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Italy 2019: Sicily/Sorrento/Amalfi/Pompeii/Rome, Orvieto/Tuscany/Siena/Florence/Cinque Terre/Milan

My wife and I traveled in Italy for 3 weeks in Aug-Sep 2019. This trip report is in 7 parts, connected as replies to this Part 1. This was our first time together in Italy. Itinerary:

  1. SICILY - CANTANIA 2 nights, with visit to ORTIGIA. – Part 2
  2. SICILY - TAORMINA 1 night. – Part 2
  3. SORRENTO 3 nights, with visits to the AMALFI COAST, POMPEII, NAPLES. – Part 3
  4. ROME 2 nights. – Part 4
  5. ORVIETO 2 nights. – Part 4
  6. Near MONTEPULICIANO 3 nights, with visits to PIENZA, MONTEFOLLOCINO, near MONTALCINO, wineries, an abbey, etc. – Part 5
  7. SIENA 3 nights, with visits to FLORENCE and SAN GIMIGNANO. – Part 6
  8. CINQUE TERRE (Manarola) 3 nights. Visited all five Cinque Terre towns. – Part 7
  9. MILAN 1 night. – Part 7


  • Though it was tourist season and I intensely dislike crowds, it was a wonderful trip. We hit a few crowds, but it was manageable.

  • Pre-purchasing entry to attractions and train tickets whenever possible saved time and anxiety.

  • Learning a little Italian was well worth the few magic Italian language moments. (For Italian study I used two free websites: – to learn – and – to practice and build vocabulary.)

  • Trains: TrenItalia and Italo:

o We rode TrenItalia (mostly 2nd class) and one Italo train. Both provided a good experience, and we bought all tickets in advance.

o The TrenItalia mobile app (as well as using their web site on a PC) was very useful for planning trips and buying tickets. Thanks to these tools, we never stood in line to buy tickets.

o We used TrenItalia extensively to travel between cities and only experienced one delay. During one journey between cities we had a 5-minute and a then a 9-minute turnaround between trains; we had no problem making the transfers – even though we had to change platforms with our luggage.

Day 1: On Aug 20 (Tue) we arrived at Gatwick Airport from Seattle, then flew from Gatwick to Catania. Blessed with a 6-hour layover at Gatwick, we had pre-purchased train tickets to London and back. We rode from Gatwick to London Bridge, from whence we walked 3 hours across London to Victoria Station. From there we rode the Gatwick Express back to the airport.

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PART 2. SICILY: Catania, Ortigia, Taormina. We want to visit Sicily again and see more.
We arrived at Catania airport early evening Aug 20 (Tue), staying 2 nights in that city and 1 night in Taormina before leaving by train for Naples/Sorrento.

LODGING (Rick Steve’s first Sicily guidebook came out after our plan was complete and we changed to lodgings in that book; both met expectations):

  • Catania. Manganelli Palace Hotel (2 nights). Surprisingly good buffet breakfast included, with outside seating. TIP: if walking to the bus or train station, use Vio Giovanni di Prima, one block of which is named after the Italian-American actor Tony Curtis. This lane is shaded, has limited traffic, and a broad sidewalk with sloped curbs (helpful for wheeled luggage).
  • Taormina. Casa Turrisi B&B (1 night). The central location was worth the cost.

Sicily Highlights:

  • The people. For example, in Catania we were walking along empty early-morning streets from the fish market when an older gentleman stopped us, asked (in simple Italian) if we liked his town, smiled broadly when we responded enthusiastically, and then shook our hands and wished us well before continuing off toward the market.
  • The Catania Fish Market. There were many retired gentlemen lining a pedestrian road that directly overlooks the market. When we walked up, a few of them spontaneously offered us their prime locations. The market was very interesting to see.
  • Godfather Tour. I am no Godfather movie fan, but my wife is, so we went on a private tour to villages used for filming. That and the included food stop exceeded expectations. I posted details on the forum:

Other activities:

  • Day trip to Ortigia from Catania. We took bus to Ortigia, and train for the return.
  • Greek-Roman Theatre in Taormina, and a Taormina town walk.
  • Granite and brioche at Bam Bar in Taormina, where we had both lunch and breakfast. Lunch was crowded but worth the wait. When we went for breakfast just after opening there were very few people, mainly locals.

