53 days in Tuscany Itinerary

53 days in Tuscany Itinerary

Created using Inspirock Tuscany holiday planner

Make it your trip
Fly
1
Florence
— 9 nights
Drive
2
Cortona
— 6 nights
Drive
3
Montalcino
— 8 nights
Drive to Porto S.Stefano, Ferry to Isola Del Giglio
4
Isola Del Giglio
— 5 nights
Ferry
5
Orbetello
— 6 nights
+2
Drive to Piombino, Ferry to Portoferraio, Drive to Capoliveri
6
Capoliveri, Elba Island
— 6 nights
Drive
7
Massa Marittima
— 6 nights
Drive
8
Livorno
— 6 nights
Fly

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Florence

— 9 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Eschew the tourist crowds and head to Piazza Santa Croce and Torre Salvucci Maggiore. Get out of town with these interesting Florence side-trips: Monteriggioni (Walls of Monteriggioni & Castello di Monteriggioni), Siena (Wine Tours & Tastings, Torre del Mangia, &more) and San Gimignano (Historic Centre of San Gimignano, Piazza della Cisterna, &more). There's still lots to do: get engrossed in the history at Corridoio Vasariano, appreciate the extensive heritage of Knights’ Square, pause for some photo ops at Monumento a Garibaldi e Vittorio Emanuele II, and contemplate in the serene atmosphere at Pieve dei Santi Giovanni ed Ermolao.

To find reviews, more things to do, traveler tips, and other tourist information, you can read our Florence trip itinerary website.

Bristol, UK to Florence is an approximately 5.5-hour flight. You can also do a combination of car and train; or take a train. The time zone changes from Greenwich Mean Time (GMT) to Central European Standard Time (CET), which is usually a 1 hour difference. March in Florence sees daily highs of 17°C and lows of 6°C at night. Wrap up your sightseeing on the 3rd (Wed) early enough to drive to Cortona.

Things to do in Florence

Historic Sites · Tours · Wineries · Museums

Side Trips

Find places to stay Mar 25 — Apr 3:

Cortona

— 6 nights

City of Art

The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
Step off the beaten path and head to Eremo Le Celle and Via di Gracciano nel Corso. Explore Cortona's surroundings by going to Villa Sant'Anna (in Abbadia di Montepulciano), Montepulciano (La Braccesca, Boscarelli Di De Ferrari Luca E Nicolo' Soc.Semp., &more) and Il villaggio dei bambini (in Chianciano Terme). And it doesn't end there: tour the pleasant surroundings at Belvedere di Cortona, contemplate in the serene atmosphere at Chiesa San Francesco, make a trip to Piazza della Repubblica, and do a tasting at Azienda Agricola Baldetti Alfonso.

For traveler tips, more things to do, maps, and more tourist information, you can read our Cortona trip builder tool.

You can drive from Florence to Cortona in 2 hours. Another option is to take a train. Finish up your sightseeing early on the 9th (Tue) so you can go by car to Montalcino.

Things to do in Cortona

Wineries · Historic Sites · Museums · Fun & Games

Side Trips

Find places to stay Apr 3 — 9:

Montalcino

— 8 nights

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Eschew the tourist crowds and head to Winery Solaria Patrizia Cencioni and Poggio Rubino. Get out of town with these interesting Montalcino side-trips: Roccalbegna (Chiesa dei santi Pietro e Paolo & Bosco Rocconi), Borgo di Lucignano d’Arbia (in Lucignano d'Arbia) and Il ghetto degli ebrei (in Santa Fiora). The adventure continues: indulge your senses at some of the top wineries in the area, contemplate the long history of San Quirico d'Orcia, learn about winemaking at Tenuta Fanti, and make a trip to Piazza Pio II.

For reviews, maps, photos, and more tourist information, read Montalcino road trip planner.

Getting from Cortona to Montalcino by car takes about 1.5 hours. Other options: take a bus; or do a combination of train and bus. In April, daily temperatures in Montalcino can reach 23°C, while at night they dip to 9°C. Wrap up your sightseeing on the 17th (Wed) early enough to travel to Isola Del Giglio.

Things to do in Montalcino

Wineries · Historic Sites · Shopping · Museums

Side Trips

Find places to stay Apr 9 — 17:

Isola Del Giglio

— 5 nights
Discover out-of-the-way places like Faraglione dell'Isola del Giglio and Punta del Capel Rosso.

To find more things to do, traveler tips, other places to visit, and tourist information, use the Isola Del Giglio online route maker.

Traveling by combination of car and ferry from Montalcino to Isola Del Giglio takes 3 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus, train, and ferry. In April in Isola Del Giglio, expect temperatures between 23°C during the day and 9°C at night. Cap off your sightseeing on the 22nd (Mon) early enough to catch the ferry to Orbetello.

