Italy’s classic sights trip

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Make this journey through Italy’s classic sights your own. Choose local stays, personalized experiences, and slow-paced days that let you feel like a resident.

Perfect for travelers seeking authentic, tailor-made trips to Italy, we offer custom options, trusted local hosts, and private touches throughout. Start planning now to secure your preferred dates, and turn Italy into a story you lived.

Italy’s classic sights trip highlights

  • Ancient Rome immersion: Walk the Colosseum and Roman Forum with a local guide, skipping lines and uncovering myths.
  • Renaissance art and private tours: See the Uffizi and Accademia with expert guides.
  • Venetian canals and hidden alleys: Glide through canals by private gondola, then explore secret courtyards and artisanal workshops.
  • Tuscan countryside and wine tasting: Taste Chianti at family-run estates, enjoy bespoke vineyard tours, and savor slow meals.
  • Tailor-made local connections: Customize every day with private drivers, local hosts, and authentic experiences.
DayLocationActivityOvernight
1Rome

• Arrival in Rome and private transfer to hotel

• Explore or relax with local suggestions

Rome
2Rome

• Small-group Colosseum and Roman Forum tour

• Walk the Via Sacra past ancient landmarks

• Free evening in Rome

Rome
3Rome

• Visit a Roman market with a local guide

• Hands-on cooking class with a five-course meal

• Dine on your own creations

Rome
4Florence

• High-speed train to Florence with private transfers

• Explore Florence using tailored recommendations

• Evening at leisure

Florence
5Florence

• E-bike tour through Florence and Piazzale Michelangelo

• Pizza and gelato cooking class

• Enjoy your homemade meal

Florence
6Chianti / Florence

• Chianti wine and olive oil farm tour

• Guided tastings and countryside views

• Return to Florence for a relaxing evening

Florence
7Lerici / La Spezia

• Regional train to La Spezia and Lerici

• Stroll Lerici’s waterfront or explore La Spezia

• Free evening with local dining options

Lerici
8Cinque Terre

• Guided hike from Monterosso to Corniglia along the Sentiero Azzurro

• Return to hotel and unwind

Lerici
9Lerici

• Free day in Lerici

• Optional boat trips or village walks

• Sunset dinner or quiet coastal evening

Lerici
10Venice

• Train to Venice via Florence with private transfers

• Scenic journey and water taxi arrival

• Local tips for your first Venetian night

Venice
11Venice

• Private walking tour of Venice

• Visit major sights and finish at Rialto

• Sixty-minute gondola ride through the canals

Venice
12Venice

• Free day in Venice

• Explore Dorsoduro or visit nearby islands

Venice
13Venice → Airport

• Final stroll and morning coffee

• Private transfer to the airport

• Departure from Venice

Places you'll visit

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Day01

Arrival in Rome

Arrive in Rome and enjoy a private transfer to your hotel. The rest of the day is yours to relax, stroll cobblestone streets, or ask your local host to tailor a gentle introduction to the city.

Colosseum with clear blue sky, Rome, Italy. Rome landmark and antique architecture. Rome Colosseum is one of the best known monuments of Rome and Italy
Day02

Colosseum half-day tour

Skip the lines to explore the Colosseum and Forum Romanum in a small group with an English-speaking guide who brings the ruins to life.

Stroll the cobblestones of the Via Sacra from the Colosseum to the Roman Forum, passing the House of the Vestal Virgins, Trajan's Column, and other ancient highlights.

Inside the old Colosseum (Coliseum), Rome, Italy © Viacheslav Lopatin/Shutterstock
Day03

Market visit and traditional cooking class

Explore a lively Roman market in a small group, sampling seasonal fruits, vegetables, cheeses, and cured meats while learning what sets Italian ingredients apart.

Then head to a hands-on cooking class, where you'll prepare and enjoy a five-course Roman meal, starting with an appetizer, followed by three types of pasta, a main dish with a side, and dessert.

Market Italy
Day04

Rome to Florence by high-speed train

Travel by high-speed train from Rome to Florence, with private transfers to and from the stations for a seamless, stress-free journey.

Explore Florence at your own pace with personalized tips from local experts: priority entry to the Uffizi or Accademia, a private tasting at a traditional trattoria, or visiting artisan workshops in the Oltrarno.

Florence cityscape © Bob Hilscher/Shutterstock
Day05

Florence e-bike tour and pizza and gelato class

Discover Florence at a relaxed pace on a small-group e-bike tour, perfect for anyone planning a Florence trip through the historic city. With an English-speaking guide, ride through the historic center and up to Piazzale Michelangelo on a pedal-assist or fat-tire e-bike.

