FREAKING OUT! Less than 30days from flying and I'm second guessing everything...

Chris, do you have reservations in the Cinque Terre? It could be interesting trying to find an accommodation on the fly there. Parking can be a real headache as well: many, many accommodations do not provide it, or are located in places where vehicles are prohibited altogether.

We stayed in a place recommended by my husbands cousin once, an agrotourismo called Spannocchia, not far from Sienna. We were a little apprehensive since my parents were with us but it turned out to be a great trip. We stayed 3 days and drove to a few hill towns from there. My parents loved it, so did we:)
http://www.spannocchia.com/

Our trip was...land in Milan, drove to and stayed in Santa Marguerita- from there took a boat to Portofino and train to CT. Then drove to Pisa to see the sights for a few hours, then to Florence for an overnight, then Spannocchia- from there saw a few hilltowns- Volterra, San Gimignano, then Greve and Sienna. then we headed to Rome.

Another trip we went to lake Como,(swung up through Lichtenstein and Bavaria) Lake Garda, Verona, Venice.

Relax and Enjoy!

If you fly to Milan Malpensa, I recommend renting a car and going to nearby Stresa on lake Maggiore for a few days (3 nights would be ideal), then you can drive down to your next destination. Since you might have a car at the Cinque Terre I recommend to stay in Monterosso or Levanto (next to Monterosso), as there is no parking in the other towns. You won't need a car there, but if it's only for a day, you can keep it parked. Then you drive back to Malpensa for the return flight. With a car I would stay again at the lake Maggiore or if you want at an airport hotel.

Since "Our goal is rest and relax - eating as much local authentic food / sampling as much wine as we can without falling down, and just being in beautiful surroundings" consider this. Train from Milan up to Lake Cumo -- do you really want to drive after a long flight? Then see about renting a car for the rest of the trip.

I agree with Roberto that if you are driving, then Monterosso or Levanto should be your destinations for the Cinque Terre area. However, I would not advise trying to arrive in Monterosso without reservations. Besides being pretty booked at that time of year, the town is divided into the old and new sections, and they are not connected by road. If you drive to one and need to be in the other, you have to drive back up three miles on winding narrow roads, then back down. Check this website for information on driving in Monterosso: www.cinqueterreriviera.com.
We did not visit Levanto, but it is quite close to Monterosso, and they have a public parking lot at the train station.

At this tourist heavy time of year be sure you have booked your car before traveling (generally much cheaper that way) and book lodging especially in places with high tourist volume and low lodging volume like the CT. We did the CT on the fly the first time we visited, but that was nearly 35 years ago and it was pretty much undiscovered by Americans -- we saw no other USers there and were the only people on the trail from Riomaggiore to Monterosso that day other than one class of Italian 14 year olds and their teacher.

Try not to let any hotel or agriturismo make or break your trip. Your sightseeing and other experiences have so much more to offer! Expecting a post-card perfect trip is setting yourself up for disappointment. Instead, try to enjoy whatever you discover on this adventure. And if you're worried about one spot not being good enough for 7 days, then maybe you should decide now to split that time. If your aim is not to book ahead, driving and deciding on short notice, then timing, budget, and standards all must be flexible.

THANKS ALL. I really appreciate hearing from the folks that have been there / done that. I'm finalizing everything this weekend - most of the agriturismo and AirBnBs I've reached out to have availability, same for cars etc.

chris,

A few thoughts on your travel plans.....

I assume you're flying from North America? Renting a car immediately after a long international flight can sometimes be a bit of an issue. One of the regular posters here has commented that it's equivalent to driving with a BAC of 0.05%.

Also note that each driver will require the compulsory International Driver's Permit, which is used in conjunction with your home D.L. You'll have to be extremely vigilant to avoid the ZTL (limited traffic) areas which exist in many Italian towns (hefty fines!). You'll also need to be vigilant to avoid the speed cameras and Traffic Tutor system, which monitors both instantaneous speed as well as an average between two points. Exceed both and you'll get two tickets.

One comment that caught my attention was "sampling as much wine as we can without falling down". Sampling wine and driving a rental car are not a good combination, especially in Europe as the penalties can be severe.

As the others have mentioned, getting a hotel booking in Monterosso on short notice could be an issue. I'm sure you'll be able to find something, but if you just show up it could take a while. As mentioned, Monterosso has the best car parks of the five towns, with one in the "new town" and one in the "old town". Which one to use will depend on where your accommodations are located. There is a road between the two parts of Monterosso, but you won't be able to drive through town. A few of the hotels have limited parking for guests.

I agree with Roberto's suggestion to start your trip with a few days in Stresa on Lago Maggiore. It's a beautiful town and a perfect place to "rest and relax" while you get over jet lag. While there you could take a day trip to Locarno (CH) via the scenic Cento Valli Railway, returning to Stresa by boat in the early evening.

Buon Viaggio!

Thanks Ken for the good advice! =)

OK THE TRIP IS BOOKED, with the only night not yet solid being our arrival day. As many have said a long drive can be rough after flying so we're playing Saturday 9/5 by ear.

Relais Villa Baldelli in Cortona 9/6~13
Oasis Hotel in Levanto C.T. 9/13~15
Hotel Villa Delle Rose near Milan MPX 9/15~17

=)

chris,

You're very welcome! If you decide to start your trip with a few days in Stresa, you can easily get there from Malpensa / MXP via Gallarate. Don't rent the car until you're ready to leave Stresa, as that should save you a few days of rental costs and parking.

Chris,
Don't freak out! you've received some helpful ideas by the others thus far.

Just make sure your passports are valid for at least three months beyond your planned date of departure from the Schengen area. (Six months recommended)

Have a wonderful trip!

Alls good. Reservations have all been made, cars booked, and rough things to see lining up. We fly in about 25days.