January 16, 2021   9:17am

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Traveling with Friends (you’d like to keep)

Just got back from your vacation … planning your trips for 2008? Thinking how great it would be to travel with friends this time around? Our “Travel” expert Susan helps you avoid a mismatch and have a great time ….

Perhaps it’s over dinner — after a few glasses of wine –that you and your friends get excited about a trip — together. It’s so easy to romanticize how much fun it’s going to be, and, before you know it, you’re out the door and on your way. Prior to taking the plunge, here are some things to think about…

Avoid a Mismatch

Traveling with friends often makes the exotic more comfortable, and what could be better than sharing costs for private cards, drivers, boat charters, house rentals and other expenses off distant shores. Having traveled often in groups of three, four, six and eight, I’ve learned that a mismatch in expectations can ruin your trip and threaten your relationship. Rules of thumb: the more complex the trip the higher risk of things going awry; and the larger the group the more personalities are in play.

Think/Talk About Before You Go:

Same or Different Travel Patterns: Do you want to stop each day for a fabulous (long) lunch, while they really want to see every (I mean every) possible museum or other site along the way? If so, avoid extensive point-to-point touring where you move from place to place and mutual scheduling is required. Instead pick a destination where you can stay awhile and explore independently. Or consider a cruise where you can make different choices and still meet up later.

Morning People or Night Owls: If your internal time clocks are not in sync, but you still want to travel together, pick a resort destination or a cruise – both of which accommodate more flexible schedules.

Easily Stressed or Easy Going: Since things are bound to go wrong (or perhaps not perfectly) on any trip, save your more complex trips (such as point-to-point touring) for friends who aren’t easily stressed by everyday life. (Think how they’ll act on the road!).

Money Matters: If finding a restaurant at the right price point for you and your friends is hard at home, it will be harder on your trip. Still want to travel with them? Pick an all-inclusive vacation – where most things are prepaid in advance.

Heavy or Light Packer: If one of the group tends to take along the kitchen sink, while others travel foot loose and fancy free, you might want to discuss this in advance. Particularly if space in a rental car, on a boat or in a private plane has limited storage … or if one thinks being able to carry bags onto a plane is important vs. checking them. TIP: There are severe weight restrictions in countries where the aircraft is small — such as Costa Rica (where my luggage and I were both weighed — in plain sight of all). Plane travel in parts of Africa and when you’re going on safari are also restricted. Check ahead!


Allow For Free Time: Too much togetherness is not a good thing. Make sure that there is free time (hopefully each day) for individual exploring, shopping or naps!

Stay In One Place Awhile: Too much moving around, early departures, long days on the road, can result in a tired and cranky group. Streamline your trip. Perhaps save some sights for another visit, and everyone will be happier.

Cater To Special Interests: If they want to visit a certain site, or eat at a special restaurant, try and make it happen (even if you decide not to go along). It’s their vacation too! And, if there’s something you want to do on your own — a special meal with your mate or with friends who live there — discuss this in advance so your needs are understood as well. All goes better when you limit the surprises, and they may very well be relieved because they want to do this to.

Be Flexible: If you get to a place no one likes, perhaps the next place on your itinerary can take you a day earlier. Its okay to adjust plans once you’re on the road – but if you find you’re stuck somewhere, don’t obsess – make the best of it and have fun together. You’ll laugh about it later!

Still not sure?

Test run a shorter trip, like a weekend away together. Or meet up for only a part of your trip — select one or two destinations of common interest on a longer trip, bot go your separate ways for the rest of your vacation.

You may have tips to share as well. Add them in the comment box below. Wishing you the best travel for 2008!

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1 Comment
Lynn says: January 24th, 2008 at 4:25 pm

We have travelled extensively with friends, some who were experienced travellers, others who were not. We have found it helps to set a few ground rules prior to the trip:
1. We are not “joined at the hip” . Make it clear that it is not required for the group to be together every minute of the day. Schedule a day where the group goes in different directions, only to meet for dinner. This gives each couple some “alone” time, and adds to the conversation at the dinner.
2. Establish a banker for the group events and pool monies. This simplifies those meals when everyone is together, and avoids the fumbling for currency when the tab must be split. Warning: don’t fall into the trap of being distressed when the couple across the table had an extra bottle of wine. After all, you could have joined in.
3. There is always a person in each group who takes the lead in arranging the schedule. If he/she doesn’t consult with the group on these events, and some of them are not your cup of tea, make it clear you will not be with the group for those events. No harm; no foul.

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