Early June Itinerary (Venice > Florence/Tuscany > Cinque Terre) + open questions

You have planned well.

I would suggest checking if you have parking when you get to Siena. It's a rather congested city (down the hill from the center city), and parking is very difficult. Many people take the bus into the Siena city center--from across the street from the Florence train station (next to McDonalds.) You could also pickup a rental car in Siena before heading to the countryside.
Tuscany is still best seen by rental car. The roads are well paved and easy to navigate.
We especially liked going the short distance over to San Gimignano and down to Volterra for a day trip.
I'd keep the car and turn it in at LaSpezia.

From Siena, you can daytrip to Montalcino but you might have to tinker with your schedule. Or (my preference) sleep in Montalcino. I love the Brunello wine!

While you are in Firenze, after the Accademia, you can go to the Museum of San Marco just up the street. Formerly a Dominican convent, each sleeping room has a fresco by Fra Angelico.

Eek! David - sounds like we may have benefited from visiting Siena first - we have already booked our stay there as after the other hilltown, so Florence to (hilltown) to Siena, then Cinque Terre - so the bus to Siena from Florence doesn't sound too good unless we drive from the hilltown back to Florence then take the bus to Siena, stay, then bus back to Florence to take the train to La Spezia?

Thank you for the recommendation on San Gimignano and Volterra, they look very charming. Any highlights from your trips there that we may want to note?

Zoe - did you go on a wine tour from Montalcino? How was it? And thank you for the San Marco recommendation, we will see if we can squeeze that in!

Are you really arriving in Venice at 10.05pm. If so, by the time you get to the hotel you will not have much time for wondering around Mark's Sq. Second, are you thinking of taking a late night train from LaSpezia to Milan and then the airport. That could be a big problem as I think the earliest trains to the airport if 0525. You may have to sleep in the airport for 0555 flight or come the day before. At 0555 that is not a direct flight to the US.

Be sure you have you International Driver's Permit and know how to ride a Vespa for the Vespa tour.

Thank you very much for your detailed observations Frank! Yes, we are really arriving in Venice that late...we were thinking if we were still jetlagged and wide awake, to enjoy the St Marks Square when there's a lot less people, but of course if we're tuckered out from the flight we'll put that to another evening or early morning!

And we were actually thinking about getting a late night train to Milan but wow, thank you for the intel on the 0525 train situation, did not know the trains don't run 24/7. We'd probably pull an all nighter in Milan's airport or spend the night in a cheap apartment there then. You're correct, we bought tickets from Aeroflot which will fly to Russia first and then the US (the price difference for flight tickets at the time was significant enough to warrant this choice for us).

Just got my IDP, husband is waiting on his, thanks for the reminder! The tour guides on the Vespa tour will be teaching everyone to ride so hopefully we pick it up quickly :)

Just a few minor observations as you have a basically very solid plan.

June 3 seems ambitious. The Accademia and Uffizi in one afternoon is a lot of museum time. Many people spend 2 or 3 hours in he Uffizi alone. Maybe save one of the museums for the 4th, after your class?

June 8 is light...you are really doing nothing which is fine, but maybe Siena is not the place for you if you are not sure what you will be doing there. Montalcino and Montelpuciano are, IMO, much more appealing. Why not three nights in a Tuscan Hill town and drop Siena? It's hard to park in Siena anyway, unless you stay outside the walls. I selected Siena as a stop on our first trip to Italy and we ended up using it only as a place to sleep and eat. I liked the other towns much more. OR try an agrtiturismo as al alternative to tour Tuscany. A totally different experience!

Rent your car in Firenze and keep it to La Spezia. From La Spezia take the train to Vernazza. You coudl stop in Lucca if you ahv a mind to.

I would probably go to Milan on Saturday and spend Sunday seeing some sights there: the Duomo, the Last Supper (get tickets through a consolidator)

I suggest swapping your Sunday and Monday activities in Venice. You plan to visit two major churches on Sunday; they will be closed to tourists part of Sunday for liturgies. At San Marco, the church will be closed to tourism most of the morning/midday on Sunday and then again in the early evening.

Also, if you're really leaving Milan at 5:55 AM, you're not going to be able to take a train that day and make your flight. I suggest spending that night in Milan. I find that the easiest website for checking train schedules is bahn.com.

Maybe spend a day in Milan. In addition to the last supper and the duomo, Milan has some wonderful art museums, some beautiful very early churches, and shopping opportunities.

If you decide to keep Siena as a two-night stop, Hotel Minerva on via Garibaldi has covered garage parking onsite and is at one of the city gates - a 10-minute walk to the Campo. Very easy to drive out to other towns.

I love Siena, especially in the early morning and late afternoon/evening.

I did not catch that your flight is at 5:55 AM. the trains I can find would put you at Malpensa at 00:02 on the 14th, having left La Spezia at 19:02 the evening prior and with 4 trains, 3 changes to do it.

What will you do for 4+ hours around the airport? For me it would make a cranky end to a lovely trip. It would be bad enough to have to get up at 03:00 to get to the airport by cab. I believe the first train from MIlano is at 4:28, not early enogh for you.

