Discovering Italy


Explore Italy’s most influential cities and important cultural sites—from the Colosseum and Vatican City in Rome, to the Renaissance art of Florence and the elegant mansions and canals of Venice. Visit iconic archaeological ruins and museums; take cooking classes with a local chef; tour the vineyards of Chianti; hike between the colorful villages of the Cinque Terre; and relax along the pristine waters of Lake Como.

Days: 16
Best time to visit: April-June, September, October
Ideal for: Couples, Families

Trip Itinerary

Day 1 – Arrive in Rome

Arriving in Rome, you will be met for a private transfer to your hotel in the heart of the city. With an overwhelming array of ancient ruins, historic churches, and world-class art museums and galleries, it’s time to start exploring. Go for an afternoon stroll in Villa Borghese Park, stop by Trevi Fountain on your way over to the Parthenon, and enjoy dinner and a glass of Chianti in one of the city’s many piazzas.


Day 2 – Vatican City Tour

After breakfast, you will be picked up and brought to the Vatican for a private, half-day tour of this collection of beautiful artwork, artifacts, and incredible architecture. The tour will take you through the incredible array of Greek and Roman sculpture, religious artworks, ancient geographical maps, and the frescoes of the Raphael Rooms. Experience the magic of Michelangelo’s paintings gracing the Sistine Chapel, and visit St. Peter’s Basilica and Square.


Day 3 – Archaeological Excursion

Dive into the history of Ancient Rome on a private, 3-hour tour encompassing the most impressive archaeological sites of this world-shaping empire. Highlights include visiting the Colosseum, Capitoline Hill and Palatine Hill, and deciphering the complex layers of the Roman Forum. After your tour, enjoy the remainder of the day at your leisure, exploring the bohemian Trastevere neighborhood, having a late lunch in Piazza Navona, or climb up to Janiculum Terrace for views over the city.


Day 4 – Train to Florence

This morning after breakfast, check out of your hotel and head to the Tiburtina Rail Station for your train north to Florence. Arriving around midday, you’ll have most of the day to stroll through this enchanting city, renowned for its artistic heritage. Spread along the banks of the Arno River, Florence is brimming with architectural gems like the Cathedral of Santa Maria del Fiore, and is a delight to explore on foot.


Day 5 – Florence Walking Tour

Get acquainted with the fascinating history, art, and architecture of Florence on a private, 3-hour walking tour. Home of the powerful Medici family and birthplace of the Renaissance, Florence’s artistic influence has spread all over the world. You will see the famous Ponte Vecchio, the Piazza della Repubblica, the Duomo, and the artisan leather market of Santa Croce. End the tour with a visit to the Accademia Gallery to see Michelangelo’s David.


Day 6 – Traditional Cooking Class

Join a small group this morning for a market tour and cooking class led by a local chef. In this 5- hour culinary course, you will learn to prepare a classic, four-course Tuscan meal, starting with selecting your seasonal ingredients at the market. For lunch, enjoy the delicious food you have learned to cook, paired with regional wines.


Day 7 – Tuscan Wine Tour & Siena

This morning, embark on a full-day Chianti wine tour en route to your next destination just outside of Siena. Take an owner-led winery tour, learning about wine production in the region, and enjoy lunch at the vineyard. After lunch, drive to Castellina di Chianti, and explore this historic and picturesque town in the Chianti Hills before your second tour and tasting. Arrive at your accommodation in the late afternoon.


Day 8 – Explore Historic Siena

This morning after breakfast, travel the short distance into the center of Siena to meet your local guide for a private sightseeing tour. Known for its art, museums, and architecture, Siena’s Old Town is a UNESCO-listed site that’s filled with landmarks like the magnificent Duomo and the Palazzo Pubblico. Next, you’ll head to the walled cities of Monteriggioni and San Gimignano. Return to your lodging, or head back to Siena for an evening in town.


Day 9 – Siena to Venice

From Siena you will board a train for Venice. Arriving in the afternoon, settle into your hotel and then spend the rest of the day exploring Venice’s hidden gems. Singular and spectacular, Venice is awash in history—filled with artistic treasures, the entire city is an architectural marvel.


Day 10 – Touring Venice

Discover Venice on a private, half-day walking tour and boat ride—customize your itinerary to take in the sites you most want to see, at your own pace. Visit the main sights around St. Mark’s Square and then make your way to the centuries-old Rialto fruit and fish market. With ornate churches and canalside mansions dotting the city, you can’t go wrong while exploring Venice. After lunch, float along the Grand Canal and smaller canals with your guide to explain the architecture and history of the buildings lining the banks. Enjoy the evening at your leisure.


Day 11 – Travel to Sestri Levante

Board a morning train to Milan, changing trains and traveling onward to Sestri Levante, a coastal town to the south of Genoa—about a 6-hour journey. You will be met at the station and brought to your hotel in the heart of town, which is perched on a picturesque promontory jutting into the Ligurian Sea. Enjoy the rest of the day exploring the Old Town and waterfront along the town’s two bays.


Day 12 – Explore the Cinque Terre

Today, explore the UNESCO-listed villages of the Cinque Terre National Park, just a short drive to the south of Sestri Levante. There is a passenger ferry that connects the colorful villages, but hiking is the best way to experience the magic of this rugged coastline. Well-marked trails, of varying degrees of difficulty, pass through vineyards and orchards and offer stunning views all along the way.


Day 13 – The Lakes Region

This morning you will board a morning train north to the Lakes Region, changing trains in Milan and arriving at Lake Como in the afternoon. A region known for its elegance, your lakefront hotel is just a first glimpse of luxury. Enjoy the remainder of the day exploring the historic center of Como and relaxing along the lakeshore. Spend the next two days here, visiting historic towns along the lake.


Day 14 – Lake Como by Boat

Boating excursions are the best way to explore Lake Como, whether on public ferries or faster-paced hydrofoils. One of the most picturesque towns on the lake is Bellagio, with its sandy-hued buildings tucked into cypress groves, climbing along steep, cobblestone lanes away from the lakeshore. Just across the water from Bellagio is the charming, former fishing village of Varenna.


Day 15 – Villas & Villages on Lake Como

On the western shore of the Lake Como, visit the lively resort town of Menaggio—19th-century architecture along the lake gives way to medieval buildings higher uphill. Make your way back from Menaggio by land and stop at the extravagant Villa Carlotta and stroll through its beautiful botanic gardens, or visit the Villa del Balbianello, which has featured in both James Bond and Star Wars movies.


Day 16 – Departure from Milan

Take the train back to Milan and board your afternoon flight home.

Remarkable Journeys has partnered with Lost World Adventures to create this journey. We partnered with Lost World due to their well-mannered relationships with tour guides, hotellers, airlines, and ground management services in the region. In our opinion, they offer the best value and experience in the region.

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