The Best Weekend Trips in the US According to a Second-Home Expert

Best Weekend Trips in the US

What if the best weekend trips in the US weren’t just trips at all, but places you could actually call yours? A home by the lake. A cabin in the desert. A cottage by the sea that pays for itself while you’re back in the city, dreaming about your next long weekend.

Three years ago, Katie Cline did something most people thought was backwards: she bought her second home before her first. Living in New York City had made buying a primary home feel impossible, so instead of waiting, she purchased a vacation home three and a half hours north near Lake George. When she’s not there, it doubles as a short-term rental, covering its costs, building equity, and turning a profit. She’s since bought two more vacation homes. Both pay for themselves. What started as a personal experiment has become Katie’s life’s work. She’s now an award-winning hospitality expert and the host of Second Home First, a podcast and business built around helping others replicate what she stumbled into.

At Flytographer, we’ve been capturing memories in the places that travellers love since 2013, connecting people with trusted local photographers in 350+ destinations worldwide. We’ve captured over six million memories for 100,000+ travellers who wanted more than a phone snap. Below, Katie shares her picks for the best weekend destinations in the US, specifically the kind of places where buying a vacation home might be the smartest decision you ever make.

Jump in

Katie’s Approach to Choosing a Second Home

1. Cape Cod, Massachusetts: Best for Classic New England Charm
2. Montauk, New York: Best for Laid-Back East Coast Weekends
3. Napa Valley, California: Best for Wine Country Weekends
4. Cannon Beach, Oregon: Best for Pacific Coast Scenery
5. Lake Tahoe, California: Best for Year-Round Escapes
6. Park City, Utah: Best for Ski Weekends and Summer Adventures
7. Sarasota, Florida: Best for Beach Culture and City Life
8. Sedona, Arizona: Best for Red Rock Landscapes
9. Joshua Tree, California: Best for Desert Escapes
10. Santa Fe Foothills, New Mexico: Best for Year-Round Culture

Photo: Ashley in Lake Tahoe for Flytographer. Camrie and family capture memories on a trip to Lake Tahoe with a family photoshoot.

Katie’s Approach to Choosing a Second Home

The first question Katie is almost always asked is: where should I buy? Her answer is disarmingly simple. Choose a place you already love. A place that ranks among your favourite weekend trips, not because someone told you to go, but because you keep going back. A place where you can picture years of holidays, long weekends, and ordinary days with the people who matter most.

The financial logic follows from the emotional one, not the other way around. A place you love is a place you’ll return to, rent well, and take care of. Start there, and the rest tends to work itself out. 💛

1. Cape Cod, Massachusetts: Best for Classic New England Charm

Closest big city: Boston (approximately 1.5 hours)

“The Cape is a summer classic. Vacation rental rules vary by town, so do a little homework before you settle into lobster rolls and chowdah.” – Katie Cline

One hundred and fifteen beaches, the Cape Cod Rail Trail for cycling past cranberry bogs and salt marshes, Wellfleet’s oyster farms, and lobster rolls from shacks that haven’t changed their recipe in 40 years. Chatham has the storybook harbour. Provincetown has the art galleries, the whale-watching boats, and an energy unlike anywhere else on the East Coast. But the Cape’s best-kept season is autumn, when the crowds thin, the light turns golden, and you can finally get a table at your favourite clam shack without a wait. That’s when second-home owners say the Cape feels most like theirs.

Photo: Cori in Cape Cod for Flytographer. Jordan and family capture memories on a trip to Cape Cod with a family photoshoot.

2. Montauk, New York: Best for Laid-Back East Coast Weekends

Closest big city: New York City (approximately 2.5 hours)

“My fellow New Yorkers, who doesn’t love a Montauk weekend!? Just know it’s a tightly regulated market, so checking the rules before you buy will save you a lot of frustration later.” – Katie Cline

Montauk runs on a different frequency than the rest of the Hamptons. More surf wax than socialite. Ditch Plains is the East Coast’s most celebrated break, and even if you don’t surf, watching from the dunes with a coffee is half the appeal. The lighthouse has been standing since George Washington commissioned it in 1796. The food scene has quietly become one of Long Island’s best, from lobster on the dock at Duryea’s to craft beer at Montauk Brewing Co. On a clear evening, the sunset from the harbour makes a three-hour drive feel like nothing.

