60 days in Tropea, Crotone & Tuscany Itinerary
Created using Klarna Trips Italy trip itinerary planner
Start: Toronto
Fly
1
Tropea
— 8 nights
Drive
2
Crotone
— 10 nights
+2
Drive to Lamezia Terme Airport, Fly to Perugia San Francesco d'Assisi – Umbria International Airport, Drive to Cortona
3
Cortona
— 7 nights
Drive
4
Montalcino
— 7 nights
+2
Drive to Piombino, Ferry to Portoferraio, Drive to Capoliveri
5
Capoliveri, Elba Island
— 7 nights
+2
Drive to Portoferraio, Ferry to Piombino, Drive to San Gimignano
6
San Gimignano
— 7 nights
Drive
7
Florence
— 8 nights
Drive
8
Pisa
— 5 nights
Fly
End: Toronto
Wed, Jun 1 - Sat, Jul 30
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View full calendar
Tropea — 8 nights

You'll find plenty of places to visit near Tropea: Abbazia di Santa Maria di Corazzo (in Carlopoli), Basilica Maria SS. delle Grazie della Quercia di Visora (in Conflenti) and Curinga (Il Gigante di Curinga & Santuario di Maria SS del Carmelo).
To see more things to do, maps, other places to visit, and tourist information, read Tropea trip planning app.
Toronto, Canada to Tropea is an approximately 12-hour flight. The time zone difference moving from Eastern Standard Time to Central European Standard Time is 6 hours. In June in Tropea, expect temperatures between 30°C during the day and 20°C at night. Finish your sightseeing early on the 9th (Thu) to allow enough time to drive to Crotone.
more
To see more things to do, maps, other places to visit, and tourist information, read Tropea trip planning app.
Toronto, Canada to Tropea is an approximately 12-hour flight. The time zone difference moving from Eastern Standard Time to Central European Standard Time is 6 hours. In June in Tropea, expect temperatures between 30°C during the day and 20°C at night. Finish your sightseeing early on the 9th (Thu) to allow enough time to drive to Crotone.
Side Trips
Curinga, Chianalea di Scilla, Praia di Fuoco, Abbazia di Santa Maria di Corazzo, Santuario di Maria Santissima dell'Itria
Find places to stay Jun 1 — 9:
Highlights from your trip
Crotone — 10 nights
Change things up with these side-trips from Crotone: Parco Avventura Principe (in Petilia Policastro), Spiaggia di Curmo (in Capo Rizzuto) and Santa Severina (Centro Storico, Chiesa di Santa Filomena, &more).
For photos, maps, more things to do, and tourist information, use the Crotone trip itinerary maker tool.
Explore your travel options from Tropea to Crotone with the Route module. Cap off your sightseeing on the 19th (Sun) early enough to go by car to Cortona.
more
For photos, maps, more things to do, and tourist information, use the Crotone trip itinerary maker tool.
Explore your travel options from Tropea to Crotone with the Route module. Cap off your sightseeing on the 19th (Sun) early enough to go by car to Cortona.
Side Trips
Find places to stay Jun 9 — 19:
Highlights from your trip
Cortona — 7 nights
City of Art
Explore Cortona's surroundings by going to Montepulciano (Tenuta Valdipiatta & Az. Agr. Poliziano) and Wine Tours & Tastings (in Siena). The adventure continues: make a trip to Eremo Le Celle, shop like a local with La Torena Arte, do a tasting at Baldetti Wine, and get engrossed in the history at MAEC - Museo dell'Accademia Etrusca.
To see traveler tips, maps, and more tourist information, read our Cortona online trip maker.
The Route module can help you plan travel from Crotone to Cortona. Finish your sightseeing early on the 26th (Sun) to allow enough time to drive to Montalcino.
more
To see traveler tips, maps, and more tourist information, read our Cortona online trip maker.
The Route module can help you plan travel from Crotone to Cortona. Finish your sightseeing early on the 26th (Sun) to allow enough time to drive to Montalcino.
Side Trips
Find places to stay Jun 19 — 26:
Highlights from your trip
Montalcino — 7 nights
City of Honey
Explore the numerous day-trip ideas around Montalcino: Tempio di San Biagio (in Montepulciano) and Fortezza di Radicofani (in Radicofani). It doesn't end there: do a tasting at Ciacci Piccolomini d'Aragona and admire the verdant scenery at Val d'Orcia.
For where to stay, more things to do, photos, and more tourist information, read Montalcino vacation planner.
You can drive from Cortona to Montalcino in 1.5 hours. Alternatively, you can drive; or take a bus; or do a combination of train and bus. Expect a daytime high around 34°C in June, and nighttime lows around 19°C. Wrap up your sightseeing on the 3rd (Sun) early enough to travel to Capoliveri.
more
For where to stay, more things to do, photos, and more tourist information, read Montalcino vacation planner.
You can drive from Cortona to Montalcino in 1.5 hours. Alternatively, you can drive; or take a bus; or do a combination of train and bus. Expect a daytime high around 34°C in June, and nighttime lows around 19°C. Wrap up your sightseeing on the 3rd (Sun) early enough to travel to Capoliveri.
Side Trips
Find places to stay Jun 26 — Jul 3:
Highlights from your trip
Capoliveri, Elba Island — 7 nights

