Itinerary & Activities
Milan (2 nights)
Our Italy and Greek Islands odyssey begins as we jet to beautiful Milan, Italy, a dynamic and influential city renowned for its fashion, design, and cultural heritage. As Italy’s financial and industrial hub, Milan is a blend of modernity and tradition, offering a range of experiences from historic landmarks to cutting-edge contemporary culture. Our first stop is the Piazza del Duomo and the iconic Duomo di Milano, where you will be awe-struck by the sheer size and intricate details of the cathedral’s imposing façade. We’ll climb to the Duomo’s rooftop, where you’ll be treated to panoramic views of Milan, and on clear days, you can see as far as the Alps in the distance. Next, we’ll tour the Sforza Castle, an imposing fortress and architectural wonder which dates to the 15th century, offering a fascinating glimpse into Milan’s medieval past and its role as a powerful military center. Next, we’ll strap on our helmets for a guided Bike Tour through the Navigli District, one of Milan’s most charming and vibrant neighborhoods. Take in the lively atmosphere as we bike along the area’s picturesque canals and oh-so charming streets. Venice (2 nights)
Our next stop is Venice, one of the most enchanting and unique cities in the world, renowned for its canals, historic architecture, and fairy-tale atmosphere. Built on a network of islands in the Venetian Lagoon, Venice offers a distinctive blend of cultural, historical, and architectural experiences. We’ll enjoy a Moonlit Gondola Ride on Venice’s canals and enjoy some gelato in Piazza San Marco, one of the most beautiful squares in the world and the heart of Venice’s social and cultural life. Get a fascinating glimpse of the city’s history when we visit Doge’s Palace, the center of power during the time of the Venetian Republic. Check out the markets and shops along the Rialto Bridge and bask in the beauty of St. Mark’s Basilica. You’ll feel like a local while enjoying your cicchetti and watching the world go by.Florence and the Tuscan Countryside (3 nights)
The next stop on our journey is Florence, a city rich in history, art, and culture, often considered the birthplace of the Renaissance. Located in the Tuscany region of Italy, this captivating city is renowned for its remarkable architecture, world-class museums, and vibrant cultural scene. Check out the Galleria dell'Accademia, where you'll marvel at Michelangelo's perfectly sculpted 17-foot-tall-marble statue "David". Learn how to make fresh pasta from scratch at our Cooking School and then feast on your culinary creation. Take in the Cathedral of Santa Maria del Fiore, better known as the Duomo, one of the most recognizable landmarks in Florence. On our way to the beautiful Boboli Gardens, we’ll stroll over the Arno River on the iconic Ponte Vecchio. Marvel at the works of Botticelli, Michelangelo, and Leonardo da Vinci at the unbelievable Uffizi Gallery and enjoy the sunset from Piazza Michelangelo. Get ready for an awesome day in the magnificent Tuscan countryside, stopping in the charming city of Siena and spending time in the Piazza del Campo, home to stunning architecture and historic landmarks. No trip to Tuscany would be complete without a stop in San Gimignano, a charming medieval town known for its well-preserved medieval architecture and beautiful surrounding landscape (and world-class gelato!).Rome (2 nights)
Welcome to the “Eternal City”, where ancient history, vibrant culture, and modern life make it an endlessly fascinating destination. Whether you’re exploring its historic ruins, savoring its culinary delights, or soaking up the atmosphere of its lively neighborhoods, Rome offers an unforgettable experience. Take a walk-through history when we visit the Colosseum, the largest amphitheater of the Roman Empire where gladiators once battled. Next, stroll through the sprawling ruins of the Roman Forum, the center of Roman commerce during ancient times. We’ll check out Circus Maximus, an ancient Roman chariot racing stadium, and step inside the Pantheon, a church originally built as a temple to the Roman gods. Walk down the Spanish Steps and toss a coin over your shoulder into the Trevi Fountain (legend promises if you throw a coin in the fountain, you will someday return to Rome). We’ll take a guided tour of St. Peter's Basillica in Vatican City and marvel at Michelangelo's artwork on the ceiling of the Sistine Chapel.Santorini (3 nights)
