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Boston to Milan, Bologna and Venice - Trip Report

My daughter wanted to go to Venice for the Bienalle and I wanted to see Italy. My partner has been to Italy so joined for the adventure. My daughter has traveled throughout Italy on her own as well so had some experience. We travel together often; Caribbean, Denmark, Spain, Sweden and beyond. We love boutique hotels and low key off the beaten path. We booked air on Air Canada Boston to Milan and Chicago Milan via Montreal. We booked in May and secured Premium Economy seats for 1100.00 We have found SAS and Iberia's PE flights were amazing so decided to try Air Canada. In short, never again.

Nov. 18-26
Our plan was to visit friends who reside near Varese, see Milan, head to Bologna so my partner could go to Ducati and then to Venice for the Bienalle as my daughter is an art curator. We stayed at Aethos in Milan, Antica Casa Zucchini in Bologna and Caneletto Apartment in Venice with Truly Venice. We also stayed with friends near Varese.

Trains
Italo - Milan to Bologna - flawless
Trenitalia Bologna to Venice and Venice to Milan - flawless
Trenord Milan to Varese - a little hurried as we needed to change stations with minutes to spare but awesome

I booked our train tickets online. It took some navigating but went well and we loved our train experience. We preferred Italo for comfort, overall.

The three of us researched food on various blogs and social media accounts. We created a Google Map Doc and Spreadsheet to insure we had our trip planned plus allowing "go with the flow " opportunities. In all 3, we walked a lot. We averaged 20k steps a day. We drank cappuccino and ate coronets (croissants) standing up at bars in all three cities. This was the highlight of our trip, meeting locals, savoring amazing coffee and eating great treats. Every experience was better than the next. We ate light, lovely lunches and a lot of cicchetti. We had one pizza in Venice that was not memorable. We had a bad meal in Milan and also one in Venice, otherwise, we loved all our dining experiences.

Weather was amazing aside from our arrival day into Venice. We wore hats, scarves and light winter wear. We were always comfortable but felt a chill in Venice. The day we arrived into Venice it was pouring rain with howling winds. it was also close to a full moon. The streets were wet with puddles but no flooding. We noticed all locals wore regular shoes. The only covered boots and ponchos were tourists.

Milan was bustling. We stayed in Naviglio which was a bit too crowded and touristy for our taste. Our food highlights were Pasta Madre, Sabbia Di Oro and Loste Cafe. We did notice the high amount of smokers in Milan. It did not mar our experience, just an observation.

Bologna was busy but not crowded at all. We walked for hours and enjoyed the historic vibe. Sfoglia Rina was our favorite meal for amazing tortellini. My partner LOVED his tour of Ducati. He took an Uber and was there for 3+ hours. He highly recommends the tour for motorcycle enthusiasts. The pro racer Francesco (Pecco) Bagnaiawas there so that was an exciting opportunity for my partner.

Venice was a dream. I have lived in the Caribbean and traveled all over the islands and parts of the UK and Europe but Venice by far, touched my heart. There was one beautiful view after another. The crowds were low so navigating the city was comfortable. We had so many great experiences as far as dining and exploring. The Biennale was amazing. We went to a few pavilions at Arsenal and the main area. The Simone Leigh sculptures blew me away. We walked everywhere vs water taxis but used private water taxis to and from the train station to our flat in Castello.

My partner speaks a little Italian and I learned some basic phrases but otherwise, we had a fine time communicating and navigating in all 3 cities. It was a fast paced trip but one that I will long remember.

Posted by
7401 posts

Glad your trip went so smoothly. Sounds as if you've got the travel thing down pat.

We too were in Venice in June, even though my wife was unable to see much of the city on her electric personal scooter. It was her third trip to Europe being mobility challenged, however she has since had surgery and should walk better in the future. We stayed by the train station--and it was okay since my wife's been to Venice many times.

I took my 10 year old granddaughter all over Venice walking as I was too cheap to pay $15 for us to step on a vaporetto. Even after 10+ trips to Venice, I still find navigating those alleys hard from time to time. Brynley asked me where we were and I told her I had no idea--and I had no idea where we were going. But we still made it back to the train station and our apartment next door. She told me she wants to return to Italy--for the food.

Posted by
760 posts

Sounds lovely Caribchakita. How nice that there were low crowds.

What was the weather like? I am considering something similar for 2023.

Posted by
61 posts

Calimom, the weather was glorious; 50's and sunny. My partner wore a hat and scarf and medium weight sweater. I wore a hat, fashionable scarf (vs wool) and thin winter jacket. My daughter wore her Burberry raincoat and a hat. One day, arrival into Venice was horrible. There were high winds, torrential rains and puddles (no flooding) everywhere. Our host wore runners. Most locals wore regular shoes. The only people wearing the colorful ponchos and shoe covers were tourists.

Posted by
2170 posts

Thanks for the report!
Can I ask what happened to put you off Air Canada?

Posted by
61 posts

S. J

Here is the long and short

For Transatlantic, we love Premium Economy. Past experiences on Iberia, SAS and Lufhansa. All three were amazing. When I did a fare search for our Milan flights, Air Canada had a great price. My daughter flew on AC to Toronto and Vancouver and endorsed it.

I realize my issues pale in comparison to the lives of others and I realize COVID has created travel challenges.

Flights were significantly delayed
Staffing on the east bound flight was limited - one trash pick up in 8+ hours, one drink service
Tight seating - the two and two Embraer from BOS to YUL had more leg room
HOT cabins, beyond bad
Dirty floors
Meals were mediocre to bad
flimsy plastic cups East bound

At YUL - Changing gates, 3 times in 2 minutes causing people to move around the terminal. Filthy bathrooms, beyond words

Arrival and departure in Milan challenging (bus from plane to terminal causing huge waits and delays due to tarmac traffic)

Arrival for transit into Canada (we were not staying in Canada) was THE most stress filled experience. No joke we showed boarding passes 5 times. We had several security checks and lines and communication was a mess. People missing connections due to delays from Milan were not supported so chaos ensued

Global Entry and Canada document machines not working properly. We were asked for our actual Global Entry cards which is not GE protocols. We had to take out all liquids and put in a special bin.

I am over it but it was my top 1 worst travel experience due to issues at YUL, AC, and Milan.

That is a short list, never again.