After 3 nights, on Aug 23 (Fri) we left Sicily by day train for Naples/Sorrento. One reason we chose to go by train was the opportunity to ride the only train ferry remaining in the world; it was fun to go on-deck for the 30-minute ride across the Strait of Messina. We chose to ride second class, which was plenty comfortable. It was a fun ride, and the Italians sitting with us changed as we travelled north, some of whom we were able to converse with. TIP: It is about a 7-hour ride and food is not served on-board, so one needs to bring a lunch. Before leaving Taormina to catch the 9:19am train, a grocery store near our lodging made us simple yet very delicious sandwiches to go.

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PART 3. SORRENTO 3 nights, with side trips to the AMALFI COAST, POMPEII, NAPLES.

Arrived in Sorrento on Aug 23 about 5:30pm. Stayed in an apartment one block from the Sorrento train station. (We found the apartment on


  • Amalfi Coast tour. A relaxing, efficient way to visit three towns (Positano, Amalfi, Ravello) was Mondo Tours "Shared Tours Mondo Guide for Rick Steves". I posted our experience with our driver/guide Vincenzo on the forum:
  • Pompeii. We spent one morning visiting the ruins at Pompeii, and then went to Naples for lunch and a walkaround. We decided to skip a visit to the Naples Archaeological Museum as the Pompeii visit was enough. Arriving at Pompeii by train shortly after 9am opening—before it became crowded—we used the Rick Steves Audioguide. That guide was very effective. The ticket office was out of the free maps, so we used the map that comes with RS Audioguide. We saw another couple who were also using Rick’s audioguide, and a person who had rented the ticket office’s audioguide came to us for assistance in finding his way around.

Other activities:

  • Naples. After our morning at Pompeii we took the 11:37am train from there to Naples. Our main objective was pizza. Both pizzerias we had chosen from the Rick Steves guidebook were closed for vacation, so we found a pizzeria on our own and enjoyed excellent pizza with beer. After doing some of the RS walk, we walked to the waterfront and took a ferry back to Sorrento. It was a pleasant town walk from the Sorrento waterfront up to our lodging near the train station.
  • David’s Gelateria. As described in the RS guidebook. Excellent gelato with varied flavors, with friendly service. It was near our apt, and we had their gelato three times.

NOTES on the Circumvesuviana train. We were told by a local that the people in the area refer to this train line sardonically as “a very special local train.” Though we never felt unsafe, we always chose to ride the first or second car to be near the driver.

  • RELIABILITY. Due to occasional outages and unannounced short-term strikes, our lodging manager advised us to take an earlier train on the day of our departure than we had planned to ensure we arrived in Naples on time for our train to Rome.

  • BUYING TICKETS (at Garibaldi Station). Unless one is buying multiple tickets, the cashiers at Garibalidi will NOT accept 20 Euro or higher notes. We witnessed one unfortunate Italian woman who protested and begged loudly to no avail.

After 3 nights, on Aug 26 (Mon) we left Sorrento, taking the Italo high-speed from Naples to ROME.

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PART 4. ROME 2 nights, ORVIETO 2 nights.

Arrived Rome Termini Station on Aug 26 about 12:35pm. Bought 48-hour ROMA Pass at a station kiosk, then walked 15 min to our lodging.

LODGING: Il Rosario in the Monti area, managed by the Dominican Sisters – from the RS guidebook. Peaceful stay with breakfast – and a midnight curfew. Internet speed via Wi-Fi from the room was a bit slow, but usable. Walking distance to most places, with bus stop for Vatican nearby.

Useful tools:

  • 48-hour Roma Pass was a good value for us, due to free entry to one site and for ease of bus-riding. [edited based on user "Kathy" helpful reply.]
  • The Probus Rome mobile phone application was useful in using the Rome bus system.

Rome Activities: Almost everything was a good experience:

Aug 26 (Mon). Rome Arrival.

