The wrath of the winter weather is quickly approaching and, with the onset of snow and sleet, mittens and misery, you may be thinking of planning an escape in the upcoming months. But where to go? If you’re traveling with the kids, here are some of the hottest family friendly destinations this winter and holiday season. 

Cruise the Caribbean:

nieuw-statendam Holland America

Half Moon Cay, Holland America, CruiseCruising is a great way to experience multiple destinations without the hassle of having to pack and unpack. I’ve discovered that it’s especially great when traveling with kids!

Holland America Line has a brand new ship called Nieuw Statendam and will offer 3, 4, 7, 10 and 14-day itineraries starting this December 2018-October 2019. The ship will be sailing from Fort Lauderdale, Florida and will cruise all through the Caribbean and Bahamas. One of the highlights is Holland America Line’s private island called Half Moon Cay. It’s been voted (several years running) as one of the top rated beaches in the Bahamas. Guests can go snorkeling, kayaking, horseback riding or just relax, and best of all, there’s a new water park for the kiddos.


horseback riding excursion for families Holland America
On board Holland America Line has Club HAL with a plethora of activities for kids of all ages, and for parents, there’s the Rolling Stone Rock Room (where you can let loose and break out your air guitar), as well as partnerships with America’s Test Kitchen, Billboard, Lincoln Center, BBC Earth and O, The Oprah Magazine (seriously, the list goes on and on). As a fun side note, Oprah was recently named Nieuw Statendam’s godmother, and she and bestie, Gayle King, will be onboard for a 3-day Girls’ Getaway cruise through the Caribbean Jan. 30, 2019. Check out to learn more about the new ship and upcoming Caribbean adventures



You can never go wrong with Hawaii. During the winter months, Oahu’s North Shore is a great choice for the family traveler. This part of the island offers up an authentic local surf vibe with delicious food truck cuisine, unique art galleries and jaw dropping big wave surfing competitions. During our trip last year, one of my favorite places to take the kids was Waimea Falls. Hiking through this sacred place with some 700 years of native Hawaiian history under its belt, you’ll see a reconstructed ancient village, several archeological sites, indigenous birds and vibrant orchids. The hike ends at a cool mountain waterfall where you can slip in for a memorable (albeit very chilly) swim. Check out my full story on traveling with the family to the North Shore.

One of the places on my personal 2019 hit list is the island of Kauai. Known as the Garden Island, it’s home to incredible flora from mountain to ocean. Between the Waimea Canyon (dubbed The Grand Canyon of the Pacific ) and the dramatic sea cliffs of the Napali Coast, there seem to be no shortage of incredible things to do there. There is a brand new oceanside hotel that just opened up on the island called Hokuala by Timbers Resorts. It looks like a gorgeous property and, best of all, it offers immersive cultural experiences for the kiddos. They can learn about endangered Hawaiian monk seals, palm frond weaving and haku lei making through art and play.

Valparaiso, Chile

Winter is a great time to visit South America. Remember that the Southern hemisphere seasons are reversed so their summer  is roughly November to February. One of my favorite countries is Chile. It’s extremely diverse and very affordable. In one day, you can go from skiing in the Andes mountains, to sweating it out in the world’s driest desert the Atacama. From there check out Valparaiso, a charming town along the Pacific where you can tour graffiti murals. Amazing culture, food, wine and there’s something for everyone here.

Circling back to cruising as a travel option to visit multiple destinations, Holland America Line offers a number of South America and Antarctica cruises this winter visiting Chile, Brazil, Argentina, as well as cruising along the Amazon River and circling around South America’s southernmost point to Antarctica.

Southhampton, Bermuda

boy Baby Beach Bermuda

Just a two-hour flight from New York City, Bermuda is a great choice for an easily accessible, high-end, family-friendly getaway. This proximity means that East Coasters can quickly go from the drudgery of winter weather to basking on the pink-sand beaches in paradise. I just got back from a trip to Bermuda with my 2 and 4 year old and it was an awesome spot for families. It has some of the nicest beaches, with powder sand and turquoise waters. My favorite beach for little swimmers is Baby Beach, located at the western end of Horseshoe Bay Beach in Southampton Parish. It’s a calm, shallow, naturally formed pool framed by picturesque rocky outcrops. From secluded beaches to historic pirate ships, kid-friendly restaurants to lighthouses and aquariums, there are plenty of activities for the whole family. If you do decide to vacation in Bermuda, be sure to check out a baby equipment rental company called Little Long Tails. They rent everything from cribs to car seats, toys to strollers. This service saves you from having to lug around all your gear during your travels. Simply make your booking online and your desired gear is delivered straight to your hotel. Super helpful, and, having access to books and toys in my room kept the kids entertained during our ‘down times’ in the hotel room. We stayed at the Fairmont Southhampton, my top choice for families with young children. Beyond their epic beach, the Fairmont has a dedicated play space with childcare, kiddie pools with slides and beach toys.


boy snowboarder colorado kids ski resort

One of the oldest ski towns in the region, Steamboat Springs remains one of the top family friendly resort towns in North America. Steamboat has a great Kids Ski Free program where children under 12 can ski free, for the same number of days as their parents’ passes. My husband and I visited last year (with the grandparents and the kids in tow) at stayed at Moving Mountains, Steamboat’s luxury property management company. It was this amazing multi-bedroom suite with a fully-equipped kitchen and laundry facilities. We were able to chill fireside with the fam and cook together in our very ‘homey’ condo. This was the perfect place for a multi-gen trip, plus traveling with built-in babysitters means you can get the parents to watch the kiddos while you hit the slopes.

I’m an Epic Pass holder so I’m planning to take the kids for their first ski experience this winter at resorts in Vail, Breckenridge, Crested Butte and Keystone (one of the most family friendly).

Keystone offers free Kidtopia programming throughout the village, with daily events like a parade with floats, dancers, music and free cookies. They have also offer a free play space for the kids who want to take a break from the slopes to build some giant Lego, craft and bun off some energy. Really great ski town for families. They also have a great Kids Ski Free program which is available to kids under 12 every day the entire season (including weekends and holidays) when you book just two nights of lodging.

Expert Budget Saving Tip:

If you’re on a budget, have flexible travel dates and are open to adventure, let “chance” decide your next family vacation. Go to Scott’s Cheap Flights, one of the best resources out there for flight deals. Sign up for one of their email alerts and their travel experts will send you hand-picked deals and mistake fares.  When I see an affordable deal I like, I pounce. It’s the deal itself that will determine my trip, not the actual destination. That said, that style isn’t for everyone. If you’re already set on a destination but not sure WHEN you should book your air and hotel travel to score the best deal turn to Hopper. Hopper is an awesome app that helps you determine the best times to fly and buy. It also suggests alternative airports and airlines to help you save money.