5 Tips for Traveling with Friends

This year, Joe and I went on two international trips with friends: in February, to Venice, Italy, then in August, to Alberta, Canada. Besides the occasional road trip with friends, we had never vacationed with others, so this was definitely a big first for us! After the break, some tips for traveling with friends.


Traveling with friends is awesome. You’re never flying solo! You have pre-identified fellow tourists to take photos of you! You’re sharing planning duties with others! You learn a ton about each other along the way – the good, the bad, and the ugly. It can bring you much closer, or at worst, lead you to book an early trip home. I’m happy to report that we had an absolute blast on BOTH our trips this year (and still love our friends as much as we did before jumping on a plane with them). Here, 5 tips to ensure smooth sailing on your next friend-venture:

1. Plan together in advance: Last year, when our friends Will and Lorraine invited us to join them on a trip to Italy, we jumped at the chance to come along. We spent the next few months eagerly sharing potential itineraries and inspirational travel blogs. This added to our collective excitement about the trip, but more importantly, gave us insight ahead of time into what kinds of travelers they were and what they were looking to get out of the trip (i.e. cool photos of famous landmarks, great dinners, unique souvenirs, etc.). This is also the time to bring up your must-dos: “I’ve got to buy a print from ___ store for my mom, let’s make sure we hit that up on ___.” We mostly planned via group text and email, but you could easily set up a Google Drive spreadsheet with itinerary suggestions or to keep track of must-dos on your trip.

2. Set expectations: As you’re planning, make sure everyone’s on the same page about “together time” and costs. Everyone travels differently, and there’s no wrong way to go about it, but be clear upfront about how you want to manage your time and money while on vacation. On both trips, we appreciated a day-by-day itinerary of must-sees, with lots of built-in time for unscheduled adventures, rest, or gelato breaks. To capture some alone time, this script worked well: “Hey, we’d like to check out ___, but I know you wanted to ___, so let’s meet back at the hotel for drinks before heading to dinner together?” Similarly with costs, pre-planning and regular communication are musts. Know if you’re ok with splitting the bill in halfsies or need to parse it out more specifically to each order. Try to get an idea of expected costs during the trip (hotels, park fees, rental cars and gas, tickets to activities or events, etc.), and bring up any issues as soon as you can.

*Side note, my younger sister Sarah added: if you’re traveling with a group, discuss going out in advance and whether it’s ok to leave the group for a hook up opportunity, or if everyone expects to stick together for the whole night.
*She also added: discuss eating habits in general, as some people need three square meals a day, and others can get by with dining on the go. Guess which category she falls in… 🙂

3. Speaking of which, make restaurant reservations: To me, dinner reservations are like beautiful, reliable endcaps to a day of travel adventure. I know many people prefer to plan dinner spontaneously, ducking into a cute trattoria or bustling tapas bar, but in general, I love to decide on dinner locations ahead of time based on recommendations from travel or local city blogs. Often, my restaurant wish lists include popular spots with small kitchens and limited seating, so it’s very helpful to call in advance, especially with 4 or more to a party. (I was sooooo sad not to get a reservation at Frenchie’s in Paris!) Making reservations also takes care of the stressful/annoying on-the-spot decision making between friends. Ever heard, “What would you like for dinner?” “I don’t care, whatever’s fine.”And so on. Decide on dinner spots ahead of time and enjoy a restful dinner while exchanging photos and catching up on the day’s highlights over a glass (or three) of wine.

4. Make playlists, share the cord: This is a small but important road trip-related point! If you’re going to be in the car for any length of time, make playlists in advance with music to your taste (if you’re on Spotify, make sure to download them to your phone ahead of time in case of spotty service on the road. In Canada we literally went 8 hours straight with zero service on the Icefields Parkway!). Switch off on DJ responsibilities in equal time increments… that way you know that if their taste in music is questionable, it’ll be your turn to pump up the jams soon.

5. Determine how you’ll take and share photos: A quick establishing comment of, “Oh, so glad we’re here together – let’s be sure to take lots of photos of each other and then exchange them later” sets expectations on photo-taking responsibilities. You’d hate to have taken a bunch of photos of the other couple, and then receive no photos of you in return. Probably unlikely, but best to be certain. Then, make sure you all have a way to share photos, whether it’s simply through texts, AirDrop (this works great for me 95% of the time), Photo Stream, or some other program. We enjoyed winding down our evenings sharing photos from the day and exchanging the best ones with each other.

I polled my family and friends on this one and EVERYONE had something to say… so expect additional posts on this topic in the near future! In the meantime… any tried and true advice to share on traveling with friends? Let me know in the comments!

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