Last minute trip to Italy in 2 weeks, have some itinerary questions

Personally I would cut a bit from Florence and add it to Venice. If you want to day trip to Bologna, why not do that on your way to Venice? I know you don't like to pack and unpack, but it seems like a lot of transiting around. You might also want to consider spending some time in a smaller place like Verona, Lucca or Siena, which will give you a very different pace than the bigger more crowded cities.

When in Rome - do try visiting the Galleria Borghese. Stunning Bernini sculptures. Check for tickets now. Timed entry. Without big crowds. So refreshing after crowded Vatican galleries. The beautiful Borghese Villa Gardens are also so lovely and inviting - a very nice place to stroll and relax.

You’ve got ALOT packed in there already. I wouldn’t try to add any more stops. If anything, I would be eliminating some. I’m going to assume you are young and jet lag doesn’t hit you so hard yet. Otherwise day 2 might be a bit exhausting. All of the day 2 sites are close to each other, so you have that going for you. It’s just a full day to see it all. I really recommend a walking tour of the Forum if you can catch one. It will help put EVERYTHING else you see in perspective.

You don’t have a “free day” until day 10. I would be ready for a chill day by day 7. Maybe relax in Florence on day 7, skip Bologna on day 9. Is Bologna a bigger foodie destination than Florence? Don’t worry, you’ll be eating amazing food everywhere!

On day 10 go to Venice. You need more time there than you’ve given yourself. If you take a day away from Milan, add it to Rome at the beginning of the trip. Give yourself a day in Rome to just “be”.

Your Day 4 trip is about 200 miles each way from Rome, and might be virtually impossible to take in Pompeii, Postiano, Sorrento and the Amalfi Coast. You might want to reconsider that trip. So many travelers spend so much time in Rome, but they ignore the many, many sights in the suburbs within an hour.
Day 7 over to Cinque Terre from Florence is about 115 miles, and you get there from LaSpezia by a slow local train. It would be a better trip in Summer and when you have more time to spend there.
Day 8 to Siena is about 1 hour south of Florence, and it's best by taking a bus. San Gimignano is also in close proximity, but Pisa is out of the way. Other than the leaning tower and a nice church, relatively few people go to Pisa other than to fly out of their airport.
Bologna is about an hour north of Florence, and it would be a good stop on the way to Venice. You could catch Verona on the way from Venice to Milan.
Lake Garda is nice, but I'm thinking they're having water level problems this year. It's a place a rental car would be needed to see. Lake Como is about 45 miles due north of Milan--a train ride. It's a special place worthy of staying for a few days.

Italy is one of those places where there's so much food, art, architecture and history that you've got to pick what's important. It's a place that's best taken slowly vs. trying to see it all in one trip. Because you will return.

You need more time in Venice.

You plans are way to short for the wonderful city of Rome. You will miss so much.
Also, your Florence plans are weak.
I would skip the day trip to Bologna. Also, Cinque Terre is good, but you are making short shrift of Rome and Florence. Frankly, I loved the Amalfi Coast. If you go to the Naples area, spend more time there, go to Sorrento and Capri as well. If not, skip it entirely and focus of Rome, Florence and Venice.
Again, your time in Venice is way too short. Are you going to St. Mark's, the Doges Palace, climb the tower do a gondola ride, explore the old Jewish section of the city??

Verona is good, especially to see the Arena, but perhaps you should focus more on Rome, Florence, Venice and Milan.

How wonderful you have an unexpected trip to Italy! I'm guessing this is your first trip & you want to see as much as you can but also have some time to explore. I agree with what everyone else has said, this trip seems really busy with very little time to sit down & have a 2-hour lunch or just hang out or experience "La Dolce de no far niente", (the sweetness of not doing anything)! Here are some suggested amendments to your itinerary. Agree you should leave the Lake District for another trip so you have more time in Rome, Florence, Tuscany & Venice. Since you're foodies, have you considered walking food tours? We did the Testaccio tour over New Years 2019 & loved it so much we took taxis back twice to eat at recommended places. The guide was a local from the neighborhood & he was fantastic. I'm sure the Florence Eating Europe Tour would be comparatively wonderful. One idea is to do the food walking tours the first or second day in each location so you have good recommendations of where to eat during your trip. https://www.eatingeurope.com/rome/taste-of-testaccio/

