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.

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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.