Explore Nantucket without the summer crowds
Once the Nantucket summer fades, this quaint island 30 miles south of Cape Cod becomes a travel afterthought — for run-of-the-mill travelers. But savvy travelers know most island businesses stay open year-round now, making this a delightfully quiet winter travel spot — and a romantic destination on the East Coast. Winter is a fabulous time to stroll Nantucket’s famous beaches. Head out to Great Point to see seals, gulls, long-tailed ducks, and Arctic birds enjoying the island’s warmer (than the Arctic) temperatures.
Driving the beach is also a blast, but you’ll need a 4×4 vehicle. You can rent one, but if you’re driving your own vehicle, you’ll need to obtain a permit to drive on the beach. It’s also wise to bring a shovel, jack, boards, and portable compressor to ensure you don’t get stuck. The effort is worth it — the views are stunning and the point is serenely peaceful. As one visitor explained on TripAdvisor: “You’ll want to stay and never go back to civilization.” The Trustee of Reservations, which oversees the point, also offers natural history and Great Point Lighthouse tours.
In town, don’t miss the popular Whaling Museum, founded in 1894 and home to a 46-foot sperm whale skeleton. The museum details the island’s whaling history and boasts a rooftop deck with amazing views. Hit the popular Cisco Brewery, where the experts will guide your drink selections, and consider staying at The White Elephant. Sure, it’s expensive (this is Nantucket, remember), but it is gorgeous, with airy interiors and plenty of island charm, and close to downtown.
Visit Pittsburgh’s world-class museums
A Pittsburgh winter is the best time to take in Steel Town’s world-class museums. Your first stop should be The Andy Warhol Museum, a seven-floor jewel celebrating the art and legacy of Pittsburgh’s most famous artistic son. Gawk at the Pop Art pioneer’s artwork, make a silkscreen, and dig through the archives (not literally), which hold 569 standard-size cardboard boxes full of Warhol’s ephemera. This collection spans a 40-year period until Warhol’s death in 1987. Admission is $25 for adults, $13 for kids.
Next, visit the August Wilson African American Cultural Center. Named for the Pulitzer Prize-winning playwright and Pittsburgh native, the AWAACC boasts three galleries celebrating African-American art and culture. A must-see is the “August Wilson: The Writer’s Landscape” exhibit, which requires reservations. It celebrates Wilson’s renowned American Century Cycle, a 10-play body of work exploring the realities of growing up black in America. The plays were inspired by Wilson’s time in Pittsburgh, and admission is free.
Don’t forget Pittsburgh’s beloved Carnegie Science Center, home to the U.S.S. Requin, a World War II-era submarine that visitors can explore. No, you can’t fire a torpedo down the Ohio River, but you can check out the Titanic Artifact Exhibition and the Miniature Railroad & Village, a detailed model that spans Pittsburgh’s history from the 1890s through the 1940s. Admission to the Center is $25 for adults and $15 for kids aged 3 to 12.
Enjoy baseball, bourbon, and fillies in Louisville
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Louisville, Kentucky, might not be as famous as other Southern cities, but its plethora of attractions and mild winter weather make it a great winter getaway. If you’re a baseball fan, you’ll want to visit the Louisville Slugger Museum & Factory ($22 for adults, $14 for kids), home to baseball’s most famous bat. Stand slack-jawed at the 120-foot bat outside the museum, and take a tour to see where these famous bats (used by legends such as Derek Jeter, Mickey Mantle, Babe Ruth, and others) are made.
After an hour or two at the Slugger Museum, take a bourbon distillery and horse farm tour (we figured bourbon after bats) through Travel The Trail. The highly regarded tour company offers tours of famous Kentucky distillers, such as Jim Beam, Wild Turkey, and Maker’s Mark, with an option to also tour famous horse farms, where you may meet an upcoming Kentucky Derby competitor. The tours can be customized, but a tour of the distilleries and horse farms will last most of the day, with an average cost of $260 per person.
If bourbon isn’t your thing, consider driving 93 miles south from Louisville to Mammoth Cave, a UNESCO Heritage Site and home to the world’s most extensive cave system. This should definitely be on your list of must-visit East Coast National Parks. Rangers give guided tours, and even if visiting in winter, the caves remain a balmy 54 degrees Fahrenheit year-round.
Sun yourself on Big Pine Key in the Florida Keys
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Escape winter and the Key West crowds by landing in Big Pine Key, a quiet, stunning part of the Florida Keys. If the beach is all you want, head to Bahia Honda State Park ($8 for parking) for white sand and turquoise waters. You can rent beach umbrellas, kayaks, and snorkel gear. If you want adventure, the highly regarded Keys Boat Tours ($145 per person) takes snorkelers to Looe Key National Marine Sanctuary, where you can swim alongside aquatic life and explore the Keys’ most vibrant reef. Keep an eye out for Atlantic bottlenose dolphins, year-round visitors to the area.
