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Planning and Executing a Large Group Trip to Europe

Ellen Singer

Several years ago I read an article in the New York Times about a B&B owner who gave workshops for folks who wanted to become B&B owners. The first day of the workshop was dedicated to all the reasons the prospects should forget they ever even considered the idea of owning a B&B. Only if he hadn't succeeded in scaring off all of the participants did the leader move on to how to run a B&B on day two of the workshop.

In a similar vein, let me suggest that if you are considering leading a large group trip you should forget the idea right now. I'm not kidding. Don't do it!

You're still reading! I said to forget the idea!

(Sigh.) Apparently your desire to pursue this foolish idea is stronger than my determination to dissuade you. If so, let me share what I learned from planning and leading a group of 15 people on a two-week trip to Italy in the spring of 2004. Some of the learnings are "things I did right", even more are "things I did wrong" and the largest group, by far, includes "things I wish I had done."

Before you begin planning a trip, there are three important topics to consider: leadership, people and behaviors. If after reflecting on these topics you still want to organize a group trip, there are three planning time frames: pre-travel, during the trip, and after the trip.


Even well established, functional groups need leadership. Fledging, temporary groups need it even more. The single biggest mistake I made regarding our trip was going into the leadership of it halfway; reluctant leadership is worse than none at all. If you assume even a little command of the situation people will rightfully begin to expect more from you. Take the time to decide if you want this responsibility. If the answer is "yes", step up to the plate and do the job fully. If you're not sure or if your answer is "no", back off and let someone else who is willing to do it take on the job. I didn't set out to plan a large group trip but I let it happen, then I refused to fully accept the responsibility. I choose the areas I wanted to focus on and ignored the others, pretending to myself that they would work themselves out somehow. They did not and everyone's good time was compromised as a result.

Now, leading does not mean doing everything yourself. The best leaders actively delegate for two important reasons: (1) it frees them to focus on the important and/or big picture issues and (2) it increases others' "ownership" of the trip and of their own satisfaction. Don't set yourself up to feel guilty if members of your group don't have a good time.

What, you may ask, should the leader do him/her self and what can be delegated? As a general rule I would suggest that the leader focus on two areas: people and behaviors. These are the overriding, big picture issues that will make or break a group experience. The specific decisions of where and when to go and what to do while there can be delegated as long as everyone agrees to certain decision rules (more on this under "behaviors.") Just keep in mind that delegating work to others doesn't mean abandoning them with it!


Have you heard of the book "Do What You Love, the Money Will Follow?" The group travel corollary is "pick the right people and everything else will be manageable." This is, without a doubt, the single most important group travel decision, more important than all the others added together, yet most groups I know of came together at least partly by happenstance rather than through thoughtful consideration.

When I asked someone from our group what we should have done differently she immediately shot back "psychological testing." She was kidding (I think), but she had a point. While it's not practical to ask everyone you're considering traveling with to submit to testing (no matter how tempting the idea is), there are some questions you can answer for yourself and ask of others. There are no "right" or "wrong" answers to these questions; their greatest value is the self-awareness and conversations they engender.

General Attitudes

What do you hope to get out of this trip?

Obviously if you have group members with vastly different or conflicting goals you have the potential for trouble. Dreamers with unrealistic expectations are a problem waiting to happen. Less obvious, but possibly more deadly, is the "I don't know" response to this or any key question. Do everything you can to ascertain if the person who doesn't know or won't say what they want is passive/aggressive (P/A). The P/A is the Achilles heel of any travel group because they can not or will not state their needs up front but they will openly complain during and after the fact if their needs are not met. Avoid them at all costs!

How much time do you want/expect to spend with the group, and how much alone?

Some people need a lot of time alone to restore their energy. Others need a lot of "people time" in order to feel alive. Most need some of each. Knowing and discussing this in advance can help people adjust their expectations of others.

What do you need to feel comfortable on your own?

Some folks in our group hadn't considered that they would be uncomfortable driving around on their own because they were unable to converse in Italian. Unfortunately, they were already in Italy before this occurred to them; I should have asked the question in advance. Other "needs" were more easily resolved, by purchasing maps or borrowing a cell phone before heading out alone.

