2 week trip in 1st half of May

Hi Mike, welcome to the RS forums -
There will be any which way to shuffle this but a couple of things to consider right off the bat?

6 different locations over two weeks are too many. You need to subtract your travel days from the total, and two nights anywhere give you only one FULL day of sightseeing once you subtract the 1/2 day you'll expend getting from one place to another. That process (packing up, checking out, getting to train station, sitting on train, getting to hotel, checking in and settled) usually takes longer than you think it will!

You definitely should fly open jaw (into one city and out of another) to maximize your time.

The very best way to get to the places you list is by train. The exception can be if exploring rural Tuscany, which can involve the need for a car. An alternative to this is basing in Florence - to avoid another physical move - and taking easy day trips to any number of places the trains/buses go. There are a few towns, like Lucca, on train lines which could work if wishing to avoid car rental but that will mean cutting something else short if this is a priority. Driving involves some homework to bone up on no-drive zones and whatnot, and I'm sure someone else will cover you off on the ins and outs.

Just as a starting place, here's a sample two-week itinerary with a Sat. departure and Sunday return. Note that I've done this by number of nights versus days as it's a more accurate method of dividing time, and dropped Milan:

S Night 1 - fly overnight (Sat) into Venice
S Night 2- Venice
M Night 3 - Venice
T Night 4 - Venice
W Night 5- Florence
T Night 6 - Florence
F Night 7 - Tuscany
S Night 8- Tuscany
S Night 9 - Tuscany
M Night 10 - CT
T Night 11- CT
W Night 12 - Rome
T Night 13 - Rome
F Night 14 - Rome
S Night 15 - Rome
Sunday - Fly home from Rome Fiumicino.

Even with Milan scrapped, this would be too many moves for us but then, we all travel differently so it may be fine for you! Still, I wouldn't give Venice any less than 3 nights - arrival day may be a jet-lagged haze - and I consider 4 nights/3.5 days a minimum for Rome. The middle could be shuffled slightly but there isn't a whole lot of margin to work with if you want to spend time in rural Tuscany. Again, keep in mind that two nights = 1.5 days of sightseeing time, three nights = 2.5 days, and so on? It all comes down to what and where you two are MOST interested in doing/seeing.

Flying into Venice and out of Rome is usually recommended as many flights from Venice depart very early in the morning.

First, have you gotten the Italy guidebook? It has a wealth of information.

With 2 weeks, are you counting days or nights? You should count nights. Day #1 is a travel day, Day #14 is a travel day. So you really only have 12 nights. You are trying to see a lot in that time, try to limit it to maybe 3 places. You also can lose 1/2 a day traveling, getting to train stations, checking in and out of hotels, etc.

The most popular idea is to fly into Venice, it is an easy city to get over jet lag. And a photographer's dream! Fly home from Rome, easier to get a flight out. Many people do Venice-Florence-(day trip to Siena)-Rome. You could squeeze in Cinque Terre, but you will be missing out time in the other places. And spend a lot of time wasted just traveling.

All travel can be done by train, EXCEPT for the Tuscan countryside. Then you will need a car, an International Driver's Permit, and knowledge of traffic signs and ZTL's (zones where cars are not allowed). Be sure to obey speed limits, they ticket you by camera and you receive the fine in the mail months later.

If you want to stay in a Tuscan countryside town and experience it as the locals do then you're going to have to devote some time in doing so. What exactly is it that you want to experience? Most locals will be getting on with their lives, going to work, running the house, shopping, eating at home and settling down for the evening in front of the TV which clearly isn't something you'll be doing. What you'll actually be doing is touristy stuff, eating out, exploring the town, visiting museums (if there are any), sampling the local produce etc. To fully appreciate this in rural Tuscany, or anywhere else for that matter, is going to take time if you actually want to experience and appreciate the area. Rushing around for a day or two trying to cram things in before moving on to the next stop is not a good way of doing this and simply serves to be a "tick list".

I would curtail your itinerary and focus on one or two areas.

Great advice from Kathy. I would follow her itinerary, renting a car at the end of the Florence section and dropping it in La Spezia on your way to the Cinque Terre town of your choice. A nice base for a Tuscan hill town experience is Montalcino. Lovely countryside to explore, wine, good restaurants.

