Traveling with Friends
August 29, 2016 • Travel
I’m in Rome today, getting ready to take another group of guests on a fabulous food and wine trip to Italy (that’s my first group in 2008 above, touring the Jewish ghetto in Rome). While this marks my 9th trip as a professional tour guide and trip organizer, the reality is I’ve organized dozens of trips for family and friends traveling together, and I’ve learned a few things over the years. Sharing your favorite travel destination with friends can be such a fun time, but you can also end up with stress and conflict on the trip if you don’t think things through ahead of time. Luckily, by following just a few guidelines, you can ensure a harmonious experience for all. So check out these proven travel tips when planning your next group adventure!Select compatible travel companions. Simply put, your best friends don’t necessarily make your best travel companions. Sharing a mutual love of opera with someone doesn’t convey anything about compatibility on the road. Examples of characteristics to consider when choosing travel mates include whether you are a morning person or a night owl, whether you prefer to soak in the culture in a street side bistro or in a museum, and how flexible you are about the day’s schedule. We have a group that loves to tour wine country together, and we never seem to disagree on the day’s plans. Great travel partners don’t need to be people you socialize with on a daily basis if you are simpatico on the road. Solicit input from the group on the itinerary and schedule. A well-planned group trip should include something for everyone (including things that challenge you a bit like this ATV ride around St. Bart), and making sure everyone’s needs are being met goes a long way towards putting people in the right frame of mind for the trip. By being part of the planning process, your friends feel invested in the trip, are less critical, and are more apt to enjoy the experience. Allow free time. Travel can be tiring and you need to plan for down time. After a big day of travel or sightseeing, plan on a low-key morning to follow. Those who feel energized can take advantage of the open schedule to break out on their own, while those needing a rest can sleep in, enjoy a leisurely breakfast in a café, take a walk, and recharge. Try not to schedule anything in the later afternoon (except perhaps plans for a glass of wine with a friend!) as people need time to rest and clean up before dinner.Compromise. Not everyone is going to have the same level of enthusiasm for each aspect of the trip, but a group can successfully travel together by compromising. For example, perhaps one friend agrees to visit the art museum early in the day if the other friend agrees to stroll through the street art later. Or in this case, we agreed to visit the Vatican only from the outside instead of burning up the day touring St. Peter’s and the Sistine Chapel.Ensure privacy. Although people opt to travel with a group because it’s fun to be together, it doesn’t usually work well to be together all the time. If you’re planning on one house for everyone, make sure there is enough private space (including bathrooms!), or consider two smaller villas. If you and a friend are planning on sharing a room, consider opting for two rooms at a less expensive hotel instead. Giving each other some space is especially important when you are away from the comfort of your own home and routine. My friend above and I shared a single bathroom in a house with 4 women for 2 years in college – now, we’re quite happy to have our own space when traveling together!Let people go it alone. Not every activity must include the full group. If someone chooses not to participate in a planned event, allow them to opt out without making them feel they have let the group down. Likewise, if one couple wants to add something to the day’s itinerary, it need not include the full group. The best trips with friends include a healthy balance of time alone, couple time, and group activities. In Paris, this group started the day with a group tour of the “must see” sights, then split up for the late afternoon, which worked well.Agree on the budget. Most friends discuss the destination, airfare, hotel, and car rental before departing. But what you do once you get there can significantly affect the overall cost of the trip. Booking a $300 dinner at a Michelin 3-star restaurant when your travel companions have budgeted $50 for the meal creates embarrassment and tension. Discuss your desires before you leave and agree on your general meal budget, what you will spend on entertainment and if and where you will splurge on the trip. Don’t pressure your friends to spend more than they are comfortable spending and stick to your agreement. Booking a cruise, like we’ve done with these friends a few times, is great because costs are known up front and everyone can opt in or out of excursions according to their interest and budget.Be flexible. The initial itinerary should serve only as a rough guide to your trip. Be willing to change plans based on the mood of the group. You never know when a chance encounter with a wine producer might lead to a fun barrel tasting like this one. Limit the size of the group. Four to eight people seems easiest for a group trip. Traveling with a larger group creates organizational challenges and complicates transportation. By limiting the group, you avoid wait time and limit frustration. If your group is larger, however, cruises are a great option because people can start the day on their own, but meet up at the scheduled dinner time and place at the end of the day.Pack your sense of humor. Don’t take yourself or each other too seriously, and learn to laugh at the mishaps on the road. These “incidents” may actually turn out to be some of your greatest memories. On my last trip to Paris with friends, we took a bike tour for the first time – as we started out on the bikes, riding up out of the garage in central Paris, my friend didn’t quite yet have her bike skills tuned, and she fell over, causing all four of us to tip over too. We laughed until we cried!One of the best parts of traveling with friends is the opportunity to reunite to share pictures and retell stories of your adventure. A fun way is through a themed dinner featuring the cuisine of your destination as it brings back the flavors and memories of your vacation. After our African safari trip, our reunion dinner included large stuffed animals for decor and everyone brought pictures and wore their safari clothes. Getting back together like this will make you smile and laugh, and you will be excitedly planning your next trip together before the evening is over. Happy Travels!