29 days in Italy Itinerary

29 days in Italy Itinerary

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Route & dates

29 days in Italy Itinerary

Start: Ottawa
Fly:  12​h 45​min
1
Verona
— 2 nights
2
Florence
— 4 nights
bus:  1​h 15​min
3
Siena
— 2 nights
Drive:  1​h 45​min
4
Assisi
— 3 nights
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.
Get some cultural insight at Piazza delle Erbe and Casa di Giulietta. Arena di Verona and Museo di Castelvecchio will appeal to history buffs. The adventure continues: take in the architecture and atmosphere at Basilica di San Zeno Maggiore, wander the streets of Quinzano, step into the grandiose world of Piazzale Castel San Pietro, and make a trip to Torre dei Lamberti.

To see where to stay, more things to do, reviews, and tourist information, read our Verona route site .

Ottawa, Canada to Verona is an approximately 13-hour flight. You can also do a combination of train and flight; or do a combination of flight and train. Due to the time zone difference, you'll lose 6 hours traveling from Ottawa to Verona. Prepare for a bit warmer weather when traveling from Ottawa in September: high temperatures in Verona hover around 30°C and lows are around 17°C. Wrap up your sightseeing on the 1st (Tue) early enough to take a train to Florence.

Things to do in Verona

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

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your cultural itinerary includes sights like Pitti Palace and Academy Of Florence Art Gallery. Gallerie Degli Uffizi and Basilica di Santa Croce will appeal to museum buffs. Take a break from Florence with a short trip to Castello del Trebbio in Santa Brigida, about 36 minutes away. There's lots more to do: take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, snap pictures at Ponte Vecchio, take in panoramic vistas at Campanile di Giotto, and relax and float downstream with a rafting and tubing tour.

To find maps, traveler tips, other places to visit, and tourist information, go to the Florence trip itinerary maker site .

Take a train from Verona to Florence in 2 hours. Alternatively, you can drive; or take a bus. In October in Florence, expect temperatures between 25°C during the day and 14°C at night. Wrap up your sightseeing on the 5th (Sat) to allow time to take a bus to Siena.

Things to do in Florence

Museums Historic Sites Wineries

Side Trip

Castello del Trebbio
Find places to stay Oct 1 — 5:
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

2
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 6th (Sun), do a tasting at Guardastelle Vineyard, take in the architecture and atmosphere at Duomo di Siena, and then explore the world behind art at Palazzo Pubblico and Museo Civico. Get ready for a full day of sightseeing on the next day: indulge your senses at some of the top wineries in the area and then make a trip to Piazza del Campo.

For where to stay, maps, and other tourist information, you can read our Siena online vacation maker .

You can take a bus from Florence to Siena in 1.5 hours. Alternatively, you can drive; or take a train. October in Siena sees daily highs of 26°C and lows of 15°C at night. Finish your sightseeing early on the 7th (Mon) to allow enough time to drive to Assisi.

Things to do in Siena

Tours Wineries Historic Sites

Side Trip

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

3
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Basilica Papale e Sacro Convento di San Francesco d'Assisi and Rocca Maggiore are good opportunities to explore the local culture. Visit Eremo delle Carceri and San Damiano for their historical value. Get out of town with these interesting Assisi side-trips: Famiglia Buccelletti Winery (in Castiglion Fiorentino), Wild Foods Italy (in Montefalco) and Castello Monte Vibiano Vecchio (in Mercatello). Next up on the itinerary: do a tasting at Tili Vini Societa Agricola, see the interesting displays at Museo della Porziuncola, take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola, and appreciate the extensive heritage of Centro Storico.

To find maps, photos, ratings, and more tourist information, you can read our Assisi day trip app .

Traveling by car from Siena to Assisi takes 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Siena in October, expect a bit cooler with lows of 12°C in Assisi. 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

Famiglia Buccelletti Winery, Castello Monte Vibiano Vecchio, Wild Foods Italy
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.
Palatine Hill and St. Peter's Basilica will appeal to history buffs. Appreciate the collections at Galleria Borghese and Vatican Museums. Take a break from Rome with a short trip to Villa Adriana in Tivoli, about 36 minutes away. Next up on the itinerary: pause for some serene contemplation at Pantheon, ponder the design of Trevi Fountain, get to know the fascinating history of Piazza Navona, and contemplate the long history of Roman Forum.

To find ratings, photos, maps, and more tourist information, read Rome day trip app .

Drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. October in Rome sees daily highs of 26°C and lows of 15°C at night. Finish your sightseeing early on the 14th (Mon) so you can drive 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.
Give yourself a bit of retail therapy at Miniaci Art Gallery and Il Gusto della Costa. Visit Lido di Ravello and Bagni d'Arienzo Beach Club, Positano for some beach relaxation. Explore the numerous day-trip ideas around Positano: Ravello (Villa Rufolo & Villa Cimbrone Gardens), Lido Capo di Conca (in Conca dei Marini) and Amalfi (Valle delle Ferriere & Duomo di Sant'Andrea). There's much more to do: enjoy the sand and surf at Fornillo, take a tour by water with Boat Tours & Water Sports, and add some adventure to your tour with a kayaking and canoeing tour.

To see maps and more tourist information, use the Positano visit planner .

Drive from Rome to Positano in 3.5 hours. Alternatively, you can do a combination of train and subway; or take a bus. Plan for somewhat warmer nights when traveling from Rome in October since evenings lows in Positano dip to 20°C. Wrap up your sightseeing on the 18th (Fri) early enough to ride a ferry to Vietri sul Mare.

Things to do in Positano

Outdoors Parks 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. You'll explore and learn at Ceramiche Cosmolena di Margherita di Palma and Ceramiche d'Arte Carmela. Do some cultural sightseeing at Pompeii Archaeological Park and Le Vigne di Raito. Change things up with these side-trips from Vietri sul Mare: Ravello (Cappella Sant'Angelo all'Ospedale, Duomo di Ravello, & more). There's still lots to do: kick back and relax at Spiaggia di castiglione, pause for some serene contemplation at Chiesa San Pietro Apostolo, contemplate the long history of Santa Maria de Olearia, and tour the pleasant surroundings at Spiaggia Lannio.

To find maps, more things to do, photos, and more tourist information, refer to the Vietri sul Mare visit website .

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. Wrap up your sightseeing on the 21st (Mon) early enough to travel to Venice.

Things to do in Vietri sul Mare

Historic Sites Parks Outdoors

Side Trips

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

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.
Visit Peggy Guggenheim Collection and Basilica di San Marco for their historical value. Appreciate the collections at Doge's Palace and Gallerie dell'Accademia. Get out of town with these interesting Venice side-trips: Padua (Scrovegni Chapel & Basilica di Sant’Antonio). There's lots more to do: make a trip to Piazza San Marco, take in the views from Ponte dei Sospiri, explore the world behind art at Museo Correr, and examine the collection at Ca' Rezzonico.

For photos, ratings, other places to visit, and other tourist information, read our Venice trip itinerary planning site .

Use the Route module to find suitable travel options 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. Cap off your sightseeing on the 26th (Sat) early enough to 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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