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Tips for planning the perfect long weekend trip

Kaz Fantone/NPR

Hannah Sampson has two rules for every trip she goes on: She always tries to visit a bookstore (ideally one that sells used books), and she always gets some local ice cream.

Beyond books and ice cream, Sampson, a staff writer at The Washington Post who covers travel news for its By The Way vertical, has tips on making the most of a long weekend trip.

If getting out of town this weekend isn't in the cards for you, use her tips as inspiration for the next long weekend (planning ahead can help with cost) or consider being a tourist in your own town, says Sampson.

Answers have been edited for length and clarity.

What sorts of destinations are ideal for long weekends?

I love a city getaway because your options are plentiful, you can likely get around on public transportation and the energy is invigorating. But if you just want to relax and enjoy nature without huge crowds, a beach town or mountain getaway can be just the ticket. Either way, for a quick trip, I'm looking for something pretty easy to reach with lots of things to do in a walkable, bikeable or public-transit-friendly area. No one wants to spend a short vacation stuck in traffic the whole time.

What should you consider in terms of transportation? Car trips only? Or are flights on the table, too?

If you can swing a vacation by car or train, that would be best for a long weekend. Flying adds so much uncertainty to the equation, especially in this era of staff shortages and delays and cancellations. Missing a flight or running into a serious delay could take a huge chunk out of the getaway. Plus, flying can be so stressful and time-consuming between showing up early and going through security and fighting for overhead space, even if the flight itself is relatively quick. If there's no choice but to fly, consider heading out on the earliest flight of the day to minimize the chance of delays.

How many hours should you spend traveling to your destination?

There's no great science to this, but ideally less than four hours. If you can spend closer to one to three hours, I think that's even better. It's far enough away from home to feel different, close enough that you're not exhausted by the journey.

What about timing? Do you recommend people leave on Friday after work and return late Monday?

I like the Friday through Monday schedule, especially if you can fit in some activity late Friday to make it feel like you kicked things off with some fun. Taking Monday off means you can look forward to a shorter work week, which is a big bonus. I try to give myself a little time on the final day of a trip to unpack, get groceries, do laundry or just unwind before jumping back into regularly scheduled programming.

Do you have any tips for making the most of a long weekend without spending a lot of money?

If you have the flexibility at work or home, it will always be cheaper to take a long weekend in "shoulder season" rather than high season. That probably means avoiding travel during holiday weekends and going when kids are back in school. September and October are great budget-friendly times to travel. If you're going at a busier time, book far in advance to have the best shot at cheap train or plane fares.

This year, I'm taking a couple of longer trips that start during holiday weekends, but by booking three and four months in advance, I was able to find plane tickets that didn't cause me actual pain. Also: don't feel like you have to eat out for every meal. Stopping at a grocery store for snacks, fruit and some lunch or breakfast staples can save some cash if you're staying somewhere with a kitchen.

How can you make the most of a long weekend at home if getting away isn't possible?

Before I moved away from Miami, where I'm originally from, I started planning "tourist in my own town" adventures. I'd take boat tours at sunset, venture out to the fruit stand and milkshake spot an hour away, listen to live music and have frozen drinks downtown on Biscayne Bay. It was so fun, and I've continued the habit everywhere I've lived since. I always try to keep a running list of nearby places to explore, restaurants to try, bookstores to check out or slightly outside-town spots to visit when I have extra time. A long weekend is the perfect occasion for that.

Final thoughts before we all book our long weekends away?

My concept of a vacation – long weekend or anything else – has changed significantly since becoming a parent nearly three years ago. Now I think about naps and bedtime, playground proximity, kid-friendly menus and whether the hotel or Airbnb has a tub as well as a shower. Still, we love to explore new places with our daughter and find her a delightful travel companion. Best of all: Like her mom, she loves to try ice cream wherever she goes.


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