Here’s Why We Love Our Multigenerational Vacations on Windstar

It’s a mild August evening at the historic Liotrivi estate in Monemvasia, Greece, and our group is transfixed by traditional Greek dancers twirling and winding through the patch of olive trees where we’ve just eaten dinner, a king’s feast of fresh olives, tomatoes, feta cheese, sausage, bread, tzatziki and wine. The trill of the bouzouki, a Greek string instrument similar in sound to a mandolin, increases its cadence, inviting the dancers to move and shift faster as they begin to grab hands of guests to dance with them around the dinner tables.

Someone beckons me to join, and I am suddenly stepping and bouncing alongside fellow guests, my hands grasping theirs in a joyous if slightly clumsy version of a Greek conga line. Although it’s Windstar’s signature event, celebrating all things Greek on the seven-day Greek Isles itinerary, it feels more like a wedding or a party.

And as I look at the table where my family is watching and clapping as the group dances around them — my husband, our two mothers, my mom’s spouse and our two teenage sons (the latter two horrified that I’m dancing, to be sure) — I’m reminded: This is why we keep coming back to Windstar with family. In fact, out of nine Windstar cruises, our first a honeymoon trip from Rome to Barcelona in November 1999, we’ve experienced eight of them with some combination of our parents and/or kids.

Here’s why we love these cruises for multigenerational vacations:

Seamless sightseeing

Let’s face it: Family vacations are often stressful. There’s the headache of multiple agendas, pieces of luggage, personalities, and timetables that offer plenty of opportunity for conflict. Add in the stress of traveling from place to place — requiring constant packing and repacking — in a short amount of time, and the chances for conflict only increase. But cruises eliminate that chaos, allowing more time for enjoying a place while eliminating the tension caused by getting there with everyone’s belongings and sanity intact. (That doesn’t even account for finding restaurants to please everyone’s taste buds.)

And on a Windstar cruise, there are few days at sea, allowing the group to visit a variety of ports without the strain of figuring out how to get there. You simply wake up and — voila! — you’ve arrived. Bonus? Onboard restaurants can please even the pickiest of eaters (myself and younger son included!). 

Free time for all

Cruises offer multigenerational guests the unique opportunity to travel as a group without demanding everyone spend the day in the exact same way because there are a variety of options. Like any self-respecting teen, for instance, my boys would rather sleep late than get up early every day of vacation for a tour. So while they and my mother-in-law happily slept in, the rest of us disembarked in Nafplio, located in the Peloponnese Region and the original capital of modern Greece, to tour the archaeological site of Mycenae. That included viewing the famed entrance to the Bronze Age citadel, Lion Gate, and the beehive tomb known as the Treasury of Atreus (or the Tomb of Agamemnon) — then finishing at the 17th-century Venetian Palamidi Castle, perched 999 steps above the city. Throughout the day, my boys were swimming and kayaking off the ship’s water-sports platform and there was no teen grousing to be heard. 

 Fellow passenger Nic Campos, 25, loved being able to enjoy activities on his own while traveling with his Aunt Sylvia, who took him on a Greek Isles cruise to celebrate his recent graduation from Houston’s South Texas College of Law. “There have been times where my aunt just wanted to sit by the beach or enjoy a glass of wine at a local winery, and we have split up so that I can go hiking up mountain paths or check out a local soccer stadium,” says Campos, who also experienced the Lisbon to Barcelona Windstar cruise with Sylvia in 2018 following his college graduation. “It just seemed like no matter where we were during the trip, there were always options to please everyone.”

Darrell Drummond, a retired financial planner from Sedro Woolley, Washington, enjoyed the cruise with his 20-year-old grandson, the fifth trip he’s taken alone with one of his grandkids. “Seeing the world through my grandchildren’s eyes excites me,” he says. And cruising is an ideal way to visit multiple places to determine where he wants to return for longer periods. Plus, he says, “smaller ships are much more relaxing and fun.”

Small ship, big payoff

There are larger ships we’ve experienced with more restaurants and kid-friendly activities that feature elaborate varieties of entertainment, especially for families. And if a thumping bar or festive kids’ clubs are your jam, great. But you won’t find it here.

Indeed, we’ve always returned to Windstar for its simplicity and high-quality crew, where the staff knows your names and preferences. There are only a couple of restaurants, a handful of activities (which vary by cruise) like music trivia and Liars Club, a genuinely marvelous crew talent show, plus a band and a musical duo (the small sailing ships provide only the latter). But this is the place where my kids get to play card games with us and their grandparents, something we rarely get a chance to do back home, and where winning the Liars Club is a top priority. (Pro tip: Kids remember weird words way more often than adults. They’re our secret weapon.) And on the last night of the cruise, it’s also the place where my 15-year-old played his first international performance when the ship’s musical duo, a brother-sister act from Argentina, invited him to accompany them on three songs. It was an unforgettable experience for him, his family and fellow guests, and one he’d not likely have enjoyed on a larger ship. 

Everyone loves a Sail Away

There’s something extra special each night as guests begin to mill about the pool deck in anticipation of the traditional Sail Away, when the ship leaves one port toward the next. Our family typically grabs our happy-hour snacks and drinks — virgin strawberry daiquiris and rum punches are a favorite for the boys — and stake out a place to view the masts. As the ship begins to move, the dramatic start of the music, Vangelis’ “1492: Conquest of Paradise” (from the 1992 movie of the same name) begins to pipe through the sound system, and the sails begin to unfurl. Will we be able to sail tonight? I never know.

But we keep coming back to find out.