• Day 1 - Land in Rome at 2 PM. GREAT! *If you don't need a nap, there are some good sunset walking tours, that would give you a good orientation, maybe "Rome Walks" (recommended in Rick's books). They offer a 2 hour "Twilight Rome Walk".
• Day 2 - Rome: Colosseum, Roman Forum, Capitoline Hill, Pantheon
• Day 3 - Rome: Vatican, Sistine Chapel, St. Peters, etc. (guided tour booked) - Does this tour include both Sistine Chapel & St Peters? (They have separate entrances 15 min walk apart AFTER your feet are aching from the Vatican Museum, which you have to walk through to get to the Sistine Chapel on almost all tours, unless they have access by a side door into the Vatican, which I've heard of but not done.)
• Day 4 - I would save Pompeii for a separate trip. This is a gorgeous region as someone else has mentioned & you can easily spend a week here. Instead how about a Rome walking food tour in the morning & visit the Borghese Gallery in the afternoon, walk back to hotel via the Spanish Steps & if you have any energy left, visit a few selected churches which have amazing art? OR swap Day 2 with Day 4 so you get some food ideas early on.
• Day 5 - Transit to Florence, play around in Florence a little.
• Day 6 - More sightseeing in Florence & hopefully it's not Monday when larger museums are closed. Not sure which museums you want to visit, but many require tickets ahead of time. This might be a good day to add a walking food tour.
• Day 7 - I would skip Cinque Terre, it was too crowded to hike peacefully 20 years ago, can't imagine what it's like now. Unless you were both avid hikers & wanted to climb into the surrounding hills & walk at a higher elevation, which I've done. You're right the little towns are very pretty but I wouldn't want to have to get there & just hang out in the villages.
• Day 8 - Small group tour to Siena, Chianti Hills, San Gimignano - Of course you could split this into 2 days. I really like Siena which you could easily reach by bus & take a wine tour to the Chianti Hills one afternoon? As others have said, I would skip Pisa, not that interesting compared Florence, Siena or more time in Venice.
• Day 9 - Transit to Venice. Explore Venice for half the day.
• Day 10 - Venice
• Day 11 - Venice
• Day 12 - Spend half day exploring Venice, and do a half-day trip to Murano & Burano. There are some good posts about a day visiting other islands on the area's lagoon, so will leave that to others.
• Day 13 - Here's more time for staying longer in either Florence or Venice!
• Day 14 - Transit to Milan. Milan is a big city & not nearly as interesting as Verona, though I'm not familiar with luggage storage there.
• Day 15 - Fly Home from Milan (morning flight) Hope you have a wonderful trip & please let us know how your final itinerary looks!

Thanks all.. I need more time to think through some of the replies and how to incorporate... but, one trend has been that I need another day in Venice. Just wanted to clarify "why" -- my guess is that it's to spend more time to explore the city, vs just the historical/touristy spots. I had 1.5 days originally based on recommendations from 2 coworkers who both just came back from Venice, as well as some random websites I had read.

I was going to follow a suggested itinerary from a website (granted I haven't gone in depth on their itinerary yet, but it was a starting point)

Day 1: Get in around 12 PM. Check out the Grand Canal, check off some of the Venice bucket list items: St. Mark's Square & Cathedral & Campanile, Doge's Palace, Rialto Bridge. They also mention Scala Contarini del Bovolo & Bridge of SIghs.

Day 2: Burano & Murano for half a day. The other half, pick one or two neighborhoods to explore: San Giorgio Maggiore, Guidecca, Dorsoduro, Castello.

Also a quick comment on Day 1. We're actually coming from a week in Amsterdam on business. So that's why we're landing and starting right away, since we'll be acclimated to the timezone already and have no significant jet lag to deal with. We're not young enough to do that otherwise, haha. (both in our mid/late 30s).

Everyone is different. On my first trip to Italy (northern Italy), we spent three nights in Venice, and I thought it was ideal. Honestly, I could have been satisfied with two nights. Venice is hot and crowded in September, so our goal was to literally see Venice and enjoy a couple highlights. We toured the Basilica one morning (early to avoid long lines) and the went up to the top of the Companile the next morning (again to avoid lines). The rest of the time, we wandered around the back streets which were blissfully empty and shady. We did not have time to go to any of the other islands, which didn't really bother me.

We appreciated having two and a half days in Venice since it was the beginning of our trip and gave us time to get over jet lag. But again, I would have been okay with two nights. So if that's all the time you have, it might be enough for you.

