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Wednesday, March 12, 2025

How I Ended Up Engaged and Living on a Vineyard in Italy

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One summer I was traveling solo in Italy with my dog, Oscar, thoroughly enjoying la dolce vita in places like Tuscany, the Amalfi Coast, Capri, and Sicily, during what I called my “Successful Girl Summer”. I had just turned 35, purchased my first apartment in full, finished a handful of amazing travel collaborations, plus a few group trips, and most importantly, I was keeping up with my goal of focusing on work first that year, instead of dating. I definitely deserved a summer of indulging in Italy with my hard earned success, and definitely did not need no man to support me!

In fact, I was so over trying to find a man who can keep up with a woman who travels the world for a living, that part of my plans for the year included freezing my eggs in Barcelona! So I manifested a year of work and life success, and low key manifested only meeting someone different from my usual toxic choices; perhaps someone older for once, and financially-happy.

Anyway, I decided to randomly go to Sardinia to see the beautiful blue waters and also some potential investment properties. When I announced I was going there on social media, a woman with a travel planning company saw my post, and reached out to ask if I’d be interested in doing a last minute collaboration where she’s from in an area called Ogliastra (which is also a Blue Zone!).

The first boat trip I did along the Baunei Coast, not knowing I’d end up moving there!

That area was also where the up and coming Insta-famous Baunei Coast is, and where I had wanted to check out as well, but was leaning towards skipping it since it would require about six hours extra of driving. But it seemed too fateful to pass up! After exploring the area I first wanted to see; the Maddalena Islands and Costa Smeralda, I headed south to the little town where she was hosting me, called Tortoli.

Part of the collaboration included a sailboat ride along the Baunei Coast, which was exactly what I had hoped to do there, and it was as stunning as the photos I’d seen on social media. The other part of the tour was visiting a winery to try local Sardinian wines, since she knew I love wine, and she wanted me to show other aspects of the area besides the beaches.

But we spent too much time on the sailboat, likely due to Prosecco and drone-time, and by the time I finally got off the boat, the winery closed. Luckily, there was another one that she knew of that was open later. I tried to cancel because I was beyond tired, but she insisted, so I pulled myself together, threw on a short light blue romper and hat, picked up Oscar, and went! Because let’s be serious, I wouldn’t be me if I passed up a free wine tasting at a vineyard on an Italian island!

When I arrived, I felt awkward strolling up solo to a wine tasting, and felt like the family sitting outside was looking at me like a crazy tourist. There’s a lot more funny moments and thoughts to this moment, but you’ll need to read the extended version of this story on my blog here.

Anyway, long story short, a guy with thigh tattoos walked by, and a few minutes later, my server was asking me out for him. At first I said no, because I thought he was asking me to join him and his family for the dinner they were currently having. Then I said I would meet him for a drink later. Oh, and she kept mentioning he was “the boss”, but all I thought was ‘Don’t blow up this man’s ego!’ and brushed that off, assuming maybe he was the manager of the cellar or something.

Sardinia winery Alyssa Ramos @mylifesatravelmovie

A year later having our engagement party at the winery!

I accepted going to drinks (barely because I almost fell asleep), and then his invitation for lunch the next day, which is when I put it together that it was actually his vineyard. He made sure to make that clear despite our severe language barrier, by continuing to order bottles of his wine. I’m not going to lie, lunch was amazing, especially since it was at one of the beautiful beaches and included a lot of pasta, but I didn’t really think I’d see this guy ever again. We didn’t even speak the same language, and it didn’t seem like he was a big traveler. He tried to ask me to stay in the area a few more days, but I needed to get to Barcelona to start my egg freezing process…since I had given up hope of meeting a good man any time soon to have a child with.

But, while I was going through the egg freezing process, and for the three weeks afterwards that I was traveling in Africa hosting my group trips, he would text me every day. From the moment he woke up to when he went to sleep. He would also mention me coming back to Sardinia after Africa, or him coming to see me in Mexico, but I really didn’t think much of it. I was actually pretty sure he probably met many cute women at his vineyard that he took out and claimed to want to go see.

But low and behold, he actually booked the flight, and after three months of texting every day, he came to see me in person where I live part-time at my cute little condo in Tulum. Of course, I didn’t let him stay with me, and even told him if he was coming just for sex to not get his hopes up. He was completely fine with getting his own place though, and told me he definitely wasn’t flying half way across the world just for sex.

Our time together in Mexico was interesting. He definitely spent way too much money on food and drinks, and didn’t understand that just because he is on vacation, does not mean that I am. So I’d work until the mid afternoon, then we’d eat and drink and eat and drink until I got sick of it and told him I needed an adventure. We ended up going to the Tulum Ruins, Chichen Itza, and Holbox, and I was extremely happy to discover he’s a pretty good traveler, and more importantly, we got along really well, and had a lot of fun.

He was so kind and respectful to me, and I could tell he really just wanted to be happy and wanted me to be happy as well. After about the second week of him being there, I felt myself start to fall for him, but of course, would not allow myself to show it.

After over a month, he left, and the next day he asked if I wanted to be in a relationship with him. It was so straight forward that I couldn’t decide if it was strange or refreshing, considering many men these days don’t want any titles at all. I told him if he’s OK with long distance then yes. He said yes, so we planned to spend another two months apart, then I would come back to Sardinia all of January.

In those two months I learned that from the moment he saw me he knew he wanted to marry me. Or at least so he says. He didn’t know who I was, or that I travel for a living, he says he looked into my soul and he knew. So it shouldn’t have been a surprise when he started asking me for my ring size. This saga of the ring really needs more detail, and you’ll have to read about it in the extended version.

