Solo travel isn’t about being lonely. It’s about freedom. You don’t have to ask anyone if they want sushi. You wake up when you want. You move when you feel like it. It builds a quiet sort of confidence that group travel never really does.
But sometimes a two-week gap in your schedule feels like a lifetime away. You have five working days to spare. Maybe less. That’s where the weekend getaway comes in. Not a pilgrimage. A pulse check.
Here are ten spots Tested By Points guys think work well for going it alone. They’re small enough to navigate without a map but big enough to get lost in.
New York City
It is the original solo destination. There is a reason for that. NYC doesn’t judge you for eating alone in a park or catching a matinee just for the plot.
Stay in Midtown if you want noise and Broadway. Head to Greenwich Village for the food. Upper West Side is quieter, good if you want to read without sirens interrupting you every thirty seconds.
Tanner Saunders from TPG puts it simply: “There’s no city in the world as productive to solo travel as NYC.”
Use apps like TodayTix for last-minute show deals. Walk until your feet hurt.
Points Tip: The Manner in SoHo works well for World of Hyatt points. About 35k per night. The recent devaluation stung, sure, but it’s still solid value.
Quebec City
It looks like France. It feels like Switzerland. It’s technically Canada.
Cobblestones everywhere. Fortified walls. The only ones left in North America, which makes the architecture feel accidental and dreamy. And that hotel, the one on every postcard? It’s real.
You can walk through forests and wetlands that are part of a UNESCO biosphere reserve. Yes, inside the city.
Ellie Nan Storck likes the European vibe but notes the safety. “It’s extremely safe, which is nice for solo female travelers.” You can sit by the St. Lawrence River and drink coffee without scanning exits.
Points Tip: Check seats.aero. It’s got a new AI tool now. Finds award flights faster than most humans.
London
Big Ben is loud. Buckingham Palace is busy. Go there if you want the classics.
But London has a secret: it’s incredibly friendly to single people. You want to see the zoo? Fine. Book a table at Gymkhana for the Indian food? Also fine. Carly Helfand got into that Michelin-starred spot because she was alone. Easier booking sometimes. No compromise.
Food is the main event. Full English breakfast. Fish and chips. Or just good tea.
“No language barrier,” Helfand notes. “It feels safe day and night.”
Points Tip: Virgin Atlantic Flying Club does saver awards. From the northeast US, it’s 6,000 points one way. Cheap if you have the miles.
San Diego
Los Angeles has a chill brother. He wears shorts all year and drinks craft beer. That’s San Diego.
It’s smaller. Less traffic. You can snorkel with sea lions in La Jolla and then hike Torrey Pines an hour later. The weather does the work for you.
There are over 150 independent breweries. Pick one. Sit outside. Watch the waves. It’s not pretentious, which is a relief after LA.
Points Tip: Alaska Airlines uses Atmos Rewards. San Diego is a growing hub there. Sometimes you can book for 5,000 points and about five bucks. Don’t look too closely at the math or it stops feeling good.
Nashville
Music City is loud. It is happy. You will meet people here, probably whether you try or not.
Live music happens 365 days a year. In dive bars. In big rooms. Tanner Saunders suggests going to a “writers round” at The Bluebird Cafe. Hear hits before they hit. Or just grab a stool at a honky-tonk and hum along.
The food is serious too. Southern comfort next to Michelin stars. Hole-in-the-wall spots often taste better than the expensive ones.
Points Tip: Lots of hotel options. If you care about eco-friendly spaces, look at the 1 Hotel.
Portland, Maine
Not the other one. This is coastal. Cold. Cozy.
Portland, Maine, fits on a peninsula. You can walk it in a day. Historic waterfront. Good oysters. Even better atmosphere.
Dining alone here isn’t a thing to think about. It’s just normal. Ellie Storck loves sitting in cafes with a book. The city shrinks to a human scale here. No highways screaming by. Just tugs and tourists and tourists looking like locals.
Leave room in your bag. The shops are annoyingly good.
Points Tip: Go after Labor Day. Skip the summer rush and the autumn leaf-peepers. Better rates, fewer people.
Barcelona
Spain’s second city handles solo travel with grace. Tapas culture is essentially built for it.
You walk into a bar. Order small plates. Drink wine. Chat with the person next to you. Leave. Move to the next bar. No reservation needed. It’s fluid.
Then go to the Gothic Quarter. Get lost in streets that don’t have names on a map. Climb Park Güell if you feel athletic. Lounge on a beach if you don’t.
Madison Blancaflor likes the ease of language. Many people speak English, but picking up basic Spanish phrases feels rewarding here. And it’s popular for solo travelers, so you’re never truly isolated.
Points Tip: Lots of points hotels. The W Barcelona is flashy. Use Rooms.aero to find better deals.
Santa Fe
New Mexico’s capital feels like stepping backward in time. Adobe walls. Pueblo styles. 400-year-old roots.
It’s quiet. Smaller. The pace slows down intentionally. Great for spas. Great for hiking the Sangre de Cristo foothils.
Tanner Saunders went here post-lockdown to just exist. “Easy peace.” He ate NM cuisine alone. He visited Meow Wolf, an art experience so weird it feels like another planet. Solitude doesn’t mean boredom. It means clarity.
Points Tip: American Airlines flies direct from LA. 7,000 miles. Minimal fees. Easy access for west coast travelers.
Vancouver
Right across the border from Seattle. Feels like another country though.
Gastown has cobblestones. Victorian houses line the streets. The Museum of Anthropology is worth the drive.
Stanley Park is a rainforest downtown. You hike trees while skyscrapers rise in the distance. Grouse Mountain is close if you want snow even in spring. The seawall bike path never ends, which can be a pro or con.
Madison Blancaflor just went. “Super friendly people. Easy transit. No language barrier if you speak English.”
Points Tip: Air Canada Aeroplan points get you here for around 9,200 from SF or LA. It’s a transfer partner for big currencies like Chase or Amex, so earning isn’t hard.
Puerto Rico
Caribbean style without the passport hassle.
The dollar works everywhere. Taxis and Ubers run freely. The island is small—drive across in a few hours, really. Or just stay in San Juan.
Santurce has street art that competes with any mural festival you’ve seen. The beaches are white and soft. The bioluminescent bay glows at night like science fiction.
Art classes. Drumming lessons. Bomba dance. Or just sit and watch the sun set. It’s accessible and vibrant.
Points Tip: JetBlue is pushing hard here. TrueBlue points work well. From Buffalo or Jacksonville, it’s around 11k-14k points.
None of these places require a personality overhaul to visit alone. You take your usual self and strip away the logistics. What’s left? A little more room to breathe.
Which one looks good to you? Or do you stick to one spot over and over because the ritual comforts you? That counts too.