Hi - just a couple of comments?

Day 4 - ??? Small group tour day trip to Pompeii, Positano.. and catch
the Amalfi coast out of our window. Iffy on this because of far away
it is, but I'm personally really interested in Pompeii

I would ask -no, BEG - you to reconsider this one, especially if it's a tour via road by van or other sort of vehicle. Rome to Pompeii and back is a really long, ugly bus or van ride. It's more time sitting in that vehicle than exploring the scavi itself! If you can't save Pompeii for a future trip when you can give the Naples/Pompeii/Amalfi/Sorrentine region the time it deserves, then I'd look at tours which start in Naples or at Pompeii itself. Take a high-speed train to Naples and a local commuter train to Pompeii, OR book a tour which starts in Naples and meets you at the train station. High-speed rail to Naples cuts a chunk of the travel time it would take by road, plus you can bring your breakfast and have a lavatory at hand to use as necessary. Plus, when your guided tour is over, you can spend more time exploring the scavi on your own. Many of the road tours from Rome give you a scant 2 hours at a site which took us 5...and we STILL didn't cover it all. Skip anything that includes a rushed look at Positano/AC; save it for another trip

As a very good alternate, look at doing Ostia Antica? It's much closer to Rome and won't kill a whole day - much of it sitting - to do.

Day 8 - Small group tour to Siena, Chianti Hills, San Gimignano, &
Pisa. My coworker told me the leaning tower is kind of hard to get to
in Pisa, and you'll waste time trying to get there via public

Too much, IMHO. No, the tower isn't hard to get to but I'd prioritize, say, more time in Siena over than one.

I think you're cutting Florence short with only 1 and 1/2 day allotted for it. As mentioned, it would REALLY be short if your full day is a Monday when some of the museums you might want to see are closed.

Skip Lake Garda or Como: you just don't have time.

I think, if you left Venice early, you could get a look at some top spots in Milan in just 1/2 day. Use the full day for an additional day in Venice or even Florence? You might consider doing a day in Siena on your own - skipping the Chianti Hills/San Gimignano/Siena/Pisa tour - and another day trip to Lucca? That's been another fave with a lot of the RS travelers.

Oh, the Ostia Antica does seem interesting. Based on some feedback I've gotten, I think I may replace Day 4 (Pompeii, et el.) with something closer by. Was thinking either the Roman Catacombs and/or Ostia Antica now. Any thoughts on that?

I am curious to visit Verona (cause I loved Romeo & Juliet as a kid) and see the amphitheater there. At the same time, I'm hearing a bit of a de-prioritization of Milan. Could I maybe cut a day there by leaving Venice in the morning, hitting Verona for half a day, then seeing Milan for the 2nd half. Then I'll only have 1 night in Milan and fly back the next day. I could then take that extra day and add it to Venice/Rome/Florence itself.

As for Day 7-10 on my itinerary (Cinque Terre, Siena/Chianti Hills/San Gimignano/Pisa, Bologna, Extra Day)... I think I want to re-order these 4 days and remove Cinque Terre. Sounds like I'll save this for potentially another future day. I've read several recommendations to skip Pisa/Leaning Tower... but... it's kind of hard for me to bite that one off. It's the leaning tower! Gotta go for my bucket list and photo op, lol. And the reason I had all that grouped together in a tour group is because my coworker commented that he wasted a lot of time waiting on trains to get to Leaning Tower from Florence, and when there only for a few days, he would have joined a tour group to be more time efficient. He said (at least when he was there) the

I do like the idea of an overnight stay somewhere though -- either Siena or Bologna. 2 people suggested I cut out Bologna... would Siena be a better option? Or is it just so I get more time to spend in Rome/Venice/Florence itself. Also my wife doesn't drink, so probably wouldn't appreciate the wineries as much (discovered this last year when we went to Nice/Cote de Azure, and wife didn't really appreciate any of the wineries there).

If I wanted to re-arrange these 4 days to still manage to get to the Leaning Tower, and maybe add a 1-night stay in either Siena or Bologna, what might folks recommend?

I've read several recommendations to skip Pisa/Leaning Tower... but...
it's kind of hard for me to bite that one off. It's the leaning tower!

LOL, you're talking to the (exhausted) couple who kicked heels in Pisa for too long whilst sorting an unexpected train strike, and chose the bar across the street from the station versus a look at the tower. Long story but we were only supposed to be in Pisa long enough for a short train change; so much for THAT! Interesting day, that.

