First trip to Italy

Since you won't be hiking in the Cinque Terre (hundreds and hundreds of steps up to the paths, as I recall), I'm not sure how you will occupy your time for 4 nights (3 days). Even within the little towns you can encounter steps and hilliness. You'd also have to be very careful about finding lodgings with an elevator--a reliable one.

Tuscany and Umbria are rather large. I'm not sure there's a single base that works well for that area. I believe you'll need to figure out which specific towns you want to visit, then zero in on that particular part of the total territory.

First question- have you already purchased your plane tickets? It would be easier for you to leave from the airport at Venice with this itinerary than to backtrack to Milan. You would also gain a day at Venice (or could use at a previous location) instead of that last Milan day.

If you’re trying to avoid hills and stairs, I would avoid the Cinque Terre area. There are so many nice locations in Italy that are flat! For a first-time trip, Verona immediately comes to mind, and it’s a handy location between Milan & Venice by train, and it’s very tourist friendly.

Between Rome and Florence you might consider two stops, Orvieto and/or Siena. You might also consider an Agritourismo which has activities on site, such as cooking classes, wine tasting, or which can arrange tours to wineries. Siena has pretty good public transport connections to Florence, or plan to take the car to the Florence airport and take the shuttle bus into town from there (easy and frequent). Take a cab to/or near to your hotel, but there will be a lot of walking around town in the pedestrian only zones from cafe to museum to cafe.

In the CT we like staying in Levanto, which is a it less touristy than the five towns, with a broader range of hotels near the station. The five towns are an easy and short train ride away.

The issues with stairs may be an issue in Venice too, with many hotels quite a walk over bridges from the nearest vaporetto stop. Check carefully before you book.

Verona and Padua are also wonderful places and smaller/less busy than the other spots you mentioned (except around Juliet's Porch in Verona which is a tourist trap).

Have a great time.

I'm going to also suggest Milan and Padua. I see you have Milan down for one night, but we spent about 4 days there a couple of years ago and had a wonderful time. And it's flat! Ditto for Padua (Padova.) We were there for three days before a RS tour, and could easily have spent more time.

I agree with the other folks here that Cinque Terre could be a problem for you. Lots of hills and stairs.

I would suggest that when you are staying at your destinations, make sure you are within walking distance from the Train Station. Each of the places you have chosen will see you doing a lot of walking. Cinque Terre area is not 'flat' and will entail a lot of walking. Staying somewhere like Rapallo and train to Cinque Terre may be a better option. The journey is under an hour. You can also visit Sestri Levante, Portofino, Santa Margherita Ligure by public transport from Rapallo. The Ferry service is great.
Find a base in Tuscany where you are able to train to the cities. We spent 3 months in Italy but never 'stayed' in the cities and the nicest part of a busy day was arriving 'home'- wandering into the Piazza for a drink, beautiful traditional food and chatting with local people. It was always the highlight of our holiday. We made many "acquaintances" and these folk gave us such valuable information from sightseeing, eating and general information for trains etc. We used Air BnB and Booking.com for our accommodation. We also had a car which gave us the freedom to visit many small towns. The most time we spent in the cities would have been 1 - 2 days but we didn't stay overnight - just day trips by train.
We based ourselves in Cortona, Grieve and Quarto d'Altino for this area of our stay. We are of the same age group as you.
Good luck and have a wonderful trip.

Rome deserves more time and the Cinque Terre less time.

What Suki said. Less of steep, hilly CT and more of Rome.

