A delicate Tuscany question

I suspect this will be a bit tricky for you, starting with when you tell the interested parties they have to commit with some money. There may be a sudden loss of enthusiasm for something 12 months in the future. All kinds of things can happen in a year, even to you. Can you work in a shorter time frame?

This is tough. If you've ever bought concert tickets for friends who later backed out you'd be scared to book a large villa for someone else. I'd suggest that you get the commitment before you book, and that you get it in actual dollars and not a promise of dollars. Maybe you could have a meeting of all serious candidates and hash this out. Price pro rated on a per person per night basis. Each person puts down an equal deposit, so at least they're out something if they drop out.

I have done something similar for about 25 years and this is how I do it. This is a ski outing and we rent a four or five bedroom house for a week. For illustration purposes say the rent is a five bedroom, $5000 a week. We have two levels of participation -- sponsor and the rest. We don't have a name for "the rest." If you are a sponsor you pay $1000 and first check received gets first choice of bedroom, second, the second choice, etc. through the five bedrooms. The rent is covered by the sponsors. Anyone else that wants to attend, pays $500 and can sleep anywhere. Only a couple of people stay the whole week while most of the folks only stay Sun through Wed or Wed through Sat or some combination there of. In the end we settle up strictly on room nights used so everyone pays an equal share for the nights they were there. We have had a few as five and as many as 18. But we never have to worry about who shows or who doesn't because the initial five sponsor have covered the rent if no one else shows.

I think you could do something similar by breaking up the two weeks and giving priority to those who pay more and pay early. But you want commitment in hard cash so that you are not stuck with the bill. It is a business arrangement -- don't let friendship interfere. And I would get the commitment PRIOR to signing the lease unless you have a cancellation clause that lets out of the lease with reasonable notice.

There is a wide, wide, gap between "I would Like To" and "Here's my Share". I would consider a place large enough to accomodate several couples, but not so large you could not swing it on your own. If you paying for all (if by yourself) is simply out of the question, then you are probably thinking too big. That is the point that I would get a commitment, a partner now, and use the same guide...too much for you two to swing on your own...then you need more commitment. Besides just the financial impact, I would also consider your company. Travel partners must be chosen carefully, there would be a big difference between going with a group where each couple likes to explore on their own, then occaisionally do things together; and a situation where you are not only the landlord, but are responsible for transporting and entertaining the group as well. When people say...Gee, I would like to go...press them on why and what plans or dreams they have. If they are clueless, then plan on giving up some of your plans to cater to them. I sense maybe I am sounding negative, I do not intend to, but this sounds like your dream, so do not let others compromise it.

Why don't you make it a group thing. Say hey let's all rent the villa, split the rent equally and then you'll see who is really interested.

I would ask for a significant deposit from everyone (half the money up front) now and the balance six months before you go (unless you need to pay the whole thing now). Make sure they know it is non-refundable unless the trip is cancelled.

I organize a golf trip for 16 guys every fall. We travel all over the southeast. I find out who is REALLY interested when I ask for half the money up front. I always have a date when I need to have the money by. On that date, that is how many I plan for.

Good luck.

It's not delicate, it's business. Get the money upfront. This request will quickly get you down to the serious ones. If you can swing it yourself, book only the space that you require, unless you will receive additional compensation for all the hassle that WILL happen.

I had another thought. There are a lot of places where you can rent a smaller flat or unit of a larger place. You could rent a 1-2 bdr unit in a villa, and let everyone else rent what they wanted. I like the ideas posted above, but this might work if you think you might wimp out on getting the money upfront. You should also emphasize that you do not want to be the group navigator (unless you do!) so you don't end up as chauffeur, etc.

Terry, I'd suggest paying a lot of attention to Paul's comments. If you have some good friends you'd been planning this with for the whole time, that's one thing. But I don't think that's the case here.

