Windstar Cruises Announces Twenty-One New Itineraries for Winter 2027-28, Featuring Extended Voyages to Iconic Locations

Windstar Cruises has unveiled twenty-one new itineraries for the winter 2027-28 season, designed to offer extended voyages to some of the world’s most iconic locations. These longer sailings provide travelers with the rare opportunity to explore destinations in greater depth, allowing for more time to immerse in the culture, history, and natural beauty of places such as the South Pacific, Panama Canal, Southeast Asia, and the Caribbean. With these extended voyages, Windstar aims to deliver a more enriching and leisurely cruising experience that larger ships simply cannot offer, giving guests access to remote and iconic spots that are often overlooked.

The 2027-28 winter season brings an array of longer sailings and unique itineraries designed to offer travelers experiences that are simply not available through larger cruise lines. Windstar’s signature small ships allow guests to reach places that would otherwise be inaccessible, offering a more personalized and immersive experience compared to the larger, more commercialized options available.

Among the most exciting new additions is a 52-night voyage aboard the Star Breeze, which will take guests from Papeete to Singapore. This extended journey offers unparalleled access to the picturesque South Pacific, allowing travelers to explore a wide range of exotic islands and coastal towns over a significant period. The 52-night itinerary is perfect for travelers who want to immerse themselves in the culture and beauty of the South Pacific while enjoying the relaxed pace and luxury of Windstar’s small-ship cruising.

The Star Pride will focus on Latin America, offering voyages that will explore Costa Rica and the Panama Canal, two destinations renowned for their natural beauty and rich cultural heritage. Cruising through the Panama Canal will give guests the chance to experience one of the most impressive feats of engineering in the world, all while enjoying the intimate atmosphere that Windstar’s ships are known for. This journey promises a one-of-a-kind experience, blending adventure with comfort and style.

In the Canary Islands, Windstar will introduce a brand-new itinerary on the Wind Spirit, sailing from Málaga to Tenerife. This route will feature a special two-day stop in Casablanca, Morocco, where guests can explore the vibrant city’s markets, cafes, and historic sites. Casablanca’s unique mix of colonial and modern architecture, combined with its cultural richness, makes it an essential destination for any traveler looking to experience the magic of North Africa.

For those drawn to the allure of Asia, the Star Seeker will offer voyages through Japan and Southeast Asia. These itineraries will give guests the opportunity to explore Japan’s rich history, from ancient temples to modern cities, as well as the beauty and vibrancy of Southeast Asia. Destinations include iconic spots like Kyoto, Bangkok, and other hidden gems that are often off the beaten path for mainstream tourists.

In the Caribbean, travelers will have the opportunity to explore some of the most idyllic islands aboard the Star Pride, Star Legend, and Wind Surf. With their intimate atmosphere and ability to visit smaller ports, Windstar’s Caribbean itineraries offer a more authentic and relaxed cruise experience. Whether enjoying the beaches of the Bahamas or experiencing the local culture of Puerto Rico, Windstar’s Caribbean offerings are designed to provide a truly memorable experience.

For those interested in exploring North America, Windstar’s late-season Canada and New England voyages offer some exciting new additions. The updated Southeast Canada Exploration includes an overnight stay in Halifax, giving guests ample time to explore the historic maritime city. Also available is the Celtic Colours Festival sailing, which offers a celebration of the region’s Scottish heritage through music, food, and traditional performances. Another remarkable option is the Greenland North Atlantic Odyssey, a unique voyage that will take guests from Reykjavik to Boston, providing rare access to Greenland’s remote landscapes and a glimpse into life in this rugged, unspoiled part of the world.

In addition to these exciting new itineraries, Windstar Cruises is offering travel advisors a limited-time promotion. Until April 30, 2026, advisors can offer clients an exclusive all-inclusive package on select winter 2027-28 sailings. This package includes Wi-Fi, unlimited select beer, wine, and cocktails, gratuities, a $100 onboard credit per guest, and an additional five percent savings when clients pay in full at the time of booking. This extra value is designed to enhance the travel experience and give guests even more reason to choose Windstar Cruises for their winter getaway.

Windstar Cruises is launching twenty-one new itineraries for winter 2027-28, offering extended voyages to iconic destinations like the South Pacific and Panama Canal, providing travelers with more time to immerse in these remarkable locations.

Windstar Cruises continues to distinguish itself as a leader in small-ship cruising by offering longer, more immersive itineraries to some of the world’s most fascinating destinations. Whether seeking adventure in the South Pacific, exploring cultural landmarks in Asia, or relaxing in the Caribbean, Windstar’s winter 2027-28 season provides travelers with unique opportunities to discover the world in style, all while enjoying the luxury and intimacy that only small ships can provide. With exclusive itineraries and added value for early bookings, this winter promises to be one of the most exciting seasons yet for Windstar Cruises.

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