In short, he sent me photos of engagement rings and asked if I liked them, but I thought it was for a birthday gift. When I told him that, he said no it’s because “we are engaged”, to which I tried to explain that you have to ask someone if they want to marry you to be engaged. He said something along the lines of, “Yes, I want to ask,” but I still wasn’t sure if he really knew what this all meant. Just in case it was for an engagement ring though, I sent him photos of some beautiful lab-grown diamond ring options I really loved. But his response was a long the lines of, “We aren’t getting married yet! Do you want me to go broke?!” So that was embarrassing as well, and I decided to pretend like the entire conversation never happened. But, a few weeks later, he ordered the one I liked from a shop in Zurich, where he wanted to pick it up to give to me on my birthday on January 4th. Again, which is why I thought it was a birthday gift.

But the company delayed production, and as I mentioned, it was a whole saga, so I spent a month and a half stressing about this damn ring and what it was for. We spent NYE in Lucerne, then Lake Como for my birthday (splitting everything now that he knew about my booming business), and afterwards went back to Sardinia where I basically moved in with this man for the month.

I spent most days working from the beach or home, and sometimes we’d go up to his winery but not for long since it’s pretty cold there in January. And of course we constantly ate great food. I tried extremely hard to forget about the damn ring, since the company kept changing delivery dates, and then one day, actually after our first ever argument, I came home from a run to see the FedEx truck.

When I came inside, another long story short, I had the worst proposal ever. But I can’t blame him, he didn’t know what to do, and proposing in Italy isn’t the same as in USA. He basically just put the entire package under his Christmas Tree, and pointed at it with a big smile, then told me to open it. So I sat on the couch in my running gear, and he sat beside me in his old-man-pajamas, as I opened the ring box myself to see the small lab-grown diamond on the twisted gold band.

“You like it?” He said as he plucked it out of the box and tried to put it on all of my fingers, leaving it on my thumb, because that’s the only one it kind of fit. Then he just got up and went back to making his lunch. Like I said, worst proposal ever. All I could say was, “So, this is my birthday gift?” to which he emphasized again that no, it was because we are engaged.

So I awkwardly explained to him how big of a deal it is to Americans to have a cute engagement proposal, and to my surprise, he was very understanding, and said he was going to do it again after we get the ring re-sized (I somehow messed up on the measurements).

A few days later, we got the ring back, and headed to one of the beautiful beaches in this area. It was Sunday, January 14, 2024, and it was supposed to be cloudy, but instead it was a beautiful sunny day.

Engaged in Italy by Alyssa Ramos @mylifesatravelmovie mylifesamovie.com

Never thought I’d be engaged and living on an island in Italy!

He found a secluded beach, that was sheltered by giant boulders, and set our matching “Re and Regina” monogrammed wine glasses on top of a boulder, with a cold bottle of his white wine, and a giant bouquet of roses. Of course, the ring was in the box in the middle.

I changed into my long pink velvet birthday dress, because I’m extra like that, and when I walked up he handed me the ring again and said, “Will you marry me in the future?” And I said yes! (Then he asked me if he did it right this time, which I thought was hilarious).

We spent the next two hours taking photos and videos and drinking the wine, and also just sitting next to each other enjoying the moment. Something I’ve never really done with someone before.

Then we went for a delicious celebratory lunch in a small town where we both got sea urchin pasta, followed by pistachio cannoli. I had wanted his dog to be there for the proposal, but since he’s a bit crazy, we decided to wait, and headed up to the vineyard to see him next. Then for some reason he thought it was the best time to take me on a walking and climbing tour of the entire vineyard, even though I was in heeled boots and a dress.

It really was the most perfect day though, and we ended it at home, where I made us ravioli (well, technically his mom pre-made them, I just added the sauce), and we drunkenly sung and danced all night. So much so, that the next day we were both completely dying and swearing off wine for the next few days.

And then, in true solo traveler form, I left two weeks later to go climb Everest Basecamp, do a collaboration in Bhutan and Socotra Island, and host a group trip in India.

When I returned, he had gotten a big one bedroom apartment built behind the cellar, and we officially moved onto the vineyard shortly after! But shockingly, I was not excited about that. We had been living in a nice apartment that’s walking distance to the beach and beach bars, and the vineyard was a bit far from them and the town. According to me at least, he will insist the beach is only seven minutes away, which is likely because he drives like an Italian cheetah. But, we got a used motorbike, and I quickly fell in love with the scenic drives from the vineyard to the beach, and the old towns.

I wake up and walk through the barrels of wine to go walk my dog outside in the rows of vines. My office is a small table under an olive tree which also overlooks the vines and the sea in the distance. When it’s time to stop working, I’m usually lured to close my laptop with offers of aperitivos. And I now can speak conversational Italian!

So yeah! I literally met a guy while doing what I love; traveling solo, drinking wine, and being with my dog, and ended up engaged and living on a vineyard in Italy! This is why I always say “My Life’s a Travel Movie”. That being said, my advice to all the single ladies (and men) reading this, is to never stop doing what you love because you think it’s preventing you from finding the right person! The right person will love and accept what you do, even if they don’t like it!

Like every love story, there is a lot of work involved, and it’s not easy at all, especially with cultural differences! But we have made it a long way together, and can’t wait to get married in a couple of months!

Please drop me a comment or follow me on social (@mylifesatravelmolvie) and my blog for wedding updates!



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