3 week Italy Itinerary

It looks like you know where you want to go; I would make different choices but we are all different. I didn't find the Amalfi area and Sorrento all that, but if you want to be there at least you are consolidating hotel to Sorrento ( a lovely place) and not moving around every night. You are also committing a few days to major spots like Rome and Venice which is good.

The one thing that leapt out to me is Siena. Arrezo is not close to as interesting as Siena. I would give Siena a full day and skip Arrezo. If you were spending a week or two in Florence then Arrezo is an interesting side trip but with your rush through this part of the world, it is a waste of time IMHO. I hate one night stops, but you have generally minimized them. Siena is a fabulous day and it is lovely in the evening. Have a drink on the Campo one evening under a full moon if you can. I'd get to a hotel in Siena as early as possible on that day (get one with parking like Palazzo Ravizza or the Athena) drop the bags and then spend the day and evening exploring Siena.

I'm a little confusted with this itinarary, but I will leave it to others to comment on the bulk of it.
My questions involve this part:

Day 5. Train to Sorrento. Sleep in Sorrento
Day 6. Museums in Naples. Sleep in Sorrento.
Day 7. Pompeii/herculaneum Sleep in Sorrento
Day 8. Capri. Sleep in Sorrento
Day 9. Train to Positano- VISIT Paestum on the way- see the ancient greek temples/ Sleep in Positano
Day 10. Explore Amalfi coast. See ravello. Sleep in Positano

** DAY 5 and DAY 6: First, you have to go though Naples to get to Sorrento, so on day 5 why go all the way to Sorrento if you plan to go back to Naples the next day? By the way, leaving from Rome by the time you get to the train station in Rome, until you get to Naples and then to Sorrento will take you at least 3 hours give or take. Why not just stay in Naples.

Same with your visit to Pompeii/herculaneum, while you can get back to those locations from Sorrento, it's a much shorter journey from Naples.

DAY 8 Again, a day trip to Capri is nice, but so far - in your itinerary, you aren't leaving yourself much time at all to enjoy Sorrento.

DAY 9: We actually did this trip. While you can get there via public transportation, we found it easier to actually do a tour from Sorrento. Here is the link for that: http://www.goldentours.it/en/salerno_e_paestum.php

Day 10 You can do a nice daytrip also from Sorrento. There are many hop on/off buses as well as public transportation.

Last comment, you might want to consider just spending some time in Sorrento. However, if you want to keep to your itinary, you might be better considering nights in Naples at the beggining, followed by Sorrento.
However, this trip should be about your preferences, but from what you've listed you might want to rethink where you are spending your nights.

Thank you guys so much!!

We don't really have much experience with Italy (we've both been to Florence, but thats about it). So we aren't quite sure where we are going, if you have other places you recommend we'd love to hear them!! We basically just picked these stops because of what Rick says in his book.

I think our main concern with Naples was just his description of it being super crowded. We figured that since we had our luggage, we probably wouldn't want to stop in Naples and do the museum that day. Your suggestions make total sense, though! Has anyone had experience with Naples at night? Is it safe to explore the streets? It just sounds pretty chaotic and dangerous from his descriptions.

Also, do you have recommendations for places to visit/stay in the Tuscany area? We are clearly struggling with finding the best places to stay overnight!

Thanks again!

Geographically, Orvieto makes more sense if you hit it between Rome and Siena.

Matera (Basilicata) and Alberobello (Puglia) are very interesting destinations, but the difficulty of reaching them, especially via public transportation, makes quick trips to that area inadvisable. Transportation across southern Italy is a challenge. According to Rome2Rio, Sorrento to Matera will take 7 to 8.5 hours, Matera to Alberobello is about 3 hours, and Alberobello to Rome is 6.5 to 8.5 hours (and you're still not in your planned base of Siena). So you'd basically just be sitting on trains or buses the whole time. I'd keep that area for another trip when you can spend at least a week down there, including travel time. You could use those two days in Tuscany.

My experience visiting Tuscan towns is in the distant past, but I spent a lot of time in other parts of Italy last summer, which confirmed my rule of thumb for preliminary planning purposes: If you're using public transportation, you can usually get to two small towns per day, as long as that day isn't Sunday or a holiday and you're flexible about Town #2. Local tourist offices usually have information about bus and train schedules to nearby places of tourist interest, but it's best to double-check that information online or (even better) at the bus/train station so you don't miss a destination due to misinformation.

I'd be surprised if there aren't bus tours from Florence and Siena visiting multiple hill towns in a single day. Depending on when you'll be traveling, those trips may run only one or two days a week, and it may take a good bit of Googling just to determine who operates them so you can email for more details. When trying to travel this way (I say from experience), it helps to have a fair amount of time in each base city so you can take advantage of opportunities that are not available every day. Once you're in Italy, you can ask the city tourist offices about tours running to nearby towns.

