Here’s How Windstar has Become Family to My Family

My husband Chris and I never saw ourselves as cruise travelers. That was for older folks. Despite being a travel writer since 1995, I did not consider myself part of that crowd.

Eventually, our first seagoing journey called. Seduced by the striking profile of Windstar’s sailing ships, I booked a cabin on a Mediterranean voyage out of Civitavecchia, Italy. The chief lure was the handsome ship. Wind Surf’s five masts supported more than a half-acre of bright white sheets, its trim hull sliced gamely through the sea, and the bowsprit looked sharp enough to parry with an iceberg. What a looker.

I was also drawn by the setting for a decktop barbecue. Dinner would be held al fresco alongside Stromboli, a diminutive volcanic isle nicknamed the “Lighthouse of the Mediterranean.” For more than two hours, the ship hovered a few hundred yards offshore as the rambunctious volcano shot off fireworks every 10 or 20 minutes and smoldering lava tumbled into the sea. We clinked glasses of wine with each convulsion.

By the end of the seven days, something else had taken hold. The waiters, bartenders and cabin stewards remembered our names and drink orders, always delivered with an easygoing smile. We started to feel at home. Chris and I won the trivia contest one night, we posed for a photo on the bowsprit, and I hung out on the bridge, where officers fielded my endless questions. And each time Wind Surf steered out of port under full sail, the Greek composer Vangelis’ theme from the film “1492: Conquest of Paradise” came booming over the speakers, tingling my spine with the spirit of seafaring adventure.

This was our first Windstar cruise; it was by no means our last. Windstar provided us with cherished memories, over and over again, with each other, sure, but also with members of our extended family, ranging in age from 20 to 80. It’s become a part of our lives together. We’ve done five Windstar trips already, and can’t wait to figure out what the next one will look like.

Connecting our moms in the British Isles

Big Ben, across London’s River Thames /Shutterstock

In 2015, Chris and I invited our septuagenarian mothers on a vacation. I surmised that a small-ship cruise would be a gentle environment for two older ladies from incongruous backgrounds to get to know each other better. I was intrigued by Windstar’s acquisition of a trio of former Seabourn yachts, which had the added benefit of suite layouts that would give the moms some breathing room.

The British Isles itinerary that Star Legend sailed for its inaugural voyage under the Windstar flag took us from London to Dublin. But rather than embarking from Southampton or Dover or another big-ship port, when I say London, I really mean London. Star Legend was svelte enough to be able sail right from the center of the city. This meant stopping traffic to raise the gaudy Tower Bridge so our ship could ease through a glide 40-some miles to the sea. As this was just before skyscrapers started to take over East London, we gazed across the rooftops at one iconic structure after another — a privileged, elevated perspective from the Yacht Club to the Tower of London, Greenwich and the Thames River Barrier.

For Chris and David, a chance to help their mom’s get better aquainted on a British Isles cruise.

Joining the cruise was Darren McGrady, former personal chef for Queen Elizabeth II and later Diana, Princess of Wales, and he left the moms starstruck as he regaled with innocuous gossip and prepared a favorite meal from Buckingham Palace. A private event for Windstar was held in Wales at Picton Castle, where a Welsh chorus serenaded us and the gardens enveloped us in color and fragrance — a treat for our green-thumbed mothers. Born on opposite coasts and each having taken different paths in life, the moms found ways to bond as we bounced from one tiny port to the next.

A family cruise

Puerto Rico is a great jumping-off point for Caribbean voyages on Windstar

In early 2019 I looked at a calendar and spotted a predicament. Every seven or so years, my husband’s birthday falls on Thanksgiving Day. Chris jokes that we should just put candles in the turkey. But his birthday usually lands over that weekend, and with family and friends located across the country, Chris gets shortchanged more often than not. I called his sisters and laid out a plan: If they’d commit to take the whole week off, I’d organize the celebration on a cruise and help out with airfare for any of our adult nephews and nieces who could join.

I attached one condition: that I pick the ship and the itinerary, and they agreed. There were more than a hundred possibilities, many of which could be eliminated based on distance, timing or cost. But as soon as I spotted a Caribbean sailing out of San Juan — once again aboard Star Legend — the choice was made. And that is how nine of us, ages 20 to 80, found ourselves celebrating Thanksgiving and toasting Chris’s birthday with Windstar.

For David Swanson, some of his most memorable cruises on Windstar have included family members from 20 – 80 years old.

