Hope your planning is progressing well. If you need some opinions on options, consider posting links here. In years past, the CC gang was so helpful to me when picking accommodations in Barcelona and in Rome too. They’d post pros/cons of places and neighborhoods of various links.
Thanks so much, Colorado_mom! Well, I’ve finally booked all the hotels and AirBnBs for an 10 night trip to Italy, with Florence as base. Pretty stressful as I fell into hours of Google-review-comparison - ugh! Also booked 2 Rome tours (there for 2 days). Might be a bit tour heavy but I was overwhelmed by all the Roman historic sites & “you must see this!” - just wanted someone to curate it. Will have half a day to wander the city each day.
Wondered:
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Do folks going to Italy usually book their train trips (between cities) before flying over? I’ve heard they are about $30 cheaper per ticket if you do that…? Wondering if I should commit to that level of pre-planning detail!
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If anyone had a rec for a one day tour of Tuscan countryside with maybe a food stop(s)…that would be much appreciated!! I don’t really drink much so a winery would be for atmosphere only. lol. Read Under the Tuscan Sun years ago and just want to see some olive groves!
Many thanks!
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There are several cheese farms In Tuscany that do lunch and a cheesemaking tour. I did one a few years ago in Pienza (it was with a private driver, but I am sure you can find something with a group). The scenery was so under the tuscan sun.
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found a few by googling - they look like what you are looking for
Using a tour can really help you use your time efficiently. Our first visit to Rome in 2012 was just a lonnnng one day shore excursion from cruise ship (including 90 minute bus ride there, then return). We were amazed how much we saw when the tourguide/bus was coordinating everything and arranging save-the-line tickets.
Our shore excursion to Pompei included a lunch at a farm that made mozzarella and limoncello - what a delightful time that was!
In 2015, I think(?) we booked train from Rome to Venice ahead of time. For our overnight train from Venice to Munich, we at first had a lot of trouble booking online… perhaps because we were trying to to do it with US credit card. Eventually we found a way, via travel service. Don’t remember all the details, only the pain of going through all the train reservation steps and then getting rejected before completion.
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This is who we used:
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I would pre-book any long distance high speed train tickets in advance. They are most likely to sell out. Ticket prices can go up the closer it gets. You’ll be able to reserve seats also.
https://www.seat61.com/train-travel-in-italy.htm
It pays to do a bit research on the different types of trains and how the ticketing works before you go.
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Thank you all so much for the feedback! I am booking trains (almost done - whew, pricey!).
I love the tour options too. Those sound amazing! I really want to squeeze in a Tuscan tour - we are pretty tightly booked, though. I’m hopeful!
Again, appreciate the info!
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Glad you’ve made progress. Looking forward to your feedback, especially Tuscany
First time I booked train travel was for Spain trip years ago. Took me forever. I fortunately found a website on how to book trains with the warning built in that the English site would suddenly turn to Spanish half way through so included a translation with directions on how to answer all the questions so print it all out beforehand. Yep! Halfway through a very lengthy reservation process (pick seats first, then date and time, all passengers–names, ages etc. It suddenly goes to Spanish. And then FINALLY pay and reserve–woe to the person reserving if there wasn’t room–you get to start the process all over!) Plus only certain credit cards were accepted so had to figure that out too. It was like talking to your cable company…
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You probably don’t need to book every train–just the major high speed trains. Unless there is a major holiday while you are visiting. Some trains (in France at least) were much more expensive than others with very little difference between them–just different lines. Pay attention to the end station–in France there were four stations for Paris, 2 for Montpelier–one station would be close and another 20 miles away from where you wanted to land. I ended up with 30 euro tickets going and 200 euros coming back–ugh.
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Thanks for the thoughts!! We did book the (pricey) high speed trains from Florence to Rome and Milan and Cinque Terre. Website said the trains from Milan to Lake Como area (spending a few days there) run very frequently - so didn’t book ahead. Hoping that works out!! 
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That’s fantastic. We will all want your trip report when you are back! I’ll especially be watching for Milan feedback.
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Years ago we drove into Milan with friends on a late afternoon on our way to Lake Como. It was dirty and ugly and our husbands had no desire to go back. So a couple days later my friend and went back (after all it’s Milan!). It was beautiful and we had a great time exploring and shopping. Appears we had driven in through the industrial side and missed the pretty part. We finally convinced husbands to try it again.
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Our Milan stop is a quickie - high speed train from Florence to there, then catching more local train to Bellagio (in Lake Como). Son wanted to see the mountains of Northern Italy so we added that jaunt. Just hoping we make the local train!!
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Sounds great! Considering a visit to Lake Como. (I’m originally from upstate NY. Had to laugh when accidentally Google-searching for “Cuomo”)
We stayed (a million years ago it seems) on Lake Como for about a week. We took the ferry over to Bellagio. It truly was gorgeous. We stayed at a rented place. Most memorable is that the kids made friends pretty fast with local kids so played soccer on local courts (very small–tennis court size or just slightly larger) with families (grandpa to the smallest) and learned a ton of curse words in Italian–seemed to be the main form of “cultural exchange” at the time for them. They had a great time. And we did too!
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gouf78 that such a great story! Makes me glad we picked Bellagio. Colorado_mom - I hope to have some good stories about Lake Como too when we return!
Back to superficial questions, lol. I’ve been reading the ideal travel outfit for spring in Europe is some kind of thinnish, water-resistent jacket, then underneath a fleece, and/or warmish vest (aka, layers).
Do I need to go buy one of those rain type jackets for trip? My daughter who’s studying abroad is living the fashion life of a 21 year old so I can’t actually go by her example, 
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A super packable water resistant jacket will be your best friend. One that you can hopefully stuff in your bag for a light drizzle or you get cold sitting outside or a cold breeze comes up. I bought a super lightweight Uniqlo wind breaker and it saved me over and over again. The weight is like air so a no brainer to carry around.
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The layers plan sounds good. Then you have some combo options. One thing I like to do is bring a thin long sleeved top (white on summer trips) that I can wear under short sleeved tops if cooler than expected.
If it’s likely to be rainy, think about your feet too…. it’s no fun touring with wet feet. We have brought small umbrella, but Rick Steves suggests just buying a small cheap one on the trees if needed.
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