Went for the food, came back with a ring! Our Italy engagement trip

Today marks two months since I became JC's fianceé. That statement in itself is an achievement: March 5th is now officially our anniversary date, because we are both just terrible at remembering dates and could never celebrate anniversaries before.

Although we haven't started planning yet, every time I gather in a group with friends, family, fellow wedding vendors, or clients, our engagement and upcoming wedding are unavoidable topics of conversation. I've worked at weddings for over a decade as a single woman, so I guess it's amusing to finally see me taking the bridal journey that over 500 clients of mine have done before me. 

We've already started dreaming about the event, sharing our priorities and expectations, and getting excited about all the chaos that's to come. I wanted to kick things off with our Italy engagement story and share some Venice Engagement portraits done by my friend and right-hand assistant Jorge Cosme.

Our Culinary Italy Trip

Although we've known each other all our adult lives, JC and I have been dating for around three years after he came back to Puerto Rico from med school.

These three years have been packed with love, friends, family, and work. My photography business has been thriving under a post-pandemic wedding boom, and he has been taking great strides in his medical career. So on the verge of burnout, we squeezed a culinary trip to Italy into our busy schedules.

We daydreamed for months about our Italy trip without any energy to plan for anything other than restaurant reservations (him) and train schedule (me). And still, it was perfect. Many friends and family had asked me about the places we visited, so I'm gonna just use this post as that trip review and send them the link everytime someone asks! If you'd like to only read about the engagement, skip until the third stop! 


First Stop: Roma

In Rome, we began our adventure, staying at the Princeps Boutique Hotel, just a few blocks from Roma Termini, as we'd later start moving North by train. We had both been to Rome before, so although we had plans to visit landmarks, we didn't make our schedule around these visits. 

Late February is an excellent time to travel: although the weather is not what you envision when traveling to Italy, it was cold but comfortable for our two Caribbean bodies. I was still a bit overdressed, as my work keeps me mostly outdoors in 90-degree weather, I'm not used to anything below 75ºF. The sites were empty compared to when we were there pre-COVID Summer.

I had the idea to visit the landmarks at night. So, on our first night, we stumbled upon Drink Kong, an award-winning bar with an incredible cocktail menu, on our way to the Colosseum. The next day, walking towards la Fontana de Trevi, we found Fincato, la Casa del Habano, one of JC's bucket list items, as he is quite the cigar aficionado. 

Perks of being a partner to a photographer: always getting the coolest photos of the trip.
Perks of being a partner to a photographer: always getting the coolest photos of the trip.

That afternoon we also visited the Altar of the Fatherland. I had a fleeting thought that JC would propose there since he acted weird and romantic when we were up high. 

Later that night, we had our first actual culinary date at Alfredo alla Scrofa. Being famous for inventing fettuccine alfredo, I expected it to be just a gimmick, but it was a great dining experience. We tried their tasting menu with wine pairing, something we did on most of our Italian date nights. 

In Rome, we also fell in love with Gallo Matto. On a review left on a napkin stapled to a wall, I read that someone from Texas said we had to try their chicken gnocchis. They were so good that it was the only restaurant we visited again on our last supper before our flight back home. In Rome we also started our tiramisu challenge, we are still debating which restaurant had the best desserts.

Second Stop: Firenze

We took the fast train north to Florence, which was the city that excited JC the most. We stayed in Hotel Croce di Malta, which had the city's best views and a balcony perfect for JC's sunset cigar. After that, we walked to Ponte Vecchio, and as recommended by a friend on Twitter, we had lunch on the rooftop of Osteria delle Tre Panche. 

We had our first Aperol spritz of the trip on the rooftop since it got pretty warm. I was excited about finally taking off all those layers I'm not used to wearing. I treated JC to a meat lover's dinner at Trattoria Dall'Oste. Although the Bistecca Alla Fiorentina was excellent, my favorite part was the pistachio cream dessert, whose name I don't remember. JC always talked about this unassuming Cuban bar where he had the best mojito ever. I thought he was romanticizing the experience as we all do when we find a fellow compatriot on our travels. Finally, we found the mythical bar, and its name was Sabor Cubano. They did have the best mojitos ever. 

Hotel Croce di Malta had a great rooftop for enjoying the city at sunset.
Hotel Croce di Malta had a great rooftop for enjoying the city at sunset.

We explored the Mercato Centrale the next day, stood in awe of the Duomo's beauty, and dedicated the morning to visiting Museums. On our way out of the Museo Nazionale, we walked into Osteria Filetto d'Oro and had the best casual lunch of our trip. JC thinks they also had the second best tiramisu of our trip.