  • We checked into Il Rosario about 1pm, and then had lunch at nearby Barzilai Bistrot. Solid fare among workers and families.
  • From 3pm to 5:45pm we toured the Roman Forum and Palatine Hill. The Roma Pass provided fast entry, and we used the RS audioguide in the forum.
  • Next walked part of RS’s Dolce Vita Stroll, going to Spanish Steps and then to (very crowded) Trevi Fountain. Dinner at Barzilai Bistrot.

Aug 27 (Tue). Rome.

  • Did early-morning tour of Vatican Museum, Sistine Chapel, and St. Peter’s Basilica, leaving lodging at 6am to catch bus. Excellent tour: my review is posted on the forum:
  • We finished the tour about 11:30am and walked to Campo de’ Fiori. There we had lunch at a restaurant we happened upon, Osteria dei Cappellari. The stern waiter explained the Roman selections, the high quality of their house-made pasta, and the fact that they used Pecorino cheese (“not Parmesan” he sniffed). Excellent fare, and the server’s expression melted into a beaming smile when my wife praised the food.
  • From Campo de’ Fiori we walked the RS Heart of Rome Walk, stopping at the Parthenon – where we used the RS audioguide, and arrived at our lodging at 4pm.
  • We walked to the 7:45pm meeting place of our Colosseum Night Tour. It was a disappointment. I had a good previous experience visiting the Colosseum during the day, and we both had good experiences visiting Roman amphitheaters in France and Croatia. My review is posted on the forum:
  • After leaving the Colosseum at 10:20pm we walked back to Monti area, had a light dinner, and were back at Il Rosario before the 12am curfew.

Aug 28 (Wed). We walked to Rome Termini Station, departing on Trenitalia at 10:30am and arriving at Orvieto at 11:43. (We purchased the tickets before we arrived in Italy)

ORVIETO. The 2-night stay was wonderful. We dropped a day trip to Civita to just spend the whole time relaxing in Orvieto.

LODGING: Affittacamere Valentina from the RS Guidebook. We had the Alva Room: very clean and comfortable. In the morning we could hear the families across the narrow street starting their day.

The top highlight was dinner at Hostaria Posterula, which I found in the Italian slow food guide “osterie d’Italia guida 2019”. Review posted on forum:

Some other activities – all enjoyable:

  • Aug 28 (Wed). Arrived at Orvieto at 11:43am. Lunch at Enoteca al Duomo. Visited the Duomo, Emelio Greco Museum, stores. Dinner at Hostaria Posterula.
  • Aug 29 (Thu). Tower of the Moor at 10am opening. St. Patrick’s Well and small battlement over city entrance. RS Orvieto Walk. Chiesa di Sant Agostino. Pozzo della Cava (Caves). (after dinner) RS Rampart Walk.

On Aug 30 (Fri) we left Orvieto for Tuscany.

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PART 5. TUSCANY: near MONTEPULCIANO 3 nights, with visits to PIENZA, MONTEFOLLONICO, etc.

Aug 30 (Fri): departed Orvieto. While walking to the funicolare we bought a picnic lunch at Pane & Cucina di Moscatelli. We then picked up a car at the Hertz office near the train station and were on the road by 10am.

We took the tollway, exiting at Chiusi from whence we did much of the Rick Steve’s Heart of Tuscany Drive. During the drive we stopped at Abbazia di Sant’Antimo in the countryside. Peaceful and interesting with few visitors. After spending about an hour inside the church buildings we had our picnic lunch on the abbey lawn with a beautiful Tuscan view; we had the lawn all to ourselves.

Afterwards we drove 5 minutes to the Ciacci Piccolomini d’Aragona winery, where we were the only people in the tasting room. Attractive grounds and interior.

LODGING. We arrived at our one-family agriturismo, I Roseti, near Montepulcino at 5:30pm. Exceptionally clean, and we were greeted with a bottle of wine, fresh fruits from the farm, and more. Outstanding atmosphere for our first 3 nights in Tuscany; I posted a review on the forum:

We had dinner a few minutes away at a restaurant from the RS Guidebook in Monticchiello. We were very lucky to get one of the 3 tables on the edge of the terrace with view of sunset; without that we wouldn’t have found it worthwhile. After dinner a young boy on a bicycle rode up to us while we were walking by the church and said something in Italian; after I replied “non parlo italiano” he gave us a friendly “Ciao!” and pedaled away into the darkness.

Aug 31 (Sat). We spent the day in Montepulicano. We parked (free) at San Biagio Church; we were unable to enter the church as there were weddings all day. One of the weddings was attended by (apparently) carabinieris in gorgeous 18th century style uniforms. We walked up to Montepulciano from the church, entering via the Porta di Grassi; from there we basically did the Rick Steve’s Town Walk in reverse. A highlight was the winery De’ Ricci Cantine. After walking through the storage caves, we emerged at the tasting room. The server poured us two wines to taste and then asked if we wanted to try anything else. My wife asked about the dessert wine; the woman glanced over at a man sitting at a computer. He silently nodded without looking up, and she pulled a precious bottle from a cabinet and poured us a taste in special goblets. Very good; we bought a bottle to take home.

On the 4-minute drive back to our agriturismo we bought dinner supplies from a grocery. We prepared dinner at the house, and then went to sleep to the chirping of crickets.

Sep 1 (Sun). We visited Pienza and Montefollonico.

The breakfast we made included excellent fresh eggs that the I Roseti agriturismo host, Gianni, had given us the night before warm from his chickens. We then drove to Pienza.

Pienza was crowded, but we found parking in a residential area and walked the 10 minutes into the walled city. While we were there a parade of people in medieval uniforms and playing music marched down the main road to the town square. There they performed with flags they were carrying, twirling and throwing them about. It was fun.

Montefollonico, in contrast, was quiet with few visitors. Highlight was the ceramics studio located in a centuries-old former church. The woman artist had some wonderful pieces, and we purchased six small unique tiles still-warm from the kiln.

We returned to this village in the evening to have a fun dinner at Ristorante 13 Gobbi, recommended by our agriturismo host.

The next day, Sep 2 (Mon), we left for Siena.

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PART 6. SIENA 3 nights, with visits to FLORENCE and SAN GIMIGNANO.

We were happy to stay in Siena with a day-trip to Florence rather than vice-versa. We found Siena relaxing and pedestrian-friendly, and Il Campo was gorgeous in the sun of the late summer days. No street peddlers in Siena: it is not allowed.

Sep 2 (Mon). Moved to Siena, with a stop at San Gimignano, etc.

We drove from the agriturismo Il Roseti at 9:15am, heading to a winery near Montalcino that our host, Gianni, had recommended. En route we made a 30-minute stop at the hotspring Bagno Vignoni. Not a must-see, but it was a pretty area.

We arrived at Uccelliera winery for our 11am appointment; it proved to be our most enjoyable tasting, anywhere, to date. One other couple joined us for the 90-minute tasting of 11 wines. Our host was a charming winery executive named Giuseppe. The tasting included the estate’s olive oil with bread. Before the tasting we awaited the other couple’s arrival while standing on a terrace admiring a view of the vineyard. An elderly woman (mother of the owner) struggled slowly over from the house to the terrace and settled in a chair in the shade. My favorite Italian language moment of the trip then occurred: gesturing toward the vineyards, I turned to her and said “Molto Bella!”. Her expressionless visage brightened into a beautiful smile and she replied with a hearty “Grazie.” NOTE: The last stretch of the road to the winery is down a short gravel road; If using a navigator it would be best to download an off-line map as the cell-phone coverage is spotty. The winery’s website:

After the tasting we drove to San Gimignano; we found it rather touristy but enjoyed 45 minutes walking the village. Afterwards we dropped our car off at the Hertz office in Siena. From there we walked 15 minutes to the train station, rode the escalators up to Siena, and then walked to the apartment we had found on, arriving at 6pm.

We had dinner at a place from the Italian slow food guide “osterie d’Italia guida 2019”, La Sosta di Violante. Great food and good service in a rustic ambiance. I posted a review on the forum.

Sep 3 (Tue) was spent sightseeing in Siena, and we also stopped at Piazza Gramsci to purchase round-trip bus tickets to Florence for the next day. We did the RS Siena Walk, including visits to the Duomo, the Duomo Museum, the Crypt, and the Baptistery. We had lunch and bought food for dinner at the Agrario Grocery.