Onward to Greece! Our first stop is the island of Santorini, officially known as Thira, one of the most picturesque and popular islands in Greece. Located in the Aegean Sea and the remnant of a massive volcanic eruption, Santorini is renowned for its stunning sunsets, dramatic landscapes, and distinctive, white-washed architecture. The island’s combination of stunning natural beauty, rich history, and vibrant culture makes it a truly enchanting destination. We’ll wander through the alleyways of the island’s bustling and vibrant capital, Fira, perched on the edge of the caldera and offering awe-inspiring views of the sea and neighboring islands. Enjoy a day of sun and relaxation on Kamari Beach, known for its distinctive black volcanic sand and crystal-clear waters. Set sail on our Sunset Catamaran Cruise, taking in the magnificent coastal scenery. Pass by the famous Red Beach and White Beach, snorkel in the crystal-clear blue Aegean Sea and swim in the thermally heated volcanic waters off the island of Nea Kameni during this enchanting experience! No trip to Santorini is complete without watching the stunning sunset over the Blue Domes and white-washed houses of Oia, the most iconic town in the Greek Islands.Naxos (3 nights)
Get ready to hit the seas as we cruise to our next stop, the beautiful island of Naxos, known for its diverse landscapes, beautiful beaches, lush valleys, and mountainous terrain. Combining its natural beauty with authentic Greek life, Naxos has become a must-visit destination in the Greek Islands. Walking through the white-washed alleyways of Hora, the old town of Naxos, you’ll discover a vibrant cultural scene reflecting the island’s ancient history. You won’t believe your eyes when you take in the spectacular sunset from the Temple of Apollo. We’ll spend time relaxing and swimming on peaceful Agios Prokopios Beach, known for its long, sandy shoreline and crystal-clear turquoise waters. Head into the mountains during our Naxos Island Tour, taking in historical sites, medieval villages such as Apiranthos and Halki, and stunning natural landscapes (look for Mt. Zas in the distance, the birthplace of Zeus!). No trip to this incredible island would be complete without a traditional Naxian Cooking Class. We’ll tour a local farm, picking the fruits and vegetables we’ll use to prepare our delicious local dishes. After our feast we will learn authentic Greek dances and take part in the traditional breaking of the dishes. Opa!Paros (3 nights)
A short ferry ride takes us to our next unbelievable destination, the island of Paros. Filled with historic villages, endless captivating sunsets, sun-drenched hilltop towns, and endless golden beaches, Paros is quintessential Greece, and a visit to this idyllic island is a must on any Greek island-hopping adventure. Visit vibrant Parikia, a historic port that is the beating heart of Paros. Walk past Panagia Ekatontapiliana church as you stroll through beautiful alleys and bustling street markets. Next up, we’ll work with professional instructors during our awesome Wind-surfing Lessons! With consistent winds, flat shallow waters, and white sandy beaches, Paros is the ideal place to learn this amazing sport. We’ll spend time in Lefkes, one of the most beautiful villages in Greece, boasting narrow stone walkways, stunning traditional architecture, and friendly locals. Grab your paddle for our exciting, guided Sea Kayaking Adventure. Explore small coves, otherworldly rock formations, and small isles as we paddle, swim, and snorkel in the magnificent Aegean Sea. Finally, no trip to Paros is complete without an evening spent in the cosmopolitan and lively town of Naoussa. Enjoy walking the white-washed streets along the bustling harbor, filled with colorful fishing boats and not-to-believed luxury yachts. Grab a bite with your friends at one of the seaside cafes and enjoy the sunset over this awe-inspiring Greek island.Athens (2 nights)
The final stop on our trip to Italy and the Greek Islands is the capital city of Athens. Offering a rich tapestry of ancient history and modern vibrancy, Athens is a fascinating destination full of storied ruins and lively neighborhoods. We’ll visit the Acropolis, one of the most iconic and significant archaeological sites in the world. You’ll marvel at the famous structures such as the Parthenon, Erechtheion, and the Temple of Athena Nike. Tour the Agora, a key historical landmark which served as a central hub for commerce, politics, and social life in ancient Athens. We’ll drive by the Panathenaic Stadium, built entirely of marble and site of the first modern Olympics. Enjoy walking around Plaka and Monastiraki, charming and traditional neighborhoods with narrow, winding streets and home to some of Greece’s best boutiques and restaurants. We’ll enjoy the final night’s dinner together as we prepare to say goodbye to our new friends and our unforgettable adventure of a lifetime.