While sailing out of South Florida would have been easier on many fronts, I like departing from San Juan, because it maximizes the range of islands that can be visited on a seven-day cruise — for example, Grenada, the Spice Island. Before arriving, I hired a guide and driver to take us on a circumnavigation of the island. This included stops at a nutmeg-processing plant, a chocolate factory, and even a rum distillery still powered by water wheel. Rather than the tourist-inundated ports the big ships call on, we were encountering life on a rural, agricultural island — a far cry from our city life at home.

We continued on to the Îles des Saintes, to St. Lucia, and to St. Maarten, but the favorite for us was Bequia, a sweet little island in the Grenadines where we all hopped into a pickup truck taxi and settled into the sand at Lower Bay. Here we rented worn beach chairs and lounged in the generous shade of manchineel trees, plaintive waves lapping at our feet. One sister made herself at home in a swing; a stray cat found Chris’ mother and made himself at home in her lap. His name, a bartender told us, was Laptop.

Unlike the mega-ships emerging from shipyards with increasing regularity, Star Legend didn’t have water slides, or a casino, or a stage for Broadway-style shows, and yet it provided an unfettered, intimate environment that was ideal for bonding with loved ones. I spoiled them all, and I patted myself on the back.

Back to just the two of us

Tortola, in the British Virgin Islands

As COVID-19 arrived, Chris and I hunkered down at home. More than a year off the road began to take its toll. Cruise lines hinted at returning and finally, in the summer of 2021, itineraries started to take shape. What cruise line did we opt for when the sea was ready to welcome us?

You know the answer, and in this case Star Breeze, along with the other two ships Windstar had acquired, had received a nip and tuck that revealed a new, 84-foot-long midsection. Fifty additional cabins were added to each ship, along with two new restaurants; the spa was glammed-up and the fitness room was expanded. But, despite 50% more cabins and crew, Star Breeze didn’t feel bulkier. The ship was still sleek enough to tuck into smaller ports for offbeat explorations.

While the sea was ready to welcome us, as was Windstar’s doting crew, the ports we thought we’d be visiting were not. One after another, the planned itinerary got thrown out the window as islands opted to keep their doors closed to cruisers. The British Virgin Islands? Nope. Anguilla and St. Barts? Nope and nope. And when we got to Barbados, the first port that would receive us, our chosen shore excursion — a simple beach day — was conducted within a bubble. We were not allowed to explore the shoreline beyond a marker on each side of our loungers.

Constrained? Of course, and yet, following a year-plus of lockdown, I wouldn’t have traded that week for anything. The ship created its own bubble (four COVID tests in eight days!), allowing us to feel comfortable socializing with strangers, something that had been off limits for what seemed an eternity. Antigua welcomed us for a couple days, St. Lucia for another couple, and while this was a distinctly atypical Caribbean cruise, it was bliss.

For someone whose wanderlust borders on an affliction, I am incredibly fortunate to have visited many of the world’s most remote corners. And yet there are plenty of places that represent a blank page in my passport. One of them is French Polynesia, and when Windstar announced it would be moving Star Breeze to be based in Tahiti year-round, I signed us up fast.

Discovering French Polynesia

firedancers in tahiti
A private island event, showcasing fire dancers, is a favorite memory from French Polynesia

Ironically, our planned itinerary for Star Breeze, one of Windstar’s traditional Society Islands routes, was blown off course by a typhoon. The good news is we wound up in the exotic Marquesas Islands and, even better, we did the unimaginable: Spontaneously, we took advantage of an extra cabin to extend our trip, part of Windstar’s fabulous back to back program. “I’m retired,” Chris said with a grin. I could work while at sea, I reasoned.

And once again, joined by a whole new cast of characters to share the staggering beauty of Polynesia with, we ambled through the Society Islands at an easy pace. We e-biked around two islands, we snorkeled at others, and in Bora Bora, I joined a dive trip and discovered a green moray eel gawking at me from inside a crevasse. When I turned my back, it slithered from the rocks and was now sliding away on the sandy sea floor, revealing its length to be well over my own.

Throughout five different trips, the start and end of my Windstar day has stayed more or less the same: a cappuccino at dawn in the Yacht Club, with a double espresso to go, brought to my still-slumbering husband. And as sunset nears, Chris orders Negronis for us at Compass Rose before dinner. It’s the closest thing to being at home.

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