Click HERE for the main Italy page!
Day One
As much as I enjoy cities, I wasn’t ready to give up my coastal vacation vibe just yet. That’s why I was very excited to go to Venice after Milan! We got to our hotel after a three hour drive and a 25 minute boat taxi. Thankfully our hotel was near the waterfront and not tucked into one of the many corridors in Venice that are only accessed by walking. Obviously walking is a very non-American thing, but Venice takes it to another level; you really need to pay attention to the maps, otherwise it’s easy to get turned around. And keep in mind that not every canal has a bridge to connect them.
Like with Lake Como, we arrived in Venice in the early afternoon. This gave me a moment to change from my travel clothes (which was re-wearing a tee shirt and pants) into a proper fit, that you can see here. This leans a bit more into the euro-Esquire Man look with a bit of travel added. I got a yellow plaid sportshirt (cotton, not rayon) tucked into grey pleated shorts that are surprisingly from Uniqlo. A beret and my navy DB keep things sartorial while being contrasted by the white sneakers. I think the look leans into the resort vibe that I want.
My late lunch was absolutely hilarious. Isabel and I went to a local place where I decided to have a pizza. I was intrigued by the “Patata” pizza, which I assumed was similar to the sweet potato pizzas I’ve eaten in LA. I was dead wrong. This was simply a margherita pizza with straight up french fries on it. It wasn’t horrible, but I could feel passerbys laughing at me. I think I deserved it.
I then joined Camden and Nicholas for a gondola ride around the city. Isabel decided to take a break that day due to all the constant travel and the fact that she had a job interview later that evening. It was fun third wheeling with them (I kid, they were very nice and made me feel welcome), getting to go through the canals and taking photos of the different buildings for an hour. It was a good thing it was the three of us, as the price for a gondola ride is a flat: €160.
Once the gondola ride was finished, we explored the touristy shops around the hotel before picking up Isabel for dinner with the family. . Nick (Richard’s eldest son) and Jess had their own plans but we were instead joined by Ty (Richard’s youngest son), his girlfriend Adri, and their friend Thanassis; it was these three that Isabel, Camden, and I sat next to during the wedding dinner. During the evening, we got to know them a little bit more and were delighted that we shared similar tastes in music as well as in what we liked to do for fun. We all decided to make plans to hang out, both on this trip and once we were all back in LA.
Day Two

The next day was full of walking. Not just to get around, but because it was our guided walking tour of Venice! We met our guide outside of our hotel and he immediately got to work sharing every nugget of information about this old city. It was here that I learned that Venice was independent for a long time and that Italy is actually young for a country.
He took us through everything, from the Doge’s Palace and St. Mark’s cathedral to seemingly random (but historical) buildings after crossing the Rialto bridge. Even though this section contains the most images, I’m sorry to say that I can’t remember every piece of info, which is why this section may be the shortest.
For the walking tour, I again went back to my vacation uniform but with a few new twists. Firstly, it was time for me to wear my sandals. Sockless, I might add, which honestly ended up being a bad move since my feet were incredibly sore after a full day of walking. The other move was finally giving my suit jacket a rest by wearing my red overshirt; I had previously only wore it during the plane and during the travel days since it’s quite a practical piece. However, it is also a stylish garment, which made for a louche piece of outerwear for the day.
Once the tour was over, Isabel and I went off to do our own thing. Our first stop was actually backtracking to Libreria Acqua Alta, a bookstore that was featured during the tour; we had also heard about the bookstore during our pre-trip research. It’s known for the plethora of cats that relax among the shelves but unfortunately we didn’t see any during our visit. We did notice that they had a cool selection of vintage books as well as a “free” spot for photos on a tethered gondola. I’m glad we found it, since Isabel had to miss the gondola ride during the previous day.
We then went to check out two exhibits from the Pinault Collection. This would be the most “modern” of the art we would check out during this whole trip. The priority was “Chronorama”, a photography exhibit curated from the 1920s-1980s Conde Nast archive, which was held at the Palazzo Grassi. It was very interesting to see how the publication’s photography curation had changed with each decade. Plus studio photography is something I don’t really get to do, which was really inspiring to me.
We then trekked further down to the Punta Della Dogana for “Icones”, which was their contemporary exhibit. This was honestly one of the best exhibits I’ve been to simply due to the curation. Each placard explained the artwork thoroughly while tying it back to the main theme. I’m a big fan of thematic continuity, so it was great to see that POV preserved instead of just being a collection of things (like the Broad).
It was getting pretty late after the museum visits and so the last thing we did before dinner was check out a vintage store. There wasn’t much in the way of regular menswear, which is why you don’t see much of that covered here. The vintage store was actually pretty good, containing a lot of suede jackets (which apparently are common in Italy) and a few sportcoats made in Italy. There was one that felt very early Armani with its slouchy fit, long length, and open weave, but it was just a bit too long for me to wear; plus I already have plenty of plaid sportcoats.
We said our thanks to the shopkeeper before we went off to dinner. I had my first carbonara here and had a side of potatoes. These potatoes were better than the pizza-french fries but not much better because they were boiled and not roasted. I’ve really gotta ask questions next time.
To celebrate Isabel’s interview, we all went out for a drink at a bar. And by we all, I mean, Isabel and I, Camden and Nick, and Ty, Adri, and Thanassis. I really like it when you get to hang out with friends while on vacation! We went to a bar called Bacaro Jazz which was honestly a misnomer because it wasn’t a jazz bar. The decor, menu graphic design, and drink names were clearly jazz themed but they were blasting 90s-Y2K rock on the speakers. I even heard Journey come up.. As you could probably expect, this place was popular with American and non-Italian tourists, but that made for some fun people watching. It was honestly a fun time simply because this was the first bar bar we’ve been to that wasn’t just having a glass of wine outside of a trattoria.
The only downside was that we had to weave through the corridors for nearly 30 minutes before we made it back home. Not a great move after an already long day of walking (and drinking). We would need our rest before heading off to Florence.
Click HERE for the main Italy page!
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