7 Reasons a Windstar Cruise is the Perfect Multigenerational Trip

When kids are young they need all sorts of entertainment on vacation — that’s where the large cruise ships come in. These massive cities on the sea keep one-upping themselves with waterslides, wave riders, ropes courses, game rooms, rock climbing walls and family-friendly shows from huge, open amphitheaters. But as kids turn to teens and teens to adults these distractions and diversions can actually take away from what you really want: quality time together. And this is where a cruise on a small sailing ship can be the perfect choice for a vacation.

Windstar operates six yachts including three sailing ships — one of which, the Wind Surf, is one of the largest in the world. But don’t let that distinction throw you. With a maximum capacity of just 310 guests, as well as 214 crew, the focus is on personalized service and a curated experience, which translates to a memorable journey for your multigenerational family. I recently sailed on the Wind Surf on Windstar’s Classic Caribbean itinerary, a week-long trip during which we visited St. Maarten, Barbuda, Dominica, St. Lucia, Guadeloupe, St. Kitts and St. Barth’s. Here’s why you should coordinate calendars and book your own Windstar adventure today.

Kelly and Captain Pedro Pinto

The service is friendly, personable and unparalleled.

The ratio of guests to staff on the Wind Surf approaches 1:1, which is quite impressive. Not only did many of the crew greet me by name at meals, they also knew my cabin number when I was ordering a drink. This means the maitre d’ will be more than happy to get your family a preferred table, the bartenders will probably bring your crew your favorite beverage before you even order and the activities director will make sure you can all get on the excursions you want to experience.

No set seating times for meals means your family can roll in whenever everyone is ready.

Maybe mom and dad are soaking in the hot tub with a margarita while the kids and kids-in-law are off ziplining in the forest on St. Lucia or taking a sunset cruise on St. Kitts. The point is, wrangling your group to make that 7 p.m. dinner seating when everyone is doing their own thing can be challenging. The main dining room on the Wind Surf has open seating from 7–9 p.m., with hardly, if ever, a wait and the menu is à la carte, not buffet (no dinners on the ship are buffet, by the way.) While the other two specialty restaurants (French-focused Stella Bistro and Candles on deck) do require reservations, they can be arranged as late in the day as you want to dine. I also just showed up once at Candles and was immediately escorted to a table. After all, isn’t easy breezy flexibility — rather than hurrying up and showing up — what laid-back family vacations are all about?

Can’t rally everyone to go ashore but still want to spend the day together? Jump off the back of the boat.

When the Wind Surf was anchored out in the harbor (i.e. on days where we had to take a tender to port instead of being docked right there) and conditions were favorable (it wasn’t too choppy or windy), the crew opened up the Water Sports Platform. Located aft on the ship, it’s a way to explore the water with included and unlimited use of equipment, including stand-up paddle boards, single and double kayaks, snorkel gear, water skis and windsurfing. I headed there the morning we moored near Les Saintes in Guadeloupe. All of the above sounded a tad too taxing, though, so I swam out to hang out on one of the large tethered floats. The attendants had also set up a large inflatable trampoline to lie on, or jump off, or unknowingly launch your sibling from as they were obviously catching some rays. The platform also has lounge chairs, a shower and cubbies for your belongings. Try doing any of that on a large ship.

Water Sports Marina. Photo: Kelly Magyarics

If you come from a family of navigational nerds you’ll geek out over Windstar’s open bridge policy.

As long as the Wind Surf is sailing and the door is open you can visit the bridge any time of day or night. While I can’t claim to know too much about sailing (and those instrument panels really meant nothing to me) it was so cool to pop into the bridge at sunset or in the evening after dinner and chat with the officers. Captain Pedro Pinto even took a selfie with me. I also got some tips on the best nights and times for stargazing based on the phase of the moon, the weather and light pollution depending on where we were traveling, and the officers used the radar to point out the other vessels — from cruise ships to private yachts — that were in nearby waters.

Open Bridge. Photo: Kelly Magyarics

… and the fact that the ship actually can sail.

Each afternoon or evening when we left port the sails were unfurled and Windstar played its theme song, “1492.” Though it doesn’t happen often, I did find out one day that the ship was able to sail solely on wind power for several hours, which makes the whole voyage more authentic (and makes for great IG photos of the sails flapping in the breeze.)

Wind Surf at night. Photo: Kelly Magyarics

Creole chicken at cooking class on Dominica. Photo: Kelly Magyarics

Your family just might end up having an excursion all to yourselves.

On large cruises guests are often corralled into dining rooms to be ushered on buses for excursions with 50 to 100 of your closest friends. Not so on Windstar. There were at least a handful of options in every port, from island tours to snorkeling to catamaran cruises, all of which were attended by intimate, manageable groups. I took a cooking class on Dominica that was just a handful of other guests during which we cooked and ate Creole chicken, red beans and rice in coconut milk and fried plantains and learned about the benefits of the various spices and herbs that grow on the island. It all made for a fab afternoon a culinary-focused family would highly enjoy.

Evening are low key … in a good way.

You won’t find any pulsating discotheques, magic shows or Vegas-style reviews onboard this ship (and I don’t consider that a bad thing). What you will find is a band, bar and ample tables in the Wind Surf Lounge (there is a dance floor, too), and seating under the stars and live music in the cozy Compass Rose bar, my favorite watering hole on the ship. Either spot is great to cap off the evening with your family.