Stopover on the way to Italy

Where are you flying from? Some of these decisions are better made depending on reasonably priced available flights and transfer hubs.

Before making a decision, investigate the time and money required to get from your planned stopover to your first Italian location. Nice, for eample, is by no means a quick train ride.

There are so many wonderfil places in Italy. I'd look to spend the time there. Padua/Vicenza/Verona or Bologna/Ravenna/Ferrara would each be good for at least 4 days, just as examples.

Choose a city as you'll have jet lag. An airline transfer city makes sense - Paris, Amsterdam, Munich, Madrid.

Good advice from previous posters.

Amsterdam and Nice are good, but why not pick places closer to where your trip starts, especially if you only have a couple of days.

A stopover at either city might cost your more than you would like to pay for airfare.

If flying into Rome, you can take a trip by rail down to Naples and visit Pompeii, Sorrento and Capri.
If flying into Venice, you could visit Verona or Ravenna.

Italy is great, you will love it.

Given the state of the GBP, I think London with its wealth of low cost flights to the continent might be worth considering. The exchange is as advantageous to the dollar as it's ever been.

A big thank you to everyone for your advice! It seems like Naples could be a good option. I've always wanted to see Capri and Pompeii so it seems like I could do easy day trips to both of those by staying in Naples or Sorento.

I also I am intrigued by Cinque Terre, but seems like that could get tricky traveling to the a train from Rome.

SharYn...to answer your question I will most likely be flying out of Milwaukee.

We visited Naples, Sorrento, Pompeii and Minori on The Amalfi Coast this March. We enjoyed them all. The weather was very pleasant and the crowds weren't bad. Your idea of statting in Italy makes sense. You'll get a taste of the language, culture and food before you start your trip with your friends.

If you are flying into Venice, then I would suggest Padua.

It's a quick train ride from Venice. Lots to see and do. The Scrovengi Chapel with Giotto's frescoes are worth the trip. Good restaurants and relatively inexpensive vs larger cities. It's home to the university so depending on time of year there are lots of students around and feels very safe.

March and Capri are not a great combination generally speaking..

End of March with favorable weather could be good for walking/hiking in Capri.. but a bit shut down at that time of year....as far as restaurants and high end boutiques...but the beauty of the island will remain....but you will not find the Amalfi Coast up and running at this time of year....

I love Naples and travel to this region every fall.
In dry weather seeing the archeological sites could be a good thing.

Not sure what your budget is like but I have stayed at Una Hotel Napoli many times...5 minutes straight ahead from Napoli Centrale train station with links to Pompeii and bus to port area just outside. It has a great roof top breakfast area, quiet modern rooms, excellent wifi and great staff. If you are going to the port for ferry to Capri and seeing Pompeii staying near the train station on a short trip makes the most sense to me....but if you are weary of the area, many people like the area near the archeological museum..and just take taxis...

If you fly from Chicago, directly to Europe (and finally to Rome or Venice) the likely choices are:
One World Alliance (AA & partners) via LHR, MAD
Star Alliance (UA & partners) via FRA, MUC, ZRH, CPH, ARL
SkyTeam alliance (Delta & partners) via CDG, AMS, FCO

There are others, like Air LIngus via DUB, and probably others.

If the price is right for an extended layover, it could be an opportunity to visit one of those gateway cities.

Otherwise go to your intended first destination in Italy a few days earlier, and visit a place nearby.
Padua or Verona are nice and near Venice, if you start your trip from Venice first (recommended).
If you start from Rome, then the Naples/Pompeii/Sorrento area is an option, but a couple days only is too short for Naples.

First off, I would discourage Naples as an introduction to Italy. Secondly, think a little about jetlag. If you go early, you'll be on your own dealing with foreign places, language, money, and zonked after the long flight and the time change. Then you'll be adjusted and raring to go when your friends arrive and have to deal with it. Can you go together with your friends and then stay a couple days after?

Although everyone knows his or her limits, don't be put off by Naples, especially if you really want to see the archeological sites and museum!

I am a woman in my 50's and travel there with a friend in her 60's we stay in Naples the first and last nights before our flights back to the US.

Naples has two things that make it a bad choice for what you propose (going to a place for a few days before you join your friends).

1) From Milwaukee, you will need to make at least two connections to get there (e.g. Milwaukee to JFK to Munich to Naples). Even if you can fly from O'Hare instead, there are no nonstops to Naples.

2) I learned to like Naples in my time there, but it's hard to imagine a worse introduction to Italy. It's a very intense, in-your-face place. The Cadogan Guide's summary, all these years later, still sticks with me as the ultimate statement about the city: The only thing subtle about Naples is its charm. Rick Steves is also accurate: If you like Italy as far south as Rome, go farther south. It gets better. If Italy is getting on your nerves, don't go farther. Italy intensifies as you plunge deeper.

From the sound of your post, you have not been to Europe before, and you have used the phrase "solo female traveler" several times (meaning you're a bit fearful). Naples is simply not a suitable first place in Europe, or Italy, for such a person. If you want to go there, definitely do it after you've gotten used to other parts of Italy first.