29 days in Italy, Split & Dubrovnik Itinerary

29 days in Italy, Split & Dubrovnik Itinerary

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Route & dates

29 days in Italy, Split & Dubrovnik Itinerary

Start: Toronto, Canada
Fly:  12​h 15​min
1
Split, Croatia
— 3 nights
Drive:  3​h
2
Dubrovnik, Croatia
— 4 nights
Fly:  5​h 30​min
3
Salerno, Italy
— 4 nights
Ferry:  1​h 30​min
4
Positano, Italy
— 4 nights
Drive:  3​h 15​min
5
Tivoli, Italy
— 1 night
Drive:  2​h 30​min
6
Siena, Italy
— 4 nights
Bus:  1​h 15​min
7
Florence, Italy
— 3 nights
Train:  2​h 15​min
8
Venice, Italy
— 4 nights
Fly:  11​h 15​min
End: Toronto, Canada

3
nights
Split, Croatia

Split ©
Experience an authentic Adriatic lifestyle in Split, the largest city along the sea's coast.
Get some historical perspective at Diocletian's Palace and Franciscan Monastery. Visiting Dubovica and River Rafting & Tubing will get you outdoors. Get out of town with these interesting Split side-trips: Hvar (Spanjola & Milna). The adventure continues: contemplate in the serene atmosphere at Cathedral of Saint Domnius, take in the architecture and atmosphere at Church Of St. Roch, and explore the ancient world of Temple of Jupiter.

To find where to stay, more things to do, maps, and tourist information, read our Split itinerary planner .

Toronto, Canada to Split is an approximately 12.5-hour flight. You can also do a combination of flight and bus. You'll lose 6 hours traveling from Toronto to Split due to the time zone difference. Traveling from Toronto in September, you will find days in Split are somewhat warmer (30°C), and nights are about the same (19°C). Cap off your sightseeing on the 13th (Fri) early enough to catcht the bus to Dubrovnik.

Things to do in Split

Historic Sites Outdoors Tours

Side Trips

Hvar, Church Of St. Roch, Dubovica Beach
Find places to stay Sep 9 — 13:
Highlights from your plan
Palazzo di Diocleziano ©
Palazzo di Diocleziano
Spanjola ©
Spanjola
Franciscan Monastery ©
Franciscan Monastery

4
nights
Dubrovnik, Croatia

Dubrovnik ©
Along the Dalmation Coast, the city of Dubrovnik has become famous for its pedestrian-only Old Town surrounded by fortress walls, and its historical heft has earned it World Heritage Site status.
Get a sense of the local culture at Old Town and Franciscan Monastery. Step out of the city life by going to Island of Lokrum and Sunj Beach. Go for a jaunt from Dubrovnik to Popovici to see Pasjaca Beach about 1h 10 min away. The adventure continues: contemplate the long history of Walls of Dubrovnik, examine the collection at War Photo Limited, get to know the fascinating history of Pustjerna, and take an in-depth tour of Rector's Palace.

To see ratings, where to stay, and other tourist information, refer to the Dubrovnik trip itinerary maker app .

You can take a bus from Split to Dubrovnik in 3 hours. Other options are to drive; or fly. In September, daily temperatures in Dubrovnik can reach 29°C, while at night they dip to 20°C. Wrap up your sightseeing on the 17th (Tue) to allow time to travel to Salerno.

Things to do in Dubrovnik

Parks Beaches Outdoors

Side Trips

Sunj Beach, Pasjaca Beach
Find places to stay Sep 13 — 17:
Highlights from your plan
Old Town ©
Old Town
Dubrovnik City Walls ©
Dubrovnik City Walls
Lokrum Island ©
Lokrum Island

4
nights
Salerno, Italy

Salerno ©
While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.
Take a break from the city and head to Spiaggia di castiglione and Spiaggia di Marina d'Albori. Get some historical perspective at Castello di San Nicola de Thoro-Plano and Il Vecchio Centro Storico di Romagnano al Monte. Change things up with these side-trips from Salerno: Spiaggia Lannio (in Cetara), Basilica di Santa Trofimena (in Minori) and Sentiero dei Limoni (in Maiori). There's still lots to do: do a tasting at Le Vigne di Raito, pause for some serene contemplation at Duomo di Salerno, take in the exciting artwork at Sol’Art Ceramiche, and stroll through Rosa dei Venti.

To see more things to do, reviews, and more tourist information, use the Salerno trip planner .

Fly from Dubrovnik to Salerno in 5.5 hours. Alternatively, you can do a combination of flight and train; or do a combination of ferry and car. Traveling from Dubrovnik in September, plan for somewhat warmer nights in Salerno, with lows around 24°C. Finish your sightseeing early on the 21st (Sat) so you can ride a ferry to Positano.

Things to do in Salerno

Parks Outdoors Beaches

Side Trips

Vietri sul Mare, Maiori, Basilica of Saint Trofimena, Spiaggia Lannio, Spiaggia di castiglione
Find places to stay Sep 17 — 21:
Highlights from your plan
Spiaggia di castiglione ©
Spiaggia di castiglione
Le Vigne di Raito ©
Le Vigne di Raito
Sentiero dei Limoni ©
Sentiero dei Limoni

4
nights
Positano, Italy

Positano ©
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
You'll enjoy a bit of beach vacationing at Fornillo and Bagni d'Arienzo. Visiting Lido di Ravello and Sentiero degli dei (Path of the Gods) will get you outdoors. Explore the numerous day-trip ideas around Positano: Amalfi (Duomo di Sant'Andrea & Chiostro del Paradiso), Ravello (Cappella Sant'Angelo all'Ospedale, Villa Rufolo, & more) and Parrocchia San Giovanni (in Vietri sul Mare).

