of small-ship sailing combined with the refined service and curated experiences of a luxury voyage. With just 148 to 342 guests aboard each of their six yachts, Windstar brings you closer to every destination and every port, granting access to secluded coves, charming village harbors, and hidden gems that larger ships simply cannot reach. Half of the fleet consists of iconic Wind Class sailing yachts with towering masts and billowing sails, while the Star Plus Class all-suite motor yachts offer a sleek, modern alternative. Onboard, you’ll find gourmet dining crafted in partnership with the James Beard Foundation, a relaxed yacht-casual atmosphere, and the kind of personalized attention that only comes from a crew who knows your name. This is intimate yacht-style cruising where the world’s hidden harbors become your playground.

Windstar operates two distinct types of vessels, each with its own character. The Wind Class sailing yachts – Wind Surf, Wind Star, and Wind Spirit – feature majestic masts and sails that capture the romance of traditional sailing. Wind Star and Wind Spirit carry just 148 guests, while the flagship Wind Surf accommodates 342. The Star Plus Class motor yachts – Star Pride, Star Legend, and Star Breeze – are sleek, all-suite vessels carrying 312 guests, with every stateroom featuring ocean views. Whether you’re drawn to the billowing sails and timeless elegance of the Wind Class or the refined, modern comfort of the Star Plus Class, both deliver the intimate, yacht-style experience that defines Windstar.

A magnificent white-hulled tall ship with full square-rigged sails deployed, sailing across calm blue ocean waters under a clear sky with scattered clouds. The vessel appears to be a modern sailing cruise ship, featuring multiple masts and traditional sailing rigging combined with contemporary maritime construction.
Two elegant cruise vessels anchored in crystal-clear turquoise waters with lush, forested mountains and dramatic clouds in the background. The left ship features distinctive white sails, while the right vessel is a modern motor cruise ship. Palm fronds are visible in the foreground, suggesting a tropical Pacific destination.
A luxury sailing cruise ship with four tall masts anchored in a pristine tropical bay surrounded by lush, verdant mountains and dramatic volcanic peaks. The white vessel is shown in calm, clear waters during golden hour, with a scenic island landscape featuring dense vegetation and colorful rock formations in the background.
A stunning aerial view of a large multi-masted sailing cruise ship anchored in pristine turquoise waters near a mountainous coastal region. The vessel features multiple tall masts and white sails, with mountains visible in the background across calm, crystalline seas.

Culinary Artistry Inspired by Every Port of Call

Windstar Cruises has elevated onboard dining into a true culinary journey, partnering with the James Beard Foundation to craft exceptional experiences that celebrate every region you visit. Fresh, seasonal ingredients are sourced from ports along the way, and each evening’s menu is thoughtfully designed to showcase the distinctive flavors of the local cuisine. The Star Plus Class ships feature four dining venues including Cuadro 44 by Anthony Sasso, celebrating Spanish cuisine. All ships offer open seating, so you dine when and with whom you choose. Special experiences include deck barbecues under the stars and destination-inspired menus that deepen your connection to each place you visit. The result is dining that feels like an integral part of the voyage itself – not just something you taste, but something you remember long after you return home.

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Destinations and Windstar Cruise Tours

Windstar sails to destinations ideally suited for small-ship exploration – the Caribbean, Mediterranean, Greek Islands, Northern Europe, Alaska, Tahiti and the South Pacific, Central America, and beyond. Their intimate vessels dock in the heart of charming town centers, pulling right up to waterfront promenades and village harbors that larger ships cannot access. You’ll discover smaller, less-visited destinations where locally authentic cultures and cuisines await around every corner. For travelers who crave genuine connection with the places they visit, Windstar’s curated itineraries and immersive shore experiences transform each port into a personal discovery rather than a crowded tourist stop.

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What’s Included In Your Cruise Package?