Thanks for the detailed replies Kathy and Charlotte! And Kathy for coming up with detailed itinerary. Firstly, I'll be flying in from Asia so I'm not sure if it makes a difference in terms of jet lag, but I will have flights that can reach Italy in the morning/afternoon. As for the number of nights, 14 nights is what I am planning, not including the flight dates, apologies for not being clear on that.

I agree that 6 locations over two weeks are too many, and the whole checking out and Travelling etc would take time. I was referring to this link https://www.ricksteves.com/europe/italy/itinerary which gives a suggested itinerary for 14 days so I thought it would be possible but maybe not on hindsight. I would prefer to spend less time in Venice(2 nights) and Tuscany(2 nights) and more nights in Cinque Terre(3) and Florence(3). Would that be practical? In terms of sightseeing in Venice, I'm okay with not seeing every single one and willing to explore off the beaten track. Or does Venice really have so much to offer that I should take more time to see everything ? I'm merely thinking out loud and waiting to hear your opinions.

As for Tuscany, I have read of agritourism places, where they have villas or farms where you get to stay with the locals, take part in activities like plucking the grapes, olives etc and seeing how they make wine, eating home cooked food, learning some cooking etc. This was our main intention of wanting to stay with them, basically to escape from the "sightseeing of museums, monuments" etc, and just enjoying the countryside and the landscape. I'm aware of the fact that I'm still a tourist, but I wish to take a break from the city life and enjoy the country. Of course I might decide to explore a nearby town or two for a day but come back to stay at the house. Also, I've always wondered where are the iconic green rolling hills that always come to mind when Tuscany is mentioned, mind shedding the light on that? Is it Val d'orcia or do most towns in the region have that?

Firstly, I'll be flying in from Asia so I'm not sure if it makes a
difference in terms of jet lag, but I will have flights that can reach
Italy in the morning/afternoon

Asia is a big continent! Where will you be flying from, how many hours will you be in the air, and will it be an overnight flight? Makes a difference in how you'll feel when you arrive.

I would prefer to spend less time in Venice(2 nights) and Tuscany(2
nights) and more nights in Cinque Terre(3) and Florence(3).

Then your itinerary might look like this:
S Night 1 - fly overnight (Sat) into Venice
S Night 2- Arrive Venice/stay in Venice
M Night 3 - Venice
T Night 4 - Florence. (which is in Tuscany, BTW)
W Night 5- Florence
T Night 6 - Florence
F Night 7 - Rural Tuscany
S Night 8- Rural Tuscany
S Night 9 - CT
M Night 10 - CT
T Night 11- CT
W Night 12 - Rome
T Night 13 - Rome
F Night 14 - Rome
S Night 15 - Rome
Sunday - Fly home from Rome Fiumicino.

I have read of agritourism places, where they have villas or farms
where you get to stay with the locals, take part in activities... I
wish to take a break from the city life and enjoy the country. Of
course I might decide to explore a nearby town or two for a day but
come back to stay at the house.

You will likely need a car for this, and cutting time from Tuscany, as you said you preferred to do, leaves you only 1 full day for your farm stay: not really enough to take part in the activities PLUS go exploring. You had said in your first post that you were interested in a "stay in a Tuscan countryside town", which is a different animal, really, than a farm stay. Personally? I'd cut this if you can't give it more than a day.

Would that be practical?

Only you can answer that question as it's a matter or prioritizing your interests. I dearly love Florence (as others of our posters adore Venice), would base there and take some day trips versus make another move. Bases allow us flexibility to choose activities according to weather and other variables but that doesn't mean it would be the right decision for you if a farm stay is a priority. If so, then something else probably needs to be given less time.

As for Tuscany, I have read of agritourism places, where they have villas or farms where you get to stay with the locals, take part in activities like plucking the grapes, olives etc and seeing how they make wine, eating home cooked food, learning some cooking etc.

Mike, late Spring isn't harvest time, so there will be no grape or olive picking. I hope someone has a recommendation of a small agriturismo where you can help cook and share dinner. Check out a recent RS video on Tuscany where he found a place very similar to what you are looking for. It is a relatively small agriturismo so you'll share the experience with a handful of other guests.