We walked a lot that day to make room for the most expected night of all the trip: our dinner night at Santa Elisabetta, a Michelin 2021 restaurant at the Brunelleschi Hotel. It was everything I could ask for and more. It was the most romantic night, and that's when I thought JC would never propose on this trip. "Dang, I should've brought a ring to propose to him myself. Maybe I'll buy one in Venice, I remember many jeweler shops there."

Third stop: Milan

We stayed in an Airbnb in the Navigli Canal; I killed it with all the lodgement reservations because they were cozy, beautiful, and ideally located! The Navigli Canal is packed with bars, restaurants, and all kinds of shops.

In Milan, we did a lot of window shopping, went to the best-stocked Casa del Habano, and kept on eating and drinking. The first night we took a cab to Zello at the Four Seasons hotel, where we also took a tasting menu with wine pairings. After that, we walked to the Duomo at night, and it was majestic. Milan was buzzing with local nightlife, not just for the tourists. Eventually, a spontaneous party started at the piazza, so we left on the search for the perfect, cozy bar for 30-somethings whose feet hurt. Later on, JC told me he wanted to propose that night before the youngsters came in dancing. We're elder millennials, indeed.

The next day we woke up early and had a fun morning out in the Sunday market, visited thrift shops, and explored the Brera District. It was probably my favorite day in Italy so far, as we saw the city alive and not just what tourists would visit. That night we walked to Sadler Restaurant, our next culinary date, where we also had a fabulous 5-course tasting dinner with wine pairing. 

That night I was just exhausted from all the daytime walking, so I wanted to rent a cab when it was time to leave. JC wanted to walk. I was slightly irritated but went on with it, as the walk would help all the heaviness of the late dinner. 

An unexpected proposal in Milan

We arrived at the Navigli canal, and it was full of people. JC wanted to keep on exploring, but after a walk around, I convinced him I was too tired for anything else. That was our last night in Milan; he was anxious. I walked into our building, and as I was going up the stairs, he held my arm. I turned around, and he was on his knee. I will never forget his cute face.

I burst out laughing, and I couldn't control it. He surprised me, as I was so tired I wasn't thinking about a ring anymore! He eventually got up and tried to put on the ring, but I reminded him: "you haven't asked me anything!"

He got back on his knee. 

  • "Will you marry me?"
  • Obviously! 

And I kept on laughing uncontrollably for many minutes. We eventually called my mom and my best friend, Angélica. Mami didn't expect it, but Angélica was in on the surprise, as she helped pick the ring, just as I did for hers.

There are no photos of this moment. Jose Carlos assumed that if he booked a proposal photographer just like my clients do, I would figure it out before it happened. Although we hadn't talked about a proposal, I suspected something might be going on by weird questions and comments made by our friends.

Still, I noticed I was getting anxious about something I had no control over, so I stopped thinking about it. It was great that he waited until the last legs of the trip so my mind was distracted by everything happening around us.

Fourth Stop: Venice for Jorge's Proposal and a Dolomiti Daytrip

For years, I traveled as a single woman on different adventures, most of them out of the cities and into the great outdoors. I didn't want to leave Italy without having that experience with JC, something he hadn't done before. So I booked the last leg to Venice, which is only two hours from the Dolomiti region, where we took a private day trip with Esse Group to the Ampezzo Dolomites and Cortina.

She drove us north through the Prosecco countryside, gave us a lot of information on the history of the region, and as we got closer to the Dolomites, also talked to us about how the first world war ended on those mountains. It was a beautiful, scenic drive, and I enjoyed every minute of the conversation!

The views from the Rifugio on top of Mount Lagazuoi
The views from the Rifugio on top of Mount Lagazuoi

We visited Auronzo di Cadore, walked over a frozen Misurina Lake, and finally took a cable car to the ski Rifugio on top of Mount Lagazuoi. The views at 10,000 feet took our breaths literally and figurately, so we stopped for a hearty alpine lunch before going back down. Our tour operator drove us down to Venice, where we met Jorge and unsuspecting Leslie for dinner a few hours before their own engagement at a Venetian sunrise.

After finishing Leslie's surprise proposal that morning, we switched places, and Jorge took some portraits of JC and me with my camera. I love these images as we never have good photos taken of us, and this trip was more memorable than I could've ever imagined. After winning in life by getting empty Rialto Bridge portraits, we wandered the Venetian mazes until we found Osteria al Cicheto. A last little culinary gem away from all the touristic buzz near Piazza San Marco.

I will never forget those two weeks and all the little moments that made it memorable. Thanks to Jorge Cosme for the happy photos from our mini engagement session. Thank you JC for making the most amazing trip even more memorable by becoming my forever sidekick. Te amo.