Problem is that some people are going plan out things in detail, others will show up in Tuscany and expect you to be their (free) tour guide. Starting with picking them up at the airport. You'll be shopping for them, too, because they'll help themselves to food but never go get any for the house themselves.

My suggestion is to come up with a set of ground rules before mentioning this any further, and when you start to get deposits from people make it clear what the rules are going to be.

Wow!! What a great group of people. Paul, you are right, it is my dream. I thought it would be neat to have friends share, but it seemed to get bigger the more I talked about it.
I think what I am going to do now is give them a price.....I have looked at lots of villas to rent, as well as apartments and farm houses. My wife and I will pick the place we feel best about, then tell the others and have them look and decide. Then in September, I will ask for a dollar committment. No dough, no go. Most places seem to have a cancellation policy. If people change their minds, which is a possibility in this economy, they will have to understand the cancellation policy.
It seemed a good idea to plan a trip with other people, enjoying great food and good company in a lovely spot.

You have all given me some good points to consider...and I thought a year out would give me a chance to have more choice. Two places I have contacted are already partially booked for 2010, so I thought the earlier the better.
Happy travelling!!

Im more fortunate as Im taking my adult children.They wont back out because dad is paying.However I organize golfoutings and Ive learned cash up front.Many are interested but few will actually go.

This is exactly what I'm trying to do in 2010 too with friends and family so appreciate all the ideas on how to do this effectively. Everyone always says they are interested, but the key is getting them to pony up cash in advance if we do one villa. I think we're going to select a week (e.g., June 2010) and then allow everyone to get their flights in June 2009 (a number of them are using points so you can book 1 year out) and then start looking at villa with prices, then require a deposit say August 2009 or so to book it. But, I also like the idea of a property where there are numerous individual units, so it allows everyone to book the one they want and there are fewer financial issues - that also encourages everyone to book soon so that they all get at the same property. Also it gives everyone a bit more privacy and allows everyone to do their own thing. In one property, it probably becomes more of a group decision on certain days as to who is doing what and who is cooking/cleaning etc.

In any case, good luck and let us know how it goes!

you might look into vacation apartments- Il Portone in Volterra is a villa divided into a number of apartments. You book yours- tell you friends the dates you will stay there and the contact information for Luciana and Allesandro and they can call and reserve their apartment for the same dates... each couple has their own fridge to stock... you can eat together in the courtyard - maybe do meals pot luck :)

http://www.residenceilportone.com/

I know there are other similarly situated establishments in tuscany - I use this as an example because I was a nanny for a family who stayed there for 5 weeks- it was a great situation - the owners are very nice and helpful all the apartments open to one courtyard area, making it very easy for relationships to flow - we met many wonderful people who stayed in the other apartments ... I personally did not stay at Il Portone, I stayed in a different, more hotel like vacation apartment building with my employer's students in town - the best of both worlds- villa life by day and townie by night :)

We rented a villa in Tuscany back in 2001. First we got an idea from our friends as to who was really interested, then we searched villas that would accommodate that many (10) and found one that actually accommodated 12. We divided the cost for ten people for that week, told our friends and said we needed a deposit ($50) from each serious traveler by a certain date. In the end only one backed out and forfeit his $50 (since it was last minute) and we divided his share among us. It was stil a very good deal. We used rentvillas.com and they were very helpful. We had a welcoming dinner the evening we arrived and a stocked frig for Sunday. We had daily maid service, with a change of linens twice during the week. We had a great time and still talk about it. We've been busy traveling to other places since then, but are about ready to go back and do it again. Hope your turns out as well.

I was thinking along Neal's lines....a place where there were several apartments and people could have their own privacy, yet we would still be "together" under a roof to enjoy communal suppers. I have looked at the villa rental site Devra mentioned, but I also visited the argoturism (I know it may be spelled incorrectly) sites on the graffiti wall and read what other travellers have said about locations. I know we may eventually have to deal with car rentals......I guess I'll cross that bridge when I come to it. Thanks again for all your help...I'll try to remember to tell Neal what the outcome was.