Sail Away on a Windstar Cruise

28th December 2017

Laura Begley Bloom takes her 4-year-old sailing in the Caribbean on the Windstar, a classic ship usually favored by couples, and discovers that it’s also the perfect mother-daughter getaway.

“So I’d like to know where, you got the notion. Said I’d like to know where, you got the notion. To rock the boat, don’t rock the boat baby. Rock the boat, don’t tip the boat over.”

Disco is the last thing I expect to hear as the sophisticated four-masted Windstar sets sail from the island of Mayreau in the Grenadines. But after playing the cruise line’s signature sail-away song, the heart-stopping “Conquest of Paradise” from the Greek composer Vangelis, the ship’s resident DJ decides to have some fun and entertain the guests on the top deck with the seventies classic.

A cool soundtrack is just one example of what makes a trip on this 148-passenger sailing yacht so special. The Windstar has all the trappings of luxury – gleaming teak everywhere, spacious cabins, multicourse gourmet meals — but it still manages to be warm and personable. And Windstar’s small size allows it to get into tiny ports that are difficult for larger cruise ships to access, like the ones I’m visiting on the “Jewels of the Windward Islands” itinerary: Barbados, St. Lucia, Grenada, and the tiny islands of the Grenadines.

Windstar is known as a romantic ship for couples, but my husband I had decided to take our daughter, Lucy, with us. When he has to cancel at the last minute because of work, I start to question whether this is the right ship for a mother-daughter getaway. And some of my travel-industry friends express concern that I am taking a 4-year-old on such a grown-up vessel. Won’t she be bored? What will you do when you need downtime? But the cruise line assures me that while the ship doesn’t have amenities for kids, children are very much welcome. Plus, I reason, I’m not looking to dump my daughter at a kid’s club. I want to spend quality time together, sailing through the Caribbean and exploring some of the region’s most charming islands.

When we board the ship in Barbados, we’re greeted with open arms by the staff, and any worries quickly melt away. Lucy immediately hits it off with Natalie, who checks us in and gives us an intro to the ship. During dinner the first evening at Candles, the alfresco restaurant set under the stars, Lucy is in hysterics watching our waiter make a little squirrel animal from a napkin. In fact, she bonds with staffers throughout the ship. There’s Yosi, a dining room attendant, who surprises Lucy one night with a sketch that he has drawn of her. And she is delighted to meet a spa therapist — also named Lucy — who spoils her with colorful mani-pedis.

We are also thrilled to meet a big family from Vancouver that is doing a multi-generational reunion and has two boys near Lucy’s age. By the end of the cruise, we’re hanging out with them by the pool and at the beach and dining with them at night. In fact, we make friends with tons of other guests on the ship. With just 74 staterooms, you quickly get to know your fellow passengers.

Another highlight of being on the Windstar is the accessibility you get to the top brass. Windstar has an open-door policy on the bridge, which is a rarity in the cruise world. So whenever you want, you can stroll over to the ship’s command center and visit with the crew and Captain Belinda Bennett, who is the first black female captain in the commercial cruise industry. It is inspiring for a little girl to see a woman in such an important role — behind the wheel of a ship. Plus, Lucy loves learning about seafaring and checking out all the radars and maps in the bridge.

Windstar is also known for its alliance with the James Beard Foundation. The aim? To elevate local culinary encounters for cruise travelers. Unlike many lines, which have to buy all their provisions in bulk, Windstar’s small size allows its chefs to create market-to-table dishes throughout the course of the journey. Passengers can even accompany the chefs into the market. On Grenada, Lucy and I head out with Executive Chef Budhi Thakur to the island’s legendary Spice Market, where we shop together for ingredients — mango, nutmeg, vanilla, star anise — and visit the fish market, where Chef Budhi buys mahi mahi straight off the boat. I’ve been on a lot of cruises, and I’ve never had food so fresh.

In fact, Windstar makes sure that passengers get a chance to have meaningful experiences everywhere they go. On Mayreau in the Grenadines, Windstar hosts a beach barbeque, complete with a local steel-drum band; between courses, we explore the little island, which is home to just 271 residents. In St. Lucia, we venture into the rain forest and get a glimpse of rare birds and plants. And on Bequia, a speck of an island in the Grenadines, we follow Captain Belinda’s advice and head to Mac’s, a little open-air restaurant by the sea, for its legendary lobster pizza. Just like sailing on Windstar, it is a taste of paradise that Lucy and I will never forget.

The Ship

The Windstar is a classic four-masted sailing ship and one of the six ships in the cruise line of the same name. 

Getting There

Windstar sails through Europe and the Mediterranean in the summer and the Caribbean in winter. The “Jewels of the Windward Islands” itinerary starts and ends in Barbados, with stops in Grenada, St. Lucia and the Grenadines.


One of the highlights of a Windstar cruise in the Grenadines is a stop at Mac’s in Bequia.

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