Your extraordinary cruise adventure comes with many included amenities from the cruise line. In addition, Extraordinary Adventures offers our clients extra complimentary benefits as well as popular upgrades to create a seamless door-to-door experience – all the more reason to select Extraordinary Adventures as your cruise travel partner!

Included in Every Windstar Cruise

  • A Variety of Dining Options
  • Onboard Entertainment
  • Use of Onboard Facilities
  • Unlimited Beverages
  • Wi-Fi
  • Complimentary Watersports Platform
  • Gratuities

Your Extraordinary Adventures Cruise Also Includes

  • Expert guidance choosing your itinerary, ship, and stateroom
  • Recommendations on shore excursions
  • Advice on cruise and travel policies and procedures
  • Emergency assistance while on your trip
  • Recommendations on travel insurance

Add Extraordinary Adventures White Glove Service to Receive

  • We arrange car service and transfers
  • We book flights*
  • We reserve hotel stays
  • We coordinate pre-cruise and post-cruise travel planning

$250 Planning Fee per stateroom.
Complimentary when you book a Windstar cruise through Extraordinary Adventures.
*Terms and conditions apply.

Frequently Asked Questions About Windstar Cruises

Windstar operates small ships – both iconic sailing yachts and all-suite Star Plus Class vessels – carrying just 148 to 342 guests. Their intimate size opens the door to small ports and hidden harbors that remain beyond the reach of conventional cruise ships. The experience combines yacht-style cruising with deeply personal service, gourmet dining crafted in partnership with the James Beard Foundation, and a casual elegance that appeals to experienced travelers seeking authentic destinations. Add the retractable Watersports Platform, the legendary Signature Sail Away ceremony, and an open-bridge policy, and you have a cruise experience unlike any other on the water.

Windstar’s fleet sails across the Caribbean, Mediterranean, Greek Islands, Northern Europe, Alaska, Tahiti and the South Pacific, Central America, and beyond. With itineraries built around small ports and overnight stays, their intimate vessels dock right at waterfront promenades where you can step ashore and begin exploring immediately. Expect hidden coastal villages, vibrant local markets, and cultural encounters that feel genuinely personal rather than choreographed. For travelers seeking immersive, off-the-beaten-path exploration, Windstar delivers beautifully.

Windstar’s All-Inclusive package covers all onboard meals, unlimited beverages (wine, beer, spirits, and specialty coffees), gratuities, Wi-Fi, and complimentary use of the Watersports Platform. Shore excursions are additional unless you have purchased a package. The All-Inclusive approach means you won’t need to sign for drinks or worry about accumulating added costs throughout your voyage. Your Extraordinary Adventures advisor can also help you secure exclusive onboard credits and VIP perks that add even more value to your sailing.

The fleet is divided into two classes. The Wind Class sailing yachts (Wind Surf, Wind Star, and Wind Spirit) carry between 148 and 342 guests beneath towering masts and billowing sails. The Star Plus Class motor yachts (Star Pride, Star Legend, and Star Breeze) are all-suite vessels accommodating 312 guests, with every stateroom offering ocean views. Regardless of which class you choose, the hallmark of Windstar remains the same: intimate scale, personalized service, and a relaxed yacht-style atmosphere that feels worlds apart from conventional cruising.

Yes, a valid passport is required for virtually all Windstar itineraries since the fleet sails to international destinations including the Caribbean, Mediterranean, Greek Islands, Northern Europe, Tahiti, Alaska, and Central America. Your passport should be valid for at least six months beyond your travel dates. Some itineraries may also require visas depending on the ports visited. Your Extraordinary Adventures advisor will review all documentation requirements specific to your chosen voyage so there are no surprises before departure.

Dining aboard Windstar is shaped by the James Beard Foundation partnership, bringing culinary credibility and creativity to every meal. Chefs draw on locally sourced ingredients picked up in port, weaving regional flavors into menus that change with each sailing. Star Plus Class ships offer four distinct dining venues, including Cuadro 44 by Anthony Sasso for Spanish-inspired cuisine, while all vessels feature open seating so you choose when and with whom you dine. From al fresco deck barbecues to intimate multi-course evenings, the food becomes a memorable thread connecting every destination on your voyage.

