Top Four Winter Family Getaways by New Canaan Travel Advisor, Michelle Jackson - New Canaan & Darien Moms
With fall in full swing and temperatures starting to drop, now is the perfect time to start planning your next family vacation. But the pressure of choosing a destination that everyone will love can feel overwhelming! So we brought in New Canaan mom and SmartFlyer travel consultant, Michelle Jackson, to share a few of her favorite destinations for a winter retreat.
1. Puerto Rico
Just a quick 4-hour flight from New York’s LaGuardia Airport, 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.
📷 Dorado Beach, a Ritz-Carlton Reserve
2. 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.
📷Jumby Bay Island, Oetker Collection
3. Montana
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, for instance 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.
📷The Resort at Paws Up
4. Disney
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!”
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.
📷Four Seasons Resort Orlando at Walt Disney World Resort

Ready to stop daydreaming and start planning? Contact Michelle at [email protected] to begin discussing your next family getaway.

Author Bio:

Michelle resides in New Canaan with her husband and two active children who enjoy sand in their toes as much as she does. Her career in the hospitality industry was inspired by a love of travel that began studying abroad in Italy and was deepened after traveling extensively through places like the Adriatic Coast, South Africa, Mexico and the Caribbean. Her favorite vacations are those that balance a variety of activities for her busy family as well as ample time for leisure and relaxation.

Michelle’s extensive travel experience has taught her that proper planning ensures enjoyable travel experiences that are memorable for all the right reasons. She looks forward to helping New Canaan & Darien families plan the itineraries to escape their stress and create lifelong memories.

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