Northern Italy + Tuscany Summer 2025

Looks like a fabulous trip! Overall it looks pretty good. Don’t forget the Accademia and David when in Florence. Personally, I don’t think you need that much time in Venice. I would add more time to Montepulciano. We stayed in an agriturismo and spent a week exploring that part of Tuscany and also Umbria. Umbria often gets overlooked but it has some wonderful sights. We took a cooking class in Cortona in the chef’s kitchen in his home!!! We had lunch beside Lake Trasimeno at a truck stop, that is not like any truck stop you are imaging. We found some natural hot springs. So much in that area if you slow down and explore! The val d’Orcia is just as stunning as you’ve ever imagined. And an agriturismo in Montepulchano is the perfect way to do it! Enjoy your trip!

Thank you very much for your input! Could you provide details on the agroturismo you've been ? And the cooking class sounds awesome, my wife would love it! How did you find it ?

I'd keep your Venice time as it is.i feel the more time you have in. Venice, the more you fall in love with this magical city. Wander away from St Marks's Square and Rialto , and explore the quieter areas. We stay in the quiet back canals in Cannaregio.
Bring bug repellent and book lodging with air conditioning.
I was a little confused where all you're sleeping, it's a bit easier to count nights. So two nights is one full day. Don't underestimate transition times between areas, and the energy it takes.
Perhaps reverse the order of your trip. It can be hard to fly out of Venice for early morning flights. And Venice is a great place for working thru jet lag.
Have a wonderful trip!

Hi! Thank you for sharing. When you say it is hard to catch an early morning flight in Venice, what do you mean by that ? Is it because the airport is harder to reach then in other places ?

Hello vincentletourneau4, and welcome to the forum,

Some thoughts:
Traditionally people here count nights in places rather than days. It's a helpful convention because you know where you are every night for lodging purposes. List where you are staying every night and the necessary travel for that day.

Is your lodging set? If not I would consider extending Florence a day and doing Bologna as a day trip from Florence. Bologna is 30 minutes on the train and I don't advocate staying anywhere for one night unless it's for logistical purposes. By the time you get car returned from Siena to Bologna and checked into a hotel your time in Bologna will be shorter than you might want.

One night somewhere is two partial days with packing, check-in/out and travel hassle without even getting a full day out of it.

Is your flight out of Venice early? Logistics of early morning flights can be tricky out of Venice can be tricky so plan accordingly. Unless you stay within walking distance of the trains station you need to catch a vaporetto (water bus), walk to Piazzale Roma and catch a cab or bus to the airport. Each stage takes a little longer than you want it to and you have to err on the side of earlier to be safe. It is a small airport and can get overrun when cruise ships depart so leave time.

The big question:
Is renting a car and driving around rural Tuscany the center of your trip? If not I would extend your time in Siena and use organized tours or guides to get out and see the countryside. You're in Siena a partial day and one night - it deserves more - and then you have a couple of days driving around listed but it's probably really not going to be enough.
If rural Tuscany is your main focus than give it more time by cancelling the night in Siena and Bologna (and maybe Lake Maggiore), renting the car in Florence and making that the core of your trip. Visit Siena as part of your Tuscany exploration and spend as much time on that part as possible.
If it's not add the core of your trip then those days in Lake Maggiore and Siena, maybe Florence, move around less and explore more. Get a taste of rural Tuscany with a guide and decide if it's worth a trip all on its own. Spoiler alert the answer is probably "Yes" but that kind of trip takes slow travel time not a flying visit.

I realize you probably have a long list of things you wanted to see and already feel like you've scratched off too many things. But it takes time to get the feel of place and experience it - this is especially true for rural Tuscany where the slower pace is part of the experience.

My $.02, hope that helps, have a great trip,
=Tod

Yes, the Venice airport is a challenge to reach for early morning flights, because of the transportation modes. These modes are charming to use when arriving in Venice ( vaporetto, water taxi, and / or Alilaguna ). But an early morning flight may require an expensive water taxi to get to the airport quickly and directly. If your departing flight is around noon, no problem.
And- I corrected the area in which we stay, which is the Cannaregio area, the Hotel Ai Mori D'Oriente, on the quiet back canals. One can take sunset pix without anyone spoiling the frame.
Have a great trip!