Take a day trip to Key West and visit the Ernest Hemingway House and Museum, where the famous writer lived from 1931 to 1940. The museum is open every day, and guided tours are offered. Keep an eye out for six-toed cats, descendants of the original six-toed feline given to Hemingway as a gift during his time here. And be sure to look for the penny the cantankerous writer pushed into the wet cement during the construction of his pricey in-ground pool, after haranguing the builders, “Here, take the last penny I’ve got!”
If you want to add a little luxury to your snowbird vacation, consider staying at the Isla Bella Beach Resort, (roughly halfway between Miami and Key West). The breathtaking hotel features five pools, a marina, a restaurant, and a luxurious spa. Every room has a waterfront view, and rooms start at $280 per night.
Try ice climbing in Michigan’s Upper Peninsula
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If you’re interested in incredible scenery and outdoor adventure, consider Michigan’s Upper Peninsula in winter. While the area is renowned for its spectacular fall foliage, you can also try winter rock climbing and surfing. Yes, surfing. In the winter. In Michigan. Of the two activities, Upper Peninsula rock climbing is definitely the most accessible. The Michigan Ice Fest is the oldest ice climbing festival in the country, held every February in Munising at the Pictured Rocks National Park, on the shores of Lake Superior. The festival is a mix of expert climbers and beginners. There are classes, presentations during the day, and a social every evening at a local watering hole.
Speaking of Lake Superior — winter surfing has become quite the thing on the largest of the Great Lakes. Winter surfing is not for beginners, but if you’re an advanced surfer and want to try riding freshwater waves, get in touch with Downwind Sports, with three locations in the area of Munising. The best waves can be had from January to March (not typos), when low-pressure systems generate the necessary conditions for winter surfing, so long as Superior isn’t frozen over.
If not stoked about cold-water surfing, there are also plenty of lookout points to watch surfers catch the gnarly-est winter waves you’ll ever see. To immerse yourself in the natural beauty of the Upper Peninsula, take a load off at the highly-rated Big Bay Point Lighthouse B&B, which sits on 40 acres of secluded, wooded property on a cliff overlooking Lake Superior.
Relax in paradise on the smallest U.S. Virgin Island
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If a cold-weather winter getaway strikes you as pure lunacy, you’ll enjoy the sun and sand on St. John, the smallest and quietest of the U.S. Virgin Islands. Americans don’t need a passport to visit these U.S. territories, which sit just east of Puerto Rico. On St. John, take in the rugged beauty of Virgin Island National Park, which covers two-thirds of St. John. In the park, you can snorkel and explore jaw-dropping coral reefs, hike through historic sugar plantations, and inspect ancient petroglyphs, courtesy of the Indigenous Taino tribe.
Don’t miss secluded Maho Bay Beach, much less crowded but just as beautiful as the more popular Trunk Bay Beach. Enjoy the crystal white beach or take a languid swim with sea turtles, all the while surrounded by verdant forests. For a place to stay, head to the Cruz Bay Boutique Hotel, a quaint resting spot with 14 guestrooms that is a short walk from downtown restaurants and the ferry dock. Travelers also recommend the cocktails at The Longboard, one of the island’s most famous bars. Try the Frozen Painkiller — according to one TripAdvisor reviewer, you will not regret it.
Go marching into St. Louis
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Skip crowded Chicago, though it’s another popular winter getaway spot, and head to St. Louis, Missouri, an underrated Midwestern burg with plenty to offer winter visitors. Hightail it to the awe-inspiring Gateway Arch, a breathtaking sight no matter the time of year. Finished in 1965, the Arch is part of Gateway Arch National Park, which boasts a museum delving into St. Louis’ history as the “Gateway to the West.” In the winter, the park also features scenic, placid grounds and an ice skating rink. For a better view, take the tram ride up to the Arch’s Observation Deck. Tickets cost between $15 to $19 for adults and $11 to $15 for kids.
In St. Louis, you’ll also want to visit the famed Anheuser-Busch Brewery, where guided tours are offered. Budweiser samples are on offer as you take in the history of this famous brew. During the winter, the tour includes a visit to Warm Springs Ranch to see the famous Clydesdales. Once you’re done horsing around, stroll through the 150-year-old Missouri Botanical Gardens downtown. Marvel at the outdoor sculpture garden, and be sure to stop by the Japanese Gardens, which covers 14 acres with charming footbridges and lanterns. There are also tea ceremonies and traditional music. To soak in the area’s history, stay at the stately Pennywell St. Louis, near the Arch, and relax with an old-fashioned at the Pennydrop Bar.
Explore wintry Yellowstone National Park
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For many, winter is the best time to visit Yellowstone National Park, the world’s first national park. It’s far less crowded than during the summer, and the park offers stunning vistas when covered in snow, along with access to its famous geothermal geysers. Snowshoeing, cross-country skiing, snowmobiling, and snowcoaching are popular winter activities, and they’re also some of the only ways to get around, as all park roads (except one) are closed from November 1 until the spring. The park offers a list of reputable tour guides to get in touch with.
