Italian Itinerary for 1st Solo Trip

I've been to Milan, Parma, Siena, Lucca, and Florence before. Like you, I like to return to favorite places, and Siena and Parma would be on my list for return visits, too. I did only a day trip to Siena and would love to spend a night there someday.

I've always found Italy easy enough to navigate solo, mostly by train.

Lucca ...don't miss it. The very wide walk along the city walls is a treat. Lots of activity up there. Rent a bike to traverse it. The city center is beautiful, lots of shops up and down the streets. The Piazza is the center of activity, street musicians and performing artists. Just a really great Italian city. Not overrun by tourists. Keep it on your list

Arezzo has a rather big-deal monthly antique market. I believe it is scheduled on the first Sunday of the month and the preceding Saturday.

I would look at flights round trip to Milan, and add a stop on the Ligurian coast. Your choice of smaller destinations will mean longer transit times and a few train connections. I’d go like this over 17 nights ...

Day
1..Arrive Milan. Train (direct) to Stresa (2N)
3..Train (via Milan) to Parma (2N)
5..Train (via Bologna) to Arezzo (2N)
7..Train (via Chiusi) to Montepulciano (2N)
9..Train (direct) to Siena (2N)
11..Train (via Empoli & Pisa) to Lucca (2N)
(or travel via Florence if you want to spend a day)
13..Train (via Viareggio) to Santa Margherita Ligure (2N)
15..Train (direct) to Milan (3N) - day trip to Cremona
18..Depart Milan

djp_syd, is there a town you would recommend on the coast? We stayed at lovely Cinque Terre several years ago before the crowds of tourists.

I have not been but would probably choose Santa Margherita Ligure.
http://www.smlturismo.it/en
Easily accessed by train, with Portofino a day trip away by bus.

I like your original plan. Arezzo and Lucca are two of my favorites.

You may find more convenient flights out of Milano, in which case I would spend your last night there, and perhaps put Stresa at the end rather than at the beginning (go straight to Cremona).

A series of 2-night stays is exhausting. I much prefer fewer places for longer stays.

Instead of Siena, where you have been, why not stay in Montepulciano?

Stresa - 3 nights (Maybe 2 if you are just staying there to recover from jetlag and since you have been prior

Cremona - 3 nights. Take a day trip the one hour to Parma to feed your need and eliminate a transfer

Arezzo - 3 nights

Montepulciano - 3 nights

Lucca - 3 nights

Firenze - not necessary to stay. If your flight is late enough you should be able to arrive from Lucca.

That is 15 nights and still pretty fast-paced. If you have more time, lengthen one of the stays. It would be awesome if you could carve out 20 nights and lengthen some stays making more time for exploring and day tours.

Here's my original plan with number of days I was thinking for each. I initially was also considering returning to Torino to see a few more museums, and I like Torino.

I would be fine with some additional days, but I think I'd rather add them to the trip my husband & I will take the following year.

Fly into Milan & head to Stresa - 3 nights
Cremona - 2 nights
Parma - 1 night
Arezzo - 3 or 4 nights
Siena - 3 or 4 nights
Lucca - 3 or 4 nights
Stay near the airport for flight the next morning.

I think you really need to fully explore departure flight options before locking down a plan. I still think Milan might remain the more feasible possibility.

Fly into Milan & head to Stresa - 3 nights
Parma - 2 nights
Arezzo - 3 nights
Siena - 4 nights
Lucca - 3 nights
Milan - 2 nights (day trip to Cremona)
Fly out of Milan

Cremona is 70 mins by train from Milan with very regular services.

Cortona and Perugia would be possible side-trips from Arezzo, though I think the train station for Cortona is Camucia-Cortona, quite some distance from (and below) the town, so you'd need to finish the trip by bus or taxi.

Thank you, everyone, for your responses - much appreciated!

I'm looking at the timing of festivals for these towns and others in the same region, so that may affect the route. I'm hoping for some classical music, opera or similar and a fun cultural festival. I see Lucca has a Lantern night festival in mid September, a tiny town has a Palio as a smaller version of Siena's, and Arezzo has the jousting. I may begin in Verona to catch an opera at their arena the last week of August. So many wonderful options!

if Lucca is your final stop, you might want to investigate flying out of Pisa instead of Florence.