You can fly nonstop between SFO and Milan. Check www.skyscanner.com.
RSE has a new Best of Italy guidebook coming out in Apr. You can download an electronic version from his app. Focus on his self-guided walking tours so you don't miss anything. If you need to break them up so it takes two days, do it.
Looks like you'll be in IT for 25 days...here's what I would do:
Day 1 – arrive in Milan and take a train to the central train station (30m) and switch lines to Varenna on Lake Como (1h 15m). Sleep in Varenna.
Day 2 – boat to Bellagio for the day (10m). Sleep in Varenna.
Day 3 – direct train to Milan (1h 15m). Sleep in Milan.
Day 4 – sleep in Milan.
Day 5 – direct train to Monterosso (3h) Cinque Terre. Sleep in Monterosso.
Day 6 – sleep in Monterosso.
Day 7 – sleep in Monterosso or you may want to make it two nights and spend three nights in Venice.
Day 8 – train to Florence but requires one transfer (4h). Sleep in Florence.
Note: purchase your Uffizi Gallery tickets ASAP. You should also buy your Accademia tickets before leaving home too,
Day 9 – Sleep in Florence.
Day 10 – bus to Siena (1h 15m). Sleep in Siena
Day 11 – sleep in Siena.
Day 12 – rent car and take the Crete Senese Drive (30m) and continue on to Pienza (45m). Sleep in Montepulciano (20m).
Day 13 – Sleep in Montepulciano.
Day 14 – drive to Assisi (1h 15m). Sleep in Assisi.
Day 15 – sleep in Assisi.
Day 16 – drive to Orvieto and drop off car. Sleep in Orvieto
Day 17 – Orvieto.
Day 18 – direct train to Rome (1h). Sleep in the Trestevere (trahs-TAY-veh-ray) neighborhood.
Day 19 – sleep in Trestevere.
Day 20 – sleep in Trestevere.
Day 21 – day trip to Vatican City and sleep in Trestevere.
Day 22 – direct train to Venice (4h).
Day 23 – Venice
Day 24 – take a late afternoon direct train to Milan ( 2.5h).
Day 25 – fly home.

I get the feeling the OP doesn't want to move around that much.

Civita di Bagnoregio is not advisable for folks with mobility issues. There's an unavoidable, rather long, uphill climb to Civita. In addition, if I wanted to drive to Ovieto and planned to go to Civita the next day, I would keep the car. I don't think buses from Orvieto to Bagnoregio are very frequent, and then one needs to take a shuttle bus from Bagnoregio to the near end of the pedestrian causeway leading to Civita. A car would save time, but I'm not sure whether one can park a car at the end of the causeway.

I like Orvieto a lot and think it's worth spending more than a day there. However, care must be taken in choosing accommodations, because the historic center is on top of a hill and is not totally flat. It should be manageable with lodgings located on the end of town near the Duomo, as opposed to the end near the top of the funivia. There's bus service from the funivia over toward the Duomo.

Forget Venice. Not worth travelling across half of Italy for just two days.

Thanks acraven, I just removed Civita. I knew it required a walk across a bridge but since there's a hand rail I thought it wouldn't be too bad. I just did more research on it and it said to expect to be out of breath.

Sorry Aussie - I respectfully disagree.

Venice is one of the big three and for a first visit nobody should skip it. As far as I remember the train trip is about 3 hours.

Debryn: Next time you come to Italy, you know if it is worth it for you visiting Venice again. But remember that Venice has more than 400 bridges, so take care when you choose your hotel. Check https://europeforvisitors.com/venice/bridges/.

Only 3 nights in Rome! That is a huge mistake. You can't do justice to that City with three nights, especially since one day will be a recovery day after your flight.

Florence is wonderful, but I would cut to 4 days (do a day trip to Siena)
Cinque Terra for four nights is a bit much.

Yep, as acraven said, I don't think our OP is interested in a bunch of 2-night stays.

I'll also agree that you need to add more time to Rome and cut some (or all) days from the Cinque Terre. If hills and stairs are a challenge, you may find yourself huffing and puffing to get around parts of the 5 villages. That said, if you decide to keep a couple of your nights there, I'd choose Monterosso as a base as most of the town is pretty flat. There are some hotels in the "new" part of town which are easy walks from the train station: take a look at La Spiaggia (but look SOON as it could already be booked up for May). That one also has a rare elevator!

We've done 5 nights in Florence and could have done more but to keep as is, add or subtract depends on how interested you are in Renaissance art .... which I loved!

The RS forum's most recommended base for Lake Como is Varenna; accommodations there also book up early.

A caution about the car? Visitors are not allowed to drive directly into all Tuscan villages so you may be parking and hauling your bags from outside of them. You might want to drill down to details about specific locations as your plan comes together

Pienza mentioned for Tuscany would be fine, but Montepulciano is the definition of one huge hill - from your request it’s one you should avoid (& I love Montepulciano).

Looks great but I think you should skip Cinque Terre based on your description of yourselves. You could maybe add one of those nights to Rome or Venice (either could benefit since you wish to see culture and art), and then choose two bases in Tuscany/Umbria.
Go get a good in-depth book on Tuscany and Umbria to help your pare down--soo many choices! There are some that are devoted to driving trips that might be helpful.
I'd rework the order too--Como between Venice and Milan, Tuscan'Umbria either before or after Florence is fine, but you might feel more comfortable exploring by car after you've had a bit more time in the country (just getting used to schedules, language, etc.).

