Detailed Itinerary | July 7-19, 2026
A journey for those who travel by taste. From the Amalfi Coast to the Tuscan countryside, from Rome’s storied trattorias to Lisbon’s tiled hills, this is a celebration of flavor, culture, and the timeless art of living well.
Day 1 ❖ Tuesday – July 7, 2026
Departure
Your journey begins as you board an overnight flight to Italy. Settle in, raise a glass to the adventure ahead, and drift into dreams of lemon-scented coastlines, vineyard tables, and sunlit piazzas waiting across the Mediterranean.
Day 2 ❖ Wednesday – July 8, 2026
Naples → Sorrento | Amalfi Coast Elegance
Arrive in Naples and transfer along the glittering Bay of Naples to Sorrento, a cliffside jewel overlooking the Amalfi Coast. After checking in, ease into southern Italy’s rhythm where lemon groves scent the air and church bells echo over the sea. An introductory walking tour reveals historic lanes and artisan boutiques, followed by a welcome aperitivo with regional small plates. Dinner is independent this evening, allowing for rest or a relaxed first taste of coastal cuisine. (T)
Day 3 ❖ Thursday – July 9, 2026
Sorrento | La Dolce Vita on the Bay of Naples
Enjoy a leisurely morning to settle into the rhythm of Sorrento — espresso in Piazza Tasso, a stroll along Marina Grande, or a quiet moment overlooking the Bay of Naples as fishing boats drift in and out of the harbor. Today is entirely yours to savor: browse artisan boutiques fragrant with lemon and leather, linger over a long seaside lunch, visit a local limoncello producer, or simply unwind in the comfort of your accommodations while soaking in the Mediterranean light. As evening falls, gather together for a refined group dinner in Sorrento, where regional specialties and thoughtfully selected Campanian wines are enjoyed against a backdrop of sweeping coastal views. (B, D)
Day 4 ❖ Friday – July 10, 2026
Sorrento → Florence | Renaissance & Wine
Transfer to Naples and board high-speed rail to Florence, where the scenery shifts from sparkling coastline to rolling Tuscan hills in under three hours. Florence welcomes you with cathedral domes, Renaissance grandeur, and honey-colored stone. The afternoon is yours to wander along the Arno, explore artisan workshops, or linger over a Negroni in a sunlit piazza before enjoying dinner independently in one of Italy’s most celebrated culinary cities. (B)
Day 5 ❖ Saturday – July 11, 2026
Florence | Art, Steak & Super Tuscans
Discover Florence’s artistic treasures beginning at Piazza del Duomo and the Baptistery before standing in awe before Michelangelo’s David at the Accademia. Stroll across the Ponte Vecchio and through elegant streets alive with history. This evening celebrates Tuscany’s culinary pride: Bistecca alla Fiorentina — perfectly grilled, boldly seasoned, and paired with robust Tuscan wines for a dinner that captures the heart of Florentine dining. (B, D)
Day 6 ❖ Sunday – July 12, 2026
Cortona, Wine Country & Assisi
Journey into the Tuscan countryside, stopping in sun-washed Cortona for panoramic views across the Val di Chiana. Continue to a family-owned winery for a guided tasting of regional wines accompanied by local cheeses, cured meats, and seasonal fare while learning the traditions behind each bottle. By evening, arrive in Assisi, Umbria’s serene hilltop town rich in history and atmosphere. (B, T, D)
Day 7 ❖ Monday – July 13, 2026
Assisi | Medieval Beauty & Umbrian Cuisine
Explore Assisi’s winding stone streets and the Basilica of St. Francis, a masterpiece of frescoed art and sacred architecture. Umbria’s culinary traditions shine this evening with a farm-to-table dinner featuring truffles, lentils, wild boar, and earthy wines, thoughtfully prepared by a local husband-and-wife team using ingredients from their nearby farm. (B, D)
Day 8 ❖ Tuesday – July 14, 2026
Assisi → Rome | The Eternal City
