Where Canvas Meets Compass: Windstar Drops Anchor with New Themed Voyages

Windstar Cruises is turning the tide on special interest travel with hand-picked experiences that flow seamlessly from ship to shore – including an opportunity for guests to pilot the ship!

MIAMI--(BUSINESS WIRE)--Windstar Cruises is charting a bold new course with the launch of its Themed Voyages Collection, a line-up of beyond-ordinary sailings designed to make passions come alive at sea. Whether it’s swapping brushstrokes with celebrated artists, taking the helm on a tall ship, or flowing with daily yoga on deck, these intimate, yacht-style journeys bring immersive fun from bow to stern.

With special-interest travel on the rise, Windstar Cruises is answering the call for those craving more than a change of scenery aboard new intimate, passion-fueled voyages. These themed sailings — launching just in time for the 2025/2026 seasons — give guests something irresistible to book now, for stories they’ll be telling long after the anchor drops.

“What I love about these new themed voyages is how they turn the whole ship into part of the adventure,” said Janet Bava, chief commercial officer of Windstar Cruises. “One cruise you’re learning to tie the perfect bowline or painting alongside a world-class artist, the next you’re dancing under the stars at a pirate party or deck BBQ. It’s the kind of small-ship magic only Windstar can provide.”

Sip, Sketch, and Sail

Forget fridge magnets — how about bringing home a memory painted at sea? Windstar’s Masterpieces at Sea voyages elevate travel into a living canvas of creativity, with artists sharing presentations about the inspirations behind each piece. On select sailings, an acclaimed Fountainhead artist will be on board creating a mural or large installation in real time, transforming the ship into a floating gallery such as Samara Ash on the November 14th Masterpieces at Sea: Brushes and Tapas voyage. A second artist also joins each voyage as an instructor, transforming The Screening Room into a hands-on art studio with intimate painting workshops, lively Paint & Sip classes, and more. Adding depth to the experience, an onboard Art Historian will deliver a series of enrichment talks, tying the destinations’ artistic heritage to the creativity happening at sea.

Beyond the ship, Windstar enhances the journey with curated art-focused excursions—think Gaudi’s playful architecture in Barcelona or Picasso’s legacy in Málaga— led by the guest artists on board. See all Masterpieces at Sea sailings below:

• 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

An Ocean Crossing That’s Anything but Ordinary

Windstar’s Knot Your Average Crossing voyages celebrate the romance and tradition of life under sail. On these one-of-a-kind crossings — setting sail beginning November 2025 — guests can step up to the flying bridge and take the helm, learning age-old seamanship skills from the crew. Days at sea are filled with engaging enrichment programs: bridge and deck officers lead hands-on workshops in knot tying, chart reading, and star mapping, while distinguished guest speakers bring maritime history to life. On the upcoming sailing, Knot Your Average Crossing (Lisbon to St. Maarten), historian and journalist Joseph Novitski will deliver a lecture series on piracy, naval order, and the origins of the U.S. Navy.

More 2026 sailings will continue this tradition, with enrichment speakers still to be announced, offering fresh perspectives on maritime heritage. Whether you’re steering the ship, tracing ancient constellations, or raising a toast to pirate lore, these crossings promise a seafaring adventure unlike any other.

Sun Salutations and Sea Breezes

Windstar’s Mind, Body, Spirit Collection itineraries take wellness beyond the spa, blending serene days at sea with transformative experiences designed for guests to nurture their whole self. Renowned yoga teacher and life coach Debbie Dixon leads daily sessions of yoga, meditation, and breathwork on open decks where the horizon becomes a peaceful focal point. Guests can sip their way to vitality at the pop-up Elixir Bar, offering fresh, nutrient-rich juices, and go deeper with guidance from an additional onboard wellness coach for personalized, one-on-one attention. It’s the perfect balance of small-yacht intimacy, expert-led rejuvenation, and Windstar’s knack for pairing mindful moments with unforgettable destinations.

Need to Know

• Best Suite Selection: Booking early ensures access to the most desirable suites.
• Contact: 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.

Images Here, credit to Windstar Cruises.

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 three Star Class all-suite yachts and three Wind Class sailing yachts, offering voyages that are both intimate and inspiring. Two highly anticipated new yachts, Star Seeker and Star Explorer, set to debut in December 2025 and 2026, expand 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.