Thank you all for your input! If something else is crossing your mind, please feel free to report it here as it will be super helpful to us while planning. Especially the early morning flight from Venice is something we didn't see coming and we will definitely consider switching things around and end in Milan instead of Venice.

To answer to your question @hiredman, the Tuscany part is kind of the core (at least I think) because my wife really wants to see the cypress and hills rolling by, as well as we enjoy agriculture, food and the arts of the table and being outside. Thing is, we also really want to see Venice and maybe the mountains around the Lakes.

Question though, how would you arrange your visit and stays considering Sienna must not be so friendly when you need parking and that many comments out there point into the direction of spending at least 2 nights there?

What would be your two weeks suggestions taking into account all that have been said above ?

Thanks alot!

Adding a maybe helpful insight here for those of you helping us figuring things out. We do like to enjoy a place slowly. Yet, Italy as so much to offer and, YES, we definitely already feel we've crossed too many things of the list. Yet, we spent 12 days in Paris two years ago, and we loved it so MUCH! We took the time to sip in the daily life without being rushed.

How could we manage to recreate this atmosphere in Italy even though it is our first trip there and literally every corner is seems to be worth seeing there!

How could we manage to recreate this atmosphere in Italy even though it is our first trip there and literally every corner is seems to be worth seeing there!

Simple answer: you can't. Don't even try. You can't recreate an experience even in the same place, let alone an entirely different country. As hard as it is, try to remember Rick's advice: plan that you WILL return another time. Don't even try to cram everything into one trip. The end result won't be good. Just savour the places that you can comfortably see in the time that you have.

As for departures from Venice: it is true that many flights going to North America leave very early in the morning, requiring you to travel to the airport before the day time vaporettos start running. But you are going to Montreal, which doesn't have a direct flight. And a quick look at a random day in August on Google Flights showed several flights with connections in either Toronto or a European hub that depart in late morning or early afternoon. So you'd be fine.

Another question regarding a car rental. For those of you who have done it in the past, was it difficult to navigate the Tuscan country side and find parking in spots like Montepulciano or Pienza or Montalcino ? How did you manage ? Thanks!

On a first trip I'd drop Bologna, Milan and Stresa (we did like Stresa a lot) and concentrate on Venice, Florence and Tuscany.

if you can fly home from Florence:
Fly in to Venice
Venice 4 nights
Train to Florence- pick up car and head to Siena (you will have better options/availability for a car rental in Florence)
Siena 2 nights- there are some nice hotels with easy access parking- don't try to drive in and out of Siena
Tuscany Agriturismo 4 nights- somewhere in Val d'Orcia (Pienza, Montepulciano)
Drop car in Florence
Florence 4 nights
Fly home

If Venice and Milan are your flight options- put Milan/Stresa at the end

Venice 3 nights
Florence 3 nights
Tuscany 4 or 5 nights- include Siena here as a day trip
Milan 1 night/Stresa 2 nights or vice versa

You can stay in Stresa night before departure- there is a direct bus to MXP

(If your flight out of Venice is 11 am or later you will be fine. Just know what your transportation options are- it's not impossible)

Thank you all!

ChristineH, you're mentionning include ''Sean'' in Tuscany, what did you mean by that, Sienna would be my guess. Thank you for your advices! :)

hey hey vincent
welcome on the forum
you'll get lots of info here from these posters what's good/bad/ugly. like many first timers they want to see it all which is "cramming" it in and not enjoying, breathe the italian air, sit at an outside cafe with a glass of wine/appetizers and people watch.
at least you know it will be crowded and hot during august but..... many cities are busy all year long, no high or low seasons anymore, many people are traveling nowdays.
things to think about: check-in to hotels are 2-4pm check-out is 10-11am. if too early drop your bags at hotel or they may have a room available.
one night stays doesn't give you much time to roam around. get ready in morning & pack up, getting to train and travel to next place, if can do a day trip more time to see the town. bus from florence to siena may be an option.
renting a car will need an IDP (caa.ca/ international driving permit) is mandatory. read up about it and the rules, laws, signage of italy). you may be able to apply online. driver's license & IDP needed at all times when driving.
main attractions/activities that are a must may need reservations ahead of time, some are date & time stamped
even with the jubilee 2025 happening, some people may want to stay away from rome because of the millions of people expected, and want to see other cities which brings the overload. just go with the flow,
which ever city you are flying out of, spend the night there before flight and having no stress. look at doing multi-city flights (into one city and out another city)
look at hotel first before booking flights and work from there.
as others have mentioned, venice can be a tough flight out. usually many flights leave at 6am with morning transportation being well planned out with what's available, could be $$$ (private water taxi). getting up at "dark thirty early morning" & packing up, getting out and to airport. always come back here for more questions and answers to help you out to go smoothly.
if taking money(euros) out of ATM, i give an odd number (75, 85, 95) so i don't get a 100E note. like to have small denominations, also carrying small coins (1, 5, 10) for small purchases, restrooms/toilets.
check out food tours, markets, cooking classes, sip & paint class, walking tours or on your own, make sure where you stay with a car there's is parking. if doing a winery tour, get a planned tour with driver/guide. (italia.it/ everything you need to know about driving in italy rules & tips)
these are some of my own opinions and thoughts, seems like a lot but once you get the handle you'll be good. get your hotel and flights kicked in and will send you people, places, and things for the fun side of enjoying your trip.
was confused about your budget overview: what does $ before items and $ after items? is one canadian and the other US dollars.
you'll have a great time when you have researched and make your plans than a lot of newcomers do.
aloha