What travel pace do you prefer?

We had at least one member in our group who felt that unless she was going somewhere, doing or seeing something every waking moment she was wasting her vacation time and money. Others were perfectly happy doing nothing. This is okay, as long as the answer to the next two questions is "completely."

How accepting are you of perspectives that differ from your own?

Getting a straight answer to this isn't easy. After all, how many of us would willingly admit we are narrow minded, judgmental and/or inflexible? Even though it's hard, do whatever you can to tease this out. You can try leading questions on politics or polarizing social issues, use an example from your past and ask for reaction, anything. Just be sure you talk about it with each and every prospective member of the group and satisfy yourself that you won't be shacking up with someone who cannot compromise. Along this line, look out for "ugly Americans." I discovered that a good friend was one on my first trip to Europe. She was perfectly fine in London but when we hit Paris she turned into someone I'd never seen before. She insisted that she was an American and she spoke only English, regardless of where she was, and she became belligerent with those who did not understand her (including me.)

How responsible are you for your own enjoyment and satisfaction?

See above.

Money Attitudes

I've read that differing attitudes about money are one of the key factors leading to divorce. If it can split up people who once planned to spend their entire lives together, just think what it can do to those who've only committed to two weeks of togetherness.

  • How do you feel about equally sharing group expenses even if you don't always equally benefit (didn't eat as much as someone else, didn't drive as many miles in the car, didn't use as much heat/electricity etc.)?
  • How do you think we should handle big expenses (damages to rental property, damage to rental car, etc.)?

Other people considerations include:

Adults only or a mix of adults and children?

We successfully mixed a group with ages ranging from 18 - 81.

Experienced travelers only or a mix of experienced and newbies?

Personally, I would not mix the two again because their interests conflict and everyone winds up compromising too much in an effort to satisfy the others.

Interests: how do the potential group members like to spend their travel time (shopping, history, culture, relaxing, cooking, beach time, etc.)?

Is the answer consistent with where you will be and the people you will be with?

How many is too many?

The answer depends on the people involved. With the wrong person two can be too many! With the right people, who knows? (Actually, just about everyone I've talked to has an answer to this question but the answers are all different!)

Two final thoughts on people; first, under no circumstances should you travel with someone you have not met beforehand. No "friends of a friend" or second cousins you haven't seen in twenty years. The potential for unpleasant surprises is too high and can ruin your entire trip.

Second, have the difficult conversations as early as possible. Saying no to someone early in the process is hard but at least you have a chance to get over it with time. Avoiding the difficult conversations can ruin your trip, their trip and your relationships. Sadly, one life-long friendship in our group has been damaged, perhaps irrevocably, because we didn't have the difficult conversations and raise the right issues before we got on the plane.


Once you've determined who will be in your group, the next set of issues to tackle are how you will interact with one another. There are five key areas of interaction to focus on: communication, decision making, roles and responsibilities, cooperation and coordination, and dispute resolution.


Like the old election advice "vote early and vote often", when planning a group trip communicate early and communicate often.

  • If at all possible, get the entire group together at least once before your trip, as soon as possible after deciding who will go. Our group met for a long lunch in early December prior to our trip in late March. Everyone got to meet everyone else and ask the questions that were on their minds. Among other subjects, we discussed cars and agreed on how many we needed and who would rent them, cell phone rentals and flight arrangements.
  • Determine how you will keep in touch and provide feedback to each other during the planning process. Email is great if everyone accesses and responds to their email daily. One couple in our group only checks their email occasionally and another member doesn't have an email address so I had to call them (or rely on someone else to relay messages). It was inconvenient and added considerably to the time required. Other possibilities are to set up a web site just for the trip, create a newsletter or arrange conference calls.
  • Establish ground rules for giving and receiving feedback. Remember the passive/aggressive? In case one of them did sneak undetected into your group, make sure you get good feedback from every member of your group throughout the planning process and during the trip. Ask a lot of questions, offer a range of possibilities and ask for reactions, anything to help people articulate what they want and don't want.
  • Practice compassionate honesty. The truth doesn't have to hurt but it does need to be communicated.