To plan Positano vacation without wasting time, ask Inspirock to design an itinerary.

You can ride a ferry from Salerno to Positano in 1.5 hours. Alternatively, you can do a combination of train and taxi; or drive. In September, daily temperatures in Positano can reach 31°C, while at night they dip to 23°C. Wrap up your sightseeing on the 25th (Wed) to allow time to drive to Tivoli.

Things to do in Positano

Historic Sites Parks Beaches

Side Trips

Ravello, Amalfi, Parrocchia San Giovanni
Find places to stay Sep 21 — 25:
Highlights from your plan
Lido di Ravello ©
Lido di Ravello
Duomo di Ravello ©
Duomo di Ravello
Fornillo ©
Fornillo

1
night
Tivoli, Italy

Tivoli ©
Tivoli is a town and comune in Lazio, central Italy, about 30km east-north-east of Rome, at the falls of the Aniene river where it issues from the Sabine hills. On the 26th (Thu), delve into the distant past at Villa Adriana and then stroll through Villa d'Este.

For more things to do, maps, other places to visit, and tourist information, read our Tivoli route builder tool .

Traveling by car from Positano to Tivoli takes 3.5 hours. Alternatively, you can take a train; or take a bus. Plan for a bit cooler nights when traveling from Positano in September since evenings lows in Tivoli dip to 17°C. Wrap up your sightseeing by early afternoon on the 26th (Thu) to allow enough time to drive to Siena.

Things to do in Tivoli

Historic Sites Parks
Find places to stay Sep 25 — 26:
Highlights from your plan
Villa Adriana ©
Villa Adriana
Villa d'Este ©
Villa d'Este

4
nights
Siena, Italy

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Siena Cathedral and Palazzo Pubblico and Museo Civico will appeal to history buffs. Do some cultural sightseeing at Guardastelle Vineyard and Piazza del Campo. Change things up with these side-trips from Siena: Fattoria di Montemaggio (in Radda in Chianti), Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Azienda Agricola Patrizia Cencioni Solaria (in Montalcino). There's still lots to do: admire the landmark architecture of Leaning Tower of Pisa, admire the masterpieces at Museo dell'Opera Metropolitana, take in the architecture and atmosphere at San Francesco, and steep yourself in history at Battistero di San Giovanni.

To see photos, reviews, more things to do, and tourist information, refer to the Siena trip site .

Drive from Tivoli to Siena in 2.5 hours. Alternatively, you can do a combination of train and bus; or take a train. In September in Siena, expect temperatures between 32°C during the day and 19°C at night. Cap off your sightseeing on the 30th (Mon) early enough to catcht the bus to Florence.

Things to do in Siena

Historic Sites Wineries Museums

Side Trips

Montalcino, Fattoria di Montemaggio, Guardastelle Vineyard, Leaning Tower of Pisa
Find places to stay Sep 26 — 30:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Duomo di Siena ©
Duomo di Siena
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona

3
nights
Florence, Italy

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get a sense of the local culture at Academy Of Florence Art Gallery and The Baptistery of St. John. Visit Cathedral of Santa Maria del Fiore and Piazza della Signoria for their historical value. There's lots more to do: admire the masterpieces at Uffizi Galleries, appreciate the extensive heritage of Piazza del Duomo, take some stellar pictures from Piazzale Michelangelo, and steep yourself in history at Museo Nazionale del Bargello.

For traveler tips, more things to do, ratings, and more tourist information, read Florence trip itinerary maker .

Getting from Siena to Florence by bus takes about 1.5 hours. Other options: drive; or take a train. September in Florence sees daily highs of 30°C and lows of 17°C at night. Finish up your sightseeing early on the 3rd (Thu) so you can catch the train to Venice.

Things to do in Florence

Museums Historic Sites Parks
Find places to stay Sep 30 — Oct 3:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

4
nights
Venice, Italy

Venice ©
Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
Peggy Guggenheim Collection and St. Mark's Square are good opportunities to explore the local culture. Basilica di San Marco and Doge's Palace will appeal to history buffs. Venture out of the city with trips to Padua (Scrovegni Chapel & Basilica di Sant’Antonio). There's still lots to do: explore the activities along Canal Grande, admire the striking features of St Mark's Campanile, admire the masterpieces at Ca' d'Oro, and wander the streets of Campo del Ghetto.

To see where to stay, reviews, maps, and tourist information, use the Venice trip planner .

Traveling by train from Florence to Venice takes 2.5 hours. Alternatively, you can drive; or take a bus. Expect slightly colder weather when traveling from Florence in October: highs in Venice hover around 22°C, while lows dip to 12°C. Wrap up your sightseeing on the 7th (Mon) early enough to travel back home.

Things to do in Venice

Historic Sites Museums Nature

Side Trip

Padua
Find places to stay Oct 3 — 7:
Highlights from your plan
Canal Grande ©
Canal Grande
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace

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