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How to Plan a Day Trip

Wondering how exactly to plan a day trip? I’ve got you covered.

There’s something very freeing about day trips. They’re this easy, low-stakes way just to GO SOMEWHERE and find inspiration from your new surroundings.

With a longer vacation comes a longer list of responsibilities, research, and stress. Don’t get me wrong, it’s very much worth it, and nothing beats the feeling of disembarking a plane in a brand new country. However, sometimes you want that pay off without worrying about making it through TSA or figuring out hotel bookings and fitting in a million things to see, eat, and experience.

Cue the day trip! Depending on where you live, a day trip is an easy car, bus, or train ride away, making it doable for everyone from solo travelers to young families and everyone in between. Below is my tried and true guide to planning one of your own.

How to Plan a Day Trip

The key to day trips is that they should not be overthought or over-planned. You really only want to pick one big must-do and then find a place for lunch or dinner, depending on how long you’ll be out. Throw in some downtown shopping to seek out cool small businesses, and that’s really it.

Unique things to do in Louisville

1. Pick your day trip destination

When it comes to picking your day trip destination, you’ll want to keep it fairly nearby. I recommend at least 30 minutes away but no more than two hours, maybe three if it’s a really unique seasonal festival or big event. Remember, however far you go in one direction, you must repeat that same distance back. Five+ hours of transport in one day sounds pretty exhausting!

If you’re struggling to figure out a destination, here are some of my secret tips to help you out:

  • Search “best places to live” in your state or nearby states. This usually means they have a fun downtown area full of great restaurants and boutiques. For example, it’s fairly easy from Brooklyn to the Hamptons, and spots like Fire Island or Sag Harbor are only around 2 hours away.
  • Look for parks, forests, and hiking trails, and then look for their nearby towns. If you want to get outdoors on your day trip, you’ll first want to pick either a forest or park to enjoy. Then you’ll want to search for their nearby town to find where to eat and wander. If you’re in Louisville, for example, Bernheim Forest is a 30-minute drive away, and the small town of Clermont sits at the edge. Try some of the bourbons from James B. Beam Distilling, snap a picture in front of their famous barn, and then grab lunch or dinner at The Kitchen Table.
  • Check for local festivals. It’s usually a good sign that a town is a nice place to visit if they have an annual festival – the quirkier, the better. Even if you don’t visit during the actual festival dates, you’ll still find some fun things to do. A great example is the town of Julian, about an hour from San Diego and 2 1/2 hours from Los Angeles. It’s most known for its Apple Days Festival, but you can still see its restored historical homes, sample apple pies, and hike one of the many trails that go through the beautiful Cuyamaca Mountains any time of year.
  • Look for independent bookstores. Here’s one of my best tips when looking for nearby destinations. Simply look for small, independent bookstores. If an independent bookstore is thriving, it’s a good indication that your day trip destination has created an ecosystem for small businesses to thrive. has a great function that lets you look for local bookstores within 15-50 miles. Even better – see if you can time your day trip with an author event.

Corning Museum of Glass, New York

2. Figure out the big thing you want to do.

Once you’ve picked your destination, it’s time to choose your big thing to do. There’s so much to choose from, and it’s really up to what you want to do! Here are some ideas:

  • Easier hikes and treks. There’s nothing like a nice hike or trek. You obviously don’t want to do a more intense hike on a day trip, but I always enjoy gentler trails that might take a few hours and offer some incredible scenic views.
  • Cool, interactive museums. You’d be surprised by how many unique museums are located well outside major cities. For example, Corning in the Finger Lakes is home to the world-renowned Corning Museum of Glass, as seen in Netflix’s “Blown Away.”
  • Seasonal festivals or events. While I don’t necessarily recommend planning your day trip around a major festival as parking and crowds sound like a nightmare, there is something to be said for visiting around those dates. For example, any cherry blossom festival will have a few blooms the week before and after, so you can still experience them even if they’re not at their peak.
  • Film location finds. TV shows and movies are often filmed all over the place, and you can always find a blog post or guide that’ll give you the exact locations. For example, Hamilton in Ontario, Canada, is a favorite for some of the most buzzed-about TV shows out there – “The Umbrella Academy,” “Handmaid’s Tale,” “The Queens’ Gambit,” and so much more. Astoria, OR is a treasure trove of Goonies locations, and Cleveland, OH has a ton of A Christmas Story locations, including the original house.
  • General sightseeing. Sometimes day trip destinations have fantastic sightseeing on their own. Cape May in the Jersey Shore is home to the second largest concentration of Victorian homes after San Francisco and Manitou Springs near Colorado Springs, and Denver has a series of carbonated springs you can sip from.

