Six Spectacular Holiday Destinations for Your Family

June 20, 2019

The holiday season means something different for everyone. But no matter your point of view, it is a time to celebrate and reflect with the people you love. Whether you’re looking for a big family celebration, a quiet couple’s escape or a unique cultural exploration, ’tis the season to get away and share an unforgettable holiday adventure. So gather your nearest and dearest and go make some memories.

1. Party in Paradise: Tortola, British Virgin Islands.

Forget the snow report. Take your New Year’s celebration to the beaches of the BVI. From your pool villa on Tortola, you can contemplate your options for December 31. The big event happens on the tiny outpost of Jost van Dyke, where people from all over the world come for the raucous annual “Old Year’s Night” party at Foxy’s Bar. Jost is reachable only by boat, so charter a sailboat and arrive a day early to secure a spot in Great Harbour, where the 500 slips fill up quickly. For a more low-key scene, Trellis Bay on Beef Island, which is attached to Tortola, is the way to go. The family-friendly celebration starts at noon, but the fireworks and fire dancers continue after dark to remind everyone that the new year is once again upon them.

2. Fresh Cultural Perspectives: London, England.

A journey overseas is certain to deliver on lasting memories, and immersion into a unique culture will only enhance. Try London for Diwali, the Indian festival of lights which marks a new year in the Hindu calendar. The most well-known party happens in Trafalgar Square, where revelers can taste Indian food and watch modern and traditional dance performances. For a more intimate experience, head to the Punjabi community of Southall to shop for sweets (try the Chhappan Bhog shop) and absorb the sights and smells of Broadway, the lively main drag. Keep your camera handy: Between the blinged-out facade of the Vishwa Hindu Mandir temple, the homemade fireworks, and the flickering candles and oil lamps along the side streets, there’s no shortage of eye candy.

3. Heritage Meets History: Chicago, Illinois.

Chicago has its classic holiday hotspots, like the Lincoln Park Zoo with its shimmery light show set to music, and the Millennium Park Skating Rink, where you can glide within view of the city skyline. Add a layer of culture by visiting during Kwanzaa to reflect on the holiday’s central themes of unity, creativity and the importance of family. The DuSable Museum of African American History is the Windy City’s Kwanzaa hub: This year they’ll host a pre-holiday event with music, dance and spoken-word performances, along with daily candlelighting ceremonies all week long. Should you get snowed in by one of the city’s signature storms, you’ll be glad you booked a suite with a fireplace and a river view: Suddenly, room service.

4. Food, Fun, Family, Sun: Hilton Head, South Carolina.

You’ll have much to be thankful for if you opt for a November trip to Hilton Head Island. Sunshine is plentiful and fall temps hover in the 60s and 70s, making it an ideal time for golfing, biking or collecting shells on the beach. Feeling game? Players of all levels can enter the David M. Carmines Memorial Tennis Championship at Palmetto Dunes, which is consistently ranked as one of the country’s top places to play. For the main meal, ditch the dirty dishes and hire a private chef to commandeer your villa’s kitchen for the day. Or drive east to Savannah, where Paula Deen serves a classically Southern spread at her The Lady and Sons restaurant. You’ll leave with a new appreciation for the phrase “food coma.”

5. Just the Two of Us: South Beach, Miami.

A sexy suite high above South Beach might be an unexpected vantage point for celebrating Hanukkah. But once you try it, we bet it will become an annual tradition. This year, the holiday overlaps with Art | Basel, the most renowned show of its kind in the country. And between the chic Shops at Bal Harbour, where biggies like Marc Jacobs and Stella McCartney are represented, and the converted warehouses of the Design District, famous for its eclectic mix of home-furnishings designers, you’ll easily cobble together eight nights’ worth of glamorous gifts.

6. Idyllic White Christmas: Whistler Blackcomb, British Columbia.

Rugged enough for skiing and snowboarding addicts, urbane enough for foodies and fashionistas, and just plain fun for the kids, Whistler is the type of destination that can please almost anyone. Book a slopeside château for the family and start some new holiday traditions, like Canadian Guided Tours’ dogsled run. After zooming through an old-growth forest, your guide will give you a turn at the reins. Keep Christmas dinner stress-free, whether you dine out (try Araxi or Bearfoot Bistro) or bring in a chef from Whistler Cooks Catering to wow your crowd with pan-seared halibut or hazelnut-crusted venison. Food and fun aside, the real bonus of spending a big family Christmas here is that you’re guaranteed a white one.

There’s nothing quite like a white Christmas. Take a family trip to Vail, Colorado or Whistler Blackcomb for a picture-perfect snowy holiday adventure