Overview

Welcome to Tuscany! Your Trek Travel guides will meet you at the Palazzo Montebello in Florence at 10:30 AM. After a one-hour shuttle, we’ll arrive at the medieval Castello di Verrazzano, whose wine-making roots trace back to the 12th century. Here, you'll receive a brief introduction and an overview of the day's plans, followed by a group lunch at the castle. Learn about Giovanni da Verrazzano—the famed European explorer who first mapped much of the U.S. East Coast—before setting out on your first scenic hike through the vineyards and olive groves of Chianti. Your hike ends at Pietra del Cabreo, a charming historic estate and your home for the next two nights. This evening, gather on the hotel’s picturesque grounds for a private cooking class followed by a wine-paired dinner.

Overview

Wake up to a sunny morning and begin your day with a perfect cappuccino and sweeping views of the Tuscan countryside. Today, immerse yourself in quintessential Tuscan scenery as you walk cypress-shaded lanes and gently curving dirt roads through rows of sun-drenched vineyards and olive groves. Along the way, pause in Montefioralle—one of Chianti’s most beautiful villages—for a wine-paired lunch featuring local specialties. Afterward, enjoy a short hike back to the hotel and relax by the pool. This evening, a brief shuttle takes you to nearby Greve, where you can admire its triangular piazza adorned with galleries. With the best recommendations from your Trek Travel guides, choose from one of many trattorias for a delicious dinner on your own.

Overview

From the hotel, we’ll continue exploring the undulating terrain of Chianti with a scenic hike filled with sweeping views to Panzano, a small and lively hilltop town known for its artisan food and wine culture. Lunch today is a true highlight—hosted at a centuries-old farmhouse surrounded by vineyards and olive trees. We'll begin with a walk through the vines, followed by a visit to the wine cellars, where you'll learn about the estate’s philosophy and winemaking process. A guided tasting of organic estate wines is paired with seasonal dishes, offering a farm-to-table experience rooted in sustainability and local tradition. After lunch, sit back and relax on the shuttle to Liguria and the colorful fishing village of Camogli. Once checked in, unwind with free time along the sea before enjoying dinner at your leisure at the hotel.

Overview

Today, a quick and convenient train takes us to Riomaggiore, the southernmost village of Cinque Terre. From here, we’ll walk the famous coastal path to Manarola, a fishing village where pastel homes cling to the cliffs above the sea. The journey continues along a trail that clings daringly to the hillside through terraced vineyards and olive groves to Corniglia, offering spectacular views of all five villages. Enjoy lunch of your choice at a local bistro, indulging in fresh seafood specialties, before exploring Corniglia’s charming labyrinth of alleys. Avid hikers can extend their route to Vernazza, the “pearl of Cinque Terre,” with its vibrant harbor. A one-hour train ride will transport you back to the hotel. Tonight, explore Camogli for dinner with recommendations from your guides for the perfect dining experience.

Overview

An incredible day awaits in the Gulf of Paradiso, where Camogli’s charm unfolds among lush hills and anchored sailboats. A short shuttle brings us to Portofino, a beacon of Italian elegance known for its colorful harbor and yachting culture. We’ll take time to wander this chic seaside village before venturing into the green expanse of the Portofino promontory, following a scenic trail to San Fruttuoso—a tranquil bay cradled between cliffs and verdant slopes—where lunch awaits. The final stretch of the hike leads to the remarkable 8th-century Benedictine monastery, nestled in one of the most secluded corners of the Ligurian coast. Enjoy time to relax, explore, or swim in the crystalline waters before boarding a scenic ferry back to Camogli. Tonight, we’ll gather for a celebratory dinner at the hotel’s panoramic restaurant overlooking the sea.

Overview

This morning, relish one last cappuccino as you take in the breathtaking views from the breakfast room. Take a final stroll through the ancient streets and along the picturesque port, bustling with fishermen at work. You’ll bid farewell to your guides at 11:00 AM at the hotel before departing for the train station to head to Milan or your next destination. Before you leave, take a moment to soak in the sights and sounds of the sea—this is Cinque Terre, the jewel of the Italian Riviera and a destination you’ll never forget.