Am I crazy to consider planning a trip for friends?

Since you do not want to be responsible for their vacation or be a tour guide for them, I would suggest that you have someone else plan this for you all, like a travel agent. You can make suggestions to your group and recommendations to the agent on things you want to do or not do. Also, since you say "to be honest, i would not want to redo all the touristy things that I have done many times before" I would definitely not plan this trip for them. I understand that sentiment, that you do not want to repeat things you have done, but if this is their first and maybe only trip to Italy, they WILL want to go to those sites (and understandably so). I think planning this yourself could potentially be pretty stressful. Bottom line, I would advise you not to plan this for your friends. However, I would say maybe take a day where you are the tour guide, and show them your favorite things in your favorite city, whether that is Rome, Florence, Siena, etc. That way you can give that day as a gift to them, seeing Italy through your experienced eyes, and they can still visit all the sites they will want to.

Are you saying there are 50 of you or all are in their 50's? As a planner I bet you are itching to help. Could backfire on you if you are not careful.Some of our posters will share their "nightmares" with you. And......no matter what......under NO circumstances will you make any final plans that require money. Money issue could ruin trip and long term relationships! As far as re-doing tourist things you have done before,DON"T. But surely there area few you enjoyed so much you wouldn't mind doing them again. For example, have you seen the new underground area in the Coliseum? Suggest using guides for areas you don't wish to see and go somewhere new. Have you REALLY seen ALL of Italy? Go somewhere new,the excitement and anticipation of something new always pumps me up. Good Luck. Keep us all informed of your itinerary.

We are in our mid 50s. I do not know how many would actually end up making a real (financial) commitment but there are 9 of us in total. I realize that i never get tired of seeing Italy again, but I also enjoy seeing different areas and doing different things. Right now it is helpful for me to see what others think and what cautionary tales they may have. I appreciate all your responses.

Last year my aunt went to Italy with an old college friend she hadn't seen in ages, and with whom she had never traveled. It was a DISASTER. Not at the time - my aunt saw what she wanted to see (barely) and the friend did too - but neither had the trip they wanted. The friend wanted American-style restaurants and church stuff (including services). My aunt wanted art history, archeology, museums, and real Italian food. The y both ended up making awful compromises (mostly my aunt) that left them unsatisfied, resentful, and irritated. And regretting the trip. It sounds like you still all hang together.... which makes it more likely that you still share things in common.... but I think that what you are proposing sounds like a HUGE risk. Better might be the "rent a house, rent a car, and everyone gets to go out and do their own thing" option. All chip in equally. No one "rules" the itinerary. Might work out best for all.

I agree with Devon 100%-- on the principle of "greatest good for the greatest number," the trip should be a "Greatest Hits" tour with plenty of time in the Big Three (or is it Big Four including the Bay of Naples?). A travel agent should do the heavy lifting on this one.

I see potential for trouble. Being their first travel to Italy would set their expectations sky-high and you already alerted you don't want to re-do "all the touristy things". On a deeper level, whenever one becomes responsible for organizing a big-deal trip, directly or indirectly it becomes responsible for whatever happens - bad weather (why haven't you alerted us that it rains a lot), bad service (where are the embedded dryers), non-working plug adapter (how didn't you think this would be a big deal to me)... My suggestion: offer to help them to organize a trip. Offer advice, send them links of various sites, have an evening together to talk about practicalities, if you are keen on that, share a spreadsheet of your expenses etc., but don't assume the position of a king-maker that decides where to go, when, and gives final opinion on everything. Also, avoid at any costs to become responsible for handling money. At most, help them fill their own online purchase screens for airfare and trains, but don't become a treasury officer for the trip... At most, it ends ok, at worst, it ends on a bad tone ("I didn't told I was ok with taking that more expensive train, why have you bought it?")

I am going w/a much smaller group - now down to 3 of us celebrating 60 (we went to high school together overseas) I did all of the planning, made deposits for the apts. and we have a good idea of what we want to see/do, and keep it mind we need to be flexible. My 2 friends have been to Italy before,
( not me, though) but not the amount of time we will be there - 12 days total. We will visit what one would expect to visit and want to go off the beaten path, also. We will be in Rome, Florence, and Venice. Hope you work it out. You can email me the end of Sept. if you want to know how it all worked out.

I have planned many group trips but not to Italy. With 6 women (if 9 swear they will go you'll get 6) it should be easy if you keep it simple. I would pick a location or two at the most. Rome and Tuscany would be good. Get an apartment or two and let everyone do their own thing. Some will go sight see and others can chill out. Discuss and get in writing any financial details like deposits and cancellations. Have them get the RS guide and download the audio tours so you don't have to be the guide. Be prepared to lose a friend over your efforts. No good deed goes unpunished.

