57 days in Milan & Tuscany Itinerary

57 days in Milan & Tuscany Itinerary

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Route & dates

57 days in Milan & Tuscany Itinerary

Start: London
Fly:  4​h 45​min
1
Milan
— 16 nights
Drive:  2​h 30​min
2
Massa
— 12 nights
Drive + ferry:  2​h 45​min
3
Portoferraio, Elba Island
— 4 nights
Drive:  3​h
4
Orbetello
— 6 nights
Drive:  1​h 30​min
5
Siena
— 3 nights
Drive:  1​h 15​min
6
Arezzo
— 2 nights
Drive:  1​h 30​min
7
Florence
— 13 nights
Fly:  5​h
End: London

16
nights
Milan

Milan ©
In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
You'll explore and learn at Palazzo Te and Villa Carlotta. La Citta Alta and Chiesa di San Maurizio al Monastero Maggiore will appeal to history buffs. Get out of town with these interesting Milan side-trips: Orrido di Bellano (in Bellano), Bergamo (Monastero d'Astino, Cattedrale (Duomo) di Bergamo e Battistero, & more) and Castello di Vezio (in Vezio). Next up on the itinerary: get engrossed in the history at Basilica di Sant'Ambrogio, take in the spiritual surroundings of Eremo di S. Caterina del Sasso, step into the grandiose world of Scaligero Castle, and explore the world behind art at Museo di Santa Giulia.

Plan a trip to Milan easily and quickly by telling Inspirock to suggest an itinerary.

London, UK to Milan is an approximately 5-hour flight. You can also take a train; or drive. The time zone difference when traveling from London to Milan is 1 hour. Plan for a bit warmer temperatures traveling from London in August, with highs in Milan at 34°C and lows at 22°C. Wrap up your sightseeing on the 17th (Mon) early enough to drive to Massa.

Things to do in Milan

Historic Sites Museums Shopping

Side Trips

Bergamo, Brescia, Verona, Sirmione, Mantua
Highlights from your plan
Palazzo Borromeo ©
Palazzo Borromeo
Palazzo Te ©
Palazzo Te

12
nights
Massa

Massa ©
Massa is a town and comune in Tuscany, central Italy, the administrative centre of the province of Massa and Carrara. You'll explore the less-touristy side of things at Duomo di Pisa and Via Giuseppe Garibaldi. You'll enjoy a bit of beach vacationing at Playa Loca Beach and Vernazzola Beach. Explore Massa's surroundings by going to Grotta Turistica Antro del Corchia (in Stazzema), Pisa (Knights’ Square, Battistero, & more) and Genoa (Galata Museo del Mare, Dialogo nel Buio, & more). There's lots more to do: take in the architecture and atmosphere at Santuario di Montenero, make a trip to Via Fillungo, stroll around Parco Dei Conigli, and stroll through Bagno Uappala.

Quickly create a custom-made itinerary for Massa using our trip planner.

Traveling by car from Milan to Massa takes 2.5 hours. Alternatively, you can take a bus; or take a train. In August, daily temperatures in Massa can reach 35°C, while at night they dip to 20°C. Wrap up your sightseeing on the 29th (Sat) early enough to travel to Portoferraio.

Things to do in Massa

Parks Outdoors Beaches

Side Trips

Genoa, Pisa, Lucca, Grotta Turistica Antro del Corchia, Santuario di Montenero
Highlights from your plan
Duomo di Pisa ©
Duomo di Pisa
Dialogo nel Buio ©
Dialogo nel Buio
Galata Museo del Mare ©
Galata Museo del Mare

4
nights
Portoferraio, Elba Island

Portoferraio ©
Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Visiting Spiaggia Di Sansone and Monte Capanne will get you outdoors. Discover out-of-the-way places like Spiaggia di Cavoli and Scuba & Snorkeling. Step out of Portoferraio with an excursion to Dolphin & Whale Watching in Marina di Campo--about 32 minutes away. There's more to do: kick back and relax at Spiaggia di Capo Bianco.

To find photos, more things to do, maps, and more tourist information, go to the Portoferraio trip itinerary maker website .

You can do a combination of car and ferry from Massa to Portoferraio in 3 hours. Alternatively, you can do a combination of train and ferry. August in Portoferraio sees daily highs of 33°C and lows of 23°C at night. Wrap up your sightseeing on the 2nd (Wed) early enough to drive to Orbetello.

Things to do in Portoferraio

Outdoors Parks Beaches

Side Trips

Marina di Campo, Monte Capanne, Spiaggia di Cavoli
Highlights from your plan
Spiaggia Di Sansone ©
Spiaggia Di Sansone
Spiaggia di Cavoli ©
Spiaggia di Cavoli
Monte Capanne ©
Monte Capanne

6
nights
Orbetello

Orbetello ©
Orbetello is a town and comune in the province of Grosseto (Tuscany), Italy. Get in touch with nature at Cascate del Mulino and La Feniglia. You'll discover tucked-away gems like Giardino dei Tarocchi and Dog Beach. Change things up with these side-trips from Orbetello: Castello di Montemassi (in Montemassi), Pitigliano (Pitigliano Centro Storico & Antico Ghetto e Sinagoga Pitigliano) and Parco Archeologico del Lago dell'Accesa (in La Pesta). The adventure continues: head off the coast to Giglio Island, make a trip to Castello Di Capalbio, enjoy the sand and surf at Spiaggia di Baratti, and contemplate in the serene atmosphere at Chiesa dei Santi Lorenzo e Mamiliano.

