5 Top Tips and Advice for Traveling with Friends and Family

I always have fun traveling with family and friends, but you have to anticipate problems before they occur.

The snoring!

I always forget about the snoring, dammit.

Across the tiny room, a KOA camping cabin in South Dakota, my brother was sawing logs like he was in a rush to fell the entire forest. That's what happens I suppose after a night of drinking whisky. Bart and I had stayed up late after another long day hiking and exploring the Badlands and Custer State Park with our spouses.

So, a good night's rest was desperately needed. Bart was going to get it, and I was not.

Neither was Colleen.

But Bart's wife, Natalie, seemed to be dozing right along with my brother, years of practice sleeping alongside that noise (it sounded at times like a five geese were getting sucked into a jet engine) apparently numbs her to the ruckus.

And Colleen and I were without our handy earplugs. Ugh!

Of course we had a wonderful time traveling together that week and knocking another destination off our list, but such are the perils of traveling with friends and family. We often fail to consider the possible downfalls in our excitement of planning an adventure.

I love to travel with friends and always ask who can join Colleen and me on our trips. We enjoy exploring new places with loved ones and creating lasting memories. Plus, you can divvy up the costs of lodging and the duties involved with planning, cooking, cleaning, driving, etc.

Colleen's brother Ryan and his girlfriend Kelly joined us on a cruise several years ago. It was their first sailing. It was wonderful to have the company, playing games and going on excursions together. In St. Kitts, we went on a hike and a tour of an old plantation and sugar mill.

Later in the day, Ryan and Kelly disappeared for a bit from our group. We found them moments later alone under a huge old tree, with Kelly having some sort of emotional reaction.

We had known Ryan was going to pop the question during our cruise, and we had anticipated being nearby to witness it. Well, he had other plans and secreted his woman off to a special spot and got the task done in private. But we were delighted to be able to celebrate their engagement immediately afterward and for the rest of the cruise.

Now, Ryan and Kelly join us often in our travels, with another couple cruises already in the books and adventures in Mexico, too.

Big occasions are a good excuse to try to get people together for a trip. Colleen and I got married in Las Vegas so that we could sell it to our friends and family as a destination wedding and ease our minds about having to provide too much of the entertainment. Celebrate on a trip, and people can find plenty to do on their own.

We had a big group of friends on a Panama Canal cruise last year to celebrate our 10-year wedding anniversary and Colleen's latest milestone birthday. Next year, we'll sail the Caribbean for my 50th birthday party — again with a group of friends.

See, the planning and anticipation of a trip with friends and family is exciting. As well as Colleen and I do together traveling as a couple, it's always exciting to have other people to talk to, play games with and learn from.

By now, though, we know that hiccups and bumps in the road always creep up because not everything works out perfectly, and you shouldn't expect it to. But there are ways to deal with problems so they don't ruin a trip -- or a friendship.

1. Know Who You are Traveling With

If you know a friend extremely well, you probably know whether they will make a good travel partner. But if you are considering a trip with casual acquaintances, be careful. Perhaps you shouldn't get a room together. (At least get a suite with separation and doors between rooms.) You don't know many of their habits that might not mesh well with yours.

2. Discuss Money Before You Go

Maybe you like to go to expensive restaurants. Your friends or family might be on a tighter budget. You don't want the stress from a dispute right before meal time. Also, make sure you all agree how you will split up any expenses for groceries, lodging, tours, etc., before you're in the middle of your vacation.

3. Be Honest and Communicate

From left, Ryan, me, Colleen and Kelly on a hike in St. Kitts.

Have a quick and light chat about how you are excited to be on the adventure together. But also state that you know something might come up that you didn't consider and if anyone has an issue, please speak up. Ensure that all input is welcome and expected because it's everyone's vacation to enjoy, and it's not worth jeopardizing friendships for a short-term problem that can be easily resolved by talking it out.

READ: Couples Fight When They Travel. Deal With It!

4. Be Flexible and Relaxed

There is absolutely no need to get tied to one idea of how the trip will go. Sometimes it rains, people run late, attractions are too crowded or closed or don't live up to the hype. Remember how lucky you all are to be together — "It's better than being back at work!" — then grab a few beers and make the best of it.

5. Do Proper Planning for Daily Activities

Do your best to set out a general daily plan by communicating well ahead of time (by emails, etc.) to discuss what everyone would like to do on the trip. Once a consensus is met, you can work out a daily schedule to try to do and see all that you want. But remember to be flexible because it will rarely go exactly as planned. Planning, though, helps you avoid that awkward and frustrating discussion we've all had when in larger groups.

"What do you want to do today?"

"I don't know."

"I don't care, whatever you guys want."

Five minutes of this type of back and forth, and someone finally yells, exasperated. "Let's just do SOMETHING!"

Yeah, nobody’s got time for that nonsense.

Back to my brother Bart. He and my friend Matt and I spent a week together in Cancun in a tiny two-bed studio at a resort last year.

Yes, two beds. Three big guys. We know! This should be a recipe for disaster if there ever was one.

But we all get along well and have for more than 35 years, so we were certain we could make it work. We just had to flip a coin to see who would be sharing a bed with Bart each night. We could deal with the cramped quarters — and snoring — just fine. Because we were having a blast, reunited in Mexico!

Happy travels to you with your friends and family.

Thanks for reading,

JR