Decision Making

How will your group make decisions? I guarantee that within any group of three or more people there will be different expectations regarding how decisions will be made. Clearly, some decisions require more input and discussion than others do. You may want to reach for consensus on the accommodation decision but be okay with delegating the rental car decision to one or two people. The important point is to identify what decisions will need to be made and clarify how they will be made, for example:

  • Consensus: everyone agrees on the solution (although it may not be everyone's first choice, it is a solution they can support)
  • Majority rule: an agreed upon percentage (more than half, three quarters, etc.) of the group supports a given solution and the rest agree to go along with it
  • Delegate: one person (or a couple) is (are) designated to make the decision on behalf of the group, and the rest of the group agrees to support whatever choice they make
  • Coin toss, draw straws, etc.: just sheer luck

For example, if some, but not all, of the bedrooms in your villa have in-suite bathrooms, how will you decide who gets them (this happened to us.)

In addition to defining how a decision will be made, agree on how much time you will devote to the decision process. It's also helpful to identify a fall back option in case the decision method you choose doesn't work out or is taking too much time.

If this sounds a bit over-the-top to you, keep in mind that professional travel groups work in part because the participants go into the trip with no expectations for input; they accept that the paid leader will make all of the key decisions for them. That doesn't mean that people are always happy with those choices or that they don't complain, but in this case the leader is paid and this is their job, not their vacation. As an unpaid, non-professional leader, don't let your discomfort with process get in the way of enjoying your own vacation.

Roles and Responsibilities

Who is going to do what? And by when? Who decides whether something is done and if it's been done correctly? Just as groups need leadership they need defined roles and responsibilities. In my experience, most people are willing to chip in and help out; they simply need to know what is expected of them. If you've agreed to take on the leadership of a group, defining the roles and responsibilities and following up to ensure things are getting done is your job. An important point to clarify up front: who will enforce decisions that the group has agreed to?

Cooperation and Coordination

You can't avoid entropy. What's that, you say? According to my eighth grade physics teacher, it is the tendency of all things to fall apart eventually. He said, and I for one have seen enough examples to believe him, that left to their own devises all systems, no matter how simple or sophisticated, will degrade into chaos. Have no doubt about it, a group is a human system and it can degenerate into a mob in a heat beat. Active leadership is necessary to ensure that members of the group are cooperating with each other and that the myriad activities of the group come together in ways that benefit everyone. Who is doing what, and when? Where are the cars going, and who will be driving them? Who's picking up food for dinner?

Dispute Resolution

Maybe you'll get lucky and they'll be no conflict within your group. If that's the case, first check to see if everyone has a pulse. Conflict is normal! Expect it, and know how you're going to address it.

Pre-travel Planning

I have friends who rarely do much pre-travel research or planning, they prefer to get on the plane and just see what happens. That's fine if you travel alone or with a like minded companion, but groups, like armies, don't get anywhere without a lot of preparation. For this trip, I relied on:

Slow Travel (www.slowtrav.com)

This is a great resource for both general and specific information on a wide range of travel topics, especially about Italy (particularly good for restaurant and accommodation reviews).

Books and other web sites

Travel books helped identify possible day trips; local web sites provided specific information (for example, we downloaded walking tours from the comune of Siena's web site).


Ask everyone you know where they've been and what they did, learned, etc.

Slow Travel Message Board (www.slowtalk.com) (and other message boards)

A wealth of information and ideas as well as a great place to get answers to detailed questions and benefit from the experience of others.

General Planning

Planning time

Allow between 12 - 18 months for peak season travel; 9 -12 months for off season

When to go

Start with a general time frame (e.g. Spring 2004) and narrow down by first identifying absolute "no" weeks, then prioritize among what's left. Once you pick, stick. Another important lesson from a friend's group: insist that everyone make a formal vacation request at work immediately. Two people in their group didn't get to asking for time off until it was too late and they dropped out weeks before the trip, causing problems for everyone.