Uh oh...I see trouble in your future. Let me bore you with my story...I leave in less than two weeks on a trip that was originally for 3 friends. We agreed from the beginning that each would pay an equal share, even if something happened and someone couldn't go. One of our destinations is Paris, where I have spent 15 nights and they have never been to. I said I didn't want to do some things for the 3rd time and wanted to be able to go off on my own. No problem. Oh, and they asked me to do ALL the planning. I did all the reasearch, made reservations, paid deposits, bought train tickets, etc. Fast forward...one person decided she wasn't going AND she has forgotten about our agreement to pay equal shares. Now the other friend and I are left to pay for lodging large enough for 3 people. It is too late to change things. I agree that this is something a travel agent can arrange for all of you, so they can't hold YOU responsible if something doesn't make them happy. Also, get ALL agreements IN WRITING so there are no misunderstandings.

Linda, I have a group of 8 friends from college that is considering a similar trip. One friend began the discussions with a joint email. The trip we are planning is for next fall, however the early start has helped to bring out everyone's interests and also shown who is most interested in planning and who is less likely to want to do that. I would be happy to email you a copy of our correspondence so you can see the format the has developed. The original email made it very clear the this person was not the "planner" or "leader" in any sense. Send me a personal message if you would like me to send our correspondence to you. Janelle

Send them to this helpline where anonymous posters come to have their most important trips planned by anonymous posters. If you brought fifty people to Heaven some would complain that the harps are too loud and the manna is not fresh picked.

I think you should decide on an RS tour, maybe one of the My Way tours... you tell them all you are going and if they would like to read about the trip, pay their money, you will be happy to hang out with them part of the time. Or take a regular tour and you can skip those sights you don't want to see. I have planned trips lots of time for others, but it is only worth it if you are getting your trip for free, or getting paid. Many times friends will ask you to plan something and then decide to micro-manage everything.... could be a disaster, however if Rick plans it all you can blame him. However, I have traveled many times to Europe with friends and despite some glitches it has been wonderful for the most part.

As a direct answer to your question, YES, you ARE! You will never be able to meet each persons unspoken expectations. Turn it over to a travel agent and let them do the work (and take the blame). Work out a way for the group to choose a tour planner. you will lose friends if you try to do this yourself. Posted by a former HR Manager who knows how people think!

I like that idea of a RS tour. You could also add on a week in a villa or a couple apartments for those who want to stay longer. Maybe someplace not far from a town or city, accessible with public transportation. Have you all taken group trips before? If you're all comfortable with each other's travel styles, it could work. But if this is truly the first big trip together, you should walk away from that planner job.

Yes with a due respect You are crazy!! some will be pleased some with be very upset and if you're lucky most will be some where in between.
50 people!!!!

You might start the ball rolling by polling your 50 friends (or 50-something friends) about dates for travel. Suggest maybe 3 different dates. When you have a date and length of trip most people want, take that info to a travel agent. Meanwhile, get realistic with your friends about the expenses involved with a European trip. Maybe even suggest that they read a Rick Steves book. I doubt you will find anywhere near 50 people, or even 10, to agree on any one trip. You may find that a one-week to 10 days schedule will work for the most people. Probably a bunch of people who love the idea of a group trip won't be able to go, or will change their minds for whatever reason. I was on a group trip once that was partially organized by a leader who used a travel agency; they set us up on an actual scheduled tour. This worked ok. My only experience arranging a "group" trip was with just one friend. I gave her my flight schedule and told her she should get a ticket on that same plane, if possible. She did that, but for the wrong date. To straighten out the schedule (she hadn't traveled to Europe before), I ended up spending two days of my time traveling to SFO, which is the only place United Airlines has a ticket office in this area. I reserved hotel rooms for us. We had no money problems; each paid as we went along. We traveled together to Europe, shared hotel rooms, and mostly spent our touring time separately. I had been to Paris before and she hadn't. I introduced her to the Metro and she took off on her own. We met for a few meals and a couple of walks in Paris. I left Paris before she did. My friend found her own way (shuttle) to CDG and on to home.

Dear latest posters, I too at first read it as she was planning the trip for 50 people, but Linda has commented and confirmed that they are in their 50's as in AGE. So she is only planning for about 9, maybe less. Still daunting, but not impossible!

