HOW TO START: The key is the organizer, since groups of friends often talk about traveling together but don't follow through. The organizer (an individual or a couple) finds the place, then everyone books his or her own flight and car rental. Some meet at the airport, others later at the lodging.
The most important issue is location. Figure out the area you want to visit and find a central location so day trips are easy. My group once considered a Tuscan villa in the old walled city of Lucca but found it was a long way from Siena and many of the most scenic towns. Montespertoli was a comparatively new city we never really toured, but it had a central location with spectacular views and direct buses to Florence.
FINDING LODGING: Dozens of resources -- specialty magazines, Web sites, travel agents and tour operators -- offer services for make-your-own-group travel. A Google search under "group travel" produces many sites that can book an entire trip, or just part of it. For example, typing in "Vacation in Tuscany" produces several villa rental sites, as does "European villa rental."
The key is finding reputable agents for good properties, with guarantees if problems arise. "Work with a reliable agency or by referral so you get what is advertised -- and no surprises," advises Alan Parker, a member of my neighborhood group. Parker and his wife, Maryellen, rented our Italian villa once through an agency and thereafter went straight to the owner. They now know enough people interested in renting in Tuscany that they have their own Web site (www.stayintuscany.com) and have become the U.S. agents for the Italian owner and her four properties in Montespertoli.
Other lodging tips: Ask for pictures, and how old they are. Find out when the home was last restored and what it involved. One reassuring aspect of our rental was the owner's full-time maintenance man, who came more than once to fix things, from a fuse to the washing machine. You can also ask for referrals from former renters.
For domestic trips, neighbor Evie Hirsch uses a travel agent who negotiates special packages for us since we come in bulk. But again, if you already know where you want to go, call and negotiate directly with the resort or spa and save on the commission. Many properties give group rates and incentives.
CHEFS: Villa owners and rental agents often have lists of local chefs willing to cook one or more meals. Some, like Matisse Chefservice (www.chiantichef.com), advertise on the Web, others in local papers. Set up arrangements in advance.
TIPS: Check what your lodging provides, from towels and dishes to soap, and what facilities it has, such as air conditioning or fans, washer/dryer and dishwasher, or computer-friendly phones. A washer/dryer means having to pack less . . . The more bathrooms, the better; one per bedroom is the best . . . Be mindful of weather, especially without air conditioning . . . Use telephone cards to avoid charges on the villa phone -- and having to sort out who made what calls . . . Find out if cleaning services at the end of a stay are included or are extra.
-- Robin Wright