How to Plan a Weekend Trip Alone

denver union station

Lately I’ve spent a lot of weekends outside Philadelphia. Travel to some conferences and meetings has taken me to Colorado and Texas and personal travel has had me all over the state of Pennsylvania, Virginia and now to New York for several upcoming weekends. While I’ve had travel companions for most of these trips, there have been some where I’ve been essentially all alone. Here’s how I make things work and have a great time even if I am totally alone in a city I’ve never explored before.

torchys denver


Book accommodations.

Okay so this is pretty obvious, but is an important first step and will shape your travel experience in a major way. I almost always start my search on Airbnb, because these are usually the most cost-effective options. I prefer to stay in places where I have the whole apartment to myself, but I have also had a great experience staying in a room in someone’s house (in Portland – the house came with dogs too!). I look for places that are close to public transit and have a good amount of reviews. The “close to public transit” thing is the most important, as I plan to spend as little time as possible in the place where I’m sleeping and as much time as possible exploring when I’m in a different city.

If Airbnb fails, a good next option to look into is hostels. These vary widely from city to city, but you can often find a cheap room (even a room all to yourself) if you’re booking far enough in advance. When I spent a night in Denver this fall, I stayed at the 8th Avenue Hostel and it was exactly what I needed: cheap, nice enough, and a private room to sleep in.

Figure out what you want to do there.

If you’re totally unfamiliar with a city, it can be hard to know what to do. There are a few tools I use to try to do at least a little bit of planning in advance.

Google Maps.

Put in the address of the place where you’re staying and just see what is nearby! There is a good chance you are close to at least one cool coffee shop or bar. After I scan the few blocks surrounding where I’m staying, I look more broadly at neighborhoods in the city to see if there are any areas with lots of things I want to explore. In my experience, like things tend to be clustered together. Museums are often next to other museums, breweries are often clustered in a few neighborhoods, and certain types of food (Italian, Thai, etc.) tend to be predominantly in one neighborhood. Figure out what you want to do and use this as a guide.


This was a hugely helpful tool when planning our trip to Acadia National Park this summer. Having never even been to the state of Maine, I had no idea what to do in Acadia to make the most of our time there. I spent some time browsing Pinterest for the best hikes in Acadia and the must-see things in the park and ended up building most of our itinerary from there. Pinterest is now a regular part of my trip-planning routine.


While Instagram may not be the most helpful for substantive overall trip planning, it can help you identify some specific things you want to check out. For example, I know I am going to be spending a few days in Brooklyn over the course of December and I know that Grace Atwood from The Stripe lives in Brooklyn. I might do a scan of her Instagram feed and see if there are places she has featured that look interesting to me. The location search feature on Instagram is also helpful if you want to learn more about a specific store, bar, or restaurant you’re thinking of going to. Seeing what photos others have posted can help in figuring out if you actually want to make the stop.

nyc subway

During Trip

Get out there (especially if you’re alone).

So you have your list of things you want to do and see, you’re in this new place, and you’re ready to get out and explore. The best thing to do from here is literally to just start going to places you’re interested in and talking to people. When I was in Denver, I went to Great Divide Brewing (one of the places on my pre-planned list) and was in the corner drinking my beer trying to decide where to go next. I struck up a conversation with a Denver local, who recommended a place for me to go next (Crooked Stave Brewing), which I never would have found otherwise. It ended up being one of my favorite stops of the night.

Take Uber Pool / Lyft Line.

If I am traveling alone in a new city, I always take the carpool option in ride sharing apps. I love having the opportunity to pick my driver’s brain about what to do in the city and asking other riders what to do. Again, locals tend to have opinions about what is good in their city and I’ve never really gone wrong following their advice. Once in an Uber Pool, I was riding with these two girls going to a Halloween party at a bar around the corner from where I was staying. They invited me to come with them, so I did and I ended up having a blast. I never would have ended up there had I just taken an UberX by myself.

 Take a backup phone charger or external battery.

While this has nothing to do with actually planning a trip, this can be a lifesaver. Just last weekend in New York, I was in a situation where my phone was dangerously close to dying while I was out at night and I really needed my phone to get an Uber back to my Airbnb and to make sure I knew the door codes for the building and specific apartment I was staying in. I am not one who likes to live on the edge when it comes to these things, so the very next day I passed by a Bestbuy and bought one of these Mophie external batteries. I think this will be a game changer.

Any tips I’m missing here?