While discussed over happy hour drinks, traveling with friends seems like a brilliant idea! You enjoy each other’s company, you enjoy traveling, and you should enjoy traveling together… Why haven’t you thought of this sooner?

Traveling with Friends can be a beautiful thing!

Yet, despite your best efforts, it doesn’t always turn out to be so enjoyable. The many decisions create a mountain of stress and ruin an otherwise enjoyable experience… What have you gotten yourself into!?


You Fool! What have you done!?

Before you allow panic to commence regarding your upcoming friend(ly) travel plans, take a moment to prepare and carefully review some points of consideration…

Specifically – AcCounting Your Points Top 5 Things to Consider when Traveling with Friends:


Don’t squabble over money – speak up and talk it out!

1 – Money Talks

Mo Money Mo Problems, right?

Travel is inherently more expensive than staying at home, despite all of your efforts to be frugal and cut costs. Even when leveraging points and miles, there are plenty of travel related expenses that cannot be avoided – meals, special events/activities, ground transportation, etc.

And because of that fact, money will most likely be the largest obstacle that you will have to navigate when traveling with friends.

In fact, every other point of consideration on this list can be directly or indirectly tied back to money!

Will you split all travel expenses down the middle?

Will pay your individual meal cost or split with the group?

Will you trade off who pays Uber/Taxi fares, or will you true-up everything at the end of the weekend?

My Advice – Be open and honest about any and all money-related topics. It can be hard to speak up when it comes to financial matters, but if you keep your mouth shut, how will anyone ever know if you are in disagreement about a particular item?

Note: I struggle with this one piece of advice, and definitely have room for improvement when it comes to speaking up, myself!

Personally, I need my space!

Personally, I need my space!

2- Personal Space (& lack thereof)

You just don’t realize how wonderful it truly is until you are without it – which is why you should be making your lodging decision with it in mind!

I have completed quite a few trips with some of my dear closest friends and have had a wide variety of lodging experiences…

Boston – 1 Hotel Room (Double Beds) – 4 to a room

(Lucky for me this was with an old college roommate and his wife, where 4 people in twin bunk beds was a part of everyday life back in our college days!)

Nashville – 2 Hotel Rooms (King Beds) –1 couple each room

Washington D.C. – 1 Hotel Suite (2 Bed &2 bath) – 5 to a suite

Santa Barbara, CA – 1 Airbnb (Entire House – 2 Bed & 1 Bath) – 4 to a house

Through all of these travels you might think that I have picked up a variety of tips and tricks, yet it all boils down to one small, but crucial, piece of advice…

My Advice – Splurge (within REASON) for space!

Research room/suite types to determine if size/spacing meets your needs, leverage your hotel loyalty status and request an upgrade, utilize AAA or corporate discount codes to cut nightly rates, and/or give hotel alternatives (like Airbnb) a try!

I am all for saving money, but a few extra square feet can make a big difference in overall team moral.

Though you may believe that you will spend most of your time outside of your hotel/rental, there will be plenty of moments early morning and late night (after a hard day of travel) where you will really want your space and when you will be wishing that you listened to me!

Please believe me!


Life is about the journey, right?

3 – Transportation

Everyone has their preferred method of transportation when traveling. While it depends on the city, I think one great transportation option is the bicycle!

If the city is accustomed to bikers and the journey is safe and is a reasonable length (under 2 miles or so), biking provides a great way to really experience the city even between points of interest! Biking is cheap (sometimes free!), logistically simple, and something that everyone has experience with… but what if you can’t [safely] ride a bike? Like my wife!

WARNING –Seek safe haven if you spot this couple biking in a town near you!


Pedestrians, bikers, automobiles, trees, and woodland creatures – BEWARE!

Other Non-Biking Options: Uber (my personal fav!) & Lyft, Metro systems, taxis, walking, and rental cars – consider all of your options and choose what suits your group!

My Advice – Be flexible; know your location, know your group, and their abilities! It is best to read up on a location and determine the best method of getting around as a group, prior to when the actual travel commences.



Eat to live and live to eat!

4 – Feeding Time

I gotta eat, and I gotta eat 3 big meals a day (at minimum)! That means no skipping breakfast and no “light lunches” for me. I am normally a very calm and easy-going individual, but do not let hunger occur, or you will feel my wrath!

That said, I am really impartial as to where we eat! Michelin Star, Zagat Rated, random back-alley food truck – I love ‘em all! Others are much more particular than I am, and view dining as a key part of the overall travel experience…

This brings me to…

My Advice – Plan group dining ahead of time! Agree on all restaurants together, or split the decision by meal, that way each couple has the opportunity to choose – and do so with my #1 Money point in mind!


California views for days...

Hiking California – views for days…

5 – Activities

My list of favorite activities when traveling goes a little something like this:

  • Outdoor Activities – running, walking, hiking, kayaking, etc. – I love it all!
  • Shopping – local farmers markets, festivals and miscellaneous shops – Anything local to the destination is worth my attention.


  • Museums – get in, “oh look at xyz, I recognize that from the guide book”, GET OUT!

I respect the fact that all of my friends do not share this same ranking system, and although it kills me, I have to compromise. I really do wish that my advice here could be “just do you, man!” but unfortunately that attitude will get you nowhere fast, and so…

My Advice – Compromise! Pick one must-do or must-see activity and suggest that the group partake. If you ask nicely, and your activity is reasonable (and not putting anyone’s life in danger), then your friends should be up for it! Note: Then you must reciprocate their willingness to fulfill your travel itinerary item!


Final Thought

I don’t always travel with friends, but when I do, I prefer to follow AcCounting Your Points Top 5 Things to Consider when Traveling with Friends!

Whether you follow these tips or not, make sure to have fun, experience something new and leave a new place better friends than when you arrived!

Do you have any tips and tricks that you rely on when traveling with friends, family, or a larger group? Let me hear them in the comments below!

Happy [Friend(ly)] Travels!