Travel with a friend…Fun or Fiasco?

By Peg Sullivan

Who is a good traveling companion? A sobering question best contemplated before you blurt out: “Wouldn’t it be fun to go to Aruba in February!” Through years of traveling I’ve learned a valuable lesson — not every friend is a traveling companion.

I took my first trip with friends at nineteen. Four of us drove back to Wisconsin from the West Coast at the end of summer. We thought, “how fun” to drive on whatever roads eventually went east. We met up in Portland and headed south. We had a “college car” without power steering or air conditioning. Its only amenity was a Coleman cooler taking up half the backseat. The cooler was a combination dinner wagon-air conditioner, holding food, soda, and a 10-pound bag of ice. The steering was so stiff, only the owner was strong enough to handle it along the rocky cliffs of California’s Highway 1. We were lost a lot in cities. One evening we slept in the car because finding an affordable hotel near San Francisco was impossible. And through the desert we drove 75 mph with the windows down while icing our faces and arms — lucky we had that cooler.


This first friends’ trip taught me to select travel friends wisely. We were young and hit the road with no expectations. Daily, we laughed in the face of adversity and were too inexperienced at traveling to care. It is a trip I cherish but as an adult looking back, it would be suicidal to repeat. I still travel with one of those maiden voyagers. We laugh about that original trip. Last year we went to Cuba and this summer we are planning a trip to Cape Cod. I accumulated a short list of friends I choose to travel with now. We have fun but the trip is always planned to avoid adversity.


Careers, limited vacation time, GPS, hotel memberships, platinum credit cards, rental cars, and rational diets have interceded over the years to make my traveling more discriminate. The first trip gives definition to the phrase “a complete fiasco.” We had no itinerary, inadequate maps, no reservations, no budget, nothing prepaid but airfare, and a complete intolerance for fussy eating habits. We drove ridiculous distances without stopping, and argued about religion, appropriate wedding attire and politics. It was a miracle we made it home; today, the trip would end by leaving several people on the roadside in Nevada.


Traveling companions start trip discussions months in advance; book airfare early to find reasonable rates and most important, good departure times. I hate arriving in a new city during rush hour or late at night. At night, it is impossible to get a feel for where you are in the city, even in a car with GPS.

We frequently book and prepay hotels, and when possible we pre-purchase tours, shows, or other expensive entertainment. Our trip to Cuba was completely paid for before leaving Miami. When you spread out expenses prior to the trip, it builds anticipation and an itinerary. Then, all you have to worry about at departure are meals and incidental expenses; costs you can control. It also forces agreement on the range of hotel prices, provides destinations and timelines for anxious spouses.


Agree on key sites to visit while planning. This gives each person input and ownership, plus it minimizes the question I hate most: “What are we doing today?” My favorite trait in a traveling companion is independence. Is the person willing to do their “own thing” on occasion? I never hesitate to go alone to a museum or show if a friend would rather shop or needs to rest. A Texas friend laughed at me when I suggested we go horseback riding through the hills around Santa Fe. “You go. I never go near those smelly animals. I’ll be on the patio reading with some tea,” she assured me. We developed a travel harmony that has included domestic and international trips.


I spent a miserable week in Napa Valley when a friend was having a family crisis at home. She called her husband almost hourly, was restless, obviously stressed, and became impatient not only with us but our B&B proprietor and the spa staff. By the time my traveling companion shared her anxiety, the trip was half over. Try to resolve problems before leaving if you can. If you can’t, let your traveling companions understand what is happening.


When traveling, I am most comfortable eating a couple of times a day, once late morning and again in the evening. So several of my traveling companions now travel with food. They snack during the day on nuts, granola bars, raisins, and other convenient food to control their blood sugar levels. I was surprised the first time I noticed a quarter of my friend’s checked luggage to Paris was food, as if there was no food to be found in France. It was a great lesson to learn because I like to travel with another friend who only eats once a day. When traveling with him, I pack snacks.


Decide early who will drive on a trip. I like to drive, it keeps me from reading. I was shocked to learn people want to talk on planes, trains and automobiles. My parents never encouraged us to babble in the car so I was surprised on a train from Dublin to Cork when a traveling companion asked in an irritated voice, “Are you going to read the whole trip?”

When I drive I abhor making small talk, so satellite radio is another favorite. I listen to conversations and respond to specific questions but mostly I focus on the road, the landscape and the GPS woman so she doesn’t have to recalculate. I have two male friends who hate to drive so don’t assume it is a masculine job; driving is an ecumenical task best performed by the most comfortable driver.


I love to see new places, meet people, walk through history, and encounter different cultures and art. Traveling is special to me; it is my favorite learning experience. I love it whether I share it or not. So ask yourself, is this friend a good person to share this experience? Will the trip be equally appreciated? If not, then she/he is the wrong traveling companion for this trip.

About the writer: Travel is an intricate part of Sullivan’s professional and personal life. Whether scouting cities and hotels for corporate events or knocking off locations on her “must see” list, she is frequently searching the internet for her next trip. 

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