To find maps, traveler tips, reviews, and tourist information, refer to the Orbetello day trip site .

You can drive from Portoferraio to Orbetello in 3 hours. Traveling from Portoferraio in September, you will find days in Orbetello are a bit warmer (32°C), and nights are about the same (19°C). Finish your sightseeing early on the 8th (Tue) to allow enough time to drive to Siena.

Things to do in Orbetello

Parks Outdoors Beaches

Side Trips

Isola Del Giglio, Pitigliano, Giardino dei Tarocchi, Parco Archeologico del Lago dell'Accesa, Dog Beach
Highlights from your plan
Cascate del Mulino ©
Cascate del Mulino
Pitigliano Centro Storico ©
Pitigliano Centro Storico
La Feniglia ©
La Feniglia

3
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Your inner history buff will appreciate Historic Centre of San Gimignano and Centro Storico di Siena. You'll explore the less-touristy side of things at Abbazia di San Galgano and Torre del Mangia. Explore Siena's surroundings by going to Eremo di Montesiepi (in Chiusdino), Abbazia di Sant'Antimo (in Castelnuovo dell'Abate) and San Quirico d'Orcia (in San Quirico d'Orcia). It doesn't end there: explore the historical opulence of Castello di Monteriggioni.

To find maps, traveler tips, reviews, and tourist information, go to the Siena trip tool .

Traveling by car from Orbetello to Siena takes 1.5 hours. Alternatively, you can do a combination of train and bus; or take a train. September in Siena sees daily highs of 32°C and lows of 19°C at night. Cap off your sightseeing on the 11th (Fri) early enough to go by car to Arezzo.

Things to do in Siena

Historic Sites Shopping

Side Trips

Chiusdino, San Quirico d'Orcia, Castello di Monteriggioni, Abbazia di Sant'Antimo, Historic Centre of San Gimignano
Highlights from your plan
Torre del Mangia ©
Torre del Mangia
Abbazia di San Galgano ©
Abbazia di San Galgano
Abbazia di Sant'Antimo ©
Abbazia di Sant'Antimo

2
nights
Arezzo

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
On the 12th (Sat), don't miss a visit to Piazza Grande a Montepulciano, then make a trip to Piazza della Repubblica, then take in the spiritual surroundings of Eremo Le Celle, and finally steep yourself in history at Fortezza di Girifalco. Keep things going the next day: step into the grandiose world of Castello dei Conti Guidi di Poppi, then don't miss a visit to Piazza Grande, then contemplate in the serene atmosphere at San Francesco, Arezzo, and finally take in the spiritual surroundings of Duomo San Donato.

Find out how to plan Arezzo trip without stress by asking Inspirock to help create an itinerary.

You can drive from Siena to Arezzo in 1.5 hours. Other options are to take a bus; or take a train. Wrap up your sightseeing on the 13th (Sun) early enough to drive to Florence.

Things to do in Arezzo

Historic Sites

Side Trips

Cortona, Castello dei Conti Guidi di Poppi, Piazza Grande a Montepulciano
Highlights from your plan
Eremo Le Celle ©
Eremo Le Celle
Castello dei Conti Guidi di Poppi ©
Castello dei Conti Guidi di Poppi
Duomo San Donato ©
Duomo San Donato

13
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Let the collections at Pitti Palace and Museo Nazionale del Bargello capture your imagination. You'll explore the less-touristy side of things at Museo Ferrari and The Baptistery of St. John. Get out of town with these interesting Florence side-trips: Canyon Park (in Bagni di Lucca), La Verna - Franciscan Sanctuary (in Chiusi della Verna) and Modena (MEF-Museo Enzo Ferrari, Piazza Grande, & more). There's still lots to do: see the interesting displays at Museo di San Marco, step into the grandiose world of Castello di Verrazzano, appreciate the extensive heritage of Centro Storico, and get the lay of the land with Walking tours.

To find maps, reviews, other places to visit, and tourist information, refer to the Florence online driving holiday planner .

You can drive from Arezzo to Florence in 1.5 hours. Other options are to take a train; or take a bus. Expect a daytime high around 30°C in September, and nighttime lows around 17°C. Wrap up your sightseeing on the 26th (Sat) to allow time to travel back home.

Things to do in Florence

Historic Sites Museums Tours

Side Trips

Modena, Maranello, La Verna - Franciscan Sanctuary, Canyon Park, Terrazza Mascagni
Highlights from your plan
Museo Ferrari ©
Museo Ferrari
Centro Storico ©
Centro Storico
Canyon Park ©
Canyon Park

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