Italy with Thrifter Junker Vintage Hunter

Welcome dinner dinner at a local restaurant is included. Your meal will typically be a 3-course menu which includes a first course, second course, dessert, and one non-alcoholic drink, subject to change. *Vegetarian and gluten free options are available; Vegan options unavailable.

After dinner, let’s slow down, relax, and just be together. We’ll gather for an easygoing evening hangout — no agenda, no rush — just a chance to bond, laugh, and swap stories about our week in Italy.

Overnight in Catania.

Breakfast at the hotel is included. Hotel breakfasts typically offer continental, full/American, or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.

In the morning, take a walking tour of Catania, one of the most beautiful cities in Sicily filled with rich history. Led by a local guide, begin your exploration in the central Piazza Duomo, the heart of Catania’s historic center. Here, you’ll find the iconic Elephant Fountain, known locally as "Liotru," which has become a symbol of the city. This intriguing statue, made from black lava stone, dates back to the Roman era and is shrouded in legend and myth. Nearby, visit the awe-inspiring Catania Cathedral, dedicated to Saint Agatha, the city's patron saint. The Cathedral's baroque façade and opulent interior, with its exquisite frescoes and relics, reflect Catania’s rich artistic heritage. Across the city tour and food tour, expect to walk 1.5 - 2 miles on paved and cobblestone streets.

Continue on foot towards the markets. Here you’ll immerse yourself in the local culture by sampling some of Catania’s famous street foods. The city’s vibrant markets and lively alleys are filled with the enticing aromas of arancini, cannoli, and fresh seafood. You’ll enjoy three different foods which will vary depending on seasonality and availability. Some options include Arancini (fried rice balls), fried fish, local cured meats and/or local cheeses, focaccia, cannolo (sweet), and ice cream. Across the city tour and food tour, expect to walk 1.5 - 2 miles on paved and cobblestone streets.

Take a private transfer to Letojanni. Stops for bathrooms/snacks will be made along the way as needed.

Dinner at the hotel is included. Your meal will typically be a 3-course menu which includes a first course, second course, dessert, and one non-alcoholic drink, subject to change. *Vegetarian and gluten free options are available; Vegan options unavailable.

After a full day of exploring Catania , let’s come together for a relaxed evening wind-down. Grab a drink, find a comfy spot, and let’s just hang out, bond, and swap stories about what we’ve seen so far. This is our chance to laugh about the little moments, share first impressions, and really start to feel like a group of friends traveling together. Think of it as our cozy “living room” time in Italy — laid-back, unhurried, and all about connection.

Overnight in Letojanni.

Breakfast at the hotel is included. Hotel breakfasts typically offer continental, full/American, or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.

After breakfast, take a 30 minute private transfer to Taormina to embark on a private guided tour of its crown jewel: the Greek-Roman Theatre - renowned for its breathtaking views and historical significance. Stroll down Via Teatro Greco to the Villa Comunale, where your tour leader will introduce you to a diverse array of botanical wonders. Continue exploring the village center, including the Cathedral, Corso Umberto I, and Piazza 9 Aprile with its charming Clock Tower and Church of S. Giuseppe. After the guided tour, you’ll enjoy time at leisure in Taormina for lunch (on your own) and in the late afternoon you’ll take a private transfer back to your hotel.

In the late afternoon, meet your driver and bus and return to your accommodations.

After a day wandering Taormina’s ancient theatre, strolling through gardens, and soaking in the charm of its piazzas, tonight we’ll gather together to unwind. Over dinner and an easy evening hangout, let’s share the little highlights — the views, the flavors, the unexpected moments — that made Taormina so special. A relaxed night to connect, laugh, and let the magic of the day linger.

Overnight in Letojanni.

Breakfast at the hotel is included. Hotel breakfasts typically offer continental, full/American, or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.

After breakfast, check out from your hotel and take a private transfer to Mt. Etna, Europe's most active volcano.

Led by a local guide, enjoy an easy hike at the base of the volcano. You’ll hike past surrounding craters, marvel at the contrast between the black lava and vibrant vegetation, and explore off-road tracks through pine forests. At the end of the hike time at leisure for lunch (on your own). Hike Distance: 2.5 miles / Elevation Gain: 330 feet / Duration: 1-2 hours / Difficulty: Easy.

In the afternoon take a private transfer to a local wine estate.

Visit a local winery to taste wines enriched by the volcanic soil’s minerals. Here you’ll enjoy 3 tastings of wines, each unique to the region.

After the wine tasting continue your private transfer to Syracuse.

After a day of hiking craters on Mt. Etna, off-road exploring, and sipping wine at a local vineyard, we’ll settle into Syracuse for the night. Dinner will fill our bellies, but the real treat comes after — an easygoing evening hangout together. Think relaxed vibes, swapping stories about the hike, laughing over wine-tasting favorites (and fails!), and just soaking in the magic of being in Italy. Nothing fancy, just us unwinding, connecting, and letting the day’s memories sink in.

Overnight in Syracuse

Breakfast at the hotel is included. Hotel breakfasts typically offer continental, full/American, or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.

Take a 15 minute transfer to begin your boat tour. Today you’ll embark on a private half-day excursion and explore the maritime wonders of Syracuse while enjoying a completely relaxing experience. Depending on the size of the group, you may be split into two small boats fitting 12 people per boat. Begin by exploring the northern coast of Syracuse, renowned for its fascinating sea caves and rock formations sculpted by nature into shapes resembling animals. Next, we will sail towards the Plemmirio Nature Reserve, passing through the picturesque Gulf of Pillirina, a pristine corner of nature. The navigation will continue around the island of Ortigia, where you can admire its most iconic historical sites, such as the former Bourbon prison, Forte Vigliena, the ancient Spanish walls, Maniace Castle, the Levante waterfront, the Alfeo waterfront, the Aretusa Spring, and the majestic Grand Harbor of Syracuse. The tour also includes a stop for a refreshing swim in the crystal-clear waters along the route (weather permitting) and a light snack-lunch on board. *Please note that the activity could be changed or canceled for safety reasons due to the sea/weather conditions. Life jackets are not provided on the boat, however safety equipment is provided on board as per national law.

Your snack lunch consists of a selection of cold cuts and cheeses, paired with bread, focaccia, other snacks and non-alcoholic drinks, subject to change.

After a day sailing past sea caves, dramatic cliffs, and Ortigia’s landmarks, tonight is all about slowing down together. Once we’ve had dinner, let’s gather for an informal hangout — no agenda, just good conversation and laughs as we relive the boat ride, the views, and the little moments that made the day special. A perfect way to cap off a coastal adventure with friends.

Overnight in Syracuse

Breakfast at the hotel is included. Hotel breakfasts typically offer continental, full/American, or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.

Farewell dinner at the hotel is included. Dinner will be a 3-course set menu which includes first course, second course, and dessert, 1 non-alcoholic drink included. Alcoholic drinks are not included.

After a day to wander, rest, or explore Syracuse however you liked, we’ll come together one last time tonight. Over dinner, let’s share our favorite moments, swap stories we might’ve missed, and raise a glass to the friendships and memories we’ve made along the way. A perfect closing chapter to our Italian adventure — simple, heartfelt, and unforgettable.

Overnight in Syracuse

Breakfast at the hotel is included. Hotel breakfasts typically offer continental, full/American, or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.