Itinerary Assistance -- First timer

Happy belated honeymoon.

I would consider spending one extra day in Florence and one less day in Montepulciano. Florence and Rome are much different from one another so don't worry about boredom.

You do not need a car based on your itinerary. All are accessible by train.

I would change the order of your trip.

Arrive Rome 4/30
Next Montepulciano 5/1-5/2
Next Siena 5/3
Next Florence 5/4-5/6
I would skip Pisa and add to Rome
Next Cinque Terre 5/7-5/8
Back to Rome 5/9-5/14

Great locations, but you will be on the go.

Enjoy

Hi..what fun! I love your itinerary..and agree..one less night in M...add a night to Florence..it is wonderful.. I might suggest a short ride up the hill..by bus..to Fiesole and have lunch at the most charming restaurant in Settignano at LA Sosta del Rossellino..stunning views of the Tuscan countryside..all 25 min.from Florence..a father daughter owned restaurant..ask for the very small charming patio..

You might want to consider flying into Florence and out of Rome. that is what we did and it saves some time getting from Rome to Tuscany and back.

Also, you hardly have any time in Florence. There is as much to see there as in Rome. And, you could consider staying in Lucca and taking a day trip to Cinque Terra.

Finally, we only used a car when we went to Tuscany. We rented the car in Siena. That way we didn't have to drive in Florence or any larger town. Lots of buses and trains going from Florence to Siena.

If you’re flying in and out of New York you can fly nonstop as an open jaw (into one city and out another) between Rome and Milan since the Cinque Terre is closer to Milan.
If you stay at an agriturismo you’ll need a car, otherwise consider sleeping in Florence, Siena and Montepulciano and getting around by train and bus or pay for an expensive taxi ride. Rick Steves IT guidebook 26th edition recommends local mom and pop tour guides to help you out while there: https://store.ricksteves.com/shop/p/italy-guidebook. Be sure to check his website for updates to his guidebooks so your information is current: https://www.ricksteves.com/europe/guidebook-updates. Following are my suggestions if you fly in and out of Rome:

Sat Apr 30 - from Rome’s Fiumicino Airport take a train to Vernazza that requires two to three transfers. Expect to climb stairs at smaller stations so pack light and do laundry to make to make it easy. It’s also best not to have many bags when traveling on regional trains to avoid pick pockets who’ll be riding with you.
Sun May 1 – Cinque Terre (add a day per hike). Taking the ferry to get around is more scenic.
Mon May 2 – Cinque Terre
Tue May 3 – train to Pisa (involves a connection); sleep in Vernazza.
Mon May 4 – train to Florence (Firenze SM Novella station and requires multiple connections).
Tue May 5 – Florence (buy tickets for the Uffizi Gallery two months out and visit David at Accademia afterwards. Don’t let the line scare you because it moves fast). ITs best museums are in Florence not Rome.
Wed May 6 – Florence
Thu May 7 – direct bus from Florence to Siena (1h 15m). Siena is worth seeing at night. After dinner ask for a to go glass of lemoncello and stroll through Il Campo square. Afterwards join the others and have a seat in the square and sleep in Siena.
Fri May 8 – direct bus to San Gimignano (1h) for the day.
Sat May 9 – take a direct train to Montepulciano (1h 15m) and a taxi to the city center; sleep in Siena.
Sun May 10 – take a direct bus to Pienza (30-minutes) and explore the old town; sleep in Siena.
Mon May 11 - hire a driver and go to Montalcino for the day or go to Rome by train (requires a transfer taking 2h 30m).
Tues May 12 - Rome
Wed May 13 - Vatican City
Thurs May 14 – fly home
As you get closer to the date you should see fewer train connections to get to and from places of interest. I used the dates you provided when checking on https://www.trenitalia.com/en.html.

Thank you all for the advice!

This gives me to think about!! I am hopeful to book my trip with points so not sure the open jaw approach is going to work (could be wrong on that) but something I will look into!

I'm wondering if Montepulciano is even a good choice at this point if we do not have a car? Are we better to stay in florence/Siena and do a day trip wine tour?

I suppose I can price out a few options and just see what the numbers look like with/without renting a car.

