Italy. 1st trip abroad

I would recommend a trip to Vernazza if you like to hike.
The hike along the coast is fabulous and Vernazza has some very cozy pensiones.

Since you've mentioned that you want the hit the 'must see' locations and that you're looking to make this a bit romantic, I think the best choice would be Venice. Keep in mind that part of the time you have allotted the itinerary (7 days) will be cut into by the trips from one destination to another, so unless you're renting a car, work around the available transportation modes and schedules.

Hi, David. It sounds like you've got an exciting itinerary, but only 7 days to cover it all. If you like history, I'd recommend visiting Pompeii while you're in the Naples area. I've never been to Capri, but Rick Steves doesn't recommend it.

As far as Rome is concerned, I'd recommend the longer visit. To say the least, Rome is saturated with history and culture. In 2012, I spent two months on a sabbatical there, and I still feel like I've only seen the tip of the iceberg.

Since you're flying out of Bologna, which is in the northeastern part of the country, I'd recommend a day in Florence, and spending the rest of your time in Venice. Milan is out of your way in the northwestern part of the country. Also, it is probably the least exciting item on your bucket list -- unless you're independently wealthy and want to shop for fashion designer clothes.

Naples, Pompeii, Rome, Florence, and Venice would be more than enough for a one week itinerary. And you can take the high speed Eurostar trains to all these cities. Getting from your final destination to Venice to Bologna is very easy by Eurostar trains. Then take a taxi to the airport.

Five cities in seven nights? You will see Italy from a train. If you can handle that great. I know I could not. If I was there for 7 nights I would only plan on two cities, plus one night in Bologna before you fly out. Rome needs three nights, then........

Of course this is all IMHO.

Five cities in the length of time you have is, in my opinion, way too many. If you can, try doing only two cities. Are you locked into flying into Naples. If not, there may be a better way to use the time available.

Since your time is relatively short and this is your first time, I would suggest a very centrally located hotel. Time is going to be key, so you want to spend as little time as possible for the trips to/from the hotel.

Appreciate the responses. I should have given more details. Just flying in to Naples to get to Capri and out of Bologna due to other obligation. No site seeing in either. Arrive Naples at noon then straight to Capri. Fly out of Bologna at 1:30 pm so catch early train out of Venice to airport.

Shaping up to be: 2 nights in Capri. 3 nights Rome. day trip to Florence on way to Venice. 2 nights Venice and train from Venice to Bologna airport.

Great information. Going to stay in local neighborhoods and not hotels.

Because Rick Steves has rated Capri as one of "Europe's top tourist traps," it will be interesting to get your take on the place when you come back. Please be sure to write a review of your experience.
http://www.transitionsabroad.com/publications/magazine/0005/rick_steves_best_worst_of_europe.shtml

Oh, and another thing... this has more to do with packing and preparation and less to do with your destination, but for short trips where you have limited time, you may want to be a bit more comprehensive with your packing and gear so that you're not spending time running around trying to find random toiletries or an extra pair of socks because you forgot to pack them. Granted, shopping can be a cultural experience, but I'm guessing you might want to save such time for the sights, this being your first time and all.

There are lots of places Rick Steves doesn't recommend, which is annoying and funny. One guidebook actually says, (these three cities) "are not worth your time". He doesn't know me or what my time is worth. Go where you want. Capri is beautiful.

By the way, count nights, not days. A night is always one night, but a day can be eaten up with transportation time. So 2 nights in Roma is really about 1.5 days.

I don't think I saw what time of year you plan to be there. The summer is super busy in the cities.

My wife and I just came back from a 10 day trip (Venice, Florence, Rome Rick Steves Tour). I'm not a huge "city" person and I found Rome to be extra crowded.

We flew in and out of Milan. I think that the worlds fair is not worth it, if you are not already in the city. Milan is not a great city.

We also went to a wine tasting and lunch in a Umbrian agriturismo. It was great, the proprietor was wonderful and the wine/food excellent.

Naples...we went there after our tour. My wife wanted to see Pompeii. The city of Naples is very dirty and actually my wife's luggage was pickpocketed as we were rolling it outside the train station. I'm not a fan.

Florence...absolutely wonderful. You could easily spend 2-3 days there. Uffizi, David, tons of things to do, great food.

Venice...wonderful. This was the first stop on the tour and I must have had strange jet lag. I would wake up about 3am and be wide awake. For the first few days, I would get up and walk around the city at 5am. It's truly the best time to "see" the city...before the crowds are there. You could walk the streets and see less than a dozen people.

If I were you I would go:

Naples-->Rome-->Florence-->Venice-->Bologna
You still do a little backtracking, but from Venice to Bologna is about 2 hours. If you don't make it to Venice, may Siena, which would be a good choice for your type of lodging.

I'd recommend limiting yourself to Rome and Bay of Naples area.
Day 1 Arrive in Naples & transfer to Sorrento
Day 2 Excursion to Capri
Day 3 Excursion to Amalfi+Positano
Day 4 To Rome via Pompeii
Day 5 Rome sights - Colosseum, Forum, Trevi Fountain, Spanish Steps, Piazza del Popolo
Day 6 Rome sights - St Peters, Vatican museums, Castel San Angelo, Piazza Navona, Pantheon
Day 7 To Bologna
Day 8 Depart from Bologna

I would absoluty recommend Florence since you will be in the northern half of Italy at the end of your trip. It is my favorite city in Europe. So much to see and do and a lot Of it is centrally located around the Uffizi.

There's no place I've been to yet in Italy that didn't have its own highlights, and usually great food and wine. The problems with going to many places in a short stay are that travel time becomes a huge percentage of your total on-the-ground time and you don't have time to enjoy the places you visit. Bear in mind that you have to drop your luggage somewhere before you start sightseeing and you need time to get to the train station (allowing for possible delays), buy tickets (there are often lines - yes, at the machines too), and find your train. In Venice, allow plenty of time - you will either have to walk or take a very slow vaporetto. For instance, from St. Mark's to the train station is about 1/2 hour on foot (if you don't get lost) but it's an hour on the vaporetto (and maybe a long wait for one). I haven't been to Capri. The hydrofoil is not very near either the airport or the train station, so you have to allow transfer time (maybe through city traffic).

Your itinerary looks like this to me:

Day 1 - Land in Naples (jetlagged? night flight?), arrive at lodging in Capri 4 hours later. Have dinner and early to bed
Day 2 - Capri (getting over jetlag?)
Day 3 - Leave Capri early, arrive Rome lodging 4-5 hours later. 1/2 day sightseeing
Day 4 - Rome, full day to sightsee
Day 5 - Rome, evening train to Florence - most of the day to sightsee in Rome, dinner in Florence
Day 6 - Florence, full day sightseeing
Day 7 - ??
Day 8 - go to Bologna airport.

You "use up" pretty much a whole day of your week to get to Capri. If this is a priority, stay another night and enjoy it. Otherwise drop it. Based on the above, you have one "spare" day, which would still give you time to see the main sights in Rome and Florence - maybe even part of Day 8 to see a little more of Florence. Florence is close to Bologna and the train station is in the historic center. If you drop Capri, you can add Venice.