Alpine skiers may also consider spending some time in nearby Jackson Hole, Wyoming. The area boasts top-notch ski resorts such as Jackson Hole Mountain Resort, Snow King, and Grand Targhee. When staying in Jackson Hole, get some rest at the acclaimed Anvil Hotel, offering 49 unique rooms with a stylish and laidback Western vibe, and stop by the Anvil’s sister property in town, Glorietta Trattoria, for exquisite handmade pasta and sumptuous wood-fired fare.
Frolic and eat in South Padre Island, Texas
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Florida, California, and Arizona might get the lion’s share of the sun-soaked press, but South Padre Island, Texas, offers its own stunning beaches and scrumptious seafood right on the Gulf of Mexico. This sliver of land stretches 34 miles and is a 45-minute drive from Brownsville. Edwin King Atwood County Park boasts a beautiful state beach perfect for families and picnics, with sand dunes edging up to the beach. Isla Blanca Beach, at the southern tip of the island, is secluded and stunning. It is perfect for both activities and lounging, and a long boardwalk runs parallel to the beach. Food, pavilions, showers, and restrooms dot the area, so all your needs are met.
If you’re looking to get onto the water and see marine life, seek out Fins to Feathers, a highly-rated local outfit specializing in dolphin watching. For 18 years, the company has been taking no more than six people at a time onto its 35-foot catamaran. The company claims the dolphins in Laguna Madre Bay “know them.” On Tripadvisor, reviewers confirm this, with Stephanie R. writing, “The dolphins were playing right around the boat, so we were able to see them up close.” Once your adventure at sea is over, pay Dirty Al’s a visit. This classic South Padre Island haunt is famous for its Oysters Rockefeller and other locally sourced fare.
Warm up in the exclusive Dunton Hot Springs
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Sure, you could spend your winter vacation hob-nobbing with the hip set in Telluride, a popular Colorado ski destination. But why do that when you can relax in utter seclusion at the luxurious and all-inclusive Dunton Hot Springs, which features 24-hour access to multiple geothermal hot springs? The hot springs, ranging in temperature from 85 to 106 degrees Fahrenheit, and their boatload of minerals, are available to guests 24/7. As a guest, you’ll have access to yoga, massage sessions, a library, coffee (made to order) delivered to your door every morning, and 5-star accommodations and food. WiFi is available, but cell service isn’t.
This chic, isolated resort sits 8,850 feet above sea level, nestled in the San Juan Mountains. Located on the site of an 1800s mining town, the resort has integrated (and refurbished) the town’s surviving structures, including the original dance hall and saloon, as part of this spectacular getaway. Each room is unique — one even features the original copper tub miners would use.
Dunton Hot Springs sits 73 miles southwest of Telluride. Ranging from $1,300 to more than $4,000 per night, depending on the suite, this experience isn’t cheap. But if you can swing it, you just might feel reborn after spending time at this rejuvenating spot.
Enjoy the Homestead Crater and skiing in Midway, Utah
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The Homestead Crater sits within The Homestead Resort in Midway, Utah, with rooms starting at $169 a night. The crater offers a refreshing geothermal experience below 55 feet of limestone and is thought to be around 10,000 years old. Resort guests can sign up for one-hour time slots in the crater, where they can relax in the 96-degree spring water, or snorkel and gaze at the crater’s incredible walls. Guests must wear a lifejacket while swimming, and don’t forget to bring a towel.
Midway, located within Utah’s Heber Valley, is close to other activities besides “crater-ing.” Excellent skiing is nearby, with Park City Mountain Resort just north, or you can check out the Utah Olympic Park for winter fun. Sundance Resort is just a half-hour’s drive southwest of Midway. If you’re hankering for some snowmobiling, rent a rig from Daniels Summit Lodge to access more than 200 miles of snowmobile trails. Also, Salt Lake City and its charming Western vibe is just under an hour’s drive away.
Visit the Big Island for Hilo and volcanoes
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Don’t get us wrong — parts of Hawaii are very crowded and very much not underrated. But for a quieter and out-of-the-way Hawaiian getaway, check out Hilo and its surrounding area on the lush and green Big Island. The star of Hilo is undoubtedly Hawaii Volcanoes National Park, home to two of the world’s most active volcanoes —Kilauea and Mauna Loa. Take a guided tour of the Park with Kilauea Ecoguides, a reputable and highly-rated tour company, for up-close and personal (not that close) looks at these incredible natural landscapes.
In town, visit the Hilo Farmers Market, featuring vendors selling fresh seafood, produce, coffee, and art celebrating Hawaii’s culture. For a secluded stay, relax at The Inn at Kulaniapia Falls, a beautiful, Asian-inspired hotel nestled amid 22 private acres. The Inn sits just 15 minutes from Hilo but feels a world away. The Inn is also home to Hawaii’s largest, privately accessible waterfall, where guests can go on guided, 120-foot rappels to the bottom of the falls.