Thank you all so much for your comments and suggestions.

We have not purchased our air yet but would like to get that done in the next day or so. The reason for flying out of milan instead of Venice is flight pricing. Our flights would go up Significantly.

I understand why many of you suggested we skip Cinque Terra due to our physical limitations. However, it’s one of those places I’ve always wanted to visit. I figure we can reduce the time though as many have suggested.

As many of you stated, our goal is to have home bases and do day trips as much as possible to reduce the time and energy of packing and unpacking. Also, we will have a car throughout Tuscany so are hoping to stay outside the cities in a countryside b&b or farmhouse. Recommendations would be so appreciated.

I so appreciate all your comments and suggestions. Please keep them coming.

If you have your heart set on CT, then just choose accommodations carefully. It would drive me batty to be there and not be on the trails getting away from the crowds, so choose a place that is sort of set away from the main drag (use map functions when searching accommodations)--even if getting up there is a slog (I am sure your host can arrange help with bags), at least you will have some peace while you are sitting on your balcony, or whatever special little outdoor feature you find. I'd still add one night to one of your other stops though. If you have no interest in adding it to Rome or Venice, for sure add it to the rural stay.
You could also consider one of the other coastal towns--Camogli is quiet pretty, as is Tellaro.

I agree that your plan shortchanges Rome. And I wouldn't skip Venice just because of all the bridges. As long as you can handle a few steps up and down every few blocks they won't be a problem.

debrynklein, if you want face-to-face advice know that there are monthly travel group meetings in the extended SFO area -- Orinda, Mountain View, Sacramento. See the "Travel Group Meetings" section of this website for details.

I can’t seem to find the travel group meetings on the website. I would be very interested in attending one. I know I need to get this trip booked in order to have options. Thanks for your help.

Here's the section of the forum with travel group meetings: https://community.ricksteves.com/travel-forum/travel-meetings

For Venice, if you plan to take more vaporetti and walk less, you can often avoid many (but not all) bridges.

If you decide to go to the Cinque Terre I would recommend Hotel La Spiaggia. It is an easy walk from the train stop in Monterosso al Mare and it has an elevator. Ask for a seafront room with a balcony and enjoy the water views. It is in a level area of town and no hills to walk to it.

As I'd noted previously, La Spiaggia is in a great location. It's just getting around the rest of the CT towns that worries me as Monterosso is the flattest of the 5. The hotel is probably closed for winter but they probably check email requests now and again.

https://la-spiaggia-it.book.direct/en-us

I always recommend starting a trip to Italy in Venice because it's an easy place to relax and soak up the atmosphere while you get over jetlag. But since you are also interesting in Lake Como, another laid-back place, flying into Milan is an excellent plan. Leaving Rome to the end means by the time you get to the big, bustling city with monumental sights, you'll be as acclimated to Italy as it's possible to be. That also allows you to avoid spending a night in Milan, one less hotel change.

I'm very aware of ups and downs, thanks to knees and hips that are much older than the rest of me, or at least that's how it seems. Venice is level. You will have to cross over bridges, most of them are 6-8 steps, usually (always?) with handrails or a low wall for balance. The only high bridges you are likely to go over are the Rialto and Accademia bridges across the Grand Canal. Take them slowly and it shouldn't be a problem. They are mostly level at the top, with space to stop and enjoy the views, and lots of shops on the Rialto bridge. You can avoid crossing them altogether by taking a vaporetto. Florence is level, except for a slight incline up from the Arno on the "other" side. The only steep climbs are to the Boboli Gardens. Well, also to Piazzale Michelangelo, but you can take a bus there. Rome, on the other hand, in built on hills. I'd allow more time there because there's a lot of walking and climbing to see the sights, especially since it's a large city and the sights are spread out. The sights of Florence are all near each other. In Venice, it depends on where you are staying. The vaporetto is a good way to save a lot of walking there. It's hard to know how crowded the CT will be in May. Expect a lot of walking up and down. I stayed overnight in Riomaggiore and 10 years ago, it wasn't easy for me to walk up from the train station. I don't think there's much there, I'd say skip it or sty no more than 2 nights. Also note that Tuscany and Umbria are hilly, the towns are built on hills. I haven't been to Como. Read all the caveats about driving in Italy. The historic centers of all the charming Tuscan and Umbrian hill towns are ZTL's - no non-resident cars allowed. That means you'll have to park and walk to the sights.

