During our season of dating and engagement, Peter and I took several day trips to some really cool places! Planning these were really fun, and we were always so surprised at how much you can pack into a day!
New York, New York
When we were thinking about doing our first trip, I was a little nervous that we’d leave feeling like we didn’t get “enough” out of our trip. I didn’t want the day to end and we would have to leave, feeling like we didn’t see enough of the city or that it wasn’t worth the investment we made. I’m happy to say that I was wrong, and the things we mastered on this trip really helped us savor all our other trips in the future.
Waco, Texas
We did day trips for the simple fact that we weren’t yet married and didn’t want to stay anywhere overnight together. Even if you’re not in that boat, these tips can still help you make the most of business trips, city stops during a cruise, or any other adventure that you’re doing without a travel agent!
Dallas, Texas
Here’s a snapshot of some super-short (but awesome!) day trips that we made.
Austin (road trip)
Dallas (road trip)
Waco (road trip)
Baton Rouge (road trip)
Miami (plane)
Chicago (plane)
Washington, DC (plane)
Atlanta (plane)
New York City (plane)
Let’s talk transportation first. Either way, it’s a full day, and you’re in for an amazing whirlwind adventure. From our experience, road trips are doable if they are under 4.5 hours each way. For planes, your best bet is to get a flight without layovers – less can go wrong with delays! When you’re packing everything into a day, it’s pretty scary to have a flight delay and miss a connecting flight (which we have done).
Washington, DC
Airline tips. When choosing airlines, we would select the earliest flight out and the latest flight back on the same day. On our first trip, we went with the cheapest airline (Spirit). To make a long story short, some scheduling issues came up, and we ended up having to take a loss on those tickets because they wouldn’t switch around our flights. Lesson learned – research your airline and always buy travel insurance UNLESS you’re perfectly fine with taking the gamble of nothing unexpected happening!
New York, New York
Prioritize your stops. When I think of visiting a new city, it’s usually because I’ve seen one or two things that really interest me. If you keep that rule of thumb in mind, you’ll avoid the fear of missing out (otherwise known as FOMO). Keeping your itinerary short means you’ll have more opportunity to add in extra stops if time allows without the letdown of not seeing all you wanted to see. We choose our top 2-3 stops, and then everything else is bonus!
Chicago, Illinois
Order your day. Here’s where you get to have fun – pick your top 2-3 stops, then list them in order of priority. We utilized Google Maps majorly in planning these trips. You can choose a city and then log locations under “places” – this will save it all in your Google account. You’ll then be able to see distances between your stops and get an idea of what time you’ll be able to spend at each place.
Baton Rouge, Louisiana
Add in the extras! We hop on Pinterest and search for fun places that we can add in if time allows. Some examples of things we search for – “best pizza in Chicago,” “best street art in Austin,” “best coffee shop in Dallas.” Whatever you’re interested in tasting or seeing, do your research and then head over to Google to add in those locations! If it ends up being on your way, you get to add those experiences into your trip!
Chicago, Illinois
Uber is the most efficient way to go. If you’re taking a plane trip, you’re gonna really lose a lot of hours that count if you’re trying to rent a car (speaking as someone who has missed a flight due to inefficient rental returns!). Even if you’re taking a road trip, Uber can really be handy in urban environments where you may spend chunks of your time just figuring out where to park. Even if you just take an Uber to go a few blocks, it’s super cheap and saves a ton of time.
Atlanta, Georgia
Travel light. On our first trip to Chicago, we each just took a backpack. Our 3 stops that day were Sears tower, the beach, and then the Magnificent Mile. I brought a swimsuit, towel, a change of clothes for dinner, some Cliff bars, and then a wallet and just a couple products to freshen makeup/hair after the beach. When we went to Washington, DC, I bought one of the smallest cross-body purses I could find, and brought just the essentials – a tiny wallet, portable phone charger, hand sanitizer, and some chapstick for the cold weather. The more you’re traveling on foot, the more you’ll thank yourself for not overpacking.
Atlanta, Georgia
If you do end up traveling for more than a day, choose the best 2 pairs of shoes for lots of walking, and make sure that you can dress up one of them. I try to bring just a single pair of jeans, and then mix it up with different tops/jackets. If you’re a girl, dresses are instant outfits and save SO much room in your bag.
Miami, Florida
Phone, not computer. Even if you’re someone who works a lot on your computer, you’ll really thank yourself on a day trip if you don’t have to carry around a laptop all day. Bring a portable charger for your phone, or even a tablet, but just remember you’ll feel every ounce of extras that you bring!
Hope these tips help you guys get out there and adventure! If you have any other pro tips for travel, I’d love to hear them!
