Where are you going with your family this winter? It depends on what you’re in the mood for. Snow-covered mountains or sandy beaches? Southern California or South Carolina? Fortunately, RedWeek can get you wherever you want to go during the colder months — and we can get you there at prices that beat hotels. Below, discover some winter family travel inspiration.
Tropical Escape: Grand Cayman, Cayman Islands
The Destination: A lot of Caribbean destinations lay claim to being a “tropical paradise” — but the term may as well have been invented to describe the Cayman Islands. With white-sand beaches, sparkling waters and an elegant ambiance, Grand Cayman is an ideal winter escape, with temperatures that generally stay in the mid-70s to low-80s throughout the season.
Can’t Miss Kids Activity: For an unforgettable aquatic experience, pay a visit to Stingray City. Located on Grand Cayman’s scenic north shore, the sandbars here are filled with — you guessed it — stingrays. These gentle creatures swim around visitors in three-foot deep, crystal-clear waters, making for an incredible eco-adventure for all ages.
Where To Stay: Morritt’s Tortuga Club
Rocky Mountain Fun: Breckenridge, Colorado
The Destination: Located just a short drive from Denver, Breckenridge is a favorite Colorado ski resort, with 2,908 acres of diverse ski terrain, encompassing four terrain parks, two half-pipes and 187 trails. The destination’s downtown is almost as fun as the slopes, with an array of restaurants, shops and winter festivals taking place throughout the season.
Can’t Miss Kids Activity: Breckenridge is renowned for its family friendly ski offerings. Just a short stroll from downtown, Peak 9 is the place for novices of all ages to begin their snowy excursions. Here, you’ll find areas specifically designed for families, alongside intermediate terrain if you want to climb to the next level.
Where To Stay: Grand Timber Lodge
Check out RedWeek’s Breckenridge travel guide.
SoCal Playground: San Diego, California
The Destination: San Diego is a year-round playground, but the southern California city really shines in the winter, thanks to fewer crowds and cooler temps. There are countless San Diego attractions that kids will love, from the San Diego Zoo to SeaWorld to LEGOLAND. But the miles and miles of pristine coastline may be the city’s greatest draw, whether you’re splashing in the waves at Ocean Beach or checking out the resident sea lions in La Jolla. The endless summer is real in San Diego!
Can’t Miss Kids Activity: “Can you tell me how to get to Sesame Street?” Newly opened in 2022, Sesame Place San Diego brings the magical world of Sesame Street to life, including a detailed re-creation of the neighborhood we’ve all come to love, live character interactions and much more. If you’re traveling with younger kids, this is a must-visit.
Where To Stay: Wyndham Oceanside Pier Resort
Discover some of San Diego’s best museums.
Winter Sun: Maui, Hawaii
The Destination: If you’re looking to really get away from it all during the colder months, Hawaii won’t disappoint. You’ve got plenty of options, but Maui might be the best Hawaiian island during the winter (hoʻoilo to locals). The water is still warm, the beaches are less packed, and the climate is just about perfect. Maui is renowned for its eco-adventures, with lush rainforests, gorgeous waterfalls and plenty of chances to see wildlife. Speaking of wildlife, winter is great for whale watching, with roughly 12,000 humpback whales enjoying a little winter vacation just like you.
Can’t Miss Kids Activity: You may have been on a family road trip. But you’ve never been on a family road trip like the Road To Hana. This Maui favorite takes you on a 52-mile journey through some of the most spectacular natural landscapes you’ll ever see. If the kids are Jurassic Park fans, make sure to stop at the Garden of Eden Arboretum where parts of the original movie were filmed. Keep an eye out for velociraptors!
Where To Stay: Westin Ka’anapali Ocean Resort Villas
Check out RedWeek’s Maui travel guide.
Hilton Head Island, South Carolina
The Destination: Hilton Head Island — AKA “America’s Favorite Island” — is an excellent vacation option during the chillier months. The climate is cooler, but not too cool, with daytime temperatures usually hovering around the mid-60s. It’s perfect weather for exploration: enjoy some incredible sunsets from Shelter Cove, kayak the Lowcountry waterways and bike on 60 miles of trails and paved paths that take you all over the destination. Take note: winter is seafood season on Hilton Head, with plenty of chances to enjoy the region’s famed oysters.
Can’t Miss Kids Activity: Experience the beauty of Hilton Head Island on horseback! Lawton Stables offers trail rides that are suitable for all ages and experience levels; kids aged seven and under will love their mellow ponies. The guided ride will take you through the extraordinary Sea Pines Forest Preserve, through peaceful meadows and forests.
Where To Stay: Mariott’s Surfwatch
Check out RedWeek’s Hilton Head Island’s top resorts.
Start planning your family’s winter vacation with RedWeek now.
