The Girlfriend’s Guide to Having a Great Trip…in Any City

For me, a key ingredient to a super fun girlfriend getaway is location, location, location. Vegas, New Orleans, Portland, Los Angeles…all of these cities are packed with promise and stocked with fabulous finds. It’s beyond easy to plan a weekend trip in a “fun” city by layering in amazing restaurants, shopping, shows, and sightseeing. And I always feel a little extra burst of accomplishment when I visit a historic site or take in a museum or two.

But what do you do when you’re headed to a less exciting location? Somewhere with a more “relaxed” pace? I almost found myself in this situation a few weeks ago, when Ginger and I were going to meet up in Hartford, Connecticut as the result of my “hot mess” mileage run. Hartford is not a city that either of us are familiar with, and I can say with confidence that it’s not a destination that springs to mind for a weekend trip…but with a few tweaks to our big-city vacation style and a little planning, we were all set to have a fantastic time.

Unfortunately, our trip got derailed due to a flight delay and a touch of pneumonia, but I saved my planning notes because I think they are a great reminder of how you can really have a great trip no matter where you go.

As someone who has taken more than my share of “girlfriend getaways” (or is that possible?), here are my tips:

1. Yelp is your friend. I like to search for “Local Flavor” and see what comes up. This spot was definitely on our list. We were going for the blend of locals and sugar.

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2. For an interesting mix of fun and creepy activities, check out Atlas Obscura. You never know what you’ll find there.

3. I always love to go consignment shopping when I’m in a new place, because fab finds vary by city. For example, New Orleans has a ton of classy dresses, while Vegas has loads of sparkles, and Los Angeles has chic basics for cheap. Again, I just use Yelp for this.

We were planning to check out Rocky Hill Uptown Consignment and Panache in West Hartford…and we will, if we ever actually make it to the area!

4. Of course, dining at unique restaurants can be a memorable experience. I like to use Chowhound and Find Eat Drink to discover new spots. Some of my best vacation memories have been of food 😉

5. Renting bikes or kayaks is something I try to do on every trip I take with a friend. I love experiencing snippets of conversation, tantalizing aromas wafting out of doorways, and all the little things that make you smile with secret delight…the small vignettes of a neighborhood.

As I write this, I realize that our trip to Hartford would have been incredible, because at the end of the day, when you’re with a good friend, you really make your own fun, don’t you think? Everything else is just icing on the cake.

That being said, I’d love to know if you’ve got any other great “icing” ideas. What do you love to do while you’re on vacation with a friend?




  1. When I took my mom to Portland for her birthday we found some great cheap entertainment. We discovered a beautiful lunchtime free piano concert in a local downtown church. We had tea and dumplings at the Chinese garden. We got discounted “last minute” theater tickets at a local playhouse for a stunning play. But the most fun we had was playing Banagrams in the lobby of the Vintage court hotel during their free wine happy hour and borrowing their free bikes to cruise along the river. Kimpton hotels always impress.
    Totally off topic, but thanks to advice I have gotten on your blog, I now have 193,000 miles accrued that I didn’t have 3 months ago! Thanks PPD!

    • Points Pixie says:

      Hottie – What a great variety of activities!

      and what a huge amount of points for 3 months!! You should write a guest post 😉

  2. I enjoy spa time with girlfriends, and love trying new spas. I like to pretend I’m a spa critique sampling for an article.

    I also love traveling for races (with girl or guy runner friends) and find running to be a wonderful way to see a new city. I’d love a rock n roll series tour pass one year.

    PS – Hottie, I love Bananagrams!

    • Points Pixie says:

      Rebecca – Spas! How could I forget about spas???

      And I guess I should try Bananagrams if 2 of my favorite readers love to play.

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