You can do the planning for the trip and still maintain your sanity! All it takes is lots of discussion with your friends. I planned a trip last April for 14 people (7 couples), and I made it known from the beginning that if I had to plan it all then I got to make all of the decisions on what we do and where we go. But our group was from a local wine society, so we knew the focus of our trip would be wine. If anyone had concerns or suggestions they would tell me and I would try to include what they wanted, but no guarantees. I did include cities where people could wander on their own, and I offered tours for those who wanted to tour the city with a guide. We got a headcount for those who wanted to visit museums as well. Everyone booked their own airfare. Only a few of us flew together to/from Italy, but people could choose 2 stops if they wanted to save money, and some people used their frequent flier miles. Everyone made their own hotel reservations, even though we all stayed in the same place. I notified the hotels that we would need 7 rooms total and people would be contacting them in the next few days. That way, if someone backed out, it was up to them to cancel their reservations. We had one common expense - the chartered bus that took us on daily excursions. We agreed that if someone backed out, the rest of us would share the cost. Luckily nobody backed out and we had a great trip! Hopefully you have a wonderful trip and return as even closer friends!

I must be crazy, too! I'm doing the same thing for a group of four women in October. I have been to Italy 6 times and my friends have never been there. We are spending one week in Rome and one week in Tuscany - rented an apartment in both places. I arranged a couple of thing (e.g. cooking class in Rome) but I am going to try to keep it informal/unstructured. I, too, do not want to be a tour guide. I'll let you know how it goes. Wish me luck!

Make it simple, join a RS Italy tour. If someone do not like it after the tour. Blame it on RS, not the friends.

Thank you so much for all of your input. I guess I am starting to shy away from the whole idea.
If I do pursue this, it would only be after a lot of talking and only with only a partial responsibility. Maybe I will plan my own trip and either invite them for a part of it or for a few days at my parents' home in a somewhat remote part of italy. And they would be responsible for getting themselves there. Kathy, I am especially interested in how YOUR trip works out. Please let me know.

I LOVE the idea of suggesting you all do a Rick Steves tour together. But only if you can keep up the pretty hectic pace that they often take.

I know myself and I do not think I would like a tour.I have been to Italy 10 times and never on a tour. I also know my friends and we would like a lot of time to enjoy a glass of wine and enjoy the scenery. A couple of us love museums and history and a couple do not. The comment that I could never meet everyone's expectations spoken and unspoken really hit home. I will have to think long and hard about the whole thing.
This is why I put this idea out there. You have all helped me understand what I may be getting into.

Just remember that if you took a canned tour, you'd be seeing all of those "must sees" that you've already seen numerous times. Since you wanted to avoid that, I wouldn't recommend a tour. I like the idea of having then tag along for a few days and you guys could do your own thing. With our trip, I was a little worried that people wouldn't like the things I had planned, but it was just the opposite. Every day someone in the group would thank me for putting it all together and doing all of the "leg work" for the group. They were just happy that all they had to do was show up and they'd be taken to a new place each day. We had a wide variety of things to do & see and the group didn't stay together most of the time when we were in the cities. At wineries we were together, of course. And each evening we'd sit out on the terrace at the hotel and chat. Maybe we're just an easygoing group, but it worked well for us. :)

Linda, the first question is: do you enjoy planning a trip. For me, it's a big part of the experience & I love it. If you decide to go ahead, get everyone together for a planning session to discuss their must sees. Yes, you'll cover some of the same ground but make sure that they understand up front that you want to see new places. I've planned trips for up to 7 people and had the best results when everyone was aware ahead of time of the itinerary and had a chance for some input. If these are long time friends they'll understand that you want to see some different places which, may in the end, be their favorite experience. In November, I'm taking my brother and SIL. We will see many of the places I've seen before but will also go several places I haven't been. We're even seeing new things at places I've been several times - Scavi tour at Vatican, Secret Itinerary tour in Venice and I'll get to see the lower section of the Coliseum for the first time. But by all means plan well and well in advance in order to book hotels and have time to make changes. Plan "either or" days so that they can choose from 2 options and be very open to the need to just wander around. I know a group of ladies who went and it was a disaster because no one had any idea of where they were going, what they were really doing and even how to pack. If you still have the courage, go for it. It can be a wonderful experience.

YES

Yes! You are completely crazy! I did this for a group of friends, and it was a disaster. Even with lots pf planning, and many group meetings, it will NOT work. Have them take the RS tour( and you go off on your own), or turn it over to a travel agent. You can do the overview with a travel agent; but DO NOT ACCEPT any responsibility for ANY part of the trip. But,,,,,,,, make them all read Rick's books. They need to get a clear expectation that they will be in Rome, and "not in Kansas anymore."

