57 days in Milan & Tuscany Itinerary

57 days in Milan & Tuscany Itinerary

Created using Inspirock Italy trip maker

Make it your trip
Fly
1
Milan
— 16 nights
Drive
2
Massa
— 12 nights
Drive to Piombino, Ferry to Portoferraio
3
Portoferraio, Elba Island
— 4 nights
Ferry to Piombino, Drive to Orbetello
4
Orbetello
— 6 nights
Drive
5
Siena
— 3 nights
Bus
6
Arezzo
— 2 nights
Drive
7
Florence
— 13 nights
Fly

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Milan

— 16 nights

Fashion Capital of World

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.
Eschew the tourist crowds and head to Museo del Novecento and Arco della Pace. Give yourself a bit of retail therapy at Bellavista and Restaurifelici. Change things up with these side-trips from Milan: Orrido di Bellano (in Bellano), Castello di Vezio (in Vezio) and Bergamo (Monastero d'Astino, Cattedrale (Duomo) di Bergamo e Battistero, &more). There's lots more to do: contemplate in the serene atmosphere at Eremo di S. Caterina del Sasso, enjoy the sand and surf at Guree Beach, admire the striking features of Arche Scaligere, and get engrossed in the history at Grande Museo del Duomo di Milano.

To find reviews, photos, more things to do, and tourist information, read our Milan road trip app.

London, UK to Milan is an approximately 5-hour flight. You can also take a train; or do a combination of car and train. Traveling from London to Milan, you'll lose 1 hour due to the time zone difference. Traveling from London in August, things will get a bit warmer in Milan: highs are around 34°C and lows about 22°C. Finish your sightseeing early on the 17th (Mon) so you can drive to Massa.

Things to do in Milan

Historic Sites · Museums · Shopping · Parks

Side Trips

Find places to stay Aug 1 — 17:

Massa

— 12 nights
Massa is a town and comune in Tuscany, central Italy, the administrative centre of the province of Massa and Carrara. Get outdoors at Grotta Turistica Antro del Corchia and Playa Loca Beach. You'll get in some beach time at Bagno Uappala and Spiaggia della Lecciona. Get out of town with these interesting Massa side-trips: Pisa (Knights’ Square, Battistero di San Giovanni, &more), Genoa (Galata Museo del Mare, Dialogo nel Buio, &more) and Lucca (Piazza Anfiteatro, St Martin Cathedral, &more). There's still lots to do: take in the architecture and atmosphere at Santuario di Montenero, stroll around Parco Dei Conigli, contemplate in the serene atmosphere at Basilica Di Santa Maria Assunta, and stroll through Clan Beach.

For where to stay, more things to do, maps, and more tourist information, read Massa online trip itinerary maker.

You can drive from Milan to Massa in 2.5 hours. Alternatively, you can take a train. In August, daily temperatures in Massa can reach 35°C, while at night they dip to 20°C. Cap off your sightseeing on the 29th (Sat) early enough to travel to Portoferraio.

Things to do in Massa

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Find places to stay Aug 17 — 29:

Portoferraio, Elba Island

— 4 nights
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 Cavoli and Spiaggia di Capo Bianco will get you outdoors. Step off the beaten path and head to Monte Capanne and Scuba & Snorkeling. Step out of Portoferraio to go to Marina di Campo and see Dolphin & Whale Watching, which is approximately 32 minutes away. There's more to do: enjoy the sand and surf at Spiaggia Di Sansone.

To find where to stay, reviews, more things to do, and other tourist information, you can read our Portoferraio trip itinerary builder website.

You can do a combination of car and ferry from Massa to Portoferraio in 3.5 hours. Another option is to do a combination of train and ferry. In August, daytime highs in Portoferraio are 33°C, while nighttime lows are 23°C. Finish your sightseeing early on the 2nd (Wed) to allow enough time to travel to Orbetello.