There are trains from Firenze SM Novella to Pisa S. Rossore in as little as 1 hour, 18 minutes, no changes. They take just a little bit longer going back, or even less if willing to make a train change along the way: see your options on https://www.trenitalia.com/en.html

Pisa S. Rossore is the closest station to Piazza dei Miracoli: an easy 5-minutes or so walk.

Sounds like your plan is solidifying with more time in fewer places, which will make the trip easier. So currently you're staying in 4 hotels - Rome, Florence, Venice & last night in Milan. Siena is a stunning town & very walkable, but maybe spend the day there so you're not wasting time moving hotels? It's really up to you, but it's more packing & unpacking when you could be out enjoying the sights! You could also consider skipping downtown Milan & just stay near the airport to free up more time along the way. (Something we've done elsewhere but not in Milan, but I'm sure others will have hotel suggestions.)

Follow up questions:

1. Any open air markets we should try to target during our trip? Last year we hit market day in Arles in France and my wife loved it.
2. I've heard de-prioritization of Milan. If I want to "check off my list" landmarks in Milan, is that a half-day thing? Can I actually do Verona & Milan together in 1 day, on the way from Venice? (so the day before I fly out, I leave Venice in the morning, spend a few hrs in Verona, then late afternoon in Milan? or will that be pushing it...)

So far.. Day 4 repurposed from Pompeii/Positano to another day in Rome. Day 7 repurposed from a blitz to Cinque Terre to another day in Florence. Day 10 was a free day, but will now add that to Venice. In total, that gives me a total of 3.5 days in Rome, 4.5 days in Florence, 2.5 days in Venice, and 1 day in Milan. Still working out which day trips I want to do from Florence though.

A few more cents:
1) agree that you need more time in Venice
2) agree that you don't have enough time for a lake
3) Pisa is VERY accessible by public transportation. Many do advise that it can be skipped, but we were like you and wanted to see it. So glad we did. The grounds are beautiful and it really did not take up much time. We added Lucca (REALLY COOL city to see and also a short train trip) to the day and had plenty of time in both.
4) Siena is also an easy, self-guided day trip (bus better than train in regards to the station location in Siena) from Florence
5) agree to add Borghese in Rome. Even if you're not a huge art fan, you won't spend much time here as the visit is limited to 2 hours. The sculptures are amazing! Read a little about them before you go.
6) Eating Europe Trastevere food tour in Rome was excellent
7) Pub crawl (and cicchetti) with Alessandro in Venice was a lot of fun (google him and email him for reservations).

You won't miss Bologna. We went there only because we have friends there to visit. I'd like CT if it were a tad bit easier to get to. I think you could skip Pisa but Siena & San Gimignano are great. Look up Tours by Roberto for THE best tours of Siena.

Oh another question. My wife is enamored with the idea of renting a Vespa for a day. We literally just went to AAA today and got our International Driving Permit for it. Any recommendations on what may be a good 1-day Vespa trip?

I google'd and found some options like.... going to Pisa, then renting a Vespa there to go to Lucca. Or from Florence, a Vespa to go to Chianti. But then I was also wondering if it's possible/logical to grab a Vespa to go Sienna and/or San Gimignano.

No idea how easy/hard it is to drive (and park) in these areas.

Are you experienced Vespa drivers?

We are not. It's more a bucket list item for my wife :D

JMO
Italy is probably not the best place to acquire that skill

100% with Christine: if you are not already experienced Vespa operators, Italy is not a place to learn.

Hmmmm well it's not on my bucket list, but if done safely with a group, maybe. I absolutely wouldn't do it, but if you're going to do it anyway, a tour with safety instructions & guides would be the way to go. (Hope you're getting travel insurance including medical?!).

• There's a Vespa tour group with over 700 reviews from Trip Advisor leaving from Florence out into Tuscan countryside, (no personal knowledge) so maybe ask others on the RS forum? If you DO go, please let us know how it went! Would love to hear about it. https://www.walkaboutflorence.com/tours/tuscany-vintage-vespa-tour-from-florence

• And here's a recent RS travel report on Venice / Florence with excellent information, including leather shopping in Florence which I think you mentioned at some point. https://community.ricksteves.com/travel-forum/trip-reports/florence-with-a-side-of-venice#bottom