3. Look into where to eat and grab a drink

One you’ve figured out the big thing to do, it’s time to figure out where you want to eat and maybe grab a drink. Most day trip destinations will have at least one or two really cool restaurants with an inventive menu and focus on local ingredients. Many will also have great breweries, wineries, and distilleries so you can sample some new concoctions. I like to look on Google Maps and Tripadvisor for reviews. Take them with a grain of salt, but I often find that if people complain about the same thing, there’s a bit of truth there. They also let you know if you need to make reservations or if those opening hours listed are more of a suggestion than a sure thing.

4. Figure out the logistics

By now, you’ve got your day trip about 90% planned! Pretty easy, right? The remaining 10% are just those little details that are easy to forget but will be a huge pain if you don’t plan for them. Here are some things to consider:

  • How are you getting there? If it’s driving, do you need to rent a car, and when does it need to be back by to avoid extra charges?If it’s public transport, just keep times in mind, so you don’t accidentally miss your train or bus and need to wait an extra hour or stay overnight.
  • Parking. For those driving, are you able to find parking easily? I’ve found this is pretty easy to figure out as you can look on Google Maps for parking locations, and there are always at least one or two reviews. Otherwise, you can google for parking advice, and there’s always some TripAdvisor forum or local website with advice.
  • Kid-friendly, Pet-friendly. If you’re traveling with kids or pets, you’ll also want to check that everywhere you’re going is friendly towards them. You can’t exactly leave your pet or kid in the car while you go get lunch!
  • Snacks, drinks, and extra cash to have on hand. Before your day trip, just make sure you have snacks and drinks just in case. This goes double for kids.

And that’s really it for how to plan a day trip! You can use this guide for pretty much anywhere in the world. Below is an example for my fellow New Yorkers.

Millterton, NY Day Trip

Example Day Trip: Millerton from NYC

Up in Dutchess County,  Millerton has everything you need for an amazing day trip. It’s only 2 hours by car from Manhattan and has plenty of parking available along Main Street.

Since it’s located right on the Harlem Valley Rail Trail, I’d recommend that your big thing to do is to walk or bike along the trail and take in the stunning Taconic Hills. This is especially a must in autumn to see all the colorful foliage.

Afterward, grab a bite at the Oakhurst Diner. They have an inspired, modern menu where you can have everything from homemade meatloaf and mashed potatoes to a vegetarian macro plate.

Walk off lunch around Main Street and check out all the local designers and antique stores, which range from old school to more modern finds. You can also, of course, find a cool independent bookstore in Oblong Books.

When you need a break, stop into the Harney and Sons flagship location. I’m a tea drinker, so this place was my jam! They have over 250 personally blended teas offered at their tea bar as well as a shop with all you could ever need to properly enjoy a cuppa.

Once you’ve had your fill, you can make the easy drive back into the city feeling refreshed and relaxed!

And there you have it. A complete guide on how to plan a day trip no matter where you live. What are some of your favorite day trip destinations?

How to Plan a Day Trip

This Post Has 4 Comments

  1. Thanks Samantha for the basic simple tips that we sometimes forget. I feel like I have to get back into how to plan a trip after not planning for so long with our covid experience filling our time.
    Coming up with the destination is the most difficult challenge. I will use your independent bookstore suggestion.! Any other suggestions on ths point?
    Happy travels,

  2. Hi Samantha,
    Thanks so much for all your inspiration and great show!!!
    I am actually presenting “Road Trippin” Day Trips to our 55 and older community this Fall. Quick day trips are the best with places to see, to eat and experience. It gives us that excitement of when we first got our drivers license and could hit the road with the wind in our hair, music playing loudly and freedom to explore. There is so much out there, waiting just around the corner!

  3. I love your show! My husband and I are saving for retirement. We do a lot of day trips. I live in Jacksonville Florida and there are many great places to go here. Savanna is next and then to Flagler Beach. I’ve always been a wanderer. My Mom said that we were two gypsies!

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How to plan a day trip
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