Windstar enhances every voyage with destination-focused enrichment that deepens your connection to the places you visit. Depending on your itinerary, you may enjoy onboard lectures from local experts, cultural demonstrations, and curated destination insights that bring each port to life before you even step ashore. The James Beard Foundation culinary partnership extends into enrichment as well, with cooking demonstrations and food-focused programming. Windstar’s smaller guest count means these experiences feel personal and engaging rather than lecture-hall style.

Windstar is an excellent choice for first-time cruisers who may feel hesitant about large-ship experiences. The intimate atmosphere, small ports of call, and yacht-style service appeal to travelers who prefer authentic exploration over mega-ship entertainment. If you enjoy boutique hotels over large resorts, appreciate fine dining, and want to visit places that feel untouched by mass tourism, Windstar is an ideal introduction to cruising. Your Extraordinary Adventures advisor can help determine whether Windstar’s sailing yachts or Star Plus Class vessels best match your travel style and preferences.

Windstar maintains a relaxed “yacht casual” atmosphere throughout the voyage. During the day, resort casual attire including shorts and polo shirts is perfectly appropriate. Evenings call for elegant casual – think nice jeans, slacks, sundresses, or dress pants. There are no formal nights, and ties and jackets are never required. The overall ambiance is sophisticated yet refreshingly unpretentious, which is part of what makes Windstar so appealing to travelers who value comfort without sacrificing elegance.

We recommend booking your Windstar voyage 6 to 12 months in advance, especially for popular itineraries such as the Greek Islands in summer, Mediterranean shoulder-season sailings, and Tahiti departures. Windstar’s intimate ships carry only 148 to 342 guests, so preferred stateroom categories and prime sailing dates fill quickly. Booking early also gives you the best selection of itineraries and access to any early-booking promotions or exclusive perks available through Extraordinary Adventures. That said, last-minute opportunities do arise – reach out to your dedicated advisor, and we’ll help you find the perfect voyage no matter your timeline.

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What Our Clients Say

Real clients. Real experiences. Never ordinary – always extraordinary.

⭐⭐⭐⭐⭐

“These two definitely know their ships, and if they don’t, they know where to find answers. We had never booked with an agent before, but after our first experience with Extraordinary Adventures, we were so pleased that we quickly booked our second cruise shortly after. Their response times are rapid, and their suggestions are immeasurable.”

Sabrina & Marty S

Verified Client · Google Review

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“Scott and Laura were very helpful and professional from the first minute. The information I got saved me money and time. Wonderful, friendly, personal, and quick service. Response within minutes to all my questions. Thank you for the great work.”

Richard & Pascal F

Verified Client

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“I gave them a budget, what I wanted, and potential dates. They did the rest! Gave me checklists for what to pack, suggestions of things to do, and the best plans for the biggest bang for our buck. They even checked on us when we returned to be sure we had an enjoyable experience.”

Kristy & Anthony R

Verified Client · Google Review

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“We have tried different venues to purchase cruises and definitely prefer working with Scott and Laura. They have always put our best interest at the forefront. They are professional and easy to contact and take the worry out of our travel plans.”

Michael & Virginia D

Verified Client · YouTube Review

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“Scott and Laura are super knowledgeable and incredibly fast to respond to questions. They helped make our last cruise worry- and stress-free. I have referred two of my friends who used their services and were very happy. They will go out of their way to help. Super friendly!”

Darla C

Verified Client

⭐⭐⭐⭐⭐

“Laura and Scott are great people to help assist with any vacation needs. I found them to be very attentive to my wants and needs. They have been very informative, provided great suggestions to help make the most of my vacation, and they are very upfront and honest. I will definitely use Extraordinary Adventures again.”

Joshua & Rachel W

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