21 day itinerary.... Venice to CT or Venice to Florence and then CT

Wise to remove the Dolomites. You have too many destinations as it is,

Fly into Venice and out of Rome. I would skip Varenna OR the Cinque Terre. Add those saved nights to Rome, Venice, and Siena, where you only have one night planned. This will make your trip more relaxing and allow some time to breathe.

Laurel,
I don’t have any places for one night. I do only have Siena for two nights. Any recommendations?
You said there was too many places, do you think that’s too many for 3 weeks? Guess I’ll have to make a second trip. Not that I would mind . 😄
Stacey

To me the pace is a lot better than 90% of the itineraries I see posted. I agree that it appears you're hardly going to see Siena at all. (It appears to me that you're only sleeping in Siena on Day 13.) You have 3-1/2 days for rural Tuscany. I am guessing you have an interest in something like wine? The hill towns are picturesque, but many are quite small and can be seen in a very few hours. I think they'd be getting rather same-y to me long before I got to the end of my stay. Not saying it wouldn't be a pleasant time, just that I'd probably rather have one of those days in Rome. Note: I don't like wine!

Definitely don't try to add Sicily. It's a great place, but it really needs 2+ weeks all by itself. The Amalfi Coast would be easier than Sicily (just about anything would be easier than Sicily), but I prefer what you're working with now.

I'd reverse this trip and start in the south for reasons of weather--fear of chilly/damp weather in the north, I mean.

I'm not sure about the best order of your first four stops, either. Go to the [Deutsche Bahn website][1] to check train times. It doesn't sell Italian rail tickets, but is very easy to use for schedule-checking. You won't be able to see April/May schedules yet; just use equivalent days of the week for later this month.

Day 13: Florence , leave late for Siena
Day 14: rent car from Siena head to Tuscany countryside

This is only 1 night in Siena.

Thank you for your comments. I will add more time In Siena. Yes, I love wine so staying in Tuscany countryside is about taking innthe views, seeing the sites, drinking wine and just breathing in the surroundings.
Stacey

The Tuscan portion might become what I call a “centerpiece” of a trip: A place you settle into for 5 nights (or more if you have time) and make it your home base. Select one town to stay in and make day trips. Montalcino has been our base a few times and I’d go back in a heartbeat for 5 nights. All those 3 night stays get old.

We also wanted to see Sicily and Alfani Coast but weren’t sure how to fit it in. Should we try or is that being over ambitious ?

Yes, too ambitious ( unless you give up the days in Tuscany)-- makes a perfect excuse for a return trip.

Venice - Cinque Terra- Florence -Siena - Tuscany countryside - Rome ?

This gets my vote

My $0.02

Take one night away from the Cinque Terre.
We always have stayed in the Chianti region between Siena and Florence. We also have stayed in Cortona, and Lucca but they are on the outside edges of Tuscany so harder to visit other villages.. Look at Castellina, Radda, Panzano for your hotels.
Montepulciano and Pienza are also very nice.
Save the Dolomites for another time but make sure you visit there on a future trip. Incredible beauty! Combine it with Verona and Lake Garda.

Day 13: Florence , leave late for Siena
Day 14: rent car from Siena head to Tuscany countryside
Day 15: Tuscany countryside
Day 16: Tuscany countryside
Day 17: Tuscany countryside

I think you could work this part of the trip two ways. Plan A would be to leave Florence earlier. Rent a car there. Head straight to the Tuscan countryside. Make Siena a day trip. We stayed just outside Greve and used it as our home base. We did day trips to Florence via a 30 minute bus ride early morning and home late evening. We drove from our agriturismo to Siena and stayed until the evening. With this plan, I'd still take a day from CT and add it to the countryside.

Plan B would be to take a day from CT and add it to Siena.

If you went with Plan A, since you've already been to Florence, I'd choose an agriturismo closer to Siena. From there, Siena, Montepulciano, San Gimignano, Volterra, Radda and even Pisa/Lucca (it would be a long day) would be accessible from your home base.

Your proposed itinerary sounds a lot like the trip we took this summer, which we LOVED. Having been to Italy a couple of times before, we were very happy with how it worked out. We flew into Venice and out of Rome. Here was our itinerary:
Days 1 and 2: Venice
Day 3: Ferrara (this is a great choice if you want to go someplace off the beaten tourist path)
Days 4 and 5: Florence with a daytrip to San Gimignano, Pisa (as a quick stop), and Lucca. In hindsight, this is the one part we would have changed. Having been to Florence before, I wish we'd skipped Florence (which we used as a homebase) and stayed overnight in San Gimignano. San Gimignano and Lucca are AMAZING.
Days 6 and 7: Orvieto
Days 8, 9, and 10: Naples with Sorrento and the Amalfi Coast as side trips. It's very easy to get to Sorrento and the Amalfi Coast from Naples, and Naples hotels cost less than HALF what Sorrento costs.
Days 11, 12, and 13: Rome
Days 14 through 20: Sciacca, Sicily. We flow to Palermo from Rome for only $70 per person! We stayed in Sciacca because my husband's family immigrated to the US from Sciacca in the late 1890s and no one had been back since. So you may not find Sciacca as wonderful as we did, and/or you may not need as much time. At the end of your stay in Sicily you can fly back to Rome and home from there (we flew from Sicily to London for $60 per person and spent a long weekend there instead before coming home).

