Heidi Sarna is the co-founder of QuirkyCruise.com, a guide to small-ship cruising.
Lingering on the ample decks of the five-masted, 342-passenger Wind Surf—billed as the flagship in the Windstar Cruises sailing fleet—I was mesmerized by nearby Mount Nevis (pictured above at right) as a moody cluster of clouds clung to its peak in the fading light of day.
Four levels of outdoor tiered teak decks—where you’ll find two bars, a pool, a hot tub, the Veranda restaurant, and lots of seating—offer generous real estate for soaking up tropical surroundings on Windstar’s classic round-trip Caribbean cruise from St. Maarten to Nevis, Dominica, St. Lucia, Les Saintes, St. Barts, and St. Kitts.
The ship’s five masts give it a majestic profile, but the sails are computer-operated and mostly for show as the ship relies on its diesel-powered engines. Though it has been spruced up over the years, Wind Surf has been on the seas since 1989.
Traveling with my husband and college-age sons, I wanted to see how the ship is holding up.
(Rainbow spotted from Windstar Cruises' Wind Surf ship)
Ship Accommodations and Onboard Experience
In our case at least, the cruise proved a smart choice for a family with (nearly) grown children. We bonded over heart-to-heart talks while sipping happy hour drinks, and formed a family team for one of the daily trivia contests (and won!).
(Veranda restaurant on Windstar Cruises' Wind Surf ship)
On-deck meals are a highlight, especially breakfast at the open-air Veranda buffet, surrounded by brilliant teal waters and a bright blue sky, and at Windstar’s weekly barbecue buffet dinner. As brushstrokes of orange, red, and purple streaked the horizon before the stars stole the show, we heaped our plates with pulled pork, ribs, grilled shrimp, cheesecake, and more.
Our family occupied a pair of side-by-side, 188-square-foot Category TX cabins, the ship’s standard rooms. There’s so much storage that several of our cabinets stayed empty.
Bathrooms likewise have generous shelves for toiletries and are stocked with L’Occitane products. The tubular showers could get tight for larger folks, however.
Glass bottles are refilled with fresh water daily and the contents of a stocked mini bar are included if you opt for Windstar’s all-inclusive package ($99 a day if booked pre-cruise). It also covers alcoholic drinks, Wi-Fi, and tips.
The somewhat tired décor in standard cabins will get a facelift in 2026. The ship already sports stylish new suites.
Classic Caribbean Ports
As a family, we enjoyed a hike up to the remains of 18th-century Fort Rodney and Signal Hill on St. Lucia’s Pigeon Island, while in charming Terre-de-Haut, Les Saintes, we unfortunately chose a disappointing and pricey ($149 per person) glass-bottom kayaking jaunt around the harbor, squinting down at cloudy images of a brain coral or two and a handful of fish.
When our sons stayed back on the ship—too lazy to bother with the tender rides to shore—my husband and I walked around tiny St. Barts’ U-shaped harbor at Gustavia, where fancy private yachts bobbed in front of a string of luxury boutiques. For us, the beauty lay beyond the bling; we trekked up to the hilltop remains of the 18th-century Swedish Fort Karl to admire the island's jagged coastline cut with arcs of white sand.
In lush Dominica, the two of us signed up for the guided “Rainforest Drive, Emerald Pool & River Tubing” tour ($109 per person), a worthwhile opportunity to appreciate the island’s thick tropical foliage on both the drive itself and in the water.
(Pictured above: scenery in St. Barts [left] and Dominica [right])
Swell Swimming Marina
Along with Wind Surf’s cascading outdoor decks, the ship’s marina was my other happy place. When at anchor, the ship’s stern opened like a giant metal robot mouth, unfolding a swimming platform nearly level with the water line. From the platform, I swam in the seawater almost every day, kicking around while hanging onto a noodle (there are paddleboards and kayaks too) and swooning over yet another picturesque Caribbean harbor.
Keep in mind, the marina operates at the discretion of the captain, and you should be a relatively strong swimmer to cope with forceful currents.
Onboard Meals, Amenities, and Entertainment
Meals on the ship are open seating and casual (T-shirts and shorts are common), with the buffet-style indoor/outdoor Veranda restaurant serving breakfast and lunch (loved the salads and daily specials like sushi).
For dinner, choose from three dining venues: the newly gussied-up Amphora dining room or two reservations-required restaurants (generally you can get in each once per week): Stella Bistro for continental fare and Candles for steaks and seafood. My sons raved about the lamb chops and steaks; my favorite was the sea bass baked in parchment paper.
Sometimes there’s a wait for tables at mealtime, but otherwise you would never have known the Wind Surf was nearly at full capacity. Passengers can easily spread out on the spacious ship, checking out prime spots for hanging out, such as the recently redecorated Main Deck (deck 4), site of a large boutique, café for quick bites and coffees, and the reception area.
Amenities on board include a large, well-stocked gym with sea views and daily stretch/yoga classes. In the spa, I had an excellent 75-minute hot stone massage for a steep $299, not including tip.
(Outdoor decks on Windstar Cruises' Wind Surf ship)
Low-key entertainment involves a few solo performers singing and playing the guitar, piano, or electric violin in the bars and main lounge. After-dinner highlights are the popular crew talent show and dancing to a DJ’s ‘80s mix.
At 36 years old, Wind Surf shows its age, for good and ill. Among the good: The vessel’s classic stepped stern decks, rarely found on new ships. Among the drawbacks: On our cruise, a broken-down tender and an out-of-service elevator were not small inconveniences.
That said, the Windstar fleet has been refurbished many times over the years (the brand-new Star Seeker debuts later this year), and the line continues to command a loyal following. Many passengers we met had cruised with Windstar before and were planning to book another voyage soon.
(The author and family boarding Windstar Cruises' Wind Surf ship)
For more information or to book a cruise, go to WindstarCruises.com.