Edited to add: I think you've got plenty of ground to cover once you pick up some more places in Tuscany, but if you want other places to consider, several posters have made positive comments on Assisi, Ravenna, Verona, and Padua, among other cities. Italy seems to have hundreds of places worth a visit.

I just wanted to add one more thing. On our trip, we only passed through Naples (the train station) and traveled to Sorrento. We didn't go to any of the museums. That was our choice. We preferred to be in Sorrento and use it for a base to other places that were easier to get to from Sorrento. On the way back to other destinations, we only passed through the train station leaving Naples. So, I just wanted to be clear, that was our decision to not spend time in Naples.

I was only suggesting that you might want to spend the night, because it seems you want to visit the museums there and it might make it logistically easier for the night or two, if that was your plan. Of course you can go to Sorrento, and then back to Naples, it's just going to take you more time to do so. Perhaps time you can use to explore Naples without having to catch the train back.

Others may like to comment if this order works better...

Day 1. Fly into Rome (land at 9 am)
Day 2. Rome
Day 3. Rome
Day 4. Rome
Day 5. Train to Salerno and visit Paestum. Sleep in Salerno
Day 6. Bus to Positano. Sleep in Positano
Day 7. Explore Amalfi Coast. See Ravello. Sleep in Positano
Day 8. Bus to Sorrento. Visit Capri. Sleep in Sorrento
Day 9. Visit museums in Naples. Sleep in Sorrento
Day 10. Visit Pompeii/Herculaneum. Sleep in Sorrento
Day 11. Train to Matera. Sleep in Matera
Day 12. Train to Alberobello. Sleep in Alberobello
Day 13. Train via Rome to Orvieto. Sleep in Orvieto
Day 14. Visit Arezzo. Sleep in Orvieto
Day 15: Train to Siena. Sleep in Siena
Day 16: Visit San Gimignano. Sleep in Siena
Day 17. Train to Lucca. Sleep in Lucca
Day 18. Cinque Terre/ Riviera. Sleep in Levanto
Day 19. Cinque Terre/ Riviera. Sleep in Levanto
Day 20. Train to Venice. Sleep in Venice
Day 21. Venice
Day 22. Venice

David, I still have an issue with the SE segment. Essentially all of Day 11 will be spent getting to Matera, and all of Day 13 will be spent getting to Orvieto. Why bother?

acraven, whilst I am not familiar with Matera and Alberobello, I too thought that more than 2 days would be needed. Day 6 (Positano) could be stolen, and the plan reworked to make 3 days for those places.

I like David's itinerary alot, but I think you should drop the difficult and awkward Matera/Alberobello stops and add those nights to Siena and Lucca. Lucca is easily worth two nights, and 3 in Siena make your planned day trip to San Gimignano easier (although I would recommend Volterra instead as I found San Gimignano to be rather fake-y and Volterra to be truly historic and charming). When you have many short stays in a long trip, you don't have time for things like laundry, researching your plans for the day, getting oriented to each stop, finding the buses, etc. That "stuff," the infrastructure of travel takes TIME. Even when I do a ton of research in advance, we are always hunting down info on arrival, changing plans because of closures, looking for restaurants, and taking care of life.

Okay! Thank you guys SO much for all your help and advice! Here is our updated itinerary (using David's as a base)

1. Fly into Rome
2. Rome
3. Rome
4. Rome
5. Train to salerno. Visit Paestum. Sleep in Salerno.
   
6. Bus to positano. Sleep in Positano
7. Explore amalfi coast. See ravello. Sleep in positano
8. Bus to Sorrento. Sleep in Sorrento
9. Pompeii/Herculaneum/Vesuvius. Sleep in Sorrento
10. Museums in Naples. Sleep in Naples.
11. Rent car in naples. Drive to Matera. Sleep in matera
12. Drive to alberobello. Sleep in matera
13. Drive back to naples to return car. Take train to orvieto.
14. orvieto, sleep in orvieto
15. Sienna. sleep in sienna
16. Visit Volterra. Sleep in Sienna
17. Visit Assissi. Sleep in Assissi
18. Train (and bus) to San Gimignano. Sleep in San gimignano
19. Train to Lucca. Sleep in Lucca
20. Cinque Terre/ Riviera a. Sleep in levanto
21. Cinque Terre/ Riviera a. Sleep in levanto
22. Train to Venice. Sleep in venice
23. Venice
24. Venice
25. Fly out of Venice

How does this look?

Hi Nicole. You need to pull up a map of the Italian rail network. Siena is on a branch from Chiusi to Empoli to the west of the main north-south line. Assisi is on a branch to the east.