Italy Itinerary

Hi Debra! Sounds like a fun trip. You may want to pair down the towns you visit in Tuscany as they are a bit scattered and would take quite a bit of time to visit them all in 5 days. However, You could do Siena as a day, Montepulciano (with Montalcino) as a day (visit Santa Guilia winery and Altesino winery - both great!) and San Gimignano for a day. I'd skip Orvieto for this trip.

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1. Are there any restaurants/wineries you could suggest?

Yes! Definitely. In Florence: Osteria Toscanella (in Santo Spirito neighborhood); Perché No (gelato shop. Best gelato we had our whole trip); All'antico Vinaio (delicious sandwich shop. There are a few in Florence and other cities now).

Wineries, as mentioned above: Santa Guillia. A lovely family run winery that makes two wines and olive oil! Altesino is another wonderful, but larger, winery. Both wineries are around the Montalcino/Montepulciano area. Also there is a really great wine bar in Montepulciano where you can taste wines from all over the region in one place Enoliteca Consorzio Vino Nobile de Montepulciano (https://www.enolitecavinonobile.it/it/index.php) AND it is built over ancient ruins so the floor is glass.

Hope you enjoy your visit!

Hi Debra,

Since you could have up to six people, I would just take the train from Milan (Milano) to Florence (Firenze) and add your Ravenna night to Florence. (Italian names for Trenitalia train website or app.) You can take the train from Florence to Ravenna in about two hours. I recommend taking the 7:55am to arrive at Ravenna at 10:16 to get to the favorite sites before they’re crowded. (Begin with the top 2.). I also recommend that route in case everyone isn’t wanting to see the mosaics; they could do something else in Florence since there’s so many options.

For Milan, your group would definitely want to see the main piazza, the Duomo & roof, check day-of-week for art museums. Since you like art, history & architecture, check out the Citta Alta part of Bergamo on-line. It’s very close to Milan, and so atmospheric. I stayed at the wonderful Gombit Hotel for two nights and also the friendly Hotel Piazza Vecchia my first night.

What time of year is this trip?

1. I'd like for you to have two nights in Ravenna. The trip from Milan will take about 3 hours, or longer, by Freccia train, usually with a change in Bologna. Driving would take at least an hour longer, according to ViaMichelin's estimate. By the time you get settled into your Ravenna hotel and have lunch, you'll be into the second half of the day. There are lots of beautiful mosaic sites in Ravenna, a mosaic museum and an art museum that sometimes has a display of contemporary mosaics. The historic center of Ravenna is quite nice, too.

2. The Duomo in Milan is magnificent. Be sure to go up to the roof. The Galleria Vittorio Emanuele II, a beautiful, early shopping mall, is very near the Duomo. I believe the Brera Gallery is considered good; I haven't been there yet. There are other museums, of course. The Navigli District is trendy. Milan's the center of the Italian fashion industry, so the Quadrilatero della Moda might be of interest. The city has a great deal of Art Nouveau architecture.

3. There really are no must-sees in the Cinque Terre. It's all about the cute towns and the views from up in the hills (some ascending of steps required) unless you want to hike. The towns themselves are very crowded during day-tripping hours unless you're there off-season, so I'd give some thought to mostly seeing the area from the ferry (which I think runs only part of the year) if you aren't hikers.

4. I think you should consider the location of the wineries you want to visit in determining where your Tuscan base should be. You'll need to figure out a way not to violate the strict DUI rules.

5. The train is faster than a car between Milan and Ravenna, as indicated above. It's also faster between Ravenna and Florence. From the Cinque Terre to Milan a car will be faster if nothing goes wrong (traffic, difficulty finding parking, etc.), but consider that if the trip overlaps the lunch hour, you'll have to stop if you're driving but can pack a lunch to eat on the train. Parking is challenging and costly in most places tourists go, so the daily rental rate is only part of the cost of having a car. I wouldn't want one in the cities, because it will be of no use whatsoever there. It won't be helpful in the Cinque Terre, either. Having the car just for the rural-Tuscany part of the trip would be smart, I think. Check on the drop charge if you're seriously considering having the car for a larger part of the trip.

First night - if you arrive in Milan in the morning, you can visit Santa Maria delle Grazie (where The Last Supper is) the same day. Sleep in Milan.
Second night - the next morning, take a train from Milano Centrale to Ravenna (3h 15m) that requires a transfer: https://www.trenitalia.com/en.html. Sleep in Ravenna.
Third night – take a train from Ravenna to Florence’s SM Novella station that also requires a connection (2h 30m). Buy tickets for the Uffizi two months out to guarantee a reservation. Sleep in Florence.
Fourth night – take a direct bus from Florence to Siena (1hr 15m). Sleep in Siena.
Fifth night – get an early start and rent a car then drive to Pienza’s old town along the SR2 then left on SP146: https://lovefromtuscany.com/scenic-drives-in-tuscany/. You’ll see rolling hills and well-maintained farm houses. From Pienza drive to Montepulciano and visit the winery there. Sleep in Siena.
Sixth night – drive to Orvieto for the day. Sleep in Siena.
Seventh night - get an early start and drive to San Gimignano and make sure all luggage is in the trunk. You only need an hour or two in San Gimignano before driving to Lucca. Drop off car in Lucca and sleep in Lucca.
Eighth night – take a train from Lucca to Monterosso in the Cinque Terre (2h 15m) that requires a transfer. Sleep in Monterosso.
Ninth night – if the ferries are running, take one from Monterosso to Riomaggiore then take the train to get between towns. In Corniglia you’ll need to take a bus from the train station to reach the top of the village or walk up close to 400 steps.
Tenth night – there’s a direct train from Monterosso to Milan’s central train station (3h 30m).