Mediterranean Dream:
Cruise ship from Italy to Greece

Depart from Los Angeles to Brindisi, Italy.

Arrive in Brindisi, the port city on the Adriatic coast, located in the Puglia region (the “heel” of Italy’s boot). Thanks to its strategic position, it was long regarded as the gateway to the East, connecting Rome with Greece and the wider Mediterranean world. Brindisi marks the end of the legendary Via Appia, still remembered through the two ancient columns standing tall by the harbor, symbols of the long journey linking Rome to Brindisi. Throughout history, it was not only a bustling center of trade, but also the departure point for legions, knights, and crusades bound for the Holy Land. Today, along the waterfront, visitors can admire the crystal-clear waters of the Adriatic, stroll along palm-lined promenades, and soak in the lively atmosphere of ships arriving and departing..
Settle into a welcoming hotel. Enjoy a delicious welcome dinner featuring local specialties. (D)

Begin your day with a guided stroll through Brindisi’s historic heart, starting from the picturesque harbor before stepping into the past at the Swabian Castle (Castello Svevo). Built in the 13th century under Emperor Frederick II, this massive fortress with its sturdy walls and towers once protected the city from invaders and served as a royal residence. Just a short walk away, discover the Piazza Duomo, one of the most elegant squares in the city, framed by historic palaces and the majestic Cathedral of Brindisi.
Continue your journey to Ostuni, the “White City,” perched on a hilltop and gleaming in the Mediterranean sun. Ostuni has a long history, with traces dating back to pre-Roman times, and it flourished during the Middle Ages as an important commercial and religious center of the Puglia region. The city’s architecture reflects the Mediterranean style, with whitewashed houses, red-tiled roofs, and intricately decorated balconies lining the winding alleys paved with white stone. Dominating the central square is Ostuni’s Gothic Cathedral, built in the 15th century, featuring an elaborately carved main entrance, stunning rose windows, and a soaring bell tower. Have free time to enjoy lunch, perhaps sampling the traditional orecchiette pasta or the creamy burrata cheese, one of Puglia’s most famous local specialties.
In the afternoon, travel to Alberobello, a UNESCO World Heritage Site famous for its unique trulli—whitewashed stone houses with conical roofs. Check in at the Grand Hotel La Chiusa di Chietri, nestled among olive groves, and savor a traditional Apulian dinner in a local restaurant. (B/D)

Explore the fairy-tale lanes of Alberobello with a local guide. Dated back to the 14th century, the trulli of Alberobello are one of the most distinctive architectural features of southern Italy, earning the town its UNESCO World Heritage status. These whitewashed stone houses with conical roofs were originally built using dry stone construction—stacking stones without mortar—so that they could be quickly dismantled if needed, a method thought to have helped residents avoid taxation on permanent dwellings. Architecturally, each trullo has thick walls that provide natural insulation, keeping interiors cool in summer and warm in winter. The conical roofs are often topped with pinnacles. Inside, the trulli are simple yet functional, often consisting of one or a few circular rooms connected by small vaulted passages. Together, these unique structures create a fairy-tale-like landscape, blending practicality with local tradition and charm.

Continue to Locorotondo, one of Italy’s most beautiful villages, famed for its circular historic center and whitewashed houses. Perched on a hilltop, the town offers panoramic views over the Valle d’Itria, with vineyards, olive groves, and scattered trulli creating a quintessential Mediterranean landscape. Dating back to the Middle Ages, Locorotondo retains its traditional Apulian architecture, with narrow winding streets, elegant balconies, and small churches, while its quiet lanes host boutiques, cafés, and artisan shops. The town is also known for its Locorotondo DOC white wine, a local specialty that reflects the region’s culinary heritage.

In the afternoon, visit Polignano a Mare, dramatically perched atop limestone cliffs overlooking the Adriatic. The town proudly celebrates Domenico Modugno, the legendary singer born here and famous for the iconic song “Volare (Nel blu dipinto di blu)”, with a statue commemorating his legacy. Stroll the cobbled streets, discover hidden sea-view terraces, and perhaps sample the town’s famous gelato. End your day with a fresh seafood dinner, enjoying the flavors of the sea. (B/D)

Journey to Matera, one of the world’s oldest continuously inhabited cities and a UNESCO World Heritage Site. Explore the mystical Sassi districts, where ancient cave dwellings are carved directly into the rock and now house boutique hotels, artisan shops, and atmospheric churches. Experience Matera in a unique way with a tuk-tuk tour through its winding streets, feeling the charm of this timeless city from every corner. Matera also gained international fame as a filming location for James Bond’s “Skyfall”, where the iconic high-speed chase scene winds through the narrow alleyways, stone staircases, and dramatic cliffside paths of the Sassi.

