Itinerary #1: Getaway to Tuscany & Rome
Spend some time in the Eternal City and a few days in the Tuscan countryside on this laid-back trip plan.
|Day 1||Arrive in Florence, Transfer to Radda in Chianti||Radda-in-Chianti|
|Day 2||Full Day Chianti Tour: Winery & Steak Poet of Fiorentina from Radda||Radda-in-Chianti|
|Day 3||Radda in Chianti to Rome by Train, Walking Tour||Rome|
|Day 4||Guided Food Tour of Testaccio & Trastevere||Rome|
|Day 5||Vatican, Colosseum, & Roman Forum Tour||Rome|
|Day 6||Goodbye Italy|
The journey begins in Florence, the capital of the region. You'll transfer to the 9th-century town of Radda in Chianti in the heart of Tuscany's wine-producing area. Go for a bike ride in the surrounding hills and explore the medieval city on foot before relaxing over a leisurely dinner. On day two, you'll go on a full-day tour of Chianti, stopping at local wineries to taste wines and touring the famous Castello di Verrazzano. After an al fresco Tuscan lunch of pasta, cured meats, and artisanal cheeses before visiting the historic butcher shop known as Antica Macelleria Cecchini to try specialties like thinly sliced carpaccio, also known as the "sushi of Chianti."
Take the high-speed train to Rome for a walking tour around the oldest part of the city. You'll get off the beaten path on day four with a guided food tour of the neighborhoods of Testaccio and Trastevere, pausing to sample wine, cheese, coffee, and gelato at hole-in-the-wall shops and marketplaces. Then you'll go on a full-day tour of the Vatican, the Colosseum, and the Forum, including stops at Saint Peter's Basilica and the Sistine Chapel. Go for a stroll in the evening to see the Trevi Fountain illuminated at night before sitting down for a classic Roman meal to finish the trip. Learn more
Itinerary #2: Relaxed Amalfi Coast & Rome
This well-balanced itinerary offers the best of both worlds: history and culture in Rome, then sand and sun on the Amalfi Coast.
|Day 1||Arrive in Rome & Transfer to Amalfi Coast, Positano Sunset Cruise||Amalfi|
|Day 2||Capri and Anacapri Day Tour||Amalfi|
|Day 3||Amalfi Coast to Sorrento, Afternoon Cooking Class||Sorrento|
|Day 4||Sorrento to Rome, Pompeii en Route||Rome|
|Day 5||Vatican & Classic Tour of Rome||Rome|
|Day 6||Goodbye Italy!|
Touch down in Rome, then transfer to the Amalfi Coast, where you'll get a striking introduction to the region during a sunset cruise around Positano. Dine on fresh seafood before the next day's boat trip to the island of Capri, where you'll walk down the villa-lined Belvedere of Tragara and explore the ruins of ancient Roman homes. You'll board another boat to see the Grotta Azzurra, a naturally hollowed-out sea cave, then relax on the beach for a couple of hours.
Move onto Sorrento the next day, where you'll take a four-hour cooking class at the Sorrento Cooking School. Take some time to enjoy the laid-back charm of the beach town while strolling through the historic streets, stopping for a gelato or a glass of wine along the way. You'll visit the fascinating ruins of Pompeii — a city lost for 1,500 years following Mount Vesuvius' eruption before it was rediscovered in 1599 — on the way to Rome. Finish with a tour of the Vatican, Colosseum, and the Forum, then enjoy one more traditional meal and make a toast to your short stay in Italy. Learn more
Itinerary #3: Cinque Terre & the Italian Riviera
On this outdoorsy itinerary, you'll hike through the scenic coastal villages of the Cinque Terre and enjoy the sunshine and local wines in Liguria.
|Day 1||Arrive in Pisa, Travel to Cinque Terre & Evening Cruise||Manarola|
|Day 2||Wine Tasting & Villages of the Cinque Terre||Manarola|
|Day 3||Cinque Terre to Portofino, Sunset Kayak & Wine Tasting||Portofino|
|Day 4||Portofino Boat Tour||Portofino|
|Day 5||Portofino to Pisa, City Tour & the Leaning Tower||Pisa|
|Day 6||Goodbye Italy!|
Kick off the trip in Pisa, then take the train to the Cinque Terre and board a boat for an evening cruise along the scenic coastline of Liguria. You'll stay in Manarola, one of the Cinque Terre's five historic fishing villages. On day two, head to neighboring Riomaggiore to tour a family-owned vineyard and taste several wines produced in the hills overlooking the sea. Take the afternoon to visit the other three villages — Monterosso al Mare, Vernazza, and Corniglia — all connected by train and hiking trails.
