My Best Friend and I Went on a 'Honeymoon' in Italy Together — Here's How It Changed Our Relationship

Attempting to honor their commitment to each other, two best friends set out on a not-quite honeymoon in Italy.

Sophie and Eliza's photos from their trip to Italy
Photo: Photo Illustration by Mariah Tyler (Source Images: Sophie Dodd; Getty Images)

Traditionally, a honeymoon is a trip taken by newlyweds to celebrate their marriage. But in recent years, the concept has exploded, Big Bang style: Buddymoons and babymoons are everywhere, with couples bringing their friends along for group getaways or jetting off on romantic vacations before welcoming a baby. Friendship doesn't hold much gravity in this landscape, which centers on romantic partnerships and family (even if pals join in on a buddymoon, the nucleus is still the newlyweds).

But what if I choose to orbit my life around friendship instead? What "moon" is there to honor that commitment?

Sophie and Eliza's photos from their trip to Italy
Photo Illustration by Mariah Tyler (Source Images: Sophie Dodd; Getty Images)

My best friend, Eliza, and I decided to make one up ourselves: something perhaps less celestial than a honeymoon, but not quite so proverbial as a girls trip. We're both writers who work remotely, so we dreamt up a plan for three weeks in Italy — split between Puglia and Sicily, with a night in Rome on each side — to celebrate our friendship, read Italo Calvino on rocky beaches, and maybe co-write a dazzling work of autofiction about our adventure.

While the two of us aren't legally bound, we recently became each other's emergency contact — a designation we put to the test on several occasions during our trip — and that on-paper (fine, mostly digital) proof of our thereness for each other felt like something to celebrate.

There are few social guidelines for how else to mark the ways we've learned to support each other over the years — in Italian hospitals and in health; in lieu of getting engaged or married, we've kept showing up. And when we've fallen short, we've taken the time to work through it.

Our culture puts all the importance on committing to romantic relationships, but our close friendships require just as much upkeep, attention, forgiveness, and quality time — and in order to thrive, they require new shared experiences. That's where travel comes in: Removed from "real life," friendships are able to grow in ways that can only happen out of context, away from the habits that prevent us from showing and seeing certain sides of ourselves and our loved ones.

Despite the lack of a proper noun to describe it, we set out on our unnamed-moon in early June.

Sophie and Eliza's photos from their trip to Italy in Ostuni in the vineyard for dinner
Photo Illustration by Mariah Tyler (Source Images: Sophie Dodd; Getty Images)

The day we arrived, planes streaked the sky with the colors of the Italian flag. Unbeknownst to us, it was Italy's Republic Day. With the city center closed to cars, our taxi dropped us on a nearby bridge and we hobbled with our luggage to Hotel Chapter Roma.

Set in a 19th-century palazzo, the property is all stone arches, colorful graffiti, and not-quite-50 shades of industrial gray, accented with vibrant orange couches and green marble floor tiles.

In our room, we were charmed by the green scalloped headboard, exposed brick walls, and black-and-brass bar cart, shimmering with crystalline coupes. The ultra-trendy decor made us feel like we could be back in Brooklyn, until we caught sight of all the gorgeous golden buildings outside our window, wreathed in bougainvillea and clotheslines waving in the warm breeze.

After an afternoon of aimless wandering and an aperitivo on the hotel's sun-soaked rooftop, we went downstairs for dinner at Campocori, where three tasting menus were on offer. A round of amuse-bouches were served on tiny black marble slabs, including ricotta-stuffed cones topped with cinnamon-dusted horse meat and gin and tonic cucumber slices dabbed with lemon curd.

That first night, we toasted to normalizing forgiveness — of ourselves and each other. In the few months leading up to the trip, our usual day-to-day proximity had been ruptured by travel and romantic relationships. We'd struggled to communicate with each other as we usually do, and we talked through how we'd each felt frustrated and disappointed by the other, going over the ways in which those feelings were and weren't fair. In a friendship, how far can you ask someone to go for you? We spent that night and many others during our trip testing the boundaries.

The next day, we traded La Città Eterna for La Città Bianca, journeying from Rome into the center of Puglia on a five-hour train ride to the medieval, all-white village of Ostuni. On separate trips, we'd both traveled through Italy by train with our exes, which heightened the contrast of our being there together. We talked about the ways in which deep friendship and romantic relationships do and don't intersect (physical intimacy being the primary differentiator), and why we were happier to be on that train together (mostly because we both love writing in transit).