Contingency planning

Plan for things to go wrong because something will. It probably won't be one of the things you've planned for, but have a clue what you would do if: someone drops out before the trip, the rental falls through at the last minute, the airline goes belly up (not so farfetched given Alitalia's current financial situation), etc.

Passports and visas

Make sure everyone knows what is needed, particularly important if you have first time travelers in your group. Check passport expiration dates and renew passports that are within six months of expiring

Language study

Even a few phrases are better than being completely unable to communicate in a foreign country. At minimum, suggest that everyone in your group buy a phrase book and familiarize themselves with key words and phrases (Please, thank you, yes, no, I don't speak., do you speak English, etc.).

Medical needs

Know ahead of time where the medical facilities nearest to your rental accommodation are. We got lucky on our trip, a local pharmacist was able to receive a prescription e-mailed from the States and fill it with equivalent drug. Next time I'd rather not rely on luck. Also, bring along standard over the counter medications and first aid items. When you're feeling ill or are hurt is not the best time to be wandering around a foreign country looking for a pharmacy.


Bring a list of the addresses and phone numbers for the embassy and consulate offices in the country (or countries) you're visiting, just in case.

Travel insurance

Check out the requirements for travel insurance before you sign your rental contract or purchase airline tickets. In some cases the insurance is tied to these purchases.

"Home secretary"

Identify an emergency coordinator at home who is willing to be available by phone 24/7 whom everyone can reach out to if all else fails

Shared items

Identify items that can be shared by two or more people in the group to minimize the load

Luggage limit

Unless everyone (or every couple) has their own car you'll probably need to set a luggage limit. In our case it was one large suitcase and two carry on bags per person (but not everyone adhered to this, which brings you back to roles and responsibilities)

Transportation, Arrival and Departure


Air travel for a group should be tightly coordinated unless everyone one (or every couple) has their own car and is comfortable finding their way to the rental on their own. Everyone in our group, save for one, was flying out of the same airport so we first investigated a group fare discount. The fares we were quoted were no better than the web fares available at the time so we didn't purchase the group rate. In hindsight, we should have. Several members of our group felt that they could do better by waiting and watching the fares on the Internet. In fact, fares did fluctuate up and down by as much as $100 over the next several weeks. Six of us went ahead and purchased our tickets at $600 in December (for a March flight). Eight others waited and watched. When they purchased, two months later, they were able to save about $25 but had to take connecting fights to get that fare. This made ground transportation in Italy really confusing and wasn't worth the savings.

If I could do it again I would insist on coordinating the flights and booking as a group.

Arrivals and departures

Publish a list of every arrival flight and time for the group and distribute a copy to everyone to ease arrival coordination, especially if one or more of the flights is delayed or cancelled. If you have rented (or own) international cell phones include the phone numbers on this manifest.

Meeting points

Set meeting points and times in case you get separated (this is good to do each day, not just arrival day). For airport arrivals, list multiple checkpoints just in case (e.g. baggage claim, exit from customs, rental car desk, etc.)

Rental cars

I have a theory about rental cars and people that is a corollary to my adults and children ratio: never have more kids than arms to grab them with. For rental cars in a group, you'll need one more than you think you need.

We thought we had plenty of padding in our needs estimation; three five-passenger cars and one seven-passenger van for fifteen people. That's twenty-two seats for fifteen rear ends, more than enough, or so we thought. Even factoring down for comfort to four people in each car and five in the van, we had two seats to spare. In fact, most days we only used three of the vehicles while the fourth sat at the villa.

It became a problem when only one or two people wanted to do something on their own and it significantly reduced our flexibility. It was more of a perceptual problem than a real one (you had the "sense" of being stranded or at the mercy of others, but not necessarily the reality of it.) It was a real problem when one couple decided they would prefer to spend the last night at a hotel near the airport rather than at the villa. If they took a car it left the rest of us, with our luggage, to cram into the remaining cars. While physically possible it would have been an uncomfortable inconvenience for everyone else. It came down to the good of the group versus the desires of one couple.


