Note: All travel is subject to frequently changing governmental restrictions—please check federal, state and local advisories before scheduling trips.
Travel came to a screeching halt in 2020, turning planned vacations into virtual escapes and “maybe next year” aspirations. But now hope is on the horizon that we all might soon be able to pack up the entire crew and travel again. If you’re unsure of where to go to make the most of your newly regained freedom, you’re in luck: Here’s a list of 12 great trips to take—one for every month—no matter what year it is.
January: Breckenridge, CO
Outdoor activities like skiing, snowboarding, fat-tire biking, and mushing a team of huskies through fresh powder make Breckenridge a perfect cold-weather getaway. Plan for a midweek trip. Fewer people are around, and you can typically snag cheaper lodging and lift ticket deals.
STAY The Lodge at Breckenridge
February: Blue Ridge Mountains, NC
Escape to the Blue Ridge Mountains for one last winter adventure before spring hits. Lift lines are shorter at Sapphire Valley Resort, giving guests more time to zip down the 1,600-foot snowboard and ski runs. Feel like tubing? Race the family down Frozen Falls Tube Park’s multi-lane steep descent. Visit mid-month to laugh and cheer on racers during The Great Outhouse Races.
STAY Club Wyndham Resort at Fairfield Sapphire Valley
March: Scottsdale, AZ
Warm weather and high-desert sunshine greet you in Scottsdale. Head out to MacDonald’s Ranch for horseback rides and tasty cowboy cookouts. Float through the sky at sunset on a hot air balloon. If your favorite baseball team is in town, enjoy hot dogs and cracker jacks at the ol’ ballpark during spring training.
STAY Mountain Shadows Resort
April: Hill Country, TX
Take a scenic drive from San Antonio to Austin to kick off road trip season. First, soak up San Antonio’s history and local flavors with a stroll down the River Walk. Fiesta celebrations—which commemorate the Battle of the Alamo and feature parades, live music and sporting events over 17 days—take place in the middle of the month. Next, head into Hill Country via TX-16 to reach Bandera and experience the cowboy way. Authentic German dishes and wineries await in Fredericksburg. When you reach Austin, pop in your ear plugs: It’s the “Live Music Capital of the World” for a reason.
STAY Hotel Havana
May: Key West, FL
May is a good time to put the top down and cruise the Overseas Highway to Key West. When you get there, azure blue waters, shipwrecks and reefs have much to offer snorkelers and scuba divers. Kayaking and paddleboard tours are a must. A ferry ride lands you on Dry Tortugas National Park, a unique eco-attraction and one of the least-visited parks in the country.
STAY The Perry Hotel
June: Crooked Road, VA
Floyd’s toe-tappin’ Friday Night Jamboree at the Floyd Country Store makes the town a must-stop destination on The Crooked Road, Virginia’s 300-mile music trail. Stay a few days in June during the region’s Mountains of Music Homecoming. Music is played everywhere from inside historic venues to street corners and alleyways.
STAY Tru by Hilton Radford, VA
Beaches, rainforests, malasadas and mountains. Maui, Hawaii’s second-largest island, has it all. Shop, eat and snorkel on the island’s west side in Lahaina and Kaanapali. A traditional cliff dive ceremony takes place outside the Sheraton Maui Resort & Spa. Break for fresh banana bread on the Road to Hana at Aunty Sandy’s. Hang with goats or sample pineapple wine in Makawao and watch the sunset atop Haleakalā.
STAY Sheraton Maui Resort & Spa
August: Mackinac Island, MI
Reach Mackinac Island by ferry (that’s the only way) on August 27 and you’ve arrived in America’s fudge capital just in time for its annual festival. Celebrate with concerts, fudge-making demonstrations and, of course, sampling each delicious variety inside the many shops. August weather is perfect for guided hikes, horse-drawn carriage rides and sailing.
STAY Lake View Hotel
September: Vancouver, Canada
Boutiques, health-conscious restaurants, and top-notch museums make Vancouver a go-to urban playground. Raft, mountain bike and kayak to explore the surrounding natural splendor. Love sampling local flavors? Take a guided tour through Granville Island’s public market.
STAY Opus Vancouver
October is more like spring season in Aruba, bringing 80° temps and brief rain showers to cool off the island from time to time. Hotels typically slash their prices in spring, as well. Lounge on the beach and enjoy water sports at Eagle Beach and Palm Beach. Shallower waters and easy waves at Baby Beach make it great for younger kids. Explore nature in Arikok National Park.
STAY Aruba Marriott Resort and Stellaris Casino
November: Argentine Patagonia
If there’s one epic outdoor adventure to take in November, this is it. Jaw-dropping scenery and reasonably priced lodging options make the trip worth your effort. Hike to penguin habit in Puerto Tombo. Whale watch when visiting Peninsula Valdés in Atlantic Patagonia. The Lake District offers great hikes and horse riding. And no trip is complete until you savor traditional cuisines and relax in the quaint lakeside villages.
STAY Chalten Suites Hotel
December: Prague, Czech Republic
During the holidays, Prague becomes an enchanted Christmas wonderland. “Pa-rum-pum-pum-pum-ing” school choirs and caroling sing-alongs take place in Old Town Square and in nearby Wenceslas Square. Shop for holiday gifts in their Christmas markets. Sample trdelník, a delicious hollowed-out pastry dough covered in cinnamon sugar and topped with ice cream. Walk the Vltava River for radiant views of the city at night, then end your day with a five-course meal and live classical music at Café Mozart.
STAY BoHo Prague Hotel
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