Have you ever had an experience and then wish you could push the rewind button, because with just a few tweeks, the experience would be a more joy filled memory? It all started with me when I was doing my usual email reading of my daily travel deals which fill my inbox without fail due to my constant searches of travel deals on the Internet. I love traveling, especially when I score a bargain.
I had longed to take a trip with my college friends of 40 plus years. Our children-adults now, many of us retired, and our partners in life encouraged our independence as travelers (since they didn’t wish to travel to all the places we dreamed of visiting). A few of us, over the years, had taken some overnight trips or day trips which required little planning. They had all gone well. So,I didn’t give it a second thought that a longer trip would require anything different.
One morning, as I skimmed my travel emails, boom!, there it was, a tour in Italy at a bargain price. My husband declined my invitation to join me on this journey because the trip was during his favorite fishing month. With that information, an immediate text went out to 10 college friends with the news of this Italian journey with a tour company for 6 nights for $699 and if we acted now, we could have $100 off that price. The trip included hotel, breakfast, transportation from Rome to Milan with overnights along the way. There were optional tours available or we could create our own days with booking our own tours. It all sounded perfect. Four girlfriends responded with “I’m in!”
The trip was 10 months aways, so all we needed to do was put a small deposit down with the tour company. Each person called the tour company with their deposit, and we were on our way to Italy. So far, so good. I have travelled quite a bit, however, because some of the women were not as experienced traveling, and I love planning, when the four women said they would be happy with me taking the lead, I thought, no problem.There was so much I didn’t know I didn’t know about planning a group trip. Hopefully, these following tips will help you be confident in joining your friends and having a successful travel adventure.
Tip 1: Utilize a travel consultant/specialist when booking a group trip.
Looking in the rear view mirror, I would have called a travel agent and outlined what we wanted for flights and the Tour company we wanted to book with and have the group have the travel agent be our guide through this group process. When my husband and I travel, I love the planning of the trip almost as much as the experience. I hadn’t realized that we all have quirks and a travel professional is accustomed to dealing with multiple personalities and needs. My husband and I have created our travel dance where we know our roles in the journey. For example, he sits on the aisle and myself in a window seat. We explore with some variety by having some plans and filling in as we go. We are comfortable with flexibility and adapting as we discover from locals what we should do. We know our stamina levels and when we should eat and stop for a drink at a local bar. I hadn’t really considered how much compromise is involved when on a multi-day trip with five independent women who have different interests, levels of fitness and adaptability. In group travel, best to be discussed in a meeting prior to planning activities.
Traveling internationally, we of course needed passports. The airline needs correct names, passport numbers and birthdates. I hadn’t anticipated how long it takes to type all this information into the airline website when booking flights. Using a travel professional to book flights will collect this information as well as the credit card information for each individual. I typed one friend’s name wrong into the system which generated an issue at the airport. (A travel professional would not likely have made this mistake.) Also, I had to wait an uncomfortably long time for a few friends to reimburse me for the flight which I had charged for them on my credit card. Better not to start off a trip with these types of issues.
As I researched which cities we would visit on our tour, think about when we should arrive before the tour started (since we were not using the flights offered from the tour company since they were more money and we didn’t have control of flying nonstop, which we preferred), how we might extend our trip, what we should do in each city, how we should get to the airport to the hotel, it became clearer to me traveling in a group was more complicated than when I plan for myself and my husband. As I discovered activities in each city, I sent texts to get the okay for everyone and ask for ideas. Everyone was game for whatever I planned. I, however, didn’t take into account my friends were not keeping track of these decisions or how one activity flowed into the next.
Tip 2: Print out the itinerary for the trip with hotel names and city names, booked activities with costs, optional add on excursions in each city with their timetables and costs.
I had depended on the tour company’s app which they provided which listed the cities to be visited, hotels names and tour information they offered on our week together. This information was sent to each of us in an email. I sent separate emails about our independently confirmed tours. I was compiling my own list of all these, but didn’t realize each of my friends hadn’t been doing this and were thinking I was going to be responsible for letting them know as we went along. I discovered that I had the whole picture of the trip in my mind and the others were living day to day and depending on me for guidance. Hindsight, why wouldn’t they? I just assumed they traveled like me and loved planning and thinking about the trip months before departure.
Tip 3: Have a group meeting prior to leaving and handout itinerary with all activities and discuss that there are no leaders in our group, we are in it together and free to exercise independence within the group.
An honest conversation must be had at this meeting about voicing concerns as they occur on the trip with no hurt feelings. On our first day in Rome, which was packed with tours from day to night, I voiced my position to the group. I didn’t want to be the leader nor the decision maker when we were looking for a place to eat. (The group was waiting for me to find the restaurant.) Even though I said it, people were tired and hungry, so therefore, not really receptive to my request at that moment. It would have been much better to have had this conversation before we departed to avoid any misunderstandings. Had we established a rule before we left that complaining is not allowed, only solutions to issues as they arise, we would have had a reference point to use as a group to address individuals’ complaints as the trip went on. Instead, as issues arose, as they will on any trip, I was looked to as the point person to solve the issue, a role I didn’t want.
Tip 4: Maximum two people per hotel room.
Tour companies have double price and single occupancy price. Often the hotel room will accommodate three, but all three people in the room still pay the price for double occupancy. We had five people, so we had three women in one room and two in the other. Hindsight, we could have had two people in each room and split the difference for adding the single room and taken turns having the single room during our tour. The extra cost split among five people would be nominal. This would have given each of us a chance to at least have a night to regroup from group dynamics as well as not require the coordination involved in shower taking and bathroom use when three share a room.
Tip 5: Create a money kitty for tips and taxi rides.
Get local currency with some coins and small denominations. Use funds for restaurant tips and taxi rides. This will save a lot of time! If you go with, I’ll get this one, you get, the next, it almost never works out equally. And, if the tip is figured by each individual putting in money for their food, plus tip, as you go for each meal, the tip is usually too big or too small. Trust me, you will be so happy about this decision.
Tip 6: Stick with the itinerary of the tour company.
Our trip with the tour ended in Milan. I had always wanted to visit Lake Como and read that Milan was only an hour train ride away. If we would have stayed with the tour company ending date, they would have arranged transportation from the hotel to the airport. We now took trains, independently arranged hotels, taxi from train to hotel and transportation back to the airport in Milan after two trains which involved a transfer. A lot of coordination required, and now we didn’t have Margarite, our tour director on the bus to give us instructions. This resulted in missing a couple of trains which led to a cascade of other unanticipated issues.
If you decide to go it on your own, use a travel professional to make all the arrangements and create the itinerary which train to catch and what time, arrange and book airport transportation in advance. Multiple people traveling with multiple suitcases to and from the airport makes it difficult to find a taxi to accomodate all travelers together and splitting up can even bring more issues.
Tip 7: Laugh when things go wrong and work together to solve any issues.
We had some things go wrong which were not solved with laughter or collegiality. If we had agreed ahead of time that laughter will be necessary and group think will be needed when the unexpected happens, it would have been easier to communicate when things went a little haywire. Traveling requires trust, honesty, a love for adventure, as well as a willingness to adapt and participate in decisions.
When I returned from this girls’ trip to Italy more than two years ago, I made a vow to never do that again! However, with time, the fun memories are more vivid than the frustrations. Looking back at the photos, we did truly have a great adventure. Next time, I will be taking my own advice. Happy travels!