We stayed just outside Greve at Castello di Verrazzano. We had a wonderful time. There are only 4 or 5 guest rooms in a building down the hill from the winery. Their breakfasts include products like honey and wild boar salami that is produced on site. Their meals are amazing - all cooked over an open flame fire and served with their excellent wine.

If you want to take a cooking class then you can sign up for a class from Mama Lorena at La Cantina which is 5 minutes down the road in Greve. Greve is a charming little town and just visiting the shops in the piazza will make you feel at home. We also shopped at the local Coop supermarket where we bought fruit and cheese for our lunch picnics. We only know a few phrases in Italian, so we considered it a small triumph when we successfully shopped there without having to resort to English!

You might consider what we did regarding Florence as well. We used Castello di Verrazzano as our base for the week. We drove all around the countryside, but Gino at Verrazzano suggested we take the bus to Florence instead of having to drive in the city. It was great advice. We caught one of the early buses (I think they start running at 6:00 am) and it took 40 or so minutes to arrive in the heart of Florence. There are buses that also run up to 10:00 pm to get you back home. Since we had been to Florence before, we only had time to visit for a day, but I'd even consider keeping the agriturismo as home base and spending the night in Florence to have two days there.

Dear Kathy,

Thanks for your reply again. I'll be flying from Singapore. The flight will be split over 2 legs of 7 hours each, with a transit at Dubai. If I want to reach Italy in the morning/afternoon, then yes it will be an overnight flight.

Yes I'm aware Florence is the capital of Tuscany. Apologies once again for the misunderstanding of the word town. It's my first time to Italy, and when I think of Tuscany I just think of countryside, so I guess I meant more of a countryside stay. The towns are more like Siena, and all? Also, any idea of the region we always see in the photos of rolling green hills?

What do you think of having just two nights in Venice, given that I have explained my preferences for sightseeing in Venice?

I hear your thoughts on the farm stay, and you are right if it's not more than a day then I'd cut it. I have heard from many of my friends who have gone to Florence that it's a beautiful city and the reason why I wish to spend 3 nights there. Your idea of using it as a base and then make day trips also sounds like a good one and something I would consider.

Florence, Rome, Cinque Terre are absolute priorities for us. We have to cut either one of Venice or rural Tuscany from the itinerary, or maybe both.

Dear DougMac,

Thanks for helping out! I shall take a look at the links you have provided, and the video as well. It sounds good, but like Kathy said, it won't make sense if I'm only staying for 2 nights.

My preference for Florence would be to stay there for 3 nights. I've read that it's not practical to drive in the main cities so I won't be doing that. Only will get a car if I'm planning to stay in rural Tuscany or doing a day trip out. Perhaps I could just do a day trip out to the countryside?

Perhaps I could just do a day trip out to the countryside?

That's an excellent alternative and there are several outfits that can help you.

After much consideration, we have decided to cut Venice from our trip. Therefore, we'll have more nights in rural Tuscany. Also, we have thought of changing the order of travel the other way around to Rome-rural Tuscany-Florence-Cinque Terre. The reason is because, we are afraid that if we keep Rome to the end, we will end up being tired to explore the city. Therefore, we keep Rome first when we are still fresh, exploring all the sights and monuments, head to the countryside to get away from the city, head to Florence to enjoy the city again, and then to Cinque Terre to enjoy the landscape. From there we'll head to Milan to explore for a day or two and fly back. How does that sound?

Also, where could I possbily rent a car to travel in rural Tuscany? From Siena? I was thinking of spending time more in south Tuscany, since we will be heading to Florence anyway which is more north.

Also, where could I possbily rent a car to travel in rural Tuscany? From Siena? I was thinking of spending time more in south Tuscany, since we will be heading to Florence anyway which is more north.

I suggest you go to Google Maps and use the directions feature to find distances and travel times between points of interest. I believe you'll find like we did that the region is not that big. We stayed in Greve and every place we visited was no more than 90 minutes away, even Montepulciano.

I suggest looking for a place around Siena. That would be a good home base for the region.