The offer is an invitation to discover some of Windstar's most compelling destinations – from the trade winds of the Grenadines and the remote atolls of French Polynesia to the volcanic landscapes of the Canary Islands and Northern Greece beyond the postcard-famous islands. Available on new bookings made July 1 through November 17, 2026, the promotion makes planning an intimate yacht voyage easier while keeping the spotlight where it belongs: on the destination.
With unlimited Wi-Fi, gratuities and select beer, cocktails and wine by the glass included, guests can linger over dinner without tallying a bill, toast another spectacular sunset without signing a receipt and simply enjoy getting to know a crew that feels more like friendly travel companions than staff. The offer removes friction from the journey before guests even leave home, beginning with a deposit of just $150 per guest to reserve a preferred stateroom or suite.
"The hardest part of planning a vacation is often saying yes," says Janet Bava, chief commercial officer at Windstar Cruises. "Whether it's sailing through the Grenadines, exploring the Marquesas, discovering the Canary Islands or seeing a different side of Greece, these are the kinds of journeys guests dream about long before they book. 'More Reasons to Say Yes' gives them one more reason to make those plans a reality, with a complimentary All-Inclusive upgrade, a low deposit and additional savings for our Yacht Club Members."
Where Can Travelers Say "Yes" During the Promotion?
The limited-time offer shines a spotlight on four regions throughout 2027:
- Caribbean: Tradewind Island hopping takes center stage with voyages through Barbados, St. Lucia, Antigua and the Grenadines, including Windward Islands Surf & Sunsets, where guests sail between idyllic islands under billowing sails, and San Juan and the Virgin Islands, a classic Caribbean voyage made personal through Windstar's smaller yachts and welcoming crew.
- Tahiti: With two yachts sailing year-round in French Polynesia — Wind Star and Star Breeze — Windstar continues to offer one of the region's most comprehensive small-yacht programs. Far Flung French Polynesia & Marquesas ventures beyond familiar lagoons to rarely visited atolls and the remote Marquesas Islands, creating an experience designed for travelers seeking genuine exploration.
- Canary Islands: Beyond the familiar Mediterranean icons, Windstar's Canary Islands itineraries explore the Fortunate Isles and Madeira, where volcanic coastlines, centuries-old maritime traditions and vibrant island cultures offer a different perspective on the region aboard an intimate yacht.
- Greece: Postcards from Northern Greece offers a refreshing perspective on one of Europe's most beloved destinations, exploring lesser-photographed ports and storied coastal communities beyond the iconic island circuit.
Additional featured 'More Reasons to Say Yes voyages include: Dreams of Tahiti, Tahiti & the Tuamotu Islands, Treasures of Southern Spain & Morocco, Vietnam & Cambodia Revealed, Tantalizing Thailand & Sparkling Singapore, Naturally Costa Rica, Costa Rica & Panama Canal, Bermuda Bliss and Windstar's signature transatlantic Ocean Crossing.
Full Offer Details
The destinations may inspire the journey, but the offer makes planning it easier. Guests booking eligible voyages receive:
- A complimentary All-Inclusive upgrade including unlimited Wi-Fi, gratuities and select beer, cocktails and wine by the glass — a value of more than $1,300 for two guests on a 7-night voyage
- A reduced deposit of $300 per stateroom ($150 per guest) on qualifying voyages outside 90 days of departure
- Exclusive Yacht Club Member savings of 5%, with the loyalty benefit increasing to 10% when booking on board
- Access to select voyages sailing through the end of 2027, giving travelers flexibility to plan well in advance
To plan a small ship cruise with Windstar book online here, contact a travel advisor, reach out to Windstar Cruises by phone at 866-258-7245, or request a call by a Windstar vacation planner.
Windstar Cruises imagery here, credit to Windstar Cruises.
Contacts:
Patricia Gonzalez, Vice President of Marketing Windstar Cruises / [email protected]
LDPR, [email protected]
About Windstar Cruises:
For four decades, Windstar Cruises has been reimagining small-ship cruising with a distinctive blend of relaxed luxury and genuine connection to the world's most captivating destinations. From its origins with motor sailing yachts tailored for upscale yet casual travel, Windstar has grown into a diverse fleet of four Star Class all-suite yachts—including its newest addition of Star Seeker in December 2025—and three Wind Class sailing yachts, offering voyages that are both intimate and inspiring. Its highly anticipated yacht, Star Explorer, is set to debut in December 2026, expanding the fleet to eight yachts accommodating 150-350 guests. Windstar's legendary Wind Class sailing yachts are also undergoing a meticulous two-phase redesign to be completed by 2027. Windstar yachts sail to more than 330 ports across Europe, the Caribbean, Costa Rica and the Panama Canal, Alaska, Canada and New England, Japan, the South Pacific, and Asia. Unlike most cruise lines, Windstar sails year-round in the Mediterranean and Tahiti, offering different destination experiences seasonally. Each Windstar voyage is designed to immerse guests in authentic cultural experiences, all while delivering the comfort, service, and style that define the Windstar difference.
Windstar Cruises is proud to be part of the Xanterra Travel Collection®, a distinguished group of global hospitality and travel companies with a legacy spanning over a hundred years. Xanterra operates iconic national parks, including Grand Canyon, Yellowstone, Glacier, and Death Valley. The Xanterra Travel Collection® is owned by The Anschutz Corporation, the ultimate owner of the Broadmoor, Sea Island, and entertainment giant AEG, Anschutz Entertainment Group.
SOURCE Windstar Cruises
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