7 Days Sailing Paradise: Yacht Journey through Capri and the Amalfi Coast

Day 1 begins with energy and elegance as our guest takes the helm near Naples, ready to chart her OBM journey across the Mediterranean.

It began with a quiet sunrise in Naples and a glass of prosecco trembling in the hand. The dock buzzed softly with expectation, but time seemed to slow the moment we stepped aboard. This wasn’t just a yacht trip. This was OBM—an odyssey curated with meaning, elegance, and memory. Here’s the story of seven unforgettable days chasing the Mediterranean sun.

Day 1: Departure from Naples

The first step into the world of OBM was aboard a pristine luxury yacht in Naples. The scent of the sea mixed with the creaminess of fresh burrata from Caseificio La Fattoria, setting the tone for what was to come. As we sailed towards Capri, the city faded behind us, and the magic of the Mediterranean took over. Dinner near Marina Piccola, prepared with the morning's catch from Pescheria Azzurra, felt like dining inside a dream.

Naples, once the heart of the Kingdom of the Two Sicilies, is a city layered with Roman, Bourbon, and Spanish influences—a cultural gem that has always looked toward the sea.

OBM Tip: Before boarding, enjoy a short stop at Gran Caffè Gambrinus for a real Neapolitan espresso and sfogliatella, just like local aristocrats once did.

Anchored near hidden coves as the OBM crew prepares a beach barbecue under a glowing Mediterranean sky.

Day 2: Capri & the Blue Grotto

Waking up with the Faraglioni in sight, we met our Caprese guide—Antonio, whose stories turned the rocks and ruins into living history. After slipping into the legendary Blue Grotto, we lunched barefoot at La Fontelina, salt still on our skin. That evening, under a sky streaked with orange, Da Paolino welcomed us with lemon-scented air and plates full of tradition.

Capri has seduced Roman emperors like Tiberius, who ruled the empire from his cliffside villa here. Its caves, cliffs, and villas still carry echoes of empire.

OBM Tip: Ask your captain to anchor by Punta Carena at sunset—fewer crowds, breathtaking views, and the golden light Capri is famous for.

Day 3: Capri to Positano

We glided toward Positano, pausing at the mythical Li Galli islands. Floating in aquamarine water, a local sommelier uncorked southern Italy’s best-kept secrets. As golden hour arrived, Positano unveiled itself. We wandered through vibrant alleyways until the candles were lit at La Sponda, where mandolin chords danced on the breeze.

According to legend, Li Galli were home to the sirens that tempted Ulysses. Positano itself dates back to the Roman era, its pastel houses cascading like a living fresco.

OBM Tip: For artisan shopping, visit La Bottega di Brunella for handmade linen garments. A timeless souvenir of Positano style.

Lunch at La Fontelina—where sea, stone, and tradition meet with Capri’s legendary elegance.

Day 4: Positano to Amalfi

A gentle sail brought us to Amalfi, where OBM introduced us to the “lemon master” in the Valle dei Mulini. His zest for citrus was contagious. That night, we dined aboard as the chef recreated dishes inspired by Trattoria da Gemma, infused with flavors passed down for generations.

Once a powerful maritime republic, Amalfi rivaled Venice and Genoa in the 11th century. Its paper mills, cathedral, and sea trade made it a jewel of the coast.

OBM Tip: Visit the Museo della Carta in the valley for a private demonstration of Amalfi’s ancient paper-making tradition.

Positano, a living postcard and one of OBM’s most beloved golden hour destinations.

Day 5: Ravello Retreat

OBM took us above the clouds, to Ravello’s serene heights. At the Belmond Hotel Caruso, we exhaled among ancient stones and panoramic serenity. A stroll through Villa Cimbrone brought us to Carmela of Ceramiche d'Arte Carmela, whose painted tiles told the story of her ancestors. That night, back on the yacht, we danced barefoot under the stars.

Ravello has inspired writers and composers for centuries—from Boccaccio to Wagner. Its lofty perch and Moorish architecture offer peace and perspective.

OBM Tip: Request a sunset aperitivo at the Terrace of Infinity in Villa Cimbrone—arguably the most stunning viewpoint on the entire Amalfi Coast.

A classic morning in Positano, where style and history echo across the shoreline.

Day 6: Hidden Coves & Local Encounters

This was the day of discovery. OBM captains led us to the hidden Fiordo di Furore, accessible only by sea. We snorkeled through secret caves, grilled sea bass on an untouched beach, and shared stories with a guitarist from Accademia Musicale Amalfitana whose serenade at sunset moved us to silence.

Furore, once a remote fishing village, became a muse for artists and writers. Its natural fjord remains one of Italy’s most untouched coastal gems.

OBM Tip: Bring an underwater camera—these caves and rock formations are nature's cathedrals and perfect for diving photography.

Day 7: Return to Naples

Sailing back to Naples, we were quieter, as if trying to hold onto every wave, every taste, every face. Breakfast was bittersweet. The crew offered each of us a handcrafted OBM memento—our own piece of the journey to carry home.

As you return, reflect on Naples' layered past—once a Greek colony, then Roman port, Spanish stronghold, and now, a modern city deeply connected to its maritime roots.

OBM Tip: End your journey with a final toast at Palazzo Petrucci, Naples’ only Michelin-starred seafront restaurant—where old world meets new luxury.