Traveling in itself requires some confidence as you escape to an unfamiliar territory, but doing so alone is a whole new ball game. Flying 35,000 feet in the air hundreds or thousands of miles from home can be scary but also very rewarding and eye-opening.
Pushing yourself out of your comfort zone to travel solo may require finding a destination where you feel secure and welcome. Luckily, the U.S. has plenty of impressive parks, modern cities, quaint historical towns, alluring valleys, and gorgeous waterfalls perfect for spending your winter safely soul searching.
The Best Solo Winter Trips to Meet New People
Being alone in your travels doesn’t have to mean spending it feeling lonely. If you’re looking to put yourself out there to meet travelers like yourself, these are the best solo winter trips to plan.
See things from a new perspective or simply searching for a healthy dose of friendliness, these locations fit the bill.
1. Boston, Massachusetts
Whether you’re a sports fan, history junkie, or just looking to explore charming cobblestone streets, Boston has something for every type of traveler. Located right on the coast, the city is easily accessible by car or public transportation.
Deacon Giles Distillery
Boston can be especially cold in the winter so warm up on a tour of the Deacon Giles Distillery to learn about the manufacture of spirits like Liquid Damnation. After sampling some of the best booze, mingle with other members of the group.
Visit the Speakeasy Lab to sip on original cocktails made from their own distilled-on-site spirits and be whisked back to the days of Prohibition.
2. Honolulu, Hawaii
One of the best solo winter trips you’ll ever take is to Honolulu where locals welcome a refreshing Aloha to everyone who visits. Honolulu is a melting pot of different cultures and nationalities, combining both urban oasis and tropical landscapes. With temperatures in the low 80s, the options of things to do are limitless. Explore the great outdoors kayaking, snorkeling, sailing, scuba diving, or hiking. Bond with fellow globetrotters over the impressive volcanic views Diamond Head has to offer. In the evening, catch an uber to the city to enjoy a tropical drink at Mai Tai Bar.
Makapuu Point
This historical place to visit is one of the best sites for body surfing or watching the whales pass through between December and May. Take a tour of the active lighthouse, a shining beacon built in 1909 on a 600-foot sea cliff overlooking the gorgeous beach.
3. Page, Arizona
Horseshoe Bend and the famous Antelope Canyon will simply blow you away. You can expect more tourists in Upper Antelope because it doesn’t involve any climbing whereas Lower Antelope involves some stairs and ladders. If you’re up for it though, Lower Antelope has some incredible photo opportunities. This part of the world attracts so many like-minded travelers so you’ll have no problem chatting with other campers nearby. Page is a mecca for outdoor enthusiasts but the temperature does dip into the 30s so be sure to pack a warm winter jacket.
The Grand Staircase Escalante
Step through geologic time at the massive national monument full of colorful cliffs and dinosaur remains. Touring this enchanting area makes you feel like you’re somewhere ethereal. For an epic adventure and an adrenaline rush, spend a few hours exploring the vast land in a UTV.
4. Portland, Oregon
Portland has an unbeatable cool factor and is often underrated. You’ll never get bored in this incredibly hip city that has Japanese gardens, bookstores galore, unique boutiques, and a legendary culinary scene. You can’t get much cooler than a city with a Hipster Santa Claus. Bundle up and prepare for some frequent rain showers but don’t let that deter you from a bar crawl to sample beers from 75+ breweries.
The Witch’s Castle
If you’re looking for something a little less “been there, done that” and a little more (creepy!?) and cool, bust away from the city and hike to the Witch’s Castle. This dilapidated house has been taken over by vines creeping up the structure. Located in the southernmost end of Portland’s Forest Park, it’s definitely a sight to see and a legend to google.
5. Orlando, Florida
Planning a solo trip to Orlando may seem intimidating or overwhelming but who wouldn’t want to take advantage of the single rider lines at the happiest place on Earth or sip on butter beer at the Wizarding World of Harry Potter? Aside from being the Theme Park of the world, there’s plenty to do in Orlando other than hitting up a park. Visit the Wheel at ICON Park, the Kennedy Space Centre, or Wax Museum Orlando. You’re bound to meet some friendly faces along the way. Orlando is a dream warm weather getaway with temperatures in the 70s all winter long.
A Day on Park Avenue
Take yourself on a day date to Park Avenue in Winter Park for some of the best dining and shopping in the Orlando area. Start at Atlantic Beer & Oyster (ABO) in the Hidden Garden courtyard and enjoy one of the many craft beers and shuck some oysters from the East ,West, and Gulf coast. Once you finish up your lunch, stroll down the avenue to shop at the many unique boutiques.