Later, join a three-hour hands-on class in central Florence to learn the secrets of traditional pizza and gelato. Get expert tips from a local chef, then enjoy the meal you’ve created.

Duomo Santa Maria Del Fiore in Florence Italy © Songquan Deng/Shutterstock
Pizza
Day06

Chianti wines and olive oil tour

Explore the rolling hills of Chianti, just outside Florence. Visit family-run farms to taste estate wines and extra virgin olive oil, learn traditional methods from local producers, and take in panoramic countryside views.

This half-day experience includes guided tastings, meetings with passionate artisans, and a deeper look into Chianti’s unique terroir: curated moments that feel both personal and unforgettable.

Chianti
Day07

Florence to Lerici and La Spezia

Take a regional train from Florence to La Spezia and Lerici, a journey of about two hours. Private transfers to and from the stations are included for a smooth connection.

Spend the afternoon strolling Lerici’s waterfront, sampling fresh Ligurian seafood, or exploring the museums of La Spezia. Use La Spezia as your base for discovering the Cinque Terre, with optional boat trips, scenic hikes, and private guided walks tailored to your interests.

Lerici Italy
Day08

Sentiero Azzurro hike from Monterosso to Corniglia

Enjoy a privately guided hike along the Sentiero Azzurro (Blue Trail) from Monterosso to Corniglia, with hotel transfers included. This tailor-made walk adds local insight and personal attention to your Italy itinerary.

The route takes about three hours and is moderately challenging. Along the way, you’ll be rewarded with sweeping views of clear blue waters and dramatic cliffs, an unforgettable coastal experience.

Hiking Vernazza Italy
Day09

Free day in Lerici

After breakfast, enjoy a free day in coastal Lerici to relax and explore at your own pace. Stroll along the seafront, visit the medieval castle, swim in hidden coves, and sample Ligurian cuisine at family-run trattorias.

For something more personalized, we can arrange private boat trips to Palmaria or guided walks to nearby villages, tailor-made to match your interests.

Lerici, Italy
Annalisa

Tips from Annalisa

Italy Travel Expert

quotes

Skip the main beach and walk 15 minutes to Eco del Mare, a hidden cove with emerald water, tucked beneath dramatic cliffs. It’s pricier than the public spots, but quiet, chic, and worth it if you want Lerici without the crowds.

Day10

La Spezia to Venice

From La Spezia, take a regional train to Florence, then connect to a high-speed train to Venice. Private van and water taxi transfers are arranged at each station for a seamless journey, no stress over luggage or timing.

This travel day becomes part of the experience, with coastal views, the charm of Florence’s station, and a dramatic arrival into Venice by water taxi. Tailor-made service keeps things relaxed, with local tips to help you make the most of your first evening in the city.

St Mark's square from the Grand canal. Venice, Italy
Day11

Venice walking tour

Begin your private walking tour of Venice in the Saint Mark’s area with a historical introduction to the former maritime republic, a must for anyone planning a Venice trip. Visit the Doge’s Palace, St. Mark’s Square, and the Basilica, then continue to San Zaccaria.

Walk along the lagoon with views of San Michele and Murano, then head into the Cannaregio district, passing churches, palaces, Marco Polo’s former home, and the historic Fontego dei Tedeschi.

Finish at the Rialto Bridge and market, an ideal spot for picking up local mementos. After the tour, enjoy a 60-minute gondola ride through Venice’s atmospheric canals.

St Mark's Square and Doge's Palace, Venice, Italy
Travel couple taking selfie picture in gondola on Venice vacation. Beautiful lovers on a romantic boat ride across the Venetian canals taking self-portrait pictures with smartphone during holiday.
Day12

Free day in Venice

Enjoy a free day in Venice to explore at your own pace. Visit the Peggy Guggenheim Collection for modern art in a tranquil canal-side setting, or take a vaporetto to the quiet island of Giudecca for local cafés and lagoon views.

Browse artisan workshops in Dorsoduro, sip a spritz in Campo Santa Margherita, or simply get lost in the backstreets far from the crowds.

Souvenirs and carnival masks on street trading in Venice, Italy
Day13

Departure from Venice

Savor your final morning in Venice with a slow stroll along the canals and one last coffee, soaking in the light and quiet corners that made your tailor-made journey special.

A private driver will meet you at your hotel for a seamless transfer to the airport, ensuring you leave Italy with warm memories and a smooth farewell.

Venice