“Private yacht style.” “The #1 Boutique Cruise Line in the world.” “Intimacy providing you with the luxuries of time, space and freedom.” Does it live up to the name?
Windstar markets itself as a small-ship, luxury experience. Its fleet includes “wind yachts” with sails and “star yachts,” small all-suite ships, sailing worldwide (Tahiti year-round, for example). I recently sailed the eight-day Spanish Symphony aboard Wind Surf, visiting Spain, Gibraltar and Portugal.
I was among the roughly 10 per cent of Canadians on board; most passengers are American, with 60 to 80 years of age clearly the sweet spot for the cruise line. And what a loyal customer base! I was amazed to meet so many passengers for whom Windstar is a second home—like Sarah from Seattle, on her 53rd Windstar cruise.
“The majority of our passengers are repeaters,” Staff Captain Tom Hunwicke told Open Jaw. “They love the family feel, the personal touch– the fact that our crew smile genuinely.”
My cruise was the last Mediterranean sailing of the season, with the ship soon repositioning to St. Martin. Of the 130 passengers on that repositioning voyage, Clare Taylor, the ship’s Hotel General Manager, said she already knew 90 of them—a testament to Windstar’s loyal customer base.
That loyalty is reinforced by the “Star Collector” program, which lets passengers link multiple cruises. Some on our sailing were continuing directly from another Mediterranean itinerary. In total, clients can spend up to 80 days at sea on back-to-back cruises, stitching together different itineraries.
There were also a notable number of solo travellers, almost all women. While some were travelling with a friend or relative, the singletons clearly felt at home.
The Wind Surf is Windstar’s original ship and the largest of the wind yachts, with 210 crew and 342 guests. Its smaller sisters, Wind Star and Wind Spirit, accommodate 148. The ships’ size allows them to access ports that larger vessels can’t.
“We can get into smaller ports than the big ships—Sorrento versus Naples, for example,” Hunwicke told me. “And there’s no queuing for passengers to get on or off.”
On this itinerary, the ship often docked close to town, so passengers could stroll ashore instead of taking a bus from a distant pier. In Cadiz, for example, I went for a walk, returned to the ship for lunch, and headed back out again. With ports open as late as midnight, some guests had dinner on board before exploring local nightlife. Embarkation and disembarkation were quick—usually under a minute, just a matter of swiping your room key.
The Onboard Experience:
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Part of Windstar’s romantic appeal is the sight of its sails. While the sails are raised at every departure, they may not be hoisted again depending on season and itinerary. On our November Med cruise, we sailed under power the entire time. Sails are more likely to be used in warmer climates. “The weather has to be perfect for us to switch the engines off,” Taylor told me.
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All staterooms are ocean view. There are no balconies, and most cabins have round portholes rather than conventional windows.
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All pricing is in USD.
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The ship has a medical centre staffed by a doctor and nurse.
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Dining: Wind Surf offers five options, none surcharged, including three a la carte restaurants (two requiring reservations) and a coffee counter serving sandwiches and pastries all day. Full room service breakfast is available.
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The Captain’s all-inclusive beverage package offers unlimited beer, wine and cocktails for $79 per person per day ($89 onboard).
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Entertainment: Low key, with live music such as Elaine presents the Swinging 60s and Join Nikki for Vocal Stylings. Highlights include a line-dancing demo by the crew—including the chef in his hat—and a staff talent show, a mix of charm and humour. (“Our group’s dance has 375 moves, so it may run long… breakfast may be served a little late,” one performer joked.) Board games, puzzles, a small library, and quiet reading nooks were also popular.
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Other facilities include a spa ($), fitness centre, and a boutique (mostly clothing).
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Windstar is the only cruise line with an open bridge policy, letting guests visit the bridge and chat with officers when it’s safe. One evening, officers treated a small group to an impromptu “name that constellation” lesson.
Excursions
Our itinerary took us from Barcelona to the island of Mallorca, then on to Gibraltar and Lisbon, with several stops along Spain’s southern coast.
Shore excursions (ranging from US$65 to $235) were plentiful, including city tours, tastings, cultural experiences such as flamenco, and coach trips to inland cities like Seville or Granada.
Passengers could also explore on their own—I enjoyed a few self-guided walking tours and a hop-on-hop-off experience—but most preferred the convenience, security, and “no surprises” reassurance of booking Windstar’s excursions.
A highlight for me was Shop with the Chef, Marcelo Malacalza. He was entertaining and informative as he led us through Malaga’s market, a foodie Pied Piper with 10 of us happily trailing behind. (“Look at this! This is how you buy fish! Fantastic!”) The experience is free, but signing up is a must.
What to Pack:
Windstar’s dinner dress code is “country club casual,” though on my trip few men wore jackets. Ladies were comfortable in dress pants or a nice dress, but I did not see much in the way of glittery cocktail attire.
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Comfy, sturdy walking shoes are a must—I racked up over 85,000 steps in a week! Cobblestones and uneven pavements are common in Europe.
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Folding umbrella. The ship provides full-sized ones, but your own folding one will be more portable.
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Water bottle.
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Bathing suit (The ship has two hot tubs and a small pool.)
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European adapter (not sold on board).
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Around-the-neck phone strap to keep your hands free while touring or shopping. (In Gibraltar, a cheeky monkey once grabbed a crew member’s phone!)
Overall, my Windstar experience showed that you can be as active or as relaxed as you like. The ship’s small size means you’re never overwhelmed, and the low-key atmosphere makes it easy to chat with fellow passengers. I lost count of how many people, when I asked “Why Windstar?,” mentioned the friendly, family-like vibe. Not intimidating at all.
About Future Bookings
Future cruises are actively promoted on board—I even overheard one passenger booking two. “Commissions are protected, as the booking goes back to the originating agent (unless the client specifically requests otherwise),” Andrea Mendelsohn, Windstar’s Regional Sales Manager for Canada, told me. “Clients benefit from all the perks and discounts from the Onboard Cruise Consultant—and advisors can add any applicable national account amenities or CAA member benefits, where relevant.”
Windstar lived up to its image: small, elegant, and visiting off-the-beaten-path ports. But also fun and approachable. Next time, I’ll cover our ports of call.