Ideal Destinations for a Party of One
We all need a little me time from time and again, whether that’s on empty white sands or sitting by a fire in a quaint cabin in the dense forest. Below are some of the best solo winter trips if you’re looking to take a little time out.
1. Asheville, North Carolina
Tucked away in the Blue Ridge Mountains, Asheville is the picture perfect space for solitude. The options for places to stay are endless from the luxury Omni Grove Park Inn to the famous Biltmore Estate with three lodging accommodations on its 8,000-acre property. If you’re seeking seclusion, scale new heights in a treehouse or glamp in a dome. The breathtaking natural scenery of Western North Carolina is just waiting to be explored. Take advantage of Asheville’s Hike Finder to plan your hikes based on skill level and accessibility then wind down at the Shoji Spa and Lodge, nestled on a mountainside.
French Cuisine with a Twist
Eating is a serious thing to do in Asheville, likely because it’s known for its chef-driven and award-winning restaurants. The ultimate culinary finesse can be found at Isa’s French Bistro where innovative, seasonally-inspired French cuisine is served. The elegant bistro celebrates freshness of the season’s harvest and local produce by creating specialized menus to give you a memorable experience.
2. Big Sur, California
Check out of reality along the coast of the gorgeous Pacific Ocean. Big Sur is a bucket list destination with some of the most beautiful campgrounds in the country. The off season is the perfect time to go because winter promises easier lodge reservations and the chance to stay in a souped-up campsite for the ultimate glamping experience. The magic of Big Sur can be felt at the Keyhole Arch Rock at Pfeiffer Beach, one of the most photogenic sunset spots on the central coast. Soak in the beauty of the jaw-dropping cliffs, waterfalls, hiking trails, and more with minimal crowds.
Bixby Creek Bridge
More than just a functional roadway across a wide and deep creek, Bixby Bridge is one of the most photographed spots in Big Sur. The unforgettable and aesthetically pleasing bridge soars 260 feet above the bottom of a steep canyon. Head up to Castle Rock Viewpoint for the best spot to snap a picture or two.
3. Boulder, Colorado
Boulder is a nirvana for nature lovers and snow bunnies. Make yourself at home at a hideaway in the foothills of the Rocky Mountains. Boulder proves to be the best solo winter trip with plenty of off-grid cabin experiences and mountainous playgrounds waiting to be wandered. If you choose to head downtown, the city is walkable, safe, and welcoming. Boulder makes it easy to independently explore coffee shops, farmers markets, and museums. If the weather cooperates, take a scenic drive cruising through the scenic farmland with gorgeous mountain backdrops.
Boulder Dushanbe Teahouse
This architectural gem is hand-carved and hand-painted in vibrant colors, serving up over 100 teas. Nestled against the Rocky Mountain Foothills, the teahouse is a local hotspot for enjoying breakfast or simply taking in the zen vibes. We can’t think of a better way to pamper yourself with a traditional afternoon tea and savory pastries.
4. Jackson, Wyoming
If you’re really craving a remote destination, the least populated state is just the ticket. Grand Teton National Park’s northern neighbor, Yellowstone National Park, typically gets all the attention so you’re guaranteed some alone time with wildlife including bears, bison, and moose. There is so much to see in the wide-open space filled with pristine lakes and alpine terrain, but the Tetons at sunrise take the cake. Jackson’s winter temperatures are unforgiving, especially in January, so pack your thermals and layer up. We promise a winter here is well worth the chill.
National Elk Refuge
For an unforgettable wildlife experience, take a horse-drawn sleigh ride through an elk herd. Refuge for the majestic beasts was established in 1912 when people became aware of the reducing numbers and took interest in helping them. Today, the refugee emcompasses an impressive 25,000 acres! Dress warm to see thousands of the animals on their home turf
5. Clearwater, Florida
One of the best solo winter trips you could take is somewhere sunny and 75. You can’t go wrong with powdery white sand and calm turquoise waters lapping against the shores.
Caladesi Island State Park
Longing to visit a secluded shoreline this winter? Finding a private beach during winter months can be hard as many snow birds flock to blue skies and sunshines but Caladesi Island State Park is the perfect under-the-radar beach hideaway.
You’ll need to take a ferry from the Dunedin Causeway to arrive at views of a blindingly white stretch of sand with 650 acres of remote nature trails. The state park is one of Florida’s best kept secrets with temperatures in the 70s throughout the winter.
The United States has some of the highest mountain peaks, tropical beaches, and the most breathtaking rock formations fit for the best solo winter trip.