En route to Bari, stop for a tasting of local delicacies—perhaps extra-virgin olive oil, robust Primitivo wine, or artisanal bread from Altamura. Arrive in Bari, the vibrant capital of Puglia, and check into the luxurious JR Hotels Grande Albergo delle Nazioni, overlooking the Adriatic. Enjoy a dinner of regional specialties, such as tiella (baked rice with potatoes and mussels) or freshly made focaccia. (B/D)

Discover Bari Vecchia, the city’s atmospheric old town, where narrow winding streets lead to medieval churches, bustling piazzas, and the revered Basilica of Saint Nicholas, one of the most important pilgrimage sites in Italy. Built in the 11th century, the basilica houses the relics of Saint Nicholas, attracting both Catholic and Orthodox pilgrims from around the world. Its Romanesque façade, intricate mosaics, and elegant bell tower reflect centuries of architectural evolution, while the quiet interior offers a serene space for contemplation. Stroll through the charming alleys, observe local life, and perhaps stop at a café to savor an espresso. In the evening, embark on your overnight voyage to Greece, relaxing on board while enjoying dinner as the ship glides across the Ionian Sea, watching the sunset and listening to the gentle rhythm of the waves. (B/D)

Arrive in Patras, the vibrant gateway to the Peloponnese and Greece’s third-largest city, known for its bustling port, colorful streets, and lively atmosphere. Take a moment to stroll through the city center, admire the historic architecture, and perhaps visit the impressive Patras Cathedral, one of the largest churches in Greece. Travel north towards Athens, and consider a stop at the Corinth Canal, a spectacular feat of 19th-century engineering that slices through the Isthmus of Corinth, connecting the Aegean Sea with the Ionian Sea. Marvel at the canal’s steep rock walls, which reach up to 80 meters high, and watch ships navigate this narrow passage, a dramatic example of human ingenuity and a popular photo spot. Continue your journey to Athens,check into a comfortable hotel for dinner and relaxation after a day of sightseeing. (B/D)

Take a ferry to Mykonos, the cosmopolitan “Island of the Winds”, famous for its vibrant nightlife, pristine beaches, and charming Cycladic architecture. Upon arrival, explore the whitewashed labyrinth of Mykonos Town (Chora), where narrow winding streets are lined with iconic windmills, bougainvillea-draped lanes, and chic boutiques offering local crafts, jewelry, and fashion. Don’t miss Little Venice, a picturesque waterfront area where colorful houses seemingly hang above the sea, perfect for photos at sunset. Visit the historic Church of Panagia Paraportiani, a striking example of Cycladic ecclesiastical architecture with its asymmetrical whitewashed walls and serene courtyard. Wander at your own pace, enjoying the vibrant local atmosphere, then conclude the day with a leisurely dinner at a seaside taverna and a restful night at your hotel, soaking in the island’s magical charm. (B/D)

Spend a full day at leisure on Mykonos, relaxing on golden beaches, exploring the island’s vibrant art galleries and boutiques, or enjoying its lively cafés and bars. For those seeking a deeper cultural experience, take an optional excursion to the sacred island of Delos, a UNESCO World Heritage Site and the mythical birthplace of Apollo and Artemis. Wander through its ancient ruins, including temples, statues, mosaics, and a theater, and marvel at the well-preserved marble streets and sanctuaries. Return to Mykonos in the evening for a dinner of classic Greek cuisine, such as grilled octopus or moussaka, while watching the sun set over the horizon. (B/D)

Sail to Santorini, the legendary island shaped by volcanic fire, famous for its whitewashed villages clinging to dramatic cliffs, stunning caldera views, and iconic blue-domed churches. Upon arrival, explore the charming streets of Fira, wandering through narrow alleyways lined with boutiques, cafes, and artisan shops, and taking in the breathtaking panorama of the Aegean Sea and the caldera. Don’t miss opportunities to visit museums, local art galleries, or simply enjoy a coffee while watching the bustling life of the island. Check into Greco Hotel, where comfort meets traditional Cycladic style, and end the day with a memorable dinner, savoring local wines, fresh seafood, and Cycladic specialties, all while enjoying a sunset that lights up the caldera in shades of gold and crimson. (B/D)

Spend your morning exploring the treasures of Santorini, from charming streets to local shops and cafes. In the afternoon, transfer to Oia, the jewel of the island, celebrated worldwide for its spectacular sunsets, often regarded as some of the most beautiful in the world. Wander through its narrow cobblestone streets, lined with whitewashed houses, blue-domed churches, and boutique shops, all perched dramatically on the cliffs overlooking the caldera and Aegean Sea. As evening falls, find a perfect vantage point to watch the sun slowly dip below the horizon, turning the sky into a mesmerizing palette of gold, rose, and crimson, a moment cherished by photographers and travelers alike. Conclude the day with an unforgettable dinner, savoring fresh seafood, local wines, and Cycladic specialties while soaking in the magic of Oia’s sunset. (B/D)

Ferry back to Athens and enjoy a farewell dinner, reminiscing about your Mediterranean & Adriatic adventure. (B/D)

Discover the wonders of Athens, the cradle of Western civilization, where ancient history meets modern vibrancy. Begin at the Acropolis, the sacred hill that has stood as the spiritual and cultural heart of Athens for over 2,500 years, and marvel at the Parthenon, dedicated to Athena, along with the Erechtheion with its Caryatid columns and the Temple of Athena Nike. Visit the Acropolis Museum to see sculptures, friezes, and artifacts that illuminate Athens’ golden age. Then wander through the Plaka district, the city’s oldest neighborhood at the foot of the Acropolis, with its narrow cobblestone streets, neoclassical mansions, charming courtyards, lively tavernas, and boutiques, reflecting centuries of history from Byzantine to Ottoman times. Conclude your journey with a final dinner, savoring traditional Greek cuisine, toasting new friends, and cherishing memories. (B/D)

Transfer to the airport for your flight home, carrying with you the sights, sounds, and flavors of the Mediterranean and Adriatic.