16 days in Italy Itinerary

16 days in Italy Itinerary

Created using Inspirock Italy trip planner
Make it your trip
Fly to Milan Malpensa, Ferry to Tremezzina
1
Tremezzina
— 2 nights
Drive
2
Siena
— 5 nights
Drive
3
Assisi
— 5 nights
Drive
4
Pitigliano
— 2 nights
Drive to Leonardo da Vinci–Fiumicino Airport, Fly to London

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Tremezzina — 2 nights

The majestic Villa Carlotta is among the most popular places to visit in Tremezzina, its neoclassical architecture complimenting the lush, neatly maintained gardens and charming walkways.
Your day by day itinerary now includes Isola Madre. Start off your visit on the 23rd (Tue): step off the mainland to explore Isola Madre, take in the awesome beauty at Valchiavenna, step into the grandiose world of Castello di Vezio, then contemplate the waterfront views at Lago di Como, and finally take in the architecture and atmosphere at Chiesa di S. Marta. Get ready for a full day of sightseeing on the next day: look for gifts at La Cantina, admire the landmark architecture of Villa del Balbianello, then pause for some serene contemplation at Chiesa di S. Bartolomeo, then take in the architecture and atmosphere at Parrocchia di S. Abbondio, and finally pause for some serene contemplation at Chiesa di San Lorenzo a Tremezzo.

To see reviews, ratings, and tourist information, go to the Tremezzina day trip planning tool.

Palermo to Tremezzina is an approximately 4.5-hour combination of flight and ferry. You can also do a combination of train and ferry; or do a combination of train and ferry. In May, daily temperatures in Tremezzina can reach 25°C, while at night they dip to 13°C. Wrap up your sightseeing on the 24th (Wed) to allow time to drive to Siena.
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Nature · Parks · Historic Sites · Shopping
Side Trips
Find places to stay May 22 — 24:

Siena — 5 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
You'll find plenty of places to visit near Siena: Montalcino (Podere Il Cocco & Castiglion del Bosco Winery), San Gimignano (San Gimignano Bell Tower, Historic Centre of San Gimignano, &more) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). Next up on the itinerary: take in the architecture and atmosphere at Duomo di Siena, don't miss a visit to Centro Storico di Siena, contemplate in the serene atmosphere at San Francesco, and deepen your understanding at Scuola di Cucina di Lella.

For maps, photos, where to stay, and tourist information, you can read our Siena trip planner.

Traveling by car from Tremezzina to Siena takes 5 hours. Alternatively, you can do a combination of ferry and train; or do a combination of bus and train. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Cap off your sightseeing on the 29th (Mon) early enough to go by car to Assisi.
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Historic Sites · Wineries · Tours · Museums
Side Trips
Find places to stay May 24 — 29:

Assisi — 5 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Venture out of the city with trips to Tempio di Sant'Angelo - Chiesa di San Michele Arcangelo (in Perugia), Vineria del Carmine (in La Bruna) and Wild Foods Italy (in Montefalco). There's still lots to do: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, steep yourself in history at Eremo delle Carceri, examine the collection at Museo della Porziuncola, and step into the grandiose world of Rocca Maggiore.

For maps, other places to visit, photos, and more tourist information, you can read our Assisi itinerary planner.

You can drive from Siena to Assisi in 2 hours. Other options are to take a bus; or take a train. Expect a daytime high around 26°C in May, and nighttime lows around 13°C. Finish up your sightseeing early on the 3rd (Sat) so you can go by car to Pitigliano.
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Historic Sites · Wineries · Wildlife · Parks
Side Trips
Find places to stay May 29 — Jun 3:

Pitigliano — 2 nights

Pitigliano is a town in the province of Grosseto, located about 80km south-east of the city of Grosseto, in Italy. On the 4th (Sun), see the interesting displays at Museo di Preistoria e Protostoria della Valle del Fiora di Manciano, take in the dramatic scenery at Cascate del Mulino, and then witness a stunning natural landmark at Terme di Saturnia - Parco Termale. Keep things going the next day: get to know the fascinating history of Sorano Centro Storico, take in the spiritual surroundings of Piccola Gerusalemme di Maremma, then make a trip to Via CAVA ETRUSCA SAN GIUSEPPE, and finally appreciate the extensive heritage of Pitigliano Centro Storico.

For maps, traveler tips, reviews, and other tourist information, read our Pitigliano travel website.

You can drive from Assisi to Pitigliano in 2.5 hours. Alternatively, you can do a combination of train and taxi. In June, plan for daily highs up to 32°C, and evening lows to 17°C. Finish up your sightseeing early on the 5th (Mon) so you can go by car back home.
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Nature · Parks · Historic Sites · Spas
Side Trips
Find places to stay Jun 3 — 5:

Italy travel guide

4.6
Landmarks · Ruins · Beaches
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.
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