Advice for Traveling with Friends – 9 Tips from the Experienced

Taking a vacation with your friends can lead to a lifetime a great memories. It also has the potential of adding an unexpected stress on your trip and relationship. My husband and I took our first trip to Maui with another couple that had been our good friends for several years. We were all seasoned travelers and we were able to anticipate and diffuse some sticky points. Still, there were a couple of slightly stressful situations that we could have avoided if only we had known then what we know now. Here are some strategies to make your travel with friends go smoothly.

1. Plan your budgets and financial matters before you go on your trip.
Money is always a awkward issue, even among friends. So set aside time to meet with your friends and discuss these issues at least a month or two in advance.

  • Who will pay for the big expenses like the hotel room or condo and the rental car? How and when will the paying party be reimbursed?
  • When commonly used expenses, like groceries or gas for examples, are purchased by one person, how will you arrange to spread the cost more evenly?
  • Will you be asking for separate checks in restaurants? If a restaurant won’t split the check, how will you handle that?
  • How will you keep track of the expenditures?

2. Plan a post vacation party.
Plan in some time to get together reminisce about the vacation and share photos. Make it a fun time, but also make sure that this time can be used as an opportunity to settle up any outstanding financial matters. You’ll avoid pent up frustrations and concerns if you plan this important party/meeting well in advance. If it is possible to meet face to face, that’s best. Even if your meeting has to be over the phone, have that time allocated in your calendars so that everyone knows there is an opportunity to get together and settle the loose financial points.

3. Share the vacation planning.
Assign vacation planning tasks to everyone so that no one person is bearing the planning load and so that everyone has input into the trip. Consider having one friend researching restaurants, another researching activities, etc. By sharing the planning, you can really invest the time that’s needed to create a wonderful vacation.

4. If you are going to be sharing a room, condo, or house, know the set up of your accommodation before you go and determine how to share it evenly.
Inevitably, one bed or room will be nicer than the other. For example, most two-bedroom condos in Hawaii have one master bed with at least a queen-sized bed and a private bath, while the second bedroom has two double beds and a shared bath. So, try to plan how you will make use of the condo in a way that is fair for everyone. Will you split the use of the better room in halves during your stay? Will the person with the better room pay a bit more? By discussing the issues well before you go, you will prevent the awkwardness of who goes where when you arrive.

5. Plan in some alone time.
We love our friends, but even the best of friends can get on each other’s nerves. One of the best things we planned when we traveled to Maui with our friends was to arrange a day for each couple to have sole use of the rental car. Another strategy for alone time is to plan to dine at separate tables for an evening or two. Generally in Hawaii resort restaurants, tables for two are set up to watch sunset. If you try to sit at a table for four, two people are going to miss the view.

6. Choose a rental car wisely.
When we traveled to Maui with our friends, they really wanted to rent a Jeep Wrangler. It was a more expensive rental, but it sounded fun and adventurous at the time. It turned out that we did not have near enough room for our luggage. We were literally spilling out of the jeep as we drove from the airport–a bag actually fell off the back of the Jeep! My friend and I had to sit in the back seat and hang our heads out of the open window. It was that packed! We all laughed at the situation and we made it work.

7. Make sure you share the driving evenly.
If one person is loaded with the responsibility of driving while the rest are enjoying the sights, it can create some frustrations. So, plan to share the load evenly. This point leads me to recommend that you make sure that your rental car contract includes all the people who will be driving.

8. Plan in some friend bonding time.
For example, if the guys want to golf or fish while the girls pamper in a spa, plan that into your vacation. Doing some separate activities will give you more to talk about when you have dinner together that evening and even years later.

9. Put your plans in writing.
I love creating a spreadsheet that details the plans for each day. It really helps you keep your trip organized. (See this Hawaii vacation planning post for more information.) If your friends are web savvy, consider using a service like Tripit that helps you organize the details online.

You might also consider putting your financial agreements in writing to be used for everyone’s reference. Sometimes, we forget what we agree to, so having a written plan helps us stick to our plans.


I hope these nine points will help you have a great vacation with your friends. Have you traveled with friends? Did you have any sticky situations? Do you have additional tips to share? Please comment.

  1. Time alone is vital! have done two sailing trips with friends on small yachts in North Queensland. Both times cabin fever set in, and I disgraced myself. Once even tipping spaghetti on someone’s head as he stood below in the galley. We were becalmed by lack of wind. I was beside myself. Okay, that’s no excuse really is it?

  2. Hi Julie – Oh my! I can definitely see how being in such tight quarters on a sail boat could create even more stress on a relationship. Thanks for sharing your experience and for your first time comment at Go Visit Hawaii!

  3. Hi Sheila,

    Your excellent article made me think how 2 couples traveling together could save money in Hawaii by sharing a car-rental and using 2 for 1 Hawaii entertainment book coupons for dining and attractions.

    You could save money, but then if each couple wants to do different things in different places a the same time, then it may make things difficult.

    I like your suggestion to plan each day before the trip so you can share resources and save money.



  4. Traveling with friends is really fun and like you said every detail needs to be discussed and agreed upon before the trip begins. And I can definitely see where alone time is vital to keeping from ending up with frazzled nerves.

    Great post very useful, thanks:)

  5. Thanks, Debo Hobo! Like you said, if you can work out the details and address any awkwardness before it happens, everybody will know what to expect. Then you can all just have a good time together.

  6. Great article! We brought a friend of ours in 2002…basically paid for the entire trip minus $700 she saved as a graduation present for her. Despite telling her everything to expect, telling her about the terrain, her seeing all of our footage from our adventures, she acted like a total baby the first 3 days. REALLY saw the Italian temper in her come out. By day 3 I had called to airline asking how much it would cost to send her home. (The vacation was 18 days) I had to have hubby speak privately with her to knock it off because she was ruining our trip and I’d spent 2 years planning it. She said she’d try and he said it was going to have to be more than that. To this day she doesn’t know I orchestrated him talking to her because I knew if I did *my* temper would come out and I could be out a 14 year relationship.

    Though the beer commercials show many friends bonding over vacations, we’ve heard more horror stories than the whole bonding experience. We’ve pretty much sworn off anything longer than a weekend. LOL! Hats off to those who can pull it off though!

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