Sep 4 (Wed). Day trip by bus to Florence, mainly to visit the Uffizi Gallery and the Accademia using pre-purchased reservations. Arriving at 8:25am, we walked to the Duomo (but did not enter), and from there did the RS Renaissance Walk.

Uffizi Gallery: We used our morning reservation to visit the gallery from 10:30am to 12:15pm. It was a bit crowded, but most people were considerate. Yet again, the RS Audioguide worked well.

LUNCH: Caffeteria delle Oblate. This place behind the Duomo was recommended by a friend whose daughter had attended school in Florence. The cafeteria is inside the university grounds. Uncrowded, close view of dome from the covered terrace, friendly fast service, and solid Italian fare at an economical price.

Accademia (David): We used our afternoon reservation to visit from 2:30 to 3:30pm, using the RS Audioguide. Exceeded expectations to see David in that setting.

Before catching a bus back to Siena we walked to the San Lorenzo market, but found nothing of interest. After walking the streets a bit more, we caught the bus back to Siena and decided to have dinner (again) at La Sosta di Violante.

The next day (Sep 5) we left by train for Cinque Terre.

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PART 7. CINQUE TERRE (Manarola) 3 nights, MILAN 1 night.

Sep 5 (Thu). Moved from Siena to Cinque Terre, riding 4 trains, departing Siena at 10:41am and arriving in Manarola about 2:30pm.


Despite visiting Cinque Terre during peak season and my hearty dislike of crowds, we had a fun experience. We encountered excessively heavy crowds only a few times, and that was on a Saturday. The local service people provided very good service, but we saw more tired expressions than smiles.

LODGING: We stayed at the Conchiglia Apt of Da Paulin (from the RS Guidebook) in Manarola. It was nicely located across from a small grocery co-op and didn’t require climbing a bunch of steps to reach it. (NOTE: there is an easy and fast back pedestrian route to the restaurant Trattoria Dal Billy from the apt; no need to walk the long way up the road.)


  • We had pre-purchased a 24-hour Cinque Terre Treno pass before arriving in Italy. Totally worth it, even if not hiking. It allowed unlimited rides on the train linking the Cinque Terre towns and use of the hiking trails, station shuttles, and station Wi-Fi. The second morning we purchased additional 24-hour passes. We should have just pre-purchased 48-hour passes for our 3-night stay.
  • The free Parco Nazionale delle Cinque Terre mobile app was very useful in understanding the trails. For example, the photos of the trailheads helped us find the entrance to one trail.
  • If travelling in peak season strive to reserve lodging early! Our #1 desired apt was already taken 13 months before we departed; our #2 choice was still available.


  • Trail: we hiked the Corniglia-to-Vernazza trail one morning, beginning the hike at 8:30am. There was almost no one on the trail until shortly before we reached Vernazza, where we encountered sweating folks climbing the stairs at that end as they began their hike. Two learnings: (1) start the hike early; (2) start the hike in Corniglia.
  • Vernazza Opera. I am not an opera fan, but really enjoyed the intimate Vernazza Opera. The old former church where it is held is quite small and was only half full. Nice experience.


  • We visited all 5 Cinque Terre towns during our stay, including Corniglia 3 times. The only time it got crazy crowded was the weekend (Sat) after 10am. Riomaggiore waterfront was a veritable mosh pit as a ferry and (our) train disgorged mobs into the area at the same time.
  • The last night we had dinner at Trattoria Dal Billy in Manarola. It was ok.

Sep 8 (Sun). Move from Cinque Terre to Milan. We departed Manarola at 10:44am and arrived at Milano Centrale at 1:53pm. Decided to ride first class from Levanto to Milano Centrale as the price differed little from 2nd class. Ride comfort was similar to what we had experienced during our 2nd class rides. Our lunch aboard train consisted of a sandwich and salad from the Manarola co-op grocery.