Thank you for your insights. The reason we had thought of starting our trip in Rome, and moving north, was because of the weather. We had hoped to allow time for the lake como area to warm up.

I understand that the towns in Tuscany are built on hills. What our plan was was to stay at a B and B outside of the cities and take day trips into them as we explore the area. We will then separately spend time in Florence to enjoy the art and history there.
Which area of Tuscany would you choose to base out of keeping in mind that we won’t be visiting Florence until after the days exploring the Tuscany countryside.? I have ordered, and am waiting for RS Tuscany guide book.

Based on all your suggestions, we will reduce the Cinque Terra area. Probably only two nights there just to see it.

With the cities we want to visit, if we were to start north heading south, would you start in Venice or Lake Como?

Thanks again for all your suggestions.

With the cities we want to visit, if we were to start north heading
south, would you start in Venice or Lake Como?

Whether to choose Milan Malpensa or Venice probably depends on which entry point you can get the most economical tickets and most desired flight itinerary (arrival time, number/length of layovers, etc) for?

(Edited typos; head full of cold medicine!)

Kathy said exactly what I was thinking when I suggested Milan. Compare options into Milan and into Venice. From SFO you can probably get a non-stop into Milan which would be my personal preference rather than having a plane change. Venice's airport is too small for the large jets on the long-haul flights. If you get a bargain into Venice, though, it may be too good to pass up.

Maybe Milan/Rome and Rome/Milan are the same price, maybe not. Sometimes the day of the week can make a price difference, so take that into account if your dates are flexible.

On a 3-week trip in May, I don't know that weather will be that different at the start and the finish. You can check historical temps day by day for May for the last 10 years here for your cities. I put in Milan (no records for Como) and looked at 2018-2019. Temps fluctuated throughout the month.

If you're coming from SFO, there are no nonstops to anywhere in Italy. That means you have to change, but on the other hand, with one change you can get anywhere in Italy. So, there's no difference in convenience among the various Italian airports - you should choose based on price, and how it flows with your itinerary.

Loot at Kayak or Google Flights to see your flight options. As Chani is saying, there is no rhyme or reason to flight prices anymore. It may cost the same to start in Milan as in Venice, or there may be a significant difference. If you're otherwise undecided, a big price difference makes a handy tie-breaker!

Be aware that the ZTL's mean that you can't drive into city centers. You have to park on the outskirts, and walk or take a bus or taxi into the center. The smaller the town, the closer the parking will be to the center. Even some very small towns have ZTL's these days.

Harold - thanks for the correction about non-stop flights to Italy. I should have checked more carefully.

even as a hiker (we hiked the Cinque Terre 40 years ago before it became a tourist trap -- there wasn't a souvenir stand or an American tourist in sight). two nights is plenty for the CT. And 3 nights is not enough for Rome. I don't even much like Rome but there are so many must sees there that you need more than 2 full days. I'd do at least 5 nights there which gives you 3 full days.

I would drop the car on the way into Florence at the airport ad take a cab from the airport into town; last time I was there there was a modest fixed price for the cab. This way you don't risk the ZTLs in Florence but you also don't have to mess with getting a train to Florence since you already have the car. Be sure you read up on Italian rules for ZTL and for parking and using the parking timer thing before driving there. The small towns of Tuscany have parking lots for tourists so avoiding the ZTLs is not difficult -- it is just important to know what you are doing.

Thank you everyone for your expertise and feedback. We have decided to skip Cinque Terra based upon the majority of comments. We are needing to purchase our plane tickets and make our reservations. Listed below is the revised potential itinerary:

Fly SFO to Milan
Milan to Lake Como- 4 nights
Lake Como to Venice-3 nights
Venice to Florence-4 nights
Florence to Montepulciano-4 nights
Rome-4 nights
Fly Rome SFO

This potential itinerary seems to work with our goal of not moving locations, and having to pack and unpack taking up to frequently. We will still rent a car for the Montepulciano portion of Tuscany to explore the region. We do have flexabiity both with our dates and number of nights in each place since nothing is booked yet. We also haven't determined the local transportation details such as train, bus etc. So your feedback and suggestions are appreciated!