Windstar Cruises has announced an inspiring line-up of themed voyages for its 2025-2026 season, offering guests a collection of immersive journeys across the Mediterranean and Caribbean. With an emphasis on art, seamanship, and wellness, these new sailings go far beyond traditional cruising, turning each trip into a hands-on adventure designed for creativity, exploration, and personal growth.
Known for its intimate small-ship experiences, Windstar is now pushing the boundaries of experiential travel. The new itineraries reflect a growing trend among travellers who seek deeper engagement with destinations while enjoying the comfort of luxury cruising.
Masterpieces at Sea: Celebrating Art on the Waves
Among the highlights of the upcoming season is the “Masterpieces at Sea” program, which invites guests to embrace their artistic side. Passengers will travel alongside acclaimed artists from Fountainhead, who will create large-scale works during the voyage. Guests can watch live mural painting, attend art talks, or join interactive workshops such as Paint and Sip sessions.
Beyond the ship, curated art excursions will connect travellers with the cultural heritage of ports along the Mediterranean and Caribbean. Onboard art historians will enrich these experiences, linking local traditions with the creativity unfolding during the sailing.
Key departures in the collection include:
- Brushes & Tapas – November 14, 2025
- Europe Winter Riviera – February 20, 2026
- Mediterranean Island Mosaic – August 13, 2026
- Gems of the Leeward Islands – October 28, 2026
These itineraries blend travel with creative expression, offering a unique chance to return home with both memories and artwork inspired by the journey.
Knot Your Average Crossing: Learning Seamanship Traditions
For travellers fascinated by maritime culture, Windstar introduces “Knot Your Average Crossing” sailings. Beginning in November 2025, these voyages will celebrate the rich traditions of seamanship. Guests can take part in hands-on lessons in knot tying, star mapping, and chart reading, taught by experienced crew members on the flying bridge.
Adding depth to the program, guest lecturers will deliver talks on nautical history, piracy, and naval traditions. Notably, journalist and historian Joseph Novitski will join the Lisbon to St. Maarten sailing, offering insights into naval order and piracy’s influence on seafaring.
This collection is ideal for travellers who want to move beyond sightseeing, instead embracing the skills and spirit of life at sea.
Mind, Body, and Spirit: Wellness Cruises for Transformation
Windstar is also responding to the rising demand for holistic travel with its “Mind, Body, Spirit Collection.” These wellness-focused voyages are designed to help passengers rejuvenate both body and mind while sailing through some of the world’s most scenic waters.
Renowned yoga teacher and life coach Debbie Dixon will lead daily sessions of yoga, meditation, and breathwork on open decks, allowing guests to connect with nature. Additional wellness coaches will provide personalized guidance, offering one-on-one coaching throughout the voyage.
To complement the program, Windstar will introduce an Elixir Bar featuring nutrient-rich juices and wellness drinks, perfect for energizing guests between activities. These itineraries focus on balance, mindfulness, and renewal, making them a top choice for travellers seeking transformation at sea.
Exploring the Mediterranean and Caribbean
Themed voyages will sail through two of the world’s most captivating regions: the Mediterranean and the Caribbean. Guests can expect itineraries that showcase not only famous highlights but also smaller, less-visited ports accessible only to Windstar’s small ships.
- In the Mediterranean, travellers will discover coastal towns rich in history, art, and cuisine.
- In the Caribbean, itineraries will highlight the charm of the Leeward Islands and vibrant local culture.
This diversity ensures that whether guests are sketching in a Mediterranean art class, tying knots under the Caribbean sun, or meditating on deck, every experience is deeply connected to its destination.
Booking and Availability
Bookings for Windstar’s themed voyages are now open, with strong interest already expected due to limited ship capacity. As always, Windstar maintains its hallmark of small-ship intimacy, with fewer guests on board and personalized service. This exclusivity enhances the immersive nature of the themed experiences.
Travellers are encouraged to book early to secure spots on these distinctive sailings, which combine luxury cruising with cultural immersion.
Reimagining the Cruise Experience
Windstar Cruises has built a reputation for delivering voyages that feel personal, authentic, and memorable. With its 2025-2026 themed collection, the company is demonstrating a fresh vision for modern travel—one that transforms the ship into more than just transportation.
By offering artistic expression, maritime traditions, and wellness programs, Windstar is creating opportunities for travellers to leave with more than souvenirs. They leave with skills, insights, and renewed energy.
Conclusion
The 2025-2026 Windstar Cruises themed voyages represent a bold step forward in experiential tourism. Guests can paint alongside celebrated artists, learn the art of seamanship, or embrace a journey of personal wellness. All while exploring the Mediterranean and Caribbean in Windstar’s intimate small ships.
These voyages are designed to turn a holiday into a meaningful adventure. For modern travellers seeking creativity, knowledge, or balance, Windstar’s new collection offers a cruise experience unlike any other.
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