Linda, I don't think you are crazy, but because of your reservations, a RS tour would take the pressure off you. I've planned trips like this for friends a number of times, and it's worked because I like doing the planning and showing friends places I love. The trade-off is that I do a lot of repeat sights, but I don't get too stressed about it because I know I will have more trips. The thought of eight travel virgins is daunting! But if 9 want to go, probably 5 or 6, at best, will come through. My best trips have been for 2 or 4 women, or 4 very compatible couples in a villa. I've gotten in trouble when friends of friends whom I didn't know were included. Even friends you know and love can show a completely different side during all that enforced togetherness. If they've never traveled, you probably can't count on a lot of independence. (Will anyone else drive?) I'm happy to make the plans, but when it comes time to make the deposits, I spread the joy around. I like to drive in Europe, but I refuse to be the money counter. It helps me if I assign everyone a city to research for sightseeing. If I'm somewhere I've never been, arranging a good walking tour guide takes a lot of pressure off me. And if we are an uneven number, I always volunteer to pay for the single room! It is like herding cats at times, but if you can make it work, it's a gift you can share that they will always remember. It helps if you accept up front that YOU are probably going to have to make some concessions so they will have a memorable trip. (Just took friends to Spain and didn't get to go to the Prado...and I'm an artist.)

Linda, I like the idea of them meeting you and staying at your parents' home in a remote part of Italy. They can start off their trip doing the cities and some of the major things that they will want to see (things you don't want to) and then they can end it (or take a break during the middle) and enjoy some relaxation all together.

Nope...wouldn't do it. I spent a lot of time helping some first time visitors to Europe plan a trip (I wasn't even going on the trip but was asked to help out since we had been so many times). I took pictures of my trips to show them and gave them the names of places we had stayed and even through in the names of places I had researched (I always keep my research information in case I go back somewhere and want to try something different). I kept in mind what they wanted to spend and even got ideas from them about what they were interested in. Bottom line, the trip they ended up taking in no way resembled what I had laid out for them and neither one of them was happy with how it turned out.

I think I am leaning toward just inviting them to my parents' home. I have done this before with other friends and they enjoyed it very much. It has been very interesting to read all the opinions, and everyone's personal experiences.

Linda, I planned a trip last summer for 12 days for 3: a friend I haven't seen/heard from in 30 years and her husband (I had never met him). It worked out so well we are going to Sicily next summer! Advice: how long a trip will it be? Can you go a little earlier/stay a little longer to do the things you really want to do? My friends and I traveled for 12 days, but I was there much longer. Everyone should be responsible for their own airline tickets. Plan to meet up in your first city. For our trip, I made hotel reservations and my friends worked out the rental car, but we reimbursed each other for our shares. I suggest getting an apartment, so if one person does decide not to go, you're not hit with a hotel cancellation fee for a separate room. Major tourist sites have on-site guides or self-guided tours; perhaps you can direct or deliver your friends to these sites, go off on your own and meet up again at mealtime or for some sightseeing together. This gives you some personal time and them some ownership of their vacation, without their feeling abandoned. Let me know how it goes - I love planning trips for friends and I've done it even when I'm not going.

I was the organizer of a girls trip to Germany and Paris last year for six over-60 tennis pals. We had such a great time we are doing it again and adding 2 more friends. We leave for Germany, Austria and Italy in a few days. I think one key to our success is what you mentioned: be a tour organizer, not a tour guide. We ate dinner together every night, but during the day we were often in groups of 2 or 3 according to our chosen activities. The other key is that we have no whiners in the group. One whiner can (probably will) spoil the trip for everyone. I made sure everyone understood my travel philosophy, kept them constantly, actively involved in planning, and explained the reason for every decision.

I would love how your trip goes. Especially related to your accommodations and how the budget was handled. Did you stay in higher end places or budget places, apartments, regular hotels, etc.
Have fun.I will be waiting to hear.

I would love how your trip goes. Especially related to your accommodations and how the budget was handled. Did you stay in higher end places or budget places, apartments, regular hotels, etc.
Have fun.I will be waiting to hear.

I meant.. I would love to hear how your trip goes.

I would not try to plan the trip (been there, done that) and I think the idea of joining a Rick Steves trip is a perfect solution. I've been on 6 different Rick Steves trips and everyone of them was wonderful.
I enjoyed every moment of each trip.