u/FreddyBeach

Our trip to Italy was in September 2025.

This subreddit was a great source of information for me, so I thought I would try to pay it back a bit.

4 nights in Rome

• Stayed near Piazza Barberini. Close to the metro so we didn't have to drag our suitcases (carry-on only) too far. While there are escalators, there are still steps that need to be managed.
• We didn't make any restaurant reservations. We did a combination of snacks from the grocery store and dinners here and there.
• I wasn't prepared for how impressive the Colosseum is in person. We just did regular entry tickets timed so that we could stick around and take pics at sunset. Crowds were very manageable at this time of day.
• The Vatican Museums were quite spectacular, but the crowds dimmed the experience somewhat. Definitely worth going once. The Vatican tour guide was very good.
• The Sistine Chapel was packed when we got there, so only stayed for a few minutes.
• Even though we had timed entry for St. Peter's Basilica, it still took almost 90 minutes to get through the line and inside. It is quite spectacular, but we were so beat down from standing in line in the heat for that long that it took a while for us to appreciate it.
• I had originally intended to get a package tour for both the museums and St. Peter's so we could take the door from the Sistine Chapel, but the prices all doubled just before I booked, so we went with the standard tickets.
• We either walked or used the Metro for the most part to get around Rome. The Metro was great for us.

3 nights in Positano (Day trip to Capri)

• We took the train from Rome to Salerno and then the ferry to Positano. I bought ferry tickets ahead of time, but it wasn't necessary.
• I bought all our train tickets ahead of time because my wife can get motion sick and she wasn't sure how she'd feel if our seats were facing backward. So I got seats that faced each other so she could choose.
• It's hard to put in words how spectacular Positano is in person.
• Briefly considered using the porters to deliver our bags, but I cheaped out. We just took a few breaks along the way and it wasn't a big deal.
• We stayed on Via Cristiforo Colombo and, as it turns out, had a great balcony, so our plans to explore through Positano were modified to buying wine and paninis and watching the sun set. We still explored, but we really didn't eat out while we were there.
• We did a day-trip to Capri. The ferry ride to Capri is stunning and it's really something else to see Capri from the water.
• Immediately after disembarking we grabbed a taxi to Anacapri and took the chairlift to Monte Solaro. It's just amazing up there. It was the highlight of our day on Capri. We had lunch there which, while expensive, was really good. The baseline panini in Italy is significantly better than the average back home in Canada. I had a Limoncello Granita there that I can still taste, it was so good.
• Capri and Anacapri were underwhelming after that. The crowds (We're part of it, I know) were quite large and the heat was getting to us, so we left earlier than planned and headed back to Positano
• Our departure day was going to involve a lot of travel, so we got a car service from Positano to Napoli Centrale. There, we caught a train to Florence. We picked up our rental car from Sixt in the train station and drove to Greve in Chianti.

4 nights in Tuscany

• We stayed at a spot just outside of Greve which was great. It was beautiful, the room was great, the breakfast was spectacular and the people were lovely.
• I booked a tour, tasting and lunch at the Antinori winery which was about 20 minutes from our resort. It was not cheap, but would do it again in a second. The winery is spectacular. The tour was very interesting (we were the only Canadians with 10 Americans) and the lunch was the best food we had in Italy.
• We drove to the Poggio Al Sole winery for an impromptu tasting which was also lovely. Their grappa was really good.
• The nearby hill town of Montefiorale, while small, is definitely worth the time. Just beautiful.
• Greve is also a lovely town. Very nice for a leisurely stroll.
• I was ok with the narrow roads in Tuscany, but my wife found it stressful.
• At the end of our stay, we drove the car back to Florence

3 nights in Florence (day trip to Venice)

• We stayed near the train station. Our hotel was perfectly fine. They upgraded us to an apartment from their basic room so we had nothing to complain about there.
• Florence was the least favourite of our stays in Italy. I think maybe at this point we were just starting to run out of gas.. We're no spring chickens.
• We didn't go in, but the Duomo from outside is spectacular. What a building.
• Ponte Vecchio was such an interesting structure.
• Took the morning train to Venice. The day started out great, weather-wise. We turned right, coming out of the train station and crossed Ponte Della Costituzione. Our destination was St. Mark's Square, but we took the long way around.
• I think this was the right choice as the streets were mostly empty along this route. It was great to see Venice in this light.
• The rain started to hit shortly after we arrived at St. Mark's Square. It really was pouring at times, so we cut our visit short, went back to the train station and waited for our train home. I'm glad we went, even for part of a day.

Final notes:

• We overdid ourselves in Rome. If we ever go back, we'd take it easier.
• The rail system in Italy is fantastic. I 100% recommend it.
• Positano is the place most different from anything I've experienced. Expensive? yes. Worth it? Yes.
• Our stay in the Tuscan countryside was restorative. I could spend the rest of my life there.
• Driving in Italy was fine. I almost accidentally drove into a ZTL when leaving Florence, but I think I avoided it (no ticket yet).
• Monte Solaro is absolutely worth the trip to Capri. Go there first and avoid the lines for the chairlift.
• Before we went, without ever having had one, I thought that Aperol Spritzes were overhyped. They are not.
• No ragrets. What a country.