29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy vacation maker
Make it your trip
Fly
1
Venice
— 3 nights
Drive
2
Trento
— 4 nights
Drive
3
Florence
— 2 nights
Drive
4
Assisi
— 4 nights
Drive to Piombino, Ferry to Portoferraio
5
Portoferraio, Elba Island
— 3 nights
Ferry to Porto Biglietterie Sud, Fly to San Vito lo Capo
6
San Vito lo Capo, Sicily
— 4 nights
Fly
7
Otranto
— 3 nights
Fly
8
Rome
— 5 nights
Fly

S M T W T F S
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24

Venice — 3 nights

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.
Get some historical perspective at Piazza San Marco and Doge's Palace. Step off the beaten path and head to Centro Storico di Venezia and Basilica of St. Anthony. Change things up with a short trip to Scrovegni Chapel in Padua (about 54 minutes away). The adventure continues: admire the landmark architecture of Basilica di San Marco, contemplate the waterfront views at Canal Grande, take in the views from Ponte di Rialto, and visit Cannaregio.

To find reviews, ratings, more things to do, and more tourist information, read Venice day trip tool.

Chicago, USA to Venice is an approximately 12-hour flight. The time zone difference when traveling from Chicago to Venice is 7 hours. In August, plan for daily highs up to 85°F, and evening lows to 66°F. Finish your sightseeing early on the 26th (Fri) so you can drive to Trento.
Historic Sites · Museums · Nature · Parks
Side Trip
Find places to stay Aug 23 — 26:

Trento — 4 nights

Tyrol's capital and one of the nation's wealthiest cities, Trento serves as the commercial and cultural center of the region.
Step off the beaten path and head to MUSE - Science Museum and Mountbaldo. You'll visit kid-friendly attractions like Lago di Molveno and Castello del Buonconsiglio Monumenti e Collezioni Provinciali. Venture out of the city with trips to Castel Thun (in Ton), Schlern-Rosengarten / Sciliar-Catinaccio Nature Park (in Tiers) and Santuario di San Romedio (in Coredo). There's still lots to do: get to know the fascinating history of Piazza Duomo.

For maps, more things to do, photos, and other tourist information, read Trento vacation maker.

Traveling by car from Venice to Trento takes 2.5 hours. Alternatively, you can take a train. In August, daily temperatures in Trento can reach 86°F, while at night they dip to 62°F. Finish your sightseeing early on the 30th (Tue) to allow enough time to drive to Florence.
Historic Sites · Parks · Nature · Museums
Side Trips
Find places to stay Aug 26 — 30:

Florence — 2 nights

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Kick off your visit on the 31st (Wed): take in the views from Ponte Vecchio, get to know the fascinating history of Piazza del Duomo, take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, then enjoy breathtaking views from Campanile di Giotto, and finally get to know the fascinating history of Piazza della Signoria. Get ready for a full day of sightseeing on the 1st (Thu): steep yourself in history at Basilica of Santa Croce, admire the masterpieces at Florence Academy of Fine Arts, then don't miss a visit to Piazzale Michelangelo, and finally explore the world behind art at Pitti Palace.

Planning Florence trip won't be overwhelming when you use Inspirock's itinerary maker.

Getting from Trento to Florence by car takes about 3 hours. Other options: take a train; or take a bus. In August, daytime highs in Florence are 86°F, while nighttime lows are 64°F. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Assisi.
Historic Sites · Museums
Find places to stay Aug 30 — Sep 1:

Assisi — 4 nights

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Step off the beaten path and head to Duomo di Orvieto and Basilica di Santa Maria degli Angeli - Porziuncola. Family-friendly places like Basilica di Santa Chiara and San Damiano will thrill your kids. Explore Assisi's surroