If you have 4–5 days to spend in Tuscany

I'm all for planning your own trip‚ and this website is set up to help you do just that—but some people might just as well prefer to leave all the planning, logistics, transportation, lodging, and gathering of information to the professionals and simply sign up with a guided tour.

Nothing wrong with that. Just take my advice and choose a tour that emphasizes small groups over large crowds, local transport over big tour buses, and fun cultural experiences over sightseeing checklists. You'll have a better time, and probably spend less for it. Here are a few of my favorite tour companies who emphasize just that.

1-5 days

• Viator.com
• City-discovery.com
• SelectItaly.com

1-2 weeks

• IntrepidTravel.com
• GAdventures.com
• Viator.com

• Multi-day tours
• Intrepidtravel.com
• Gadventures.com
• Viator.com
• SelectItaly.com
• Infohub.com

• Momondo.com
• AutoEurope.com
• Vayama.com
• CheapOair.com
• Cheapflights.com
• DoHop.com
• CheapTickets.com
• Priceline.com

• Autoeurope.com
• Momondo.com
• Priceline.com
• RentalCars.com
• CarRentals.com
• AutoSlash.com
• Europebycar.com
• Renaultusa.com

• Short-term leases
• Autoeurope.com
• Europebycar.com
• Renaultusa.com

• Car resources
• Emergency service/tow: tel. 803-116
• Highway agency: Autostrade.it (traffic info, serivce areas, toll calculator, weather)
• Italian automotive club (~AAA): Aci.it
• ZTLs: Ztl-italia.blogspot.com (lightly outdated, but handy, links to cities' traffic-free zones)

• ItaliaRail.com
• Raileurope.com
• Trenitalia.com
• Seat61.com

Lodging: Booking.com, Bedandbreakfast.com, Airbnb.com, Rentalo.com, Vrbo.com, Belvilla.com, Hostelworld.com, Hostelbookers.com, Couchsurfing.com, Homeexchange.com

Packages: SelectItaly.com, Gotoday.com, Orbitz.com, Expedia.com, Travelocity.com

Maps & guides: Amazon.com, Maps.google.com, Tuttocitta.it

A tall order for just two weeks? You bet. But there are three tricks to fitting all you can into such a short time here.

1. Two weeks actually lasts 16 days (figuring you leave on Friday night for your overnight flight, and you don’t return until two Sundays after). » more 
   
   
2. You're going to fly "open-jaws" into Rome and out of Milan.This will save you a full day of traveling back to where you started to pick up the return flight. » more 
   
   
3. You are going to take some guided daytours to visit the towns and sights outside the big cities in order to (a) pack as much sightseeing as possible into a limited amount of time, (b) get a professional guide, and (c) provide all transportation so you can spend your time seeing the sights and not waiting on train and bus connections.
   

Don't forget to pay attention to the "What to do before you leave" section (next) covering all the details you need to take care of before leaving home—and be sure to read the "Foolish Assumptions" page about how these itineraries are meant to work.)

• Book plane tickets
• Book key hotels
• Check train times
• Book entry tickets:
  • Rome: Galleria Borghese
  • Florence: Uffizi, Accademia (David)
  • Venice: "Secret Itineraries" tour
  • Milan: Last Supper
  • Lake Como: Villa Serbelloni tour
• Learn more about Italy
• Practice your Italian

The basic itinerary above is pretty packed—a lot of early morning wake-ups, a lot of churches and museums—because there's simply so much to see and do in Italy.

By all means, feel free to prune this itinerary down to something a bit slower paced if you don’t want to spend so much time running around (say, leaving out a few hilltowns—Pienza or Orvieto—or perhaps the Cinque Terre, or maybe Pompeii). I've even gone ahead and whipped up a sane version of this itinerary that leaves out Pompeii and the Cinque Terre.

Think of this more as a blueprint to squeezing in the maximum possible. You should, above all, have fun.

I will freely admit to being as guilty as anyone of this, but: Please try not to overplan your trip to Italy. That's a two-fold plea:

1. Plan everything, but don't feel compelled to stick to the plan. I think it's a fine idea to work out all the details of what you plan to do—if nor no other reason than it will help you get a handle of what you are able to get done, and start making the hard choices of what you have time for and what you should leave for the next trip to Italy. (Always assume you will retrun!)
   
   But then do not book absolutely every second in advance (that leaves no room to adjust things as you go to accommodate changing interests, sudden festivals, or unexpected invitations), and please do not attempt to stick to the schedule if it turns out to be overly ambitious and startrs making you miserable.
   
   Rememeber Clark W. Griswold, the Chevy Chase dad in the Vacation movies, always bound and detemrined to get to WallyWorld come hell or dead aunties? Yeah, don't be that guy. No one in that family was having any fun.
   
2. Don't try to pack too much in. A vacation is not meant to be all about checking sights off a list or dashing from place to place to fit in as much as humanly possible. It's about enjoying yourself.
   
   So do that. Enjoy yourself. Take a hint from the Italian concept of la bel far' niente—the beauty of doing nothing—and take a break from the sightseeing every once in a while.
   
   Leave some time to stop and sip the cappuccino.