14-Day Italy Guide

Rest and acclimate as you arrive in Rome. Enjoy the spa amenities at your hotel. Take in the atmosphere of a nearby piazza or stroll in the Borghese Gardens. After a chance to rest, enjoy dinner at Taverna Trilussa located in the charming neighborhood of Trastevere.

Visit famous sights including the Trevi Fountain, Spanish Steps, Pantheon, Castel Sant'angelo, Monument of Vittorio Emanuele II, Colosseum and the Roman Forum. Wander at your own leisure or with a guide. 

Be sure to reserve tickets in advance for entrance to the Colosseum. At the end of the day, enjoy traditional Emilian cuisine at Dal Bolognese in Piazza del Popolo.

I highly recommend a guided tour to make the most of your time visiting Vatican City. What a Life Tours offers a variety of small group or private tours. View the Sistine Chapel in the morning before it opens to the general public or during an evening VIP tour. Then book yourself a reservation for lunch or dinner at Roscioli.

Book the express train from Roma Termini to Firenze Santa Maria Novella. Settle into your hotel and visit la Accademia to see Michelangelo’s famous statue of David. Be sure to book a timed-entry ticket for the museum and dinner reservations at Il Latini to experience typical Tuscan cuisine.

If you’re up for it, wander through the San Lorenzo Market before or after your visit to the Accademia.

Wake early and head to the Uffizzi Gallery to admire the famous artwork of Botticelli. A timed-entry ticket is highly recommended. After visiting the museum, walk along the Arno river towards the Ponte Vecchio. From here, you might continue on to visit the Pitti Palace & Boboli Gardens in the Oltrarno (timed-entry ticket recommended) or the Scuola del Cuoio (School of Leather) in Santa Croce to see leather bags crafted by local artisans. 

End the afternoon relaxing in Piazzalle Michelangelo which offers stunning views overlooking the city. For dinner, enjoy fresh homemade pasta and pizza at Yellow Bar or more views of the Ponte Vecchio at the Golden View.

Head out of the city to visit the vineyards of Chianti or medieval towns of Siena, San Gimignano, Lucca, or Pisa. Fun in Tuscany offers a range of tours and activities to choose from for this memorable day trip.

Don’t let your time in Florence end without seeing Brunelleschi’s Duomo up close. Entrance to the cathedral is free, but you’ll want a timed-entry ticket to climb to the top of the Duomo or Giotto’s Belltower for the magnificent views. Enjoy a carousel ride in Piazza della Repubblica or an afternoon of shopping. 

Make sure to reserve a table at La Giostra and save room for the tiramisu.

Book the express train from Firenze Santa Maria Novella to Venezia Santa Lucia. If your hotel is not walking distance, ask the concierge desk to set up a private water taxi to the hotel. Sit back, relax and enjoy sights along the Grand Canal. Wander around the canals while shopping or join a walking food and wine tour to sample the best of Venetian bàcari.

Book your timed-entry ticket for entrance to San Marco Basilica and the Doge’s Palace. 

For dinner, try a local favorite, Al Covo.

Spend a day exploring the islands of Murano and Burano. Pick up Line 12 from the Vaporetto stop in Fondamente Nove, Venice’s Old Town. Stop first in Murano, known for its hand-blown glass. Watch the experts demonstrate their craft as you tour the factory and showroom. Then, take the same vaporetto line to Burano, a colorful fishing village also famous for its lacemaking. 

Don’t miss lunch or dinner at Trattoria al Gatto Nero in Burano.

Take the afternoon train to Como arriving in time for an aperitivo and dinner after settling in to your hotel. Alternatively, hiring a private car transfer allows for an early start and visit to Bergamo; a stunning hilltop city with architecture dating back to the 16th century.

Visit the town of Cernobbio and famous villas such as, Villa d’Este and Villa Bernasconi.

Enjoy lunch in Piazza Risorgimento at Harry’s Bar.

Spend the day leisurely exploring the towns of Varenna and Bellagio. End your trip with a sunset sail along the lake.

Spend the day in Milan shopping, visiting the Cathedral or admiring Leonardo Da Vinci’s famous painting of The Last Supper.