3. Napa Valley, California: Best for Wine Country Weekends

Closest big city: San Francisco (approximately 1 hour)

“Napa is wine-country perfection. For short-term rentals, where your home is located matters. A house inside city limits can be rented very differently than one just outside them.” – Katie Cline

Five hundred wineries, and somehow every visit turns up a new favourite. The Oxbow Public Market is the kind of place you wander into for coffee and leave two hours later with olive oil, local cheese, and a plan for dinner. Calistoga’s mud baths and hot springs make the northern end of the valley feel like a wellness retreat with better wine. Catch a sunrise hot-air balloon over the valley floor and watch the fog burn off the hills below you. An hour from San Francisco, the Napa Valley manages to feel like a different country entirely.

Photo: Flytographer in Napa-Sonoma. Audra and family capture memories on a trip to the Napa Valley with a family photoshoot.

4. Cannon Beach, Oregon: Best for Pacific Coast Scenery

Closest big city: Portland (approximately 1.5 hours)

“This dreamy coastal town is in high demand, but vacation rentals are limited. Make sure a home is properly approved before you picture yourself sipping coffee by the sea.” – Katie Cline

Haystack Rock, 235 feet of basalt rising straight from the sand, is the postcard. But the life around it is what keeps people coming back: tide pools teeming with sea stars at low tide, puffins nesting on the rock’s face from May through August, art galleries that would hold their own in any major city, and winter storm-watching with a glass of Oregon Pinot in hand. National Geographic named it one of the 100 most beautiful places in the world. Ninety minutes from Portland, Cannon Beach feels like the edge of everything.

Photo: Whitney in Portland for Flytographer. Kyle and partner capture memories on a trip to Cannon Beach with a family photoshoot.

5. Lake Tahoe, California: Best for Year-Round Escapes

Closest big cities: Sacramento (2 hours)

“If you already plan your year around ski weekends and lake days, owning a place here can make those escapes feel effortless. Just be sure to choose a town that’s friendly to short-term rentals if you want the home to pay for itself.” – Katie Cline

Lake Tahoe never goes quiet, which is exactly why it works as an investment. Eleven ski resorts carry the winter, with Heavenly and Palisades Tahoe leading the way. Come summer, the lake turns a shade of blue that photographs struggle to do justice, and the hiking, paddleboarding, and long sunset dinners on the South Shore take over. The North Shore runs quieter and more upscale, with boutique restaurants tucked between pines and Sand Harbor’s boulder-studded beach. It’s the kind of place where Friday arrivals and Sunday departures start to feel like a rhythm, not a trip.

Photo: Flytographer in Lake Tahoe. Jasper and partner capture memories on a trip to Lake Tahoe with a couples photoshoot.

6. Park City, Utah: Best for Ski Weekends and Summer Adventures

Closest big city: Salt Lake City (45 minutes from the international airport)

“A skier’s paradise! Only certain areas allow short-term rentals, which means choosing the right neighbourhood is just as important as choosing the right house.” – Katie Cline

As the largest ski resort in the country, Deer Valley is a groomed luxury resort and is home to the famous no-snowboard policy. Sundance every January turns historic Main Street into a global film-industry village for two weeks. Then summer arrives, and the same mountains become 400-plus miles of hiking and biking trail, with alpine coasters and outdoor concerts for good measure. What makes Park City rare among resort towns is the airport transfer: 45 minutes from the gate, not four hours. A long weekend here is actually a long weekend.

Photo: Becky in Park City for Flytographer. Marlene and family capture memories on a trip to Park City with a family photoshoot.

