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.
DayMorningAfternoonEvening
Day 1Arrival in Rome; private transfer to hotelExplore or relax with local suggestionsOptional stroll through cobblestone streets
Day 2Small-group Colosseum and Forum tourWalk the Via Sacra past ancient landmarksFree evening in Rome
Day 3Visit a Roman market with local guideHands-on cooking class with five-course mealDine on your creations
Day 4High-speed train to Florence; private transfersExplore Florence with tailored recommendationsEvening at leisure
Day 5E-bike tour of Florence and Piazzale MichelangeloPizza and gelato cooking classEnjoy your homemade meal
Day 6Chianti wine and olive oil farm tourGuided tastings and countryside viewsReturn to Florence and relax
Day 7Regional train to La Spezia and LericiStroll Lerici’s waterfront or explore La SpeziaFree evening with local dining options
Day 8Guided hike from Monterosso to CornigliaPanoramic views along the Sentiero AzzurroReturn to hotel and unwind
Day 9Free day in LericiOptional boat trips or village walksSunset dinner or quiet coastal evening
Day 10Train to Venice via Florence; private transfersScenic journey and water taxi arrivalTips from locals for your first Venetian night
Day 11Private walking tour of VeniceVisit major sights and end at Rialto60-minute gondola ride through canals
Day 12Free day in VeniceExplore Dorsoduro or the islandsSip a spritz in a quiet square
Day 13Final stroll and morning coffeePrivate transfer to airportDeparture from Venice

Places you'll visit

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Rome
Rome
Venice
Venice
Florence
Florence
La Spezia
La Spezia
Day01

Day 1: 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

Day 2: 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

Day 3: 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

Day 4: 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

Day 5: Florence e-bike tour and pizza and gelato class

Discover Florence at a relaxed pace on a small-group e-bike tour. 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

Day 6: 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

Day 7: 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

Day 8: 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

Day 9: 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

Day 10: 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

Day 11: 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. 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

Day 12: 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

Day 13: 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