Decide before you leave who will be driving, or even might be driving, and determine if they know how to drive with a manual transmission. If they don't you'll need to factor that into your rental decision. Insist that every driver get an international drivers license. Finally, group cars and drivers and ensure that when you fill out the paperwork you list every potential driver. We didn't think to do that and lived with a certain amount of anxiety each time an uninsured driver was behind the wheel.


Make sure you have maps for every car. I printed step-by-step driving directions from the airport to the villa with detailed maps of each intersection along the route and made copies for each car in case we got separated along the way. Maps provide freedom from the tyranny of the leader - don't leave home without them! (A compass doesn't hurt either, especially if you're used to driving a car at home with one built in.)

Bungee cords (the stretchy cords with hooks on each end)

Throw a few in your suitcase just in case you have a wise guy (or gal) in your group who can't count and shows up with more than the allotted luggage. (This is usually more of a problem on the return trip.)



Get all of your needs down on paper before you contact a rental agent. And by all means, with a large group use an agent. They've been down this road before and can be invaluable throughout the planning process. I prefer to deal with someone here at home whom I can contact easily and often. I found it easiest to keep track and compare properties on a spreadsheet with columns for each of the important considerations, including:

  • Location (city, just outside a city, rural)
  • Number and type of beds (our group had three married couples and nine singles so twin beds were a priority for us) and number of bedrooms (a villa that sleeps eight may include two on a couch bed in the living room, for example)
  • Number, type and location of baths (in suite baths limit, or at least increase the difficulty of sharing; also consider the shower vs. bathtub question - some in our group had a very hard time adjusting to the bathtub shower so the one stall shower got a real workout)
  • Amenities (the most common include a dishwasher, clothes washer, pool; for our group a dishwasher was a must)
  • Extra charges (find out in advance if electricity and heat are included; if not, how and when will these charges be collected. One group I know of was shocked at their electric bill after two weeks of steady use of the air conditioning, dishwasher and twelve hair dryers going twice a day.)
  • Parking availability (how many cars can you park on the property, how far away is additional parking if needed)
  • Cleaning (is cleaning included, if not, do you want it, if so, what is the charge and how often will you need it). Cleaning was not included with our villa but with so many people using the kitchen and bathrooms we agreed to every-other-day maid service. It was a great investment in group harmony and comfort.


You may need to rent hotel rooms if you arrive a day or more before you can access your villa, if you want to take an overnight trip from the villa or if you want to stay near the airport on the night before your departure. I had great success finding group rates via the Internet for an overnight in Venice. I sent email requests to three hotels for rates on eight rooms and wound up with large doubles in a nice hotel just off St. Mark's Square for 149 euro/night the week before Easter.



Determine in advance what your group's intentions are regarding eating at home during the trip. If you intend to eat some meals at home, who will be responsible for meal planning, shopping, cooking, and cleaning up? A couple of us in our group brought recipes with us and I even brought the spices I knew I would need (they're light and pack easily and it can be difficult to find exactly what you need when you need it at the local market) as well as some dried chilies I knew I would need.


When you're buying for a couple or one family the local market will usually meet all your needs. With a large group it helps to find a larger store (in Italy, a Coop or supermercato); you can usually get this information from the rental agent or from Slowtrav.com or Slowtalk.com. Ask for food preferences from your group in advance (what % milk, which flavors of juice and jam, what types of cheeses, what kind of bread, etc.). A few people in our group do not like Italian coffee so they brought American coffee with them (a sacrilege to many, I know) and an old coffeepot that they planned to leave behind. We also brought peanut butter with us, having learned from folks on the Slow Travel Message Board that this wasn't available in Italy.

Eating out

Collect restaurant reviews for towns near your rental and for places you plan to visit from the Slow Travel website, books and message boards. Even restaurants that normally don't require reservations need some prior notice to accommodate a large group, so always call ahead if at all possible. Determine in advance how you will pay the bill (we agreed to always use cash in restaurants and to divide the bill equally rather than try to determine individual amounts.)