7. Sarasota, Florida: Best for Beach Culture and City Life

Closest big city: Tampa (approximately 1 hour)

“Sarasota has that rare combination of white-sand beaches, arts and culture, and year-round sunshine. Personally, it’s a place that’s on my radar thanks to direct flights from New York. Like many places, short-term rental rules vary by neighborhood, so working with a knowledgeable realtor will be key.” – Katie Cline

Siesta Key’s sand is 99% pure quartz crystal. It doesn’t burn your feet in August, it’s been rated the best beach in America more than once, and it’s free. That alone sells the weekend. But Sarasota surprises people with what happens off the sand: the Ringling Museum on its 66-acre bayfront estate, Marie Selby Botanical Gardens (recently named to TIME’s World’s Greatest Places list), and a dining scene that sharpens every year. The Rosemary District has become a neighbourhood worth exploring on its own, with galleries and a weekend farmers’ market that draws locals and visitors in equal measure. An hour from Tampa, it has the culture of a much bigger city and the pace of a much smaller one.

Photo: Tami in Sarasota for Flytographer. Tricia and family capture memories on a trip to Sarasota with a family photoshoot.

8. Sedona, Arizona: Best for Red Rock Landscapes

Closest big city: Phoenix (approximately 2 hours)

“Sedona welcomes short-term rentals, but the city is serious about being a good neighbour. Thoughtful management and a well-designed home will make all the difference here.” – Katie Cline

Cathedral Rock in Sedona at golden hour looks retouched even when it isn’t. The red sandstone formations shift from coral to crimson depending on the light, and the 400-plus miles of trail through them range from easy creek-side walks to scrambles that reward you with views that stay with you. Four energy vortex sites draw the spiritual seekers. Tlaquepaque Village draws the art collectors. The Verde Valley wine region is 30 minutes away, and the Grand Canyon is a two-hour day trip. Two million visitors come every year, but the town still feels like it belongs to the landscape more than the tourists.

Photo: Whitney in Sedona for Flytographer. Darlene and family capture memories on a trip to Sedona with a multigenerational photoshoot.

9. Joshua Tree, California: Best for Desert Escapes

Closest big city: Palm Springs (approximately 1 hour)

“Joshua Tree is wildly popular with travellers, but because every Airbnb here looks like it was pulled from the pages of Architectural Digest, you’ll need to invest in great design to stand out.” – Katie Cline

Joshua Tree National Park is 800,000 acres of surreal boulder fields, twisted trees, and some of the darkest skies in southern California. On a clear night, the Milky Way looks close enough to touch. The town is Pappy & Harriet’s on a Saturday night, live music in a 1940s Western movie set that operates somewhere between fever dream and institution. Sunday morning is a sound bath at The Integratron. In between, art installations appear at the side of the road with no explanation and no apology. An hour from Palm Springs and a couple from Los Angeles, it’s close enough to be a weekend but remote enough to feel like a real escape.

Photo: Jamie in Palm Springs for Flytographer. Emilyn and family capture memories on a trip to Palm Desert with a family photoshoot.

10. Santa Fe Foothills, New Mexico: Best for Year-Round Culture

Closest big city: Santa Fe (approximately 1 hour)

“Santa Fe is a year-round cultural hub, which means the right home here can stay in demand long after peak tourist season fades. The city limits the number of vacation rentals, so finding a property that’s already approved is a huge advantage.” – Katie Cline

The oldest capital in North America, founded in 1610, with over 250 galleries lining Canyon Road alone. The Georgia O’Keeffe Museum. Meow Wolf’s immersive installations. An open-air opera house set against the Sangre de Cristos, where the sunset becomes part of the performance. The food is shaped by centuries of Native American, Spanish Colonial, and Mexican traditions: green and red chile enchiladas, blue corn pancakes, carne adovada. At 7,000 feet, summer days stay warm and dry while the rest of the Southwest swelters, and skiing is 16 miles from the Plaza in winter. It’s the kind of place that doesn’t feel like anywhere else, which is exactly why people keep coming back.

Photo: Stephanie in Santa Fe for Flytographer. Christian and partner capture memories on a trip to Santa Fe with a couples photoshoot.

The Memories Are the Point

Katie spent a fair amount of time explaining her decision to her well-meaning family, who didn’t quite get it. But watching her daughter jump off the dock at their lake house, waking up to birdsong instead of sirens, she stopped explaining and started inviting them up. She didn’t want to wait for someday. She wanted to build memories now, in a place that also happens to be building her family’s future.

If any of these destinations become yours, a Flytographer will be there to help you capture it. Find a local photographer near you.