Continue onto Portofino on day three for a sunset kayak tour followed by a tasting of locally produced wines. You'll spend part of the next day on a boat, making a stop at beautiful San Fruttuoso Beach, located beside a medieval abbey. Then follow your guide for a snorkeling tour around the submerged Christ of the Abyss statue. Return to Pisa for sightseeing in one of Tuscany's most famous destinations, pausing for the obligatory photo op at the Leaning Tower and stops at the Duomo cathedral and the 12th-century botanical gardens at the University of Pisa. Learn more
Itinerary #4: Luxury Italian Highlights
On this high-end trip plan catering to luxury travelers, you'll see the finer sides of Venice and Florence.
|Day 1||Arrive in Venice, Private Guided City Tour||Venice|
|Day 2||Bacaro & Private Squero Tour in Venice||Venice|
|Day 3||Venice to Florence, Private Guided City Tour||Florence|
|Day 4||Private Guided Accademia Gallery & Boat Tour||Florence|
|Day 5||Free Day in Florence||Florence|
|Day 6||Goodbye Italy!|
The adventure starts in Venice with a private tour of cultural and historic highlights, including the ornate Doge's Palace, Piazza San Marco, the quaint Bridge of Sighs, and the Grand Canal. On day two, you'll dine in style at a traditional Venetian bacaro (wine bar), sampling fresh seafood from squid skewers to salted codfish canapès. Then take a private tour of a squero, a small boatyard where tradesmen build and repair gondolas, before lingering over a candlelit dinner along the canals.
On day three, take the train to Florence. You'll see the Galleria dell'Accademia, home of Michelangelo's 'David' sculpture, on a private tour, then walk across scenic Ponte Vecchio bridge and climb to the bell tower atop the Italian Gothic Cathedral of Florence. You'll have dinner with wine pairings at Enoteca Pinchiorri, Florence's 3-star Michelin restaurant. Nearing the end of the trip, you'll board a traditional boat for a sunset cruise on the Arno River, passing monuments including the Uffizi Gallery, the Vasari Corridor, and Palazzo Corsini as the day comes to a close. Finish by raising a glass at one of the many wine bars in the neighborhood of Sant'Ambrogio. Learn more
Itinerary #5: Cycling in Tuscany
Pedal through Pisa, Lucca, and other Tuscan destinations on this active itinerary.
|Day 2||Pisa – Lucca||Lucca|
|Day 3||Lucca – Montecatini Terme||Montecatini Terme|
|Day 4||Montecatini – Vinci – San Miniato||San Miniato|
|Day 5||San Miniato – Pisa||Pisa|
Take it easy in Pisa on the first day of the trip before heading off on two wheels on the second day towards the historic city of Lucca. You'll pedal along a beautiful cycling path across the Serchio River — or, alternatively, past Massaciuccoli Lake in the Chiarone Nature Reserve — before breaking for the evening in Lucca, a wonderfully preserved Tuscan gem. On day three, continue on your bicycle through the Lucchesia Hills, pedaling along country roads to the town of Collodi, best known as the birthplace of Pinocchio. Take a break in the green gardens of Villa Garzoni before ending up in the spa town of Montecatini, where you'll spend the evening.
Cycle across the Padule di Fucecchio wetlands to the town of Vinci, the hometown of Leonardo de Vinci, on day four. You'll pass vineyards and villas before crossing the Arno River and the famed San Miniato fortress. The next day is your last full day of cycling, starting in the hills of San Miniato before heading downhill towards Bientina and Vicopisano Castle. You'll pedal along the Arno River all the way back to Pisa, where you'll treat yourself to one last Italian meal before flying out the next day. Learn more