First day dinner

This can be a tough one to predict. Some people sleep well on flights and will be ready to go on the first night, others will not. We opted to eat in on our first night and made a simple pasta and salad meal.

Initial food shopping

We made our list before we left home and stopped at a Coop on the way to the villa.


Day trips, side trips and itineraries

We identified all of the likely places we might want to visit while on our trip and gathered information on each, including step-by-step driving directions and maps (from mapblast.com, mappy.com or viamichelin.com) and created a three ring notebook that everyone could access for ideas. We intended that if a group decided to go to a particular place, they would take those pages from the book and put them back (with comments, hopefully) when they returned for others to use. As it turned out we pretty much stayed together for the entire trip but the idea was good.

Guides and/or instructors

Determine in advance if you will want guides for the large cities or specific sites (lots of people like to use guides for the Vatican, ancient Rome, and Pompeii for example) so you have time to research and locate the best guides for your group. Instruction, particularly cooking, is another popular group activity.


Group vs. shared expenses

Determine this in advance (see decision methodologies and conflict resolution, this can be a tough one.) We shared equally the costs of the rental, cleaning, food, car rental and gas.


Create a cash kitty to cover group expenses. We did this for food, the villa deposit and the cleaning costs. For some reason I forgot to include gas in the kitty and it was a little confusing - we should have paid for gas from the common fund as well, it would have been much easier. I asked everyone to give me 130 euro upon arrival in Italy based on my projection of expenses for the two weeks, it was more than enough.

Trip budget

Create a trip budget and share it openly. Don't emulate, or allow anyone else to, the Enron guys who thought it was okay to make up new accounting rules as they went along. This is such a touchy subject for many people that I advise you to err on the side of over communicating. Don't forget to include planning expenses such as faxes, phone calls, photocopying.

Payment procedures

For our group I collected the funds for all deposits and planning expenses and wrote checks from my account, or used my credit card to make reservations. You may want to consider setting up a special checking account just for the trip to increase transparency.


Determine in advance how much cash you will need on the first day and how you will get it. I told our group that they would need to hand me 130 euro in cash at the airport and left it up to them to decide if they wanted to exchange money here at home or wait and use an ATM or money changing service at the airport. A group of us who wanted to change money here at home got together and made one big transaction and shared the transaction fee.

Banking/ATM locations

Although I've never had a problem finding an ATM in Italy, you may want to ease your mind and find out from your bank or credit card provider where the ATM locations are nearest to your rental.

Final day cash

Remember that if heat, electricity and/or maid service are not included in your rental fee you'll be asked to pay for this in cash when you return your keys. Some of this, perhaps all, may be covered by the damage deposit you gave them when you checked in but don't count on it. Just as you are getting ready to go home is not the time to be scrounging around looking for money to pay your next to last group bill.

During Travel


Itinerary development

Develop a process for developing/adjusting itinerary each day, even if it's just a quick conversation around the dinner table. As your vacation progresses your interests may change; keep in mind that even the best laid plans are merely a guide, not an imperative.


If you will be in the car for long periods bring some CDs as most rental cars now have CD players. We listened to Italian language discs on a long drive to Venice.



Keep receipts for everything paid out of the kitty.


Do your accounting each day so you always know where you are and periodically check the usage rate of the kitty funds in case you need to add to it during the trip.

Post Travel


  • Share photos (digital pictures really lend themselves to this).
  • Write a trip report and submit it to the Slow Travel website.
  • Collect and share your learnings about leading a large group and add it to our collective knowledge.


Do final accounting ASAP (don't wait for the next credit card billing cycle, call or check on-line with credit card companies to get all charges (example - final rental car charges).


If you've made it this far and you're still reading, you must be serious about leading a group trip. My advice may seem like overkill to many, even regimented, but remember that a large group is akin to a small army and the usual rules of behavior are often not enough. The point is to do everything you can to enjoy your vacation and, if you have accepted the mantle of leadership, to help your entire group to have the best possible experience.

© Ellen Singer, 2004

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