Things to do in Portoferraio

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay Aug 29 — Sep 2:

Orbetello

— 6 nights
Orbetello is a town and comune in the province of Grosseto (Tuscany), Italy. Discover out-of-the-way places like Spiaggia di Baratti and Giglio Island. Your inner history buff will appreciate Antico Ghetto e Sinagoga Pitigliano and Castello Di Capalbio. Explore the numerous day-trip ideas around Orbetello: Pitigliano Centro Storico (in Pitigliano), Cascate del Mulino (in Saturnia) and Giardino dei Tarocchi (in Pescia Fiorentina). The adventure continues: enjoy the sand and surf at Dog Beach San Vincenzo, appreciate the extensive heritage of Parco Archeologico del Lago dell'Accesa, tour the pleasant surroundings at La Feniglia, and take in the spiritual surroundings of Chiesa dei Santi Lorenzo e Mamiliano.

To find reviews, where to stay, other places to visit, and other tourist information, use the Orbetello trip planner.

You can do a combination of ferry and car from Portoferraio to Orbetello in 3.5 hours. Another option is to do a combination of ferry and train. Expect somewhat warmer weather when traveling from Portoferraio in September: highs in Orbetello hover around 32°C, while lows dip to 19°C. Finish up your sightseeing early on the 8th (Tue) so you can go by car to Siena.

Things to do in Orbetello

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Sep 2 — 8:

Siena

— 3 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Satisfy your inner culture vulture at San Quirico d'Orcia and Centro Storico di Siena. Popular historic sites such as Eremo di Montesiepi and Castello di Monteriggioni are in your itinerary. Change things up with these side-trips from Siena: Abbazia di San Galgano (in Chiusdino), Abbazia di Sant'Antimo (in Castelnuovo dell'Abate) and Historic Centre of San Gimignano (in San Gimignano). The adventure continues: enjoy breathtaking views from Torre del Mangia.

For more things to do, traveler tips, maps, and more tourist information, use the Siena tour itinerary tool.

Traveling by car from Orbetello to Siena takes 1.5 hours. Alternatively, you can take a train; or do a combination of train and bus. In September, daily temperatures in Siena can reach 32°C, while at night they dip to 19°C. Wrap up your sightseeing on the 11th (Fri) early enough to take a bus to Arezzo.

Things to do in Siena

Historic Sites · Shopping

Side Trips

Find places to stay Sep 8 — 11:

Arezzo

— 2 nights

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Kick off your visit on the 12th (Sat): don't miss a visit to Piazza Grande a Montepulciano, don't miss a visit to Piazza della Repubblica, then contemplate in the serene atmosphere at Eremo Le Celle, and finally contemplate the long history of Fortezza di Girifalco. Keep things going the next day: explore the historical opulence of Castello Dei Conti Guidi Di Poppi, make a trip to Piazza Grande, then take in the spiritual surroundings of San Francesco, Arezzo, and finally pause for some serene contemplation at Arezzo Cathedral.

For where to stay, photos, other places to visit, and more tourist information, go to the Arezzo trip itinerary builder website.

You can take a bus from Siena to Arezzo in 1.5 hours. Alternatively, you can drive; or take a train. Finish your sightseeing early on the 13th (Sun) to allow enough time to drive to Florence.

Things to do in Arezzo

Historic Sites

Side Trips

Find places to stay Sep 11 — 13:

Florence

— 13 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your cultural itinerary includes sights like Castello di Verrazzano and Chiesa di Santa Maria degli Angeli del Paradiso. You'll explore the less-touristy side of things at La Verna - Franciscan Sanctuary and Officina Profumo-Farmaceutica di Santa Maria Novella. Venture out of the city with trips to Modena (MEF-Museo Enzo Ferrari, Piazza Grande - World Heritage Site, &more), Canyon Park (in Bagni di Lucca) and Maranello (Museo Ferrari & Adrenaline & Extreme Tours). The adventure continues: bet on your favorite at Autodromo del Mugello, get the lay of the land with Walking tours, engage your brain at Museo Galileo - Institute and Museum of the History of Science, and don't miss a visit to Terrazza Mascagni.

For ratings, reviews, other places to visit, and other tourist information, use the Florence driving holiday site.

Traveling by car from Arezzo to Florence takes 1.5 hours. Alternatively, you can take a train. In September, daytime highs in Florence are 30°C, while nighttime lows are 17°C. Finish your sightseeing early on the 26th (Sat) so you can fly back home.

Things to do in Florence

Historic Sites · Museums · Tours · Outdoors

Side Trips

Find places to stay Sep 13 — 26:

Tuscany travel guide

4.4
Landmarks · Art Museums · Historic Walking Areas
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.