This schedule is very doable - we accomplished it while dragging four teenagers and two 70-something grandmas with us. Our blog has a lot of stories from the trip we took this summer, if you want more detailed information or recommendations.

hi staceypina
if you like wine, while in Rome, a short train ride to Frascati, known for their white wines. oldfrascatiwinetours.com stop by ceralli.it a bakery, pizza oven and the “best” porchetta, saw on a tv travel show.
aloha

@suki So you stayed in Chianti region and visited Siena and Florence from there? I would love to do that, but I was under the impression driving in Siena or Florence was difficult for parking. Any thoughts?

@princesspupule Thank you for the information about the wine tour. We will definitely be adding that into our activities.

@Dougmac. You said take Siena as a day trip. So if I use Tuscan countryside as home base, could we drive to Siena or would we leave car and catch a bus or train?

Another question:
I am watching airfare as it seems to be fluctuating. However I know Rome, Venice and Florence hotels and Airbnb’s book quickly, should I book these before I have purchased the airline tickets or just wait until we have our tickets to book our lodging?
Thank you for all of your help.
Stacey

There's no harm in booking lodging if you can cancel for free, but I always do airfare first. Often it's possible to save a good bit of money by shifting the dates forward or back a day, or possibly even reversing the trip. And as you continue to plan, you may very well learn about an additional sight or event you want to see that requires a tweak to the itinerary.

Keep watching the airfare daily. Something good may happen.

@Dougmac. You said take Siena as a day trip. So if I use Tuscan countryside as home base, could we drive to Siena or would we leave car and catch a bus or train?

From our agriturismo just outside Greve to Siena was less than an hour down the famous 222. Greve is about as far north as you would want to stay. There are many agriturismos just outside Siena that are 20-30 minutes away.

There's plenty of parking in Siena. I'd suggest driving to Siena and parking. Parcheggio Santa Caterina is a good place to park, very convenient to the duomo. 2 euro an hour.

One thing no one has mentioned during the timeframe you're looking at. So you need to plan well. There are two major holidays. (Easter is April 21) places will be crowded the week before and after.( May 1 ), since it falls on a Wednesday, celebrations could last thru the weekend. Prices for lodging could also be higher.

I'm with Laurel, pick either Varenna or Vernazza.

If you pick Vernazza, fly into Venice out of Rome.
Your itinerary would look like this.

Venice>Florence>Vernazza>Tuscany> Rome.
Pick up your rental car in La Spezia as you're leaving the CT. Drop it in Rome by Tiburtina station. Taxi into Rome.

If Varenna is where you wish to settle in, fly into Rome out of Milan Start in Rome. This would be your path.

Rome>Tuscany>Florence >Venice>Varenna.

Pick up your car by Rome Tiburtina station.

Those three extra days could be added where your interest lie, and make this a much more relaxing trip.

Thanks for all of your advice. We have revised our plan as follows:
Fly into Venice ..:stay 3 nights
Florence 4 nights
Rent car in Florence and drive to countryside
Tuscan countryside 4 nights
Drop car in Orvieto and train to Rome
Rome 3 nights
Train to sorrento and bus to Amalfi coast
Amalfi stay 4 nights
Bus back to sorrento and train to Rome
Rome 2 nights
Fly home to San Jose ca

Question:
We have one extra night ....which place should we add it to?
Also should we just go to Amalfi Coast first then stay Rome until we leave or break it up as I have it now?
We wanted to do cinque Terre but I think your advice is correct to focus longer in areas we are most interested in.
Thank you
Stacey

My gut instinct would be to add a night to Venice, take a night from Rome add that to the AC, path would be Orvieto to Amalfi, ( this will take about 5 hrs. so your first day would be a waste) ending with 4 nites Rome.

Edit: to save about an hour transit time between Naples and Amalfi, a private driver would be perfect. Look at Sorrento silver star, should be about €120.

I would do all my Rome days at the end. Saves you one hotel transfer; one less day interrupted with travel.

I think I would add the extra day to Venice, but there is no 'wrong' choice among your destination; just depends on your preferences.

Thank you! I will add a day to Venice and switch our stay to ending with Rome.
My husband had another question. I have us staying 4 nights in Florence and 4 nights in the countryside.
Has anyone had a similar itinerary? Our question is whether we should opt for less nights in Florence and more in the countryside or just keep it as it is now?
I love art, but I also enjoy wine and the idea of a relaxed pace and driving the countryside is appealing.
Appreciate all your comments.

Stacie, keep Florence as it is, there are some great day trips from there by train. Here are three. Lucca, around 1 hr 20 min. Montecatini Terme 50 min combine it with Pistoia (15min) great medieval center (40m) back to Florence.
Bologna 45m. Beautiful covered walkways, less tourists, fab food.

Agree completely with this post:
Fly into Venice and out of Rome. I would skip Varenna OR the Cinque Terre. Add those saved nights to Rome, Venice, and Siena, where you only have one night planned. This will make your trip more relaxing and allow some time to breathe.

Your trip involved zipping across Italy back and forth from Milan, Varenna to Venice and then back across to CT. Not good.

I went to Amalfi by bus from Sorrento but I have read that you can also take a train to Salerno and then a ferry to Amalfi. It might be more efficient and something to consider.

Beth