Things to do in Isola Del Giglio

Outdoors · Parks · Beaches · Nature
Find places to stay Apr 17 — 22:

Orbetello

— 6 nights
Orbetello is a town and comune in the province of Grosseto (Tuscany), Italy. You'll discover tucked-away gems like Cavallo Natura and Tagliata Etrusca. Explore the numerous day-trip ideas around Orbetello: Jacobelli Liquori (in Capalbio), Abbazia Di San Bruzio A Magliano (in Magliano in Toscana) and Montemerano (Villa Acquaviva - La Fattoria & Chiesa di San Giorgio). The adventure continues: explore the striking landscape at Spacco della Regina, head outdoors with Pescaturismo Sirena, explore the historical opulence of Forte Filippo, and explore by horseback at Maneggio Barbazzale.

To see other places to visit and other tourist information, read Orbetello road trip planning site.

Ride a ferry from Isola Del Giglio to Orbetello in 2 hours. In April in Orbetello, expect temperatures between 23°C during the day and 9°C at night. Finish up your sightseeing early on the 28th (Sun) so you can travel to Capoliveri.

Things to do in Orbetello

Outdoors · Parks · Wineries · Historic Sites

Side Trips

Find places to stay Apr 22 — 28:

Capoliveri, Elba Island

— 6 nights
Capoliveri is a comune (municipality) on the island of Elba in Italy. You'll explore the less-touristy side of things at Castello del Volterraio and Casetta Drouot. Explore the numerous day-trip ideas around Capoliveri: Spiaggia di Forno (in Scaglieri), Madonna del Monte (in Marciana) and Gulliver - Terre d'Autore (in Marciana Marina). And it doesn't end there: admire the striking features of Forte Longone, stop by Elba Nostrale, stroll through Acqua marina, and head outdoors with Stabilimento Balneare Batignani.

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

You can do a combination of car and ferry from Orbetello to Capoliveri in 3.5 hours. Alternatively, you can do a combination of train, ferry, and bus. While traveling from Orbetello, expect a bit cooler days and about the same nights in Capoliveri, ranging from highs of 19°C to lows of 11°C. Cap off your sightseeing on the 4th (Sat) early enough to travel to Massa Marittima.

Things to do in Capoliveri

Outdoors · Parks · Trails · Nature

Side Trips

Find places to stay Apr 28 — May 4:

Massa Marittima

— 6 nights
Massa is a town and comune in Tuscany, central Italy, the administrative centre of the province of Massa and Carrara. Explore hidden gems such as Viale dei Cipressi and Eremo di Montesiepi. Get out of town with these interesting Massa Marittima side-trips: Montemassi (Podere Ristella Vineyards and Winery & Rocca di Montemassi), Tenuta Poggio Rosso (in Populonia) and Piombino (Acquanauta & Promontorio Piombino). There's much more to do: admire the striking features of Palazzo Comunale, take in the dramatic natural features at I Canaloni Del Torrente Farma, contemplate in the serene atmosphere at Church of Saints Stephen and Lawrence, and pause for some serene contemplation at Chiesa di San Martino Vescovo.

For other places to visit, maps, and tourist information, read our Massa Marittima route builder app.

Traveling by car from Capoliveri to Massa Marittima takes 2.5 hours. Traveling from Capoliveri in May, you will find days in Massa Marittima are somewhat warmer (27°C), and nights are about the same (13°C). Finish up your sightseeing early on the 10th (Fri) so you can go by car to Livorno.

Things to do in Massa Marittima

Historic Sites · Outdoors · Parks · Nature

Side Trips

Find places to stay May 4 — 10:

Livorno

— 6 nights

Naples of the North

Considered one of Tuscany's newer cities, the busy port city of Livorno boasts modern charm uncharacteristic of the region.
Discover out-of-the-way places like Costiera di Calafuria and Castello dei Vicari. Change things up with these side-trips from Livorno: SATOR Winery (in Pomaia), Museo Giorgio Kienerk (in Fauglia) and Monumento ai Caduti (in Viareggio). There's much more to do: take in the architecture and atmosphere at Santuario di Montenero, explore the historical opulence of Castello Boccale, contemplate in the serene atmosphere at Cripta San Jacopo Livorno, and make a trip to Scogli Piatti.

To find maps, ratings, where to stay, and tourist information, refer to the Livorno vacation planner.

You can drive from Massa Marittima to Livorno in 1.5 hours. In May, daytime highs in Livorno are 25°C, while nighttime lows are 13°C. Cap off your sightseeing on the 16th (Thu) early enough to catch the flight back home.

Things to do in Livorno

Historic Sites · Wineries · Parks · Museums

Side Trips

Find places to stay May 10 — 16:

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.