29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy trip planner

This plan was created by another user. Make it your plan

Route & dates

Start: Ottawa
+2
Fly + Bus + Train:  12 h 45 min
1
Verona
— 2 nights
Train:  1 h 45 min
2
Florence
— 4 nights
Bus:  1 h 15 min
3
Siena
— 2 nights
Drive:  1 h 45 min
4
Assisi
— 3 nights
Drive:  2 h 15 min
5
Rome
— 4 nights
Drive:  3 h 15 min
6
Positano
— 4 nights
Ferry:  1 h 30 min
7
Vietri sul Mare
— 3 nights
Drive + Fly:  4 h 45 min
8
Venice
— 5 nights
+2
Fly + Bus + Train:  12 h 15 min
End: Ottawa

2
nights
Verona

Verona ©
The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Visit Arena di Verona and Piazzale Castel San Pietro for their historical value. Your cultural itinerary includes sights like Piazza delle Erbe and Quinzano. And it doesn't end there: take in the spiritual surroundings of Basilica di San Zeno Maggiore, examine the collection at Casa di Giulietta, take in the architecture and atmosphere at chiesa di San Lorenzo - Verona, and contemplate the long history of Museo di Castelvecchio.

To see traveler tips, more things to do, photos, and more tourist information, you can read our Verona online vacation planner.

Ottawa, Canada to Verona is an approximately 14- hour combination of flight and train. You can also do a combination of train and flight; or fly. The time zone difference moving from Eastern Standard Time to Central European Standard Time is 6 hours. Traveling from Ottawa in September, expect Verona to be a bit warmer, temps between 30°C and 17°C. Finish your sightseeing early on the 1st (Tue) to allow enough time to take a train to Florence.

Things to do in Verona

Historic Sites Wildlife Nature
Find places to stay Sep 28 — Oct 1:
Highlights from your plan
Piazza delle Erbe ©
Piazza delle Erbe
Arena di Verona ©
Arena di Verona
Basilica di San Zeno Maggiore ©
Basilica di San Zeno Maggiore

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Popular historic sites such as Cathedral of Santa Maria del Fiore and Campanile di Giotto are in your itinerary. Get some cultural insight at Piazzale Michelangelo and Basilica of Santa Croce. Step out of Florence to go to Santa Brigida and see Castello del Trebbio, which is approximately 36 minutes away. Next up on the itinerary: explore the world behind art at Florence Academy of Fine Arts, get to know the fascinating history of Piazza della Signoria, take in the views from Ponte Vecchio, and get a sense of history and politics at Palazzo Vecchio.

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

Traveling by train from Verona to Florence takes 2 hours. Alternatively, you can drive; or take a bus. October in Florence sees daily highs of 25°C and lows of 14°C at night. Finish your sightseeing early on the 5th (Sat) to allow enough time to take a bus to Siena.

Things to do in Florence

Historic Sites Museums Wineries

Side Trip

Castello del Trebbio
Find places to stay Oct 1 — 5:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts

2
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Start off your visit on the 6th (Sun): do a tasting at Guardastelle Vineyard, then take in the architecture and atmosphere at Duomo di Siena, and then ponder the world of politics at Palazzo Pubblico and Museo Civico. Get ready for a full day of sightseeing on the next day: indulge your taste buds at Food & Drink and then make a trip to Piazza del Campo.

For reviews, where to stay, more things to do, and more tourist information, you can read our Siena trip app.

Take a bus from Florence to Siena in 1.5 hours. Alternatively, you can drive; or take a train. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Finish up your sightseeing early on the 7th (Mon) so you can go by car to Assisi.

Things to do in Siena

Tours Historic Sites Wineries

Side Trip

Guardastelle Vineyard
Find places to stay Oct 5 — 7:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Duomo di Siena ©
Duomo di Siena
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico

3
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Get some historical perspective at Basilica Papale e Sacro Convento di San Francesco d'Assisi and Basilica di Santa Chiara. Tili Vini Societa Agricola and Museo della Porziuncola are good opportunities to explore the local culture. You'll find plenty of places to visit near Assisi: Wild Foods Italy (in Montefalco), Famiglia Buccelletti Winery (in Castiglion Fiorentino) and Castello Monte Vibiano Vecchio (in Mercatello). There's much more to do: don't miss a visit to Eremo delle Carceri, contemplate in the serene atmosphere at Cripta di San Francesco, appreciate the extensive heritage of Piazza Superiore di San Francesco, and take in the architecture and atmosphere at Basilica di Santa Maria degli Angeli - Porziuncola.

For ratings, other places to visit, where to stay, and more tourist information, refer to the Assisi trip planner.

Getting from Siena to Assisi by car takes about 2 hours. Other options: take a bus; or take a train. Traveling from Siena in October, Assisi is slightly colder at night with lows of 12°C. Finish your sightseeing early on the 10th (Thu) so you can drive to Rome.

