Your Advice on our Itenerary

Amy, Plan on about 3 hours overall from Milan to the CT. Assuming that you arrive in Milan in the morning, this isn't too much first day travel. " In the Cinque Terre I want to stay somewhere with a balcony over looking the water, romantic and cozy. ". Try : www.elisabettacarro.it Have a great trip!

What is your price point?

I would like to pay no more than $225 per night.

Amy, on my first trip to Italy 2 years ago I had the same thought as you about Rome and ended up LOVING it! I think it is also a great end to a trip - kind of a historical "best of"!! 4 nights in the CT seems like too many - especially when you are only allowing 4 nights for Florence/Siena/Tuscany - and taking into consideration you are also going to the AC for 3 nights on the same trip. But then again, I am not really into hiking! So you are not planning on spending the night in Florence?

And when is it you're going to be there? You'll get better recommendations if you include that.

Amy: Great job paring it down to the trip you will enjoy! I agree with the previous poster that 4 nights in the CT is too much. Cut that to 3 and add the night to Rome so you have time to enjoy Rome, not just see the big sites. IF you ahve the budget, consider a private guide for a tour of the ancient sites: Colosseum, Palatino, and Forum. Francesca Caruso (FrancescainRoma@gmail.com) made that area come alive for us. 200 euros for a 4 hour tour we will never forget. Was able to take my head out of the guidebook and just enjoy and learn from an expert. Priceless! In Siena, look at Antica Residenza Cicogna, a B&B. Very old building, beautifully renovated with original frescos, run by a lovely young woman and her father. Delightful breakfast buffet, too. Far less than your budget $$. Rome: Palazzo Olivia is an apartment building near Piazza Navona. Fabulous area. We are returning there on our second trip to Rome later this year. Buona fortuna!
Laurel

We much preferred Manarola to Vernazza-the town is just as picturesque, but not as packed with day-tripping tourists (and grumpy fatigued shopkeepers.) Manarola also give you access to the easier sections of the Blue Train, heading to Riomaggiore or to Corniglia, instead of teh sections leading out of Vernazza which are the steepest and most rugged. For swimming, there is deep-water access just out of town. We loved swimming there from the rocks. La Torretta, at the top of the town, is very romantic, has lovely views, and nice rooms with balconies (some). Our "classic" room had a balcony nxt to a bouganvilla-covered arbor, with views to the sea and to the vineyards. The host, Gabriele, is very gracious. My husband described this place in our photo album as "the best hotel in the owrld" (and we travel extensively so that is saying a lot!)

EKC, Michael, Laurel and Lola, Thank you all so much for the input so far! I think 3 nights in the Cinque Terre and 3 nights in Rome might work out well. I will also certainly look at Maranola in the CT. The view from my room is my number one priority here. We would love to relax by the beach for portions of our stay while in the CT as well. I do plan to spend time in Florence, should I plan an overnight there? Maybe split up the time between Sienna, Florence and a small hill town such as Montepulchiano? We are going September 9th - 23rd 2011.

I would do 2 nights in Siena - 1 day for Siena and 1 day for touring hilltowns - then drop your car outside of Florence and do 2 nights in Florence, then train to Rome. But, then again, I love Florence! ;-)

Amy, Sept is the time we've done most of our traveling to Italy and I think its a good choice. A few comments: (1) you are thinking about splitting up time between Sienna, Florence and a small hill town such as Montepulchiano. I hope you mean day trips and not moving each day; by the time you get out of the hotel to the new place and get settled in its usually noon. (2) If you have a car and are staying in Florence, be very careful of the ZTL where you get expensive tickets for driving if not registered by your hotel (3) I don't think 4 nites in CT is excessive. I think more time in fewer places makes for a better trip. With 4 nites you have a chance to walk part of the trails each day, relax on the beach, take the train out of town for a day trip to someplace such as Santa Margherita Ligure, and you have a better chance of getting a day or two of sunny weather for the beach (4) since so much of your itinerary is in the north of Italy, I'd suggest spending all of it up there. Its going to be a long slog from Tuscany to the Amalfi coast and you won't be settled in there before mid-afternoon if you're taking the hi-speed train to Naples (later if you're driving); realistically you'll only have 2 days there. There is so much to do (Amalfi coast drive, Capri, Sorrento, Herculaneum or Pompeii) that I'd suggest saving it for another trip.
(5) while the RS books don't cover it, Bologna and vicinity is the food capital of Italy (think balsamic vinegar, ham, cheese, etc) and has some splendid towns to explore such as Parma. If it was me, given your itinerary start, I'd drop Amalfi/Rome and add in the Bologna area. Anyway, just throwing a few ideas out there for you to think about. Have a great trip!

I would spend all 4 nights in Tuscany in one place to minimize moving around. The best place we stayed in 3 weeks in Italy was Agriturismo Marciano in Siena. We were there 4 nights, which works out to 3 full days. We spent 2 days touring hill towns (1 day north of Siena and 1 day south of Siena), and you can usually get a least 2 towns done in a day. The 3rd day we spent in Siena. You could take a day from CT and add it to Tuscany, if that area is very important to you. Or you could stop in Florence on your way from CT. Spend a night there, then pick up a car to go to wherever you are staying in Tuscany. We spent 2 nights in Florence, and I wish we would have spent those nights at the agriturismo.

Hmm...it's your anniversary and you're skipping Venice? One of the most romantic cities on earth!

Camille, I know...It's killing me not to go to Venice, but I think I read that it's a 5 hour train ride to Venice from Milan. We couldn't get our free airfare into Venice which was my original plan. What's the advice...skip Almalfi and hit Venice before CT? That would change the itenerary to: Venice 2 nights CT 3 or 4 nights Tuscany/Florence 5 nights
Rome 2 or 3 nights That eliminates the Almalfi Coast Just not sure if we would enjoy Venice more than the Almalfi Coast. I have heard such lovely things about Positano and the day trip to Capri being so romantic!!!! So many options it's mind boggling!

Amy:
I'd suggest either the Cinque Terre OR the Amalfi Coast. Full disclosure: I have not gone to the AC yet (will in Dec), but we did do the CT and Venice last October. Venice is so magical and romantic! I'd give it 3 nights though, and as I said before, keep the CT to 3 nights. If you give 3 to Rome, then that leaves 4 for Tuscany. Also, the Amalfi Coast is pretty far south, adding significantly to your travel time. But it is YOUR TRIP. Only you can finally decide the best plan. Read everything you can and then go for it. Make sure you look up the train schedules on the Trenitalia site so you know what to expect. Add time at each end to get to the station and then to your lodging. CT to Siena can be a long train trip; Not in miles, but in many changes of trains and thus hours in transit. The only thing I'd really caution you about is not changing locations every two nights. It's not conducive to a relaxing experience.

the train ride from milan to venice is 2 1/2 hrs

Amy Where did you get 5 hours from Milano to Venezia SL? David is right, its only half that. Your source must have been going by donkey cart.