We arrived in Milan at 1:53pm. Before walking across a street to our hotel (NYX Milan) we confirmed location of the platform from which our next-morning Malpensa Express train would depart for the airport; we were glad to have checked, as the platform is located a bit farther “back” than the other platforms.

We took the subway to the Duomo station, spent a few hours walking about the Galleria and the “fashion” stores nearby, and were back at the hotel a bit after 6pm.

Dinner was at a nearby restaurant we had found in the Italian slow food guide “osteria d’Italia guida 2019”. By chance it was located one subway station away (Giao) from Milano Centrale and was open Sunday. Named Ratana, it was a decent “last supper” for us in Italy. As we walked back to the subway station after dinner we were pleasantly surprised by a free outdoor classical concert taking place in a park.

The next morning, Sep 9 (Mon), we caught the 7:55am Malpensa Express and began our return to Seattle.

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5260 posts

Thanks for sharing your trip report, it sounds like you had a wonderful time exploring many special places in beautiful Italy!

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16110 posts

Nice report, Jeff! Lots of useful info, and it sounds like it was a great trip!!! 🙂

Just one comment on Rome for first-timers?

48-hour Roma Pass was a great value, not only for free entry to one
sight but for ease of riding the bus (for our one bus ride).

I wouldn't personally have purchased € 32.00 passes just for the Forum/Palatine (you bought a separate night tour for the Colosseum) + a single bus ride. The advance Forum Super Pass ticket costs just € 18.00 (including booking fee) and allows for open entry, meaning you don't have to reserve a specific entry day/time. A single bus (or metro) BIT ticket is only €1.50. Total: € 19.50. You might even have found the ticket line at the Palatine entrance short enough to buy a day-of ticket for € 16.00 without much of a wait but I understand not wanting to take the risk.

If wanting to visit the Colosseum too, an advance, timed-entry ticket is also just € 18.00 and includes entry to the Forum/Palatine on the same day. It doesn't include special Forum/Palatine SUPER sites but with this ticket you can buy that additional piece at the entrance for € 4,00.

IMHO, as the Roma Pass now requires making a timed-entry reservation for the Colosseum, it doesn't provide quite the value/convenience it used to.

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Kathy, thank you for the rich economic analysis about the ROMA Pass. The peace of mind was worth it to us (ease of riding bus, line privileges), though it surely might not be for others. As it was we didn't need to ride the bus as much as expected. If I can find a way to do it within the character limitations of the forum, I'll made an edit recognizing your point. Have a great day!

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6378 posts

Thanks for a great report, Jeff. Love the detail!

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16110 posts

Jeff, I'm not surprised that you didn't need the bus as much as expected! Rome is a city that's most fun when experienced on one's own two feet, eh? Also helps work off all that pasta and gelato! :O)

No criticism at all intended about the passes; we all travel differently and that's cool! Just thought I'd add the "economic analysis" (LOL!) for folks traveling on really tight budgets. For a family of 4, all of whom are over age 17, the cost savings for the same scenario as yours would be substantial, and with the same avoidance of ticket queues. Anyway, again, great job with the report!

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Kathy: the content of your reply was helpful, and I don't take it as criticism at all. It adds value to the report and is appreciated. Jeff

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3961 posts

Grazie Mille for sharing your Italy journey. Well done! It’s reports like yours that inspires us to keep returning to Italy. Back to Sicily next fall!

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1057 posts

Jeff, this looks like a brilliantly planned and executed trip, with lots of fun and enough down time along the way. I have previously read most of your reviews, but I really appreciate the time you took to pull this together (and feeling some guilt for not writing up my trips.) The detail is just right to help others and really show us the arc of your trip. Well done, when is your return trip (ha)?

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7463 posts

Jeff, I really appreciate your excellent trip report, including links to additional info, also. Some parts of it brought back fond memories and other parts gave me ideas for my Italy trip this year.

Thanks so much!

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582 posts

What a great trip report! I like the way you summarized each day and included interesting tidbits. Very easy to read the way you laid it out. I've been to several of the places you discussed, and now of course I want to go back! Well done.

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3903 posts


Excellent trip report. I greatly enjoyed reading it. Thanks for sharing your experience with us.

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Thank you for the great report...will be very helpful for our trip.