Thank you all! ChristineH, you're mentionning include ''Sean'' in
Tuscany, what did you mean by that, Sienna would be my guess. Thank
you for your advices! :)

Haha- yes- typo- corrected to Siena

Driving in Tuscany is easy and delightful
Parking is always going to be outside the walls in parking lots- towns are mostly pedestrianized or ZTLs.

Familiarize yourself with driving in Italy and you'll be fine
Make sure all drivers have an IDP- you can get at AAA- required by law

After a few researches, Montreal has direct flights on Milan, Rome and Venice. Since we will not be heading to Rome. We have Milan and Venice left. I've found a great price on a roundtrip ticket on Venice but not sure if it's worth it since we would need to go back and forth by train. Another option is to take a flight from Florence to another international hub like Zurich or Munich then return home from there.

Also, the flight outbound from Venice to Montreal is around 12h20. So my guess is that t is enough time to get to the airport in time by vaporetto or taxi.

On the other hand, I've also found that we could get a plane in Florence early in the afternoon to Frankfurt (layover time of 2h15) then a flight to Montreal. Although this is 500$ more expensive then the roundtrip option, we would save on twice the train tickets and the back and forth. We never had such a short layover, is it too short if we have a checked baggage ?

Any thoughts ?

OP, have you looked at a multicity ticket instead of round trip? Any increase in price may be offset by the cost/time/effort of back tracking to your arrival airport.

Are you using Google Flights for your research? It's a great tool to see a range of available flights. Good luck!

Yes, I'm actually looking at multi-city since the beginning and using Google Flights amongst other sites like Air Canada since it is the main provider for those destinations here in Montreal.

Inbound Milan or Venice, same for returning home. Direct flights both ways. It is our first choice. So it is making me think that something like this would be our best option :

a) Starting in Venice (3-4 nights)

b) Then Tuscany via Florence (car rental including 2 nights in Siena (hotel for parking purposes) then agroturismo in Pienza/Montepulciano) (5 to 7 nights)

c) Back to Florence (3-4 nights) (maybe daytrips to Fiesole and Bologna)

d) Finishing on Milan (2-3 nights)

14 to 18 night total

Above option looks great. Have a wonderful trip. Safe travels!

Thank you Pat!

Sounds great

See this thread for hotels with parking
https://community.ricksteves.com/travel-forum/italy/siena-hotel-with-parking-on-premises

Thanks ChristineH! :) Will look at the thread for sure!

https://www.agriturismolabruciata.it/en/
This is where we spent a week - it’s less than 3 miles outside of Montepulciano. We had a car so we could explore a lot during the day and come back to heaven every afternoon/evening! Let me private message you about the cooking class. I’m never sure how much I can share on the public forum!

Sounds like a wonderful trip! I understand your time is limited and you will travel in August! We did that back in 2016 and found out that a lot of Italian people take the month of August off! Our disappointment was that many of the good restaurants were closed for 2 to 4 weeks. Ciao!

Thank you Gigi ad Jewell.

And yes, we don't really have the choice when it comes to vacation since we both work in schools! Anyhow, it was the same when we got the Paris two years ago and we had a lot of fun anyway! :) I think it's mostly with which mindset you begin the trip with that makes it most of the time!