How a ‘Buddymoon’ in Italy Enhanced My Friendship

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

Traditionally, a honeymoon is a trip taken by newlyweds to celebrate their marriage. However, in recent years, the concept has evolved into a phenomenon, with Buddymoons trending alongside babymoons. Couples are now inviting their friends for group getaways or embarking on romantic vacations before expanding their families. This shift highlights the growing importance of friendships, a dynamic often overlooked in a landscape predominantly focused on romantic and familial relationships.

Yet, what if one desires to center their life around friendship? What “moon” exists to celebrate that bond?

My best friend, Eliza, and I set out to create our own: something perhaps less celestial than a honeymoon but not quite the typical girls trip. As remote writers, we devised a plan for three weeks in Italy—divided between Puglia and Sicily, with a night in Rome at each end—to celebrate our friendship, engross ourselves in Italo Calvino’s writings on pristine beaches, and perhaps co-write an intriguing piece of autofiction documenting our adventure.

While we may not share legal bonds, we became each other’s emergency contacts—a designation we tested during our trip—highlighting our commitment and support for each other. Society frequently emphasizes the importance of romantic commitments, yet our close friendships demand similar maintenance, attention, forgiveness, and quality time to truly flourish.

Moreover, travel fosters unique shared experiences that cultivate stronger friendships. Removed from day-to-day routines, friendships can expand in ways that only a change of scenery can facilitate, allowing us to explore new dimensions of ourselves and our loved ones.

Therefore, we embarked on our unnamed-moon in early June.

The day we arrived, vibrant planes crisscrossed the sky in the colors of the Italian flag, coinciding with Italy’s Republic Day. With the city center closed off to vehicles, our taxi dropped us off at a nearby bridge as we trudged towards Hotel Chapter Roma.

Housed in a 19th-century palazzo, the hotel features stone arches and colorful graffiti, presenting a blend of industrial chiciness with vibrant orange furnishings. Our room charmed us with its green scalloped headboard, exposed brick walls, and a classy bar cart that shimmered with crystal coupes. This trendy decor transported us back to Brooklyn until we gazed outside at the charming golden buildings adorned with bougainvillea swaying in the gentle breeze.

After an aimless afternoon followed by an aperitivo on the hotel’s sun-dRENCHED rooftop, we indulged in dinner at Campocori, where we were presented with three tasting menus. The amuse-bouches served on tiny black marble slabs were a delightful mix, including ricotta-stuffed cones with cinnamon-dusted horse meat and cucumber slices garnished with lemon curd.

On that first night, we toasted to normalizing forgiveness—of ourselves and each other. In the few months leading to our trip, typical routines had been disrupted by various travels and relationships. Consequently, feelings of frustration and disappointment surfaced, leading us to work through our emotions that evening and many others during our journey.

Next, we traded La Città Eterna for La Città Bianca, embarking on a five-hour train ride from Rome to the all-white village of Ostuni in Puglia. Having each traveled through Italy by train with past partners, we noticed the marked difference this time. We engaged in conversations about how deep friendship and romantic relationships intersect, enjoying our shared love for writing in transit.

Upon arriving in Ostuni, we dropped our bags at our Airbnb, which showcased a grand cactus-lined terrace overlooking the city. Our intent for a quick run to explore soon turned into a minor mishap; Eliza tripped over cobblestone and fractured her wrist. Understandably flustered, we learned that the Ostuni hospital catered exclusively to COVID-19 patients. We called a car to the emergency room at Monopoli, where we spent hours playing charades with the nurses to explain what had happened.

Eventually, we left the hospital feeling both drained and exhilarated, with Eliza’s wrist snugly encased in a cast, and all the medical services rendered free of charge. Laughing in disbelief, we left the parking lot to continue our adventures.

Our evening progressed spectacularly as we arrived at Masseria Montenapoleone, a renovated farmhouse typical of the region, which provides engaging and elevated tourism experiences. Dining amidst rows of locally grown susumaniello grapes, we soaked in the ambiance of enchanting classic Italian ballads.

The dishes were made from produce grown around the property—like olives stuffed with fava bean puree—creating an unforgettable gastronomic experience.

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The following day, we strolled around the property, delighting in plucking lemons and apricots while admiring the quirky antiques and velvet furniture. We then visited a nearby minimalist masseria—Masseria Le Carrube—which boasts stunning turquoise pools. I settled into one with an Aperol spritz, ready to unwind.

At Le Carrube, situated on a sprawling olive orchard, the highlight is the Michelin-recommended vegetarian restaurant. Each night brings a fresh menu based on what the chef foraged that morning. In disbelief with every delightful dish presented, we experienced moments of pure joy, savoring pasta that brought me to tears.

Post-pasta tears, we redistributed ourselves to Masseria Torre Coccaro in Fasano, where we stayed in a cozy whitewashed cave formerly an olive mill. This magical place included a private lounge area, perfect for getting some work done. There, we stumbled upon the underground spa, where we reveled in couple’s massages, relaxed in the sauna, and swam in the heated pool as rain cascaded onto the skylight above.

The next morning, we crossed the stone courtyard to a fine-dining breakfast where a complimentary spread exceeded all expectations. Our early arrival allowed us to leisurely enjoy every course: succulent fruits, prosciutto, slippery burrata, and pastries. After breakfast, we hopped on a private shuttle to one of their two beach clubs, which featured a seafood restaurant offering platters of fresh fish for guests to choose from.

With sandy feet from the beach, we returned to Ostuni by taxi to check into Paragon 700, an 18th-century palazzo initially home to the city’s first mayor. This boutique hotel, a true jewel with each room named after a precious stone, granted us the only pool in central Ostuni. Our stay in the Amber room provided an extraordinary experience that awed us both.

After resting, we journeyed to Hotel Eden for our last night, a five-star luxury hotel conveniently located near the Spanish Steps. Greeted warmly in lavish surroundings, we found it difficult to leave our spacious suite, but we decided to toast with complimentary Champagne and wander through the enchanting Borghese Gardens.

Throughout our stroll, we engaged in playful debates about the best route to take, with tensions arising as we each took turns leading. These moments encapsulated the essence of our friendship, teaching us more about our individual travel styles and preferences.

In hindsight, it wouldn’t be entirely accurate to say we learned each other anew on this trip. Instead, three weeks of Italian experiences illuminated parts of ourselves and each other, unveiling aspects that we had yet to understand.

Back at the hotel for dinner that fateful night, we ascended to La Terrazza, indulging in a marvelous Mediterranean banquet while soaking in sweeping views over Rome.

Reflecting on our journey, I realize that not all memories remain vivid; some have faded, yet they all contribute to the story of our adventure. What was initially envisioned as a celebration of our friendship transformed into a robust testing ground, solidifying our bond through resilience and joy.

As we returned home, we forged a remarkable friendship—one grounded in honesty, vulnerability, and open communication—ready to navigate the future together, no matter the unpredictability. The joy of exploration and commitment formed the essence of our journey, encouraging us to embrace the beauty of friendship, even when the journey takes us far away, as long as it leads to Italy.

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