8 days

How will you be getting around?

Train between cities (and walking or taxi within cities).

I wish you had more time (so do you I'm sure). You'll be spending eight full days on the ground and traveling between cities on three of them, leaving five full days for sightseeing unaffected by transportation/hotel logistics. I haven't been to Cinque Terre but it seems like you're trying to do an awful lot there in whatever part of Thursday you have after arriving from Florence. I hope this trip is in June when the days are longest.

I spent 17 full days on the ground in Italy this fall, pretty much your trip minus CT. It was about right for me, any less and I'd have regretted missing things. But you'll experience enough to know whether you want to go back for longer.

I would consider two stops for a trip of this length: Rome and Venice.

I think squeezing CT into this short of a trip is not the best idea.

Add one more night at one of the other destinations.

Your situation is a classic example of 'less is more'

with only 8 days, I would skip one city/area, probably CT.

Two nights in Florence is hardly enough, you are really only giving yourself 1.5 days there. If you really wanted, you could take a day trip to CT and back from Florence. Or, I would suggest Lucca instead of CT.

I think I'll do that then (remove staying in La Spezia overnight and instead stay another night in Florence and do a day trip to Cinque Terre). If I'm doing a day trip, I definitely won't be hiking much but at least I'll get a glimpse of it. Do you guys recommend getting dinner in Cinque Terre or should I go back to Florence for dinner?

If you are able to, I'd recommend reversing the itinerary. Venice is a great place to start, you can get over jetlag in this low key town and just soak up the atmosphere, wandering the back canals on foot and watching the city drift by as you ride the vaporetto, both in daylight and after dark. Rome is intense - big and bustling with major sights.

Looking at your current plan, I don't think you're leaving enough time for Venice. It's at least 4 hours by train (with 2 train changes) and then you have to get to your hotel and check in. That could take another hour. That gives you barely 1-1/2 days. It looks like you've only got 1-1/2 days in Florence too.

I'm in the camp of less is more. 8 days is barely enough for Rome, Florence and Venice.

When is your trip? That might make our advice different.

Doing CT as a day trip really does not improve your itinerary.

Doing it as a day trip vs, staying the night there is mostly 'rearranging the deck chairs', not solving the underlying problem; in your case its cramming too many places into too few days.

Chani has a good thought in doing the trip the reverse of what you outline.

Checkout the "Itinerary" section of this tour to get an idea of what you are trying to do on your short trip
https://www.ricksteves.com/tours/italy/venice-florence-rome

This trip is in March. Unfortunately, there are no flights that go to Venice feasibly from where I live (although there are flights that go from Venice back to my home).

I'm thinking of just cutting out Cinque Terre completely and staying an extra night in Florence.

I'm mostly interested in trying great food/cheese on this trip (not wine though - I'm 19 and don't like the taste of wine yet), so do you think a day trip to Bologna would be a good idea when I'm in Florence? Also, do you think doing one of those "guided food tours" would be a good idea? Like this: https://www.tripadvisor.com/Attraction_Review-g187895-d3595558-Reviews-Florence_Food_Tour-Florence_Tuscany.html

I'm also hoping that Eater's guides to Italy are good:

https://www.eater.com/maps/best-restaurants-florence-italy

https://www.eater.com/2018/5/9/17308980/where-to-eat-rome

In general, I'm just worried that if I don't do a guided tour, I won't be appreciating anything with context. If anyone has any experience with guided tours, please let me know! I'm definitely doing tours for the Vatican and the Colosseum, but I'm not sure if I should also do a "guided tour of Rome/Florence" or if those are usually a waste.

We really liked the VIP David & Duomo Tour with Walks of Italy. We are not into art, so this was a perfect taste for us. Started at 8 AM to see David so crowds not bad. Then takes you through the Baptistery, the museum, and up to the Duomo Terrace which is not open to the public, and then you can walk up to the top yourself. They have other tours as well and I've seen other people on the forum recommend the company.

I second the Walks of Italy tour in Florence, it was a great half day tour. While I understand many of the people who have responded to you I think a big question you need to ask yourself is what do you want to see and will you be back to Italy in the near future. The perfect trip may be multiple days in one city but the best plan for you may be to see more if you are not going back soon. I think 2 days in Florence and in Venice are enough to see the highlights and walk much of the cities. I do agree that a side trip from Florence is a good idea, be it Cinque Terre or possibly Siena, Lucca/Pisa, or Bologna. I would suggest looking into travel time between cities to see how much time you will lose travelling.

March is very iffy for the Cinque Terre, because poor weather can make it miserable, so it's just as well to skip it. Instead of a day trip to Bologna, you could easily stop for a few hours on the way to Venice, since the train stops there anyway. There's luggage storage at the train station.

I find that 2-3 hour walking tours of any city are a good way to learn more about the place and leave an indelible impression. Also, the guide will point out little things that you would probably not notice, but that you'll start looking for/at and appreciating. This is an excellent one in Venice - you need to register in advance but there's no penalty for no-shows. It's free, you're expected to tip the guide at the end of the tour. I took the morning one and learned a great deal about the city that I never knew, in spite of several previous visits. Feel free to ask your guides for tips on where to eat and what to see.

Skip CT for this trip and focus on Rome and Florence.