Top Six Winter Family Getaways

Contributed By Michelle Jackson

With fall in full swing and temperatures starting to drop, now is the perfect time to start planning your next family vacation.

Choosing where to take the kids can be daunting. With varying ages and interests, we know how hard it can be, but that’s what our travel advisors are here for. As a mom of two and expert in family travel, we chatted with Connecticut-based travel agent Michelle Jackson to hear her top picks this season.

Puerto Rico

Dorado Beach

Dorado Beach, A Ritz-Carlton Reserve

Just a quick 4-hour flight from New York, Puerto Rico is a great destination for families with only a few days to unwind. Post-Hurricane Maria, the island of Puerto Rico has made a full recovery and invested millions of dollars in renovations. Resorts are back stronger than ever and ready to welcome tourism with the knack for service they’ve long been known to provide guests for decades! Dorado Beach, a Ritz-Carlton Reserve particularly stands out after its October 1st reopening, complete with a fresh facelift sure to wow families.

Kids of all ages will enjoy the Watermill, an aquatic playground designed after a traditional Puerto Rican sugar mill, complete with 30-foot waterslides, lazy rivers and multiple pools. Through the resort’s Goodwinds Water Sports program, guests can kitesurf, paddle and sail their days away! Plus, when the kids get hungry for lunch at The Watermill Grill, mom and dad can use the resort credit received when booking with a SmartFlyer advisor.


The Resort at Paws Up

Paws Up Resort

for a family adventure away from the beach

If you’re looking for a family adventure away from the beach, The Resort at Paws Up offers a phenomenal winter program. Known for their outdoor activities like skiing, snowmobiling and ice skating, there’s non-stop action here! Plus, if you’re going over the holidays, families can enjoy horse-drawn sleigh rides, gingerbread house contests and their New Year’s Eve party, where American Idol’s Chrystal Bowersox was last year’s musical performer.

For moments when mom and dad want to do some adult activities, book a day at the spa and enjoy a Brown Butter Sugar Cookie Hot Stone Massage, the young ones can hang at the Kid’s Club. Paws Up Little Explorers programs starts at age three, or the Kids Corps of Discovery for the older kids has a half or full day program offering age appropriate supervised activities.


Jumby Bay Island

Jumby Bay Antigua

For families looking to take advantage of the seven days off from school (or, twelve if you have a preschooler, but who’s counting?), Jumby Bay Island just off the coast of Antigua is the perfect spot. This destination will have you in a complete state of relaxation before your first sundowner! Plus, the entire property was designed with families in mind, but doesn’t sacrifice an air of sophistication married with island vibes.

Jumby Bay is an all-inclusive property offering three unique restaurants (none of which have a strict dress code), so you can truly just stay put. With daily activities like water skiing, snorkeling, sunset cruising, cooking classes and rum tasting included in the rate, why would you ever want to leave? To top it off, the resort’s kids’ program, Jumby Explorers, offers outdoor excitement tailored for children ages three and up. The Hawksbill Turtle Program is unique to Jumby Bay and allows youngsters the opportunity to participate in the island’s conservation efforts, too.

Walt Disney World®

Four Seasons Resort Orlando

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Four Seasons Orlando is redefining the meaning of the “Most Magical Place on Earth!”

Although it might not be on the top of your bucketlist, Disney® is an iconic family destination for a reason. In order to make your trip as comfortable as possible, a stay at the Four Seasons Resort Orlando at Walt Disney World Resort is highly recommended. The property’s indulgent spa, Tom Fazio-designed golf course, four eclectic dining options and Kid’s Club (available for ages four and up), will show you how Four Seasons Orlando is redefining the meaning of the “Most Magical Place on Earth!”

With a perfect blend of Four Seasons experiences and Disney offerings, including access to EXTRA MAGIC HOURS benefit and DISNEY FASTPASS+ up to 60 days prior to arrival, magical moments are practically guaranteed. When you head back from the park, Four Seasons will be your oasis from a jam-packed day. The resort’s family pool transforms into a dive-in movie theater every Saturday night, showcasing Disney classics, of course! Avoid the chaos of Magic Kingdom at night and view the firework spectacular from Four Season Orlando’s rooftop restaurant, Capa.


Mustique Island

A private island in the West Indies about 100-miles west of Barbados, Mustique is a hidden gem often overlooked by even the most seasoned Caribbean travelers. But to know Mustique is to love it, evident in its history of being a favorite spot for British Royalty, actors, musicians and moguls. The beauty of this 1400-acre private island is that despite its impressive guest list, the vibe is completely low-key. Families return annually because its ethos is about a return to authenticity and community. Here, you’ll be welcomed with open arms; from Tuesday night’s Island Cocktail Party to the 22 picnic spots around the island.

When it comes to accommodations, a villa rental is recommended to truly embrace the life of luxury this oasis offers travelers. Your travel agent can help you choose the perfect villa for your needs, and whether it be in the hills of the lush landscape or closer to the beach, you’ll be taken care of by house staff who handles meals, laundry service and of course, housekeeping. They’ll also come along for the day as you beach hop to explore activities like daily yoga, tennis, snorkeling, kayaking and nature hikes.

Park City, Utah

Montage Deer Valley

Interested in visiting North America’s #1 ranked ski slopes this December? Montage Deer Valley is a fantastic destination located in Park City, combining the love of the great outdoors with the charm of Park City’s robust ski village. As a true ski-in ski-out hotel, Montage Deer Valley aims to make ski experiences carefree for families.

Montage Deer Valley
Montage Deer Valley

During weekends in December, the resort offers Family Tubing Nights, an opportunity for all ages to enjoy Utah’s magical alpine setting. Paintbox, the resorts children’s program, offers outdoor activities including mountainside scavenger hunts and snowshoeing for children ages 5-12. A visit with the hotel’s canine ambassadors, Monty and Parker, is not to be missed; these beloved Bernese Mountain Dogs love playing in the snow and posing for family portraits! After one trip to Montage Deer Valley, you’ll see why families traveling with multiple generations choose this property to return to year after year.

Contact Michelle today to begin planning your family’s next retreat.

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