Sophie and Eliza's photos from their trip to Italy, showing Ostuni, luxury hotel stay and seafood
Photo Illustration by Mariah Tyler (Source Images: Sophie Dodd; Getty Images)

On arrival in Ostuni, we dropped our bags at our Airbnb, which opened into an enormous cactus-lined terrace overlooking the city. We decided to go for a run to get the lay of the land — the first of our many ill-hatched plans. The city is all slick stones and shades of white. It gleamed as we passed by arched alleyways, men selling olive oil, and tourists clipping around corners in tuk-tuks. The narrow streets were hilly and cobbled, and Eliza tripped on a stone and fractured her wrist.

The Ostuni hospital, we learned upon arrival, was exclusively open for COVID-19 patients. We called a car to the emergency room in Monopoli, 40 minutes away, where we spent the next seven hours playing a high-stakes game of charades with the nurses in an attempt to explain what had happened.

We eventually emerged, at once exhausted and euphoric, with Eliza's wrist sheathed in a cast; the entire rigamarole of X-rays and cast-fitting had been completely free. Feeling like fugitives who surely owed at least a few hundred dollars, we smudged on our makeup in the parking lot as we waited for a taxi, laughing hysterically at the spectacle of ourselves.

Twenty minutes later, we entered the gates of heaven, which goes by the more practical name of Masseria Montenapoleone. A masseria is a renovated farmhouse situated on agricultural land, typical of the region and often dating back to the 16th century. Now repurposed as hospitality venues, masserie (groups of farmhouses) offer intimate and elevated tourism experiences.

Perhaps one of the most unique experiences is on offer at Masseria Montenapoleone, where we dined in the shabby-chic vineyard amidst the rows of susumaniello, a locally grown grape, as a soundtrack of classic Italian ballads set the scene.

The night was pure movie magic, featuring dishes made from the produce grown around the property, like olives stuffed with fava bean puree and risotto with roasted turnips and burrata.

The next day, we wandered about the property, plucking lemons and apricots off trees and marveling over the scattered nooks of mismatched antiques and velvet furniture in shades of fuchsia and ochre. The masseria's pristine, lagoon-like pool was the perfect place to lounge after digging into the elaborate breakfast buffet.

Sleepy with sun exposure, we made our way to another, more minimalist masseria nearby, Masseria Le Carrube. The more laid-back sibling of ultra-luxurious celebrity hot spot Borgo Egnazia, Le Carrube has a classic whitewashed stone exterior and not one, but two of the sexiest turquoise pools I've ever seen, where I promptly set up camp with an Aperol spritz and a book.

The main draw at Le Carrube, also situated on a massive olive orchard, is the Michelin-recommended vegetarian restaurant of the same name. The menu changes nightly, as chef Massimo Santoro forages on the property each morning for the freshest ingredients, whipping up whatever inspires him. That night, we exchanged looks of pure delight with every new dish that arrived, from bites of asparagus foam topped with popcorn and wildflowers to a pasta that almost made me cry.

Pasta tears aside, we then headed to Masseria Torre Coccaro in nearby Fasano. The property was the most family-friendly of any we stayed at (there's a playground tucked behind the pool area, and children's cooking classes are on offer). There, we slept in a cozy whitewashed cave formerly used as an olive mill, with a private lounge area out front that was perfect for spreading out and catching up on work. A few caves over, we discovered the underground spa, where we giggled through a couple's massage, warmed up in the sauna, and took a dip in the heated pool as rain began streaming onto the skylight overhead.

Crossing the stone courtyard the next morning to the hotel's fine-dining restaurant, we swooned over breakfast: the complimentary buffet spread (my three favorite words) took over an entire room of the airy, pothos-lined restaurant and exceeded all expectations. Eliza and I got there early to pace ourselves through several courses: juicy tropical fruits, thinly sliced prosciutto, slippery bulbs of burrata, pastries, and more. From there, we hopped on the private shuttle to one of their two beach clubs, located on a sandy cove a few minutes' drive away and home to a seafood restaurant where they bring out platters of fresh fish for you to handpick your catch of the day.

Still sandy from the beach, we called a taxi for the 20-minute ride back to the center of Ostuni. There, our destination was Paragon 700, an 18th-century palazzo that was initially home to the city's first mayor. The 14-room "red palace," named for the striking color of the building's facade, boasts the only pool in central Ostuni and is a true jewel box of a boutique hotel and spa, with each room named after a precious stone. Eliza checked into the Amber room, while I was on a call. I quickly received a barrage of text messages: "You're going to faint when you see our room," she wrote.