Venture out of the city with trips to Spiaggia di Cotoncello (in Marciana) and Spiaggia di Chiessi (in Chiessi).
For where to stay, reviews, maps, and more tourist information, use the Capoliveri online travel route planner.
Getting from Montalcino to Capoliveri by combination of car and ferry takes about 3.5 hours. Other options: do a combination of bus, train, and ferry. Expect little chillier weather when traveling from Montalcino in July: highs in Capoliveri hover around 33°C, while lows dip to 24°C. Cap off your sightseeing on the 10th (Sun) early enough to travel to San Gimignano.
more
For where to stay, reviews, maps, and more tourist information, use the Capoliveri online travel route planner.
Getting from Montalcino to Capoliveri by combination of car and ferry takes about 3.5 hours. Other options: do a combination of bus, train, and ferry. Expect little chillier weather when traveling from Montalcino in July: highs in Capoliveri hover around 33°C, while lows dip to 24°C. Cap off your sightseeing on the 10th (Sun) early enough to travel to San Gimignano.
Side Trips
Find places to stay Jul 3 — 10:
Highlights from your trip
San Gimignano — 7 nights
Town of Fine Towers
Venture out of the city with trips to Castello Monterinaldi (in Radda in Chianti), Siena (All'Orto de' Pecci, Duomo di Siena, &more) and Poggio al Bosco (in Chiostrini). Next up on the itinerary: learn about winemaking at Guardastelle Vineyard, take in the architecture and atmosphere at Duomo di San Gimignano, make a trip to Piazza della Cisterna, and contemplate the long history of Torre Grossa.
To find more things to do, traveler tips, maps, and tourist information, go to the San Gimignano online visit planner.
You can do a combination of car and ferry from Capoliveri to San Gimignano in 4 hours. Alternatively, you can do a combination of bus, ferry, and train. In July in San Gimignano, expect temperatures between 35°C during the day and 21°C at night. Wrap up your sightseeing on the 17th (Sun) early enough to drive to Florence.
more
To find more things to do, traveler tips, maps, and tourist information, go to the San Gimignano online visit planner.
You can do a combination of car and ferry from Capoliveri to San Gimignano in 4 hours. Alternatively, you can do a combination of bus, ferry, and train. In July in San Gimignano, expect temperatures between 35°C during the day and 21°C at night. Wrap up your sightseeing on the 17th (Sun) early enough to drive to Florence.
Side Trips
Find places to stay Jul 10 — 17:
Highlights from your trip
Florence — 8 nights

Birthplace of the Italian Renaissance
Step out of Florence with an excursion to Castello del Trebbio in Santa Brigida--about 36 minutes away. Next up on the itinerary: explore the world behind art at Florence Academy of Fine Arts, take in the views from Ponte Vecchio, don't miss a visit to Piazzale Michelangelo, and examine the collection at Pitti Palace.
For maps, ratings, and other tourist information, go to the Florence day trip site.
You can drive from San Gimignano to Florence in 1.5 hours. Other options are to drive; or take a train; or take a bus. Expect a daytime high around 35°C in July, and nighttime lows around 21°C. Cap off your sightseeing on the 25th (Mon) early enough to go by car to Pisa.
more
For maps, ratings, and other tourist information, go to the Florence day trip site.
You can drive from San Gimignano to Florence in 1.5 hours. Other options are to drive; or take a train; or take a bus. Expect a daytime high around 35°C in July, and nighttime lows around 21°C. Cap off your sightseeing on the 25th (Mon) early enough to go by car to Pisa.
Side Trips
Find places to stay Jul 17 — 25:
Highlights from your trip
Pisa — 5 nights

Venture out of the city with trips to Lucca (Torre Guinigi, Chiesa di Santa Caterina, &more), Villa Reale di Marlia (in Marlia) and San Miniato (Podere Pellicciano - Agrisole & Cattedrale di Santa Maria Assunta e di San Genesio). And it doesn't end there: admire the landmark architecture of Leaning Tower of Pisa, steep yourself in history at St Martin Cathedral, make a trip to Le mura di Lucca, and awaken your taste buds at Italy Shore Drivers.
For other places to visit, photos, reviews, and more tourist information, you can read our Pisa online attractions planner.
You can drive from Florence to Pisa in 1.5 hours. Other options are to drive; or take a bus; or take a train. Expect a daytime high around 35°C in July, and nighttime lows around 21°C. Wrap up your sightseeing on the 30th (Sat) to allow time to fly back home.
more
For other places to visit, photos, reviews, and more tourist information, you can read our Pisa online attractions planner.
You can drive from Florence to Pisa in 1.5 hours. Other options are to drive; or take a bus; or take a train. Expect a daytime high around 35°C in July, and nighttime lows around 21°C. Wrap up your sightseeing on the 30th (Sat) to allow time to fly back home.
Side Trips
Find places to stay Jul 25 — 30:
Tuscany travel guide
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.