2nd Italy trip for me 1st for my friend - suggestions

It's easy to group these options into chunks appropriate for 8 days by looking at geography:
Just Sicily
Florence and parts of rural/village Tuscany (bus is usually better option vs train unless you rent a car)
Florence + Rome + maybe a village in between
Rome + Amalfi Coast (tight, but "doable")
Venice + Florence (you could squeeze in all three of the "big three," but I wouldn't)

I would choose based on the best flights you can get because that is the biggest expense, and any of those options would be good for a first (or fiftieth) trip

I have been to all those places except Sicily, and I'll be there this summer. Since you have been to Sicily I would say you know best if you would incorporate that into the next trip. Tuscany is the least train friendly, so I would skip that. The Amalfi Coast is spectacular, but not easy to navigate and not by train. Get to Naples by train and hire a driver for a wonderful day (mine included Pompeii for an hour and a half, which was enough for now). I would choose flying into Venice, and taking the train to Rome (fly home from there)
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The time of year should factor in. You can go anytime, but the summer will be very very crowded so that would increase the times needed for activities. Also, August 15 is a huge holiday in Italy, so many places close around that time.

If you go to Florence, I would highly recommend a day trip to Assisi. It was a beautiful bus ride through the countryside. We stopped at Cortona, I think for about 1.5 hrs. It was fine but not necessary. Assisi was a gorgeous surprise. It’s high up on a hill and the views were breathtaking. The town is also so lovely. In the summer, it was less crowded than Florence or Siena and window boxes were over-flowing with colorful flowers. I would love to return there.

A young coworker (24 yrs) loved it better than Florence because it was so peaceful comparatively. She stayed there for three days. Due to your time constraints, a day trip might be just fine.

Recommend having her review Rick’s Italy book so she can decide on the places that most interest her. Then you can plan together how to make the trip come together. Be sure to remember, travel days take longer than folks typically expect. I have found visiting less places an experiencing then for a few days is more rewarding. Sounds like you did this in Palermo, where we went for 10 days last November and never ran out of things to do and see.

There’s absolutely nothing wrong with a classic Rome-Florence-Venice trip. Though with 8 days, I’d probably narrow that to two and throw in a day trip or two in either Rome or Venice depending. Ostia or Orvieto are straightforward from Rome, and any of the Veneto triad (Padua, Verona, Vicenza) from Venice.

I’d drop Amalfi and Sicily for both time of year, and just general time versus logistics. I’d consider them both “deeper dives” to take on exclusively with a couple more sats in your pocket.

Since this is her first trip to Italy, consider flying into Venice. It is much easier to fly into than out of, and is a wonderful place to recover from any jet lag. It's also one of the most unique places in Europe. It should sweep her off her feet. Several day trips can be made from there to Verona, Vicenza, Padau, and others.

Due to the limited amout of time available, consider only one other place. You will lose at least one half day each time you relocate.

Depending on her interest, the other city could be Florence or Rome. Or a place in Tuscany. Rule out Sicily and the Amalfi Coast as they are too far south to work well with your time frame.

With 8 days (8 full days on the ground?), I would fly into Venice and fly out of Bologna. Visit the wonderful markets in Padua (30 minutes from Venice) and eat & wander in Ferrara (30 minutes from Bologna).

We were just in Sicily late March to mid-April. It's really hard to beat for interesting & excellent food. I'm glad that's where you finally decided to go on your first trip to Italy --- a bold decision!

Keep it simple - Venice, Florence, Rome. I just got back from 11 nights there which wasn’t enough, but on my first trip I took 8 nights.

Be sure to book any ‘must dos’ in advance - St. Mark’s, Florence art museums, Colosseum, Vatican Museum.

For great Rome advice, I recommend Youtuber channels Romewise and Rozier Roma

Thank you all!!

Another vote for a two centre trip - Venice and Florence and arriving in Venice from the airport by boat - the most wonderful experience.

I assume you're not planning to do them in THAT order! Also, you didn't mention your flight plan - which city (cities) you are flying in and out from. Are you in and out of Rome? (that will require some backtracking, of course.) Are you into Sicily and out of Venice or vice versa? That would save some time, for sure.

Even so, in 8 days you're planning to cover the distance from Venice to Sicily which is about the same as going from New York City to Atlanta, GA and stopping in Washington DC, Williamsburg VA, the Blue Ridge Mountains, and the Outer Banks along the way! Maybe doable if all you're doing is stopping for a day in each location, but a hectic pace and no time to really enjoy any one place.