Thanks so much!
Kaitlyn

You have alloted only 1 day to Florence, and that day is a national holiday. Even if it weren’t, you should expect to be jet lagged. You need more time there. In my opinion, the Cinque Terre are seriously over-hyped as a tourist destination. If the weather is good, they are likely to be crammed with day-trippers. (It’s unimaginable unless you’ve actually been there!). If bad, there is nothing to do. If you can’t be persuaded to omit them from this visit, at least cut a day and add it to Florence. By the way, there are many utterly charming villages in Tuscany, which could satisfy your desire for some small town experience combined with wine tasing.
Regarding your husband’s love of meat . . . There is a Tuscan town, Panzano, about half way between Florence and Siena, where a butcher/ restauranteur has an establishment. I haven’t been there, as I am not a meat lover; but the guy has an international reputation among carnivores.

When I use miles to book my travel I usually book two one-way tickets. So far, I haven’t found any advantage to booking a round trip.

hey hey kncrotty
happy late honeymoon. italy is a great place to visit with so much to see and do. i'll just put in my 3 cents worth on different things and places.
no car needed take the trains. know the train station in italian: rome - roma termini florence - firenze santa maria novella
using italotreno or trenitalia
add more days to florence and you can take day trips
one less day in montepulciano, no nights in cinque terre. as rosalyn says it is soooo overated and packed to the gills with all the crowds. put those days in lucca, smaller walled center to ride bikes and roam around. see small towns like pisa, pistoia,

many places you want to see is what a lot of other travelers want so it gets really crowded during day/bus tours. some of those tours do only places they get kickbacks from unless you ask for really $$$ private ones.
the famous butcher in panzano is dario cecchini. italaianfoodforever.com/ dario cecchini
read up about him, loves rock and roll music and plays in his shop, watch his craft of butchering, friends did tour and LOVED it.
tuscan-wine-tours.com/ super chianti
tripsavvy.com/ pistoia italy travel guide
tripsavvy.com/ pisa guide: planning your trip
more to pisa than tower, roam around the small town and along arno river. opapisa.it offical site to buy tickets to tower
tripsavvy.com/ best things to do in lucca
luccatours.com, comeandseeitaly.com, fattoriaaldotto.it winery and tasting, bus or taxi, apartmentslucca.com, take the train to viareggio beach, extravirginlucca.com and lacucinaitaliana.com cooking classes and one has accomodation
this went into "novel mode" ha ha giving you another opportuniy of seeing tuscany at a different level. so much to think and decide, but one thing to tell yourself, you can't see it all. you next trip will be talked about on flight back home.
aloha

Thank you for sharing info about Dario! My husband will be thrilled! haha!!

Definitely add more time to Florence! Our favorite restaurants were there! We stayed near Montepulciano for five days a couple of years ago but we had a car, which is really necessary if you want to explore the surrounding area. I would add days to Florence and check out winery/ Tuscany day trips from there. We loved CT but found two nights enough..we spent a full day exploring the five villages via train and boat. We stayed in Riomaggiore at https://www.allamarina.com/apartment-atlantis-en.php which had a wonderful balcony overlooking the harbor. One night an impromptu jazz band set up on a balcony across from us and it was magical!

I like Threadware's suggestions. Rome is worth a lot of your time. CT is OK, but pales compared to Rome.

I did your entire itinerary this summer. Yes, the rental car was expensive in Tuscany. But the most beautiful part of Tuscany was the drive between Siena and Montepulciano. I might spend at least a night in Siena to break up the drive (I did two nights there and it worked out perfect). You can follow the drives in the RS Italy book for the best views of the area.

Bill -- Would you be willing to share your itinerary. Where did you get your rental from/drop off?

Any info you could share would be great!

Thank you!

From Florence to Rome, this was my itinerary this past summer:

Florence: (5 nights)
Day trip to Arezzo

Lucca: (2 nights)
Day trip to Pisa

Cinque Terre (Vernazza): (3 nights)
Train to Pisa Airport, pick up car with Sixt

Tuscany Road Trip:
Volterra (2 nights)
Day trip to San Gimignano
Siena (2 nights)
Crete Senesi drive on day 2 (RS Florence/Tuscany book)
Montepulciano (2 nights)
Best of Tuscany drive on day 2, stops in Bagno Vignoni and Rocca d'Orcia (RS Florence/Tuscany book)
Orvieto (3 nights)
Cortona/Assisi on the way to Orvieto
Day trip to Civita di Bagnoregio

Rome: (5 nights)
Tivoli on the way to Rome
drop off car at Termini train station

Thank you Bill! Sounds like an incredible trip!