Upstairs, in a gesture of true honeymoon-like affection, she put her hands over my eyes and guided me into the room, where I managed, just barely, not to faint. Sky-high cathedral ceilings soared overhead, dangling with enormous, floral-shaped brass chandeliers that reminded me of Marni designer earrings. The spacious terrace looked out over the pool and garden, and as if we weren't smitten enough, there was an outdoor shower, too. Golden hour in that room was something magical, and a beam of liquid light spilled across the bed that basically begged us for a photo shoot. Surrounded by mind-boggling original frescoes, it was like staying in a private museum, but with linen bathrobes and scented bath salts.

Careful to avoid any sudden movements on the streets of Ostuni this time around, we said a slow goodbye to the splendor of Paragon 700 before catching the train to Bari, where our trip shifted from luxury vacation to proper travel. We didn't see much of our Airbnb that evening. After walking through the city and splitting a bottle of wine in the port, we stopped in at Mostofiore, a buzzy natural wine bar where we soon befriended a trio of handsome Italian poets who traipsed around the city with us for the rest of the evening on an impromptu bar crawl.

Throughout the night, Eliza and I would look at each other and wink, tipsy on skin contact wines and the delight of being 28 in a new place. This sort of night out holds a special place in my heart; there's an open-endedness that has a different texture to it than when I've visited a city with a romantic partner, whom I tend to be less inclined to break away from in order to make new friends.

Ten days and as many new pals later, after a whirlwind trip around Sicily that saw us hike the active volcano of Mount Etna, take a pilgrimage to meet famed natural winemaker Frank Cornelissen, inch a rental car along the steep switchbacks of Taormina, and attempt to become regulars at Dal Barone, a natural wine bar that we fell in love with in Palermo, we made our way back to Rome.

Sophie and Eliza's photos from their trip to Italy, it Palermo, Sicily and Rome with images of Mount Etna and a small orange car
Photo Illustration by Mariah Tyler (Source Images: Sophie Dodd; Getty Images)

For our last night, we took a page from Stanley Tucci's Searching for Italy playbook and checked into Hotel Eden, a five-star luxury hotel a stone's throw from the Spanish Steps and Borghese Gardens.

In the lavish marble lobby, the staff greeted us warmly and showed us to our room. Decorated in elegant, muted tones, the spacious suite — complete with Bottega Veneta toiletries, fresh flowers, a dazzling marble bathroom, and the most heavenly mattress I've ever slept on — made it difficult to pull ourselves away for some final explorations around Rome. After toasting to our trip with the complimentary Champagne, we meandered through the Borghese Gardens.

On our walk, we argued about the best route to take. We're each used to taking the lead while traveling with others, which was cause for friction at times. I also have a bad habit of claiming a place — of making it seem like I know oh-so-much about it after just a few days there, which I was doing in that moment, as I insisted I knew a quicker route. After apologizing, we discussed the ways we'd learned to travel growing up and how they've shaped the ways we move through unfamiliar places now: Eliza has always valued the journey, whereas I often am overly enthusiastic — one might say impatient — to get to the destination. That moment encapsulated many of the conversations that traveling together prompted for us: a pushing-past of momentary discomfort to learn something new about someone you love, to better understand why they are the way they are.

It wouldn't be quite right to say that we learned each other all over again during our trip — it was more that three weeks of Italian golden hours illuminated budding and shifting parts of ourselves to each other, from the ways we move through a new city to how we choose to document it and what it looks like when we need to decompress alone.

Back at the hotel for dinner that night, we took the elevator up to La Terrazza, the Michelin-starred restaurant that offers sweeping views over Rome and a lively menu of Mediterranean cuisine, from exquisitely cut octopus carpaccio to decadent savory cannoli.

I'm not sure what we toasted to, looking out over all that splendor. It's funny which memories stick out now, and how some have earned a permanent spot in the story of our trip, while others have faded into the background, no less important or less central to the narrative of what it was to be two best friends on a not-quite-honeymoon. I wonder which moments I'll forget that she'll remember and vice versa.

I'd anticipated the trip would be a time for us to deepen our connection, to spend quality time doing the things we love most (drinking wine, writing, wandering around, and making up stories for strangers). And in large part, it was. I'd envisioned it as a time for us to celebrate our commitment to our friendship, but what we actually did was test and renew it. Every single day.

We came home with a different friendship than when we left — one that's more honest and communicative and vulnerable than before. One that feels elastic enough to navigate the inevitable: that one or both of us will fall in love with new people and maybe start a family or move away. We know that we'll need flexibility and forgiveness as we make our way down that road — sometimes meanderingly and other times in a rush, sometimes a little exasperated with one another, but always in agreement that when it comes to how far best friends should go for each other, even when things aren't quite so sweet, the moon and back isn't too much to ask — especially if we can stop in Italy along the way.

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