Laurel - thank you for your "minor observations", they are very helpful. We thought we'd have a "museum" themed day on the 4th but you're probably right that it seems a little crammed and may "museum" us out early on. Hopefully we will have enough familiarity with the city by then to seamlessly add it in after our cooking class. Also, would you mind expanding on why Montalcino / Montepulciano was more appealing for you? We initially picked Siena based on coworker's recommendations of the dining scene there, of course RS's take on Il Campo, and it seems like a lot of people enjoy the late night "feel" of the place, which sounds very charming for us. Ah, agriturismo living does sound lovely too! I wonder if spending two nights in a hill town and two nights in an agriturismo is enough to take advantage of agriturismo living?

Sherry - great point on the Sunday / churches not available for tourists issue, we didn't even think about that. We will shuffle things around to make the most of it!

And to the both of you - Thank you for adding additional color to the last day of our trip and how a 0555 flight from Milan would be potentially quite problematic! We certainly don't want to be doing a 3-transfers hectic train-juggling schedule the last night of our trip. I think leaving Cinque Terre earlier, perhaps the morning of the 13th, gets us to Milan in the afternoon, we can walk around and enjoy the city and then make our way to the airport after a late night dinner with plenty of time to spare.

And thank you for the hotel recommendation Zoe! We had originally booked (flexible cancellation policy, thankfully) an Airbnb in the center of the city but the room does not have parking. How "bad" is it, walking-wise, if we left the car outside of the city for that stay? If it's not that ideal at all we will probably move our reservation.

Also Zoe, any highlights of Siena you might want to share? I imagine early mornings and late nights to have that lovely feeling that you have the town to yourself?

We just visited sienna today and the two other m towns. We liked sienna but loved the other ones. We are based on Florence. Rented car for a day. Follow RS advice and you'll be fine with parking. Check sienna hotel to see if they have special parking for you. While in Montepulciano, you must see the older gentleman who speaks little English but you see his wine cellar. We went due to RS book. While in Montalcino, you absolutely must go to a restaurant RS recommend. The name starts with re maybe? He speaks of Antonio and you get a 4 course meal for $25 euros and can pair it with wine for each course at $17 euros. It was devine!!!
We were just in vernazza a couple days ago. You must check out a restaurant called LA Torre. From train station walk to pharmacy, turn left and climb. You will pass a tower, keep going. Great family run place and the views are astounding! Sunset dinner possibly.
We've been here just over a week. Couple more weeks to go. You will love it!!!

Sounds like a great itinerary! My husband and I took the train from Rome to Cinque Terre then on to Florence. Driving in Tuscany was very easy and a great way to explore the countryside and hill towns. When renting a car, be sure to inspect it VERY carefully and maybe even take pictures to record any pre-existing damage, scratches, etc . When returning the rental in Rome they said the wheel rims (all 4) were scratched and we were charged 400 Euro for "damages"!

I'm speaking as a total novice but I do know that there is a hotel in terminal one of Malpensa and another, less expensive one in terminal two so that could be a good option the night before departure.

Your Itinerary looks fairly well organized, but a few thoughts......

• Combining a Vespa tour with a wine tasting may not be the best idea. The DUI laws are very strict there.
• I agree with Laurel that it would be a good idea to return the rental car in La Spezia, and then take the local train to Vernazza.
• Note that for driving in Italy, each driver will require the compulsory International Driver's Permit, which is used in conjunction with your home D.L. You'll need to be vigilant to avoid the ZTL (limited traffic) areas which exist in many Italian towns and cities (hefty fines!).
• Regarding "sleeping in Vernazza", I hope you've got lodgings booked. If not, you could have some trouble finding a vacancy at this late date.
• Regarding your "hiking days", were you planning to hike only the Sentiero Azzurro trails, or a wider variety of trails in that area? Note that some segments of the S.A. are currently closed, and will likely remain that way for some time. At the moment, the Monterosso-Vernazza and Vernazza- Corniglia segments are open, as well as a short segment of the Via dell' Amore from the Manarola end. Note that you'll need a Park Pass to hike the S.A. trails (easily purchased there, even from the small booths at the start of the trails).
• I noticed that Monterosso was absent on your list. There are some good restaurants there if you're interested.
• Especially for such an early flight I'd suggest staying in Milan for the last night, perhaps close to the airport. The first Malpensa Express doesn't depart from Cadorna station until 04:27, arriving at the airport at 05:02. That would likely be too late to connect with your flight.

What a great trip!

If you are not planning on having a guide at the Accademia or Uffizie I highly recommend downloading the RS Audio Europe app and then downloading the tours of those galleries. Once they are saved to your phone you don't have to take your phone out of "airplane" mode to listen so no data or roaming charges.

The other audio tours that we enjoyed were the Florence walk, Venice's Grand Canal and St. Marks Basillica.

Have a great time!

I didn't do an official tour, but I was traveling with friends, we had a car, and we stopped at a couple of places on the way from Siena to Montalcino.

I do love Siena when the day trippers are gone. It's easy to park at one of the public garages and take the elevator or city bus into town, if you don't spend the night there.

Your departure plan scares me too. I would stay at Malpensa the night before a 5.55am international flight.