Things to do in Assisi

Historic Sites Wineries Wildlife

Side Trips

Wild Foods Italy, Famiglia Buccelletti Winery, Castello Monte Vibiano Vecchio
Find places to stay Oct 7 — 10:
Highlights from your plan
Museo della Porziuncola ©
Museo della Porziuncola
Eremo delle Carceri ©
Eremo delle Carceri

4
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Vatican Museums and Musei Capitolini will appeal to museum buffs. Satisfy your inner culture vulture at Colosseum and Palatine Hill. Step out of Rome to go to Tivoli and see Villa Adriana, which is approximately 36 minutes away. And it doesn't end there: explore the world behind art at Galleria Borghese, make a trip to Piazza Navona, contemplate the long history of St. Peter's Basilica, and pause for some serene contemplation at Santa Maria in Trastevere.

To find photos, traveler tips, ratings, and tourist information, refer to the Rome trip planner.

Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. In October, daily temperatures in Rome can reach 26°C, while at night they dip to 15°C. Finish up your sightseeing early on the 14th (Mon) so you can go by car to Positano.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trips

Vatican City, Villa Adriana
Find places to stay Oct 10 — 14:
Highlights from your plan
Piazza Navona ©
Piazza Navona
Vatican Museums
Vatican Museums
Pantheon ©
Pantheon

4
nights
Positano

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.
Get a sense of the local culture at Villa Cimbrone Gardens and Duomo di Sant'Andrea. Visiting Fornillo and Lido di Ravello will get you outdoors. Explore the numerous day-trip ideas around Positano: Lido Capo di Conca (in Conca dei Marini), Valle delle Ferriere (in Amalfi) and Villa Rufolo (in Ravello). There's still lots to do: cast your line with a fishing tour, stroll through Bagni d'Arienzo Beach Club, Positano, savor the flavors at Il Gusto della Costa, and view the masterpieces at Miniaci Art Gallery.

For ratings, maps, traveler tips, and more tourist information, go to the Positano online trip maker.

You can drive from Rome to Positano in 3.5 hours. Alternatively, you can do a combination of train, subway, and bus; or take a bus. Traveling from Rome in October, Positano is somewhat warmer at night with lows of 20°C. Wrap up your sightseeing on the 18th (Fri) to allow time to ride a ferry to Vietri sul Mare.

Things to do in Positano

Parks Outdoors Beaches

Side Trips

Ravello, Amalfi, Lido Capo di Conca, Il Gusto della Costa
Find places to stay Oct 14 — 18:
Highlights from your plan
Lido di Ravello ©
Lido di Ravello
Fornillo ©
Fornillo
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens

3
nights
Vietri sul Mare

Vietri sul Mare ©
Vietri sul Mare is a town and comune in the province of Salerno, in the Campania region of southern Italy. For shopping fun, head to Ceramiche Cosmolena di Margherita di Palma or Sol’Art Ceramiche. You'll get in some beach time at Spiaggia di castiglione and Spiaggia Lannio. Change things up with these side-trips from Vietri sul Mare: Ravello (Cappella Sant'Angelo all'Ospedale, Duomo di Ravello, &more). The adventure continues: delve into the distant past at Pompeii Archaeological Park, take in the architecture and atmosphere at Chiesa San Pietro Apostolo, do a tasting at Le Vigne di Raito, and contemplate the long history of Santa Maria de Olearia.

To find photos, more things to do, where to stay, and tourist information, read our Vietri sul Mare planning app.

Traveling by ferry from Positano to Vietri sul Mare takes 1.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 26°C in October, and nighttime lows around 20°C. Cap off your sightseeing on the 21st (Mon) early enough to travel to Venice.

Things to do in Vietri sul Mare

Historic Sites Beaches Parks

Side Trips

Ravello, Cetara, Santa Maria de Olearia, Pompeii Archaeological Park
Find places to stay Oct 18 — 21:
Highlights from your plan
Duomo di Ravello ©
Duomo di Ravello
Spiaggia di castiglione ©
Spiaggia di castiglione
Pompeii Archaeological Park ©
Pompeii Archaeological Park

5
nights
Venice

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.
Appreciate the collections at Doge's Palace and Museo Ebraico di Venezia. Get some historical perspective at Piazza San Marco and Basilica di San Marco. You'll find plenty of places to visit near Venice: Padua (Scrovegni Chapel & Basilica of St. Anthony). And it doesn't end there: explore the activities along Canal Grande, explore the world behind art at Peggy Guggenheim Collection, take in the views from Ponte di Rialto, and see the interesting displays at Ca' Rezzonico.

To find other places to visit, ratings, where to stay, and other tourist information, you can read our Venice vacation builder site.

The Route module can help you plan travel from Vietri sul Mare to Venice. Prepare for slightly colder weather when traveling from Vietri sul Mare in October: high temperatures in Venice hover around 22°C and lows are around 12°C. Finish up your sightseeing early on the 26th (Sat) so you can travel back home.

Things to do in Venice

Historic Sites Museums Nature

Side Trip

Padua
Find places to stay Oct 21 — 26:
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

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