In Lucca, if you enjoy classical music, ask about the Puccini concerts. Also, I recommend a cooking class at Extra Virgin. I went to Lucca right after Florence last summer, and it was a welcome escape from the crowds. I talked to several residents who used to live in Rome or Florence but moved to Lucca for a more relaxed lifestyle. On every trip I like to find an "I could live here" place, and Lucca was it for me.

Regarding the Ligurian coast, I stayed in Levanto, just five minutes by train from Monterosso. It had good transportation options to other places on the coast. My favorite town was actually Portovenere, but it's harder to get around from there.

I travel solo regularly because my husband doesn't enjoy European travel the way I do; I spent a month solo in Italy last summer and had a wonderful time. The only negative for me is that lodging costs more because you don't have anyone to share the room with (and even when you can get a single room, it costs more than half a double).

I reserved my flight, so it's official - yeah! I couldn't use miles & fly back home from Florence, so I have a RT to Milan.

Here's more of a firm itinerary. I've reserved hotels/apartments with free cancellations for flexibility for further planning during the next few months.

Fly to Milan & head to Stresa - 3 nights (Stresa Music Festival - ends Sept. 1)
Milan - 1 night (staying next to the Duomo to see the main sites)
Verona - 2 nights (Purchased a ticket to Aida opera Aug. 29 at the Roman Arena)
Ravenna - 2 nights
Arezzo - 2 nights (Jousting Festival on 1st Sunday of Sept.)
Montepulciano - 2 nights
Siena - 1 night (I've been to Siena twice; this is mostly to break up the transportation leg, plus I'm traveling by myself and thought it would be nice to step into a familiar town)
Lucca - 4 nights (thanks for the cooking class & concert ideas, Melissa!)
Milan - night before I fly back

Wow. Fantastic job Jean. I’m very jealous of what I’m sure will be a wonderful trip.

A few more updates. Thank you for your recommendations!

Fly into Milan.
Stresa - 3 nights (Stresa Music Festival - ends Sept. 1) My last night will be staying in a boutique hotel on Isola Bella!
Milan - 1 night (switched to Hotel Berna)
Verona - 2 nights (Aida opera Aug. 29 at the Roman Arena)
Ravenna - 2 nights
Arezzo - 2 nights (Jousting Festival on 1st Sunday of Sept.)
Montepulciano - 3 nights (added day to Montepulciano; eliminated Siena since I've been there twice)
Lucca - 4 nights
Milan - night before I fly back (hoping to reserve a ticket for La Bayadère ballet w/ Moscow Bolshoi Ballet at La Scala)

Activities that sound fun so far besides those focused on music, art, museums & photography: renting an e-bike in Montepulciano, a cooking class and biking the wall in Lucca. I'm open to other ideas!!

Love, love Lucca. One of my favorite places. I took a cooking class there. Bought my favorite leather purse in Lucca. Let me know if you want hotel and restaurant recommendations.
Siena is also a fav....but you have been there. Also, I love Stresa......love Lake Maggiorie area. I would recommend a boat ride or drive up to Cannobio. My favorite town on the lake.

Nice job!! I hope that you're enjoying your trip!

Hi, Jean,

Nice trip...suggestion re Cremona,
I haven't been for several decades, but lived there, part time, in the 80s. Lovely town, can get quite foggy from the Po River, usually in the fall, though.
The town breathes violin makers, and for that is fascinating. Lots of luthiers, and students studying with them from other countries. My favorite time was late afternoon, sitting with a glass of prosecco and watching the declining sun change the colors of the marble on the duomo. A great town for relaxing. And cheese!

1. I agree with the post that suggested flying out of Pisa from Lucca, since you can change at Pisa Centrale to a train that goes right to the airport, at least you could two years ago. However, Florence has a Navetto from the central train station that goes to the airport, so not much of a problem there--it really depends on the best and fastest connection back to Seatac. (I'm in Western Washington, too!) Lili

Hi Lili, thanks for your comments. Living in Cremona with all of the musicians and the backdrop of an Italian city must have been wonderful! Unfortunately, it didn’t make the final count....which just means it’s on the list for the next time I’m able to go to Italy. I’m sad that I won’t be stopping at the Parma Cathedral, too, on this trip but excited for new places to visit.