Granted, the train system in Italy will get you to most destinations quicker than driving a car down the eastern seaboard, but it still gives you an idea of the distance you are planning to cover in a week. Maybe pare it down to either northern or southern Italy for this trip rather than try to cover ALL of it in a week.

During the time of year you’re considering the ferries may not be running along the Amalfi Coast, so I would choose something else. But, if you decide a different month, a train from Rome to Salerno is easy. Then a ferry to Amalfi as a hub for the area works fine. You could easily do that during your time.

Sicily - I would pick something else. Transportation is harder, and it felt like a 3rd or 4th trip to Italy location, instead of a first time itinerary.

Venice, Florence or Rome lend themselves well to day-trips from any of them. Just a comment - when you’re staying at any of those three, you’re paying more for lodging than you would at your day-trip destinations. There’s a lot of options for mini-van tours from Florence to go see some of the Tuscany smaller towns, or wine tours out to those areas. Remembering the time of year, it would probably be more the towns vs. the vineyards.

The big 3 - Venice, Florence & Rome are wonderful options to pick two. But, try to add a smaller city for a less touristy feel of Italy, too.

FYI- avoid the week before and after Easter, as the crowds increase drastically, as Europeans are on holiday then, also.
I could spend eights days in Venice, but Venice and Florence would five two different perspectives.
Have a great trip!

My sister’s dream was to visit Tuscany so I took her to Florence and then Lucca. The combination of city/small town was ideal.

We built our schedule together. In Florence — a morning in Santa Croce and the leather school, wandering around Sant’Ambrogio market, a day-long wine tour, poking around Oltrarno and a wonderful visit to David. Lots of walking around, window shopping, apertivi and people watching.

Then we trained to Lucca for a couple of days. Very relaxed. We walked the wall, ate and drank good Tuscan wine, took a cooking course, and checked out the local gelato.

Then we returned for a final day in Florence and flew home from there.

This was a great first trip for her and fun for me too. … Il Dolce Far Niente.

Thank you all for the great suggestions!

Hi Susan - I believe we are going to mimic your itinerary with a few slight changes :) Thank you for sharing!!!

Any recommendations on great places (areas) to stay or restaurants we must try? I found what helped me we I went was the restaurant recommendations from others.

Thanks again!

8 days recommend Rome and Florence, with 5 days Rome and 3 in Florence.

In Florence we like to stay in the Oltrano neighborhood. Last time we stayed at the San Pier Novello in Oltrano B&B. They have a three night minimum, but it is a charming place run by a lovely family. They offered a spectacular breakfast and recommendations for nearby restaurants and apertivi.

I second Becky’s suggestion to stay in the Oltrano neighborhood of Florence. Also highly recommend wine tour or similar activity to see the countryside. There are many, many such day tours from Florence (my favorite city!)

Hi! Let me do a little research and I will get back to you with some suggestions. Back to you in a day or so, ok? Susan

Here are a few places to consider:
In Lucca
La Boheme B&B is in a great location; it’s comfortable, spotless and the staff is friendly. Good breakfast. Ask for 2 beds. Be aware that there are steps. https://www.boheme.it/en/

Pizzeria la Felice is right behind La Boheme. It’s tiny and very popular with people who live in the neighborhood. They make traditional, very thin local pizza accompanied by a small glass of wine. Not fancy but authentic. https://www.pizzeriadafelice.it/

In Florence— we stayed at a great 2 bedroom apartment a few blocks away from the center. If you want the info I will private message you. But, I agree with other posters that Oltrarno is wonderful. In fact we are staying in a place there when we return to Florence in November.

Here are some of our favorite places in Florence (Oltrarno)

https://www.trattoriasabatino.it/ — casual family- run place. Reasonable prices. Regulars go there and there is always a line. Good home cooking.

https://www.levolpieluva.com/home-english — local wines and small plates. I’ve been there multiple times and it’s always good!

https://www.formaggiotecaterroir.it/ is a wine and cheese specialty store. They also run Grape Tours— a very nice way to check out a few vineyards and have a farm-based lunch.

https://www.lapellesrl.it/ Leather goods. Beautiful.

I also recommend that you watch Stanley Tucci’s new show on Nat Geo. The Tuscany episode features some places I’m excited to try.

Have a fabulous time!