This morning we journey south from the serenity of Assisi into the grandeur of Rome, where empire, faith, and artistry converge in magnificent layers. After settling into our hotel near Vatican City, we step into the vast embrace of St. Peter’s Basilica to behold Michelangelo’s luminous Pietà, resting in quiet power beneath the soaring dome and centuries of devotion. As evening unfolds, we gather for a Roman welcome dinner celebrating the city’s beloved culinary traditions — carbonara, amatriciana, and gricia — paired with regional wines, followed by a gentle stroll through softly illuminated piazzas where fountains shimmer and the Eternal City reveals its timeless magic under the night sky. (B, D)
Day 9 ❖ Wednesday – July 15, 2026
Rome | Ancient Glory & Trastevere Evenings
Today we step into the grandeur of Ancient Rome, where history rises from stone and empire still echoes in the air. The mighty Colosseum stands before us — a monument to spectacle, power, and endurance — followed by the vast expanse of Circus Maximus, once alive with the thunder of chariots racing beneath imperial gaze. From there, we pause at the famed Bocca della Verità, the legendary “Mouth of Truth,” immortalized by Audrey Hepburn and Gregory Peck in Roman Holiday — a playful yet enduring symbol of Rome’s layered storytelling. Crossing the Tiber, we enter the enchanting quarter of Trastevere, where cobblestone lanes and ivy-draped facades reveal a more intimate Rome. Here we visit the ancient churches of Santa Cecilia and Santa Maria in Trastevere, luminous with early Christian devotion and golden mosaics that shimmer in candlelight. This evening is yours to savor independently in this beloved neighborhood, where trattorias spill into lantern-lit streets and the aromas of cacio e pepe and wood-fired pizza fill the night air. (B, ID)
Day 10 ❖ Thursday – July 16, 2026
Rome by Golf Cart | Hidden Corners & Grand Icons
Explore Rome by private golf cart, gliding past the Spanish Steps, Trevi Fountain, Pantheon, Piazza Navona, and Bernini’s Fountain of the Four Rivers while discovering hidden courtyards and lesser-known corners. The afternoon and evening remain free for final indulgences before departing for Portugal the next morning. (B, ID)
Day 11 ❖ Friday – July 17, 2026
Lisbon | Tiles, Tarts & the Tagus
Fly to Lisbon, where Atlantic light dances across tiled façades and hilltop viewpoints overlook the Tagus River. Explore the historic center and enjoy an independent lunch at the vibrant Time Out Market before visiting Belém Tower and Jerónimos Monastery, monuments to Portugal’s Age of Discovery. No visit to Lisbon is complete without savoring a warm Pastel de Nata, fresh from the oven. Dinner introduces you to Portugal’s rich culinary traditions. (B, D)
Day 12 ❖ Saturday – July 18, 2026
Alfama & Farewell Feast
Today we wander the winding lanes of Lisbon’s historic Alfama district, where tiled façades, hidden courtyards, and sweeping views over the Tagus reveal the soul of the city as the city’s iconic yellow streetcars rattle and glide along the narrow hillsides. Nearby we visit the Lisbon Cathedral (Sé de Lisboa), the city’s oldest church, founded in the 12th century shortly after the Christian reconquest and long a spiritual anchor for the people of Lisbon. Just steps away we continue to the Church of St. Anthony, built on the saint’s birthplace. Here we learn about the beloved Lisbon native—preacher, miracle worker, and patron of lost things—and take part in a charming local tradition: tossing a coin toward St. Anthony’s open breviary while praying for the grace of a good spouse. Legend says that if the coin lands on the book, luck in love will follow. The afternoon is free for final discoveries before we gather this evening for a festive farewell dinner celebrating Portuguese hospitality. With grateful hearts, we raise a final toast to friendship, faith, and the lingering spirit of saudade. (B, D)
Day 13 ❖ Sunday – July 19, 2026
Rise and shine as your journey comes to a close. Make your way to the airport for your flight home, carrying with you the flavors, friendships, and unforgettable moments of Italy and Portugal — memories that linger long after the journey ends.
Dining Codes:
B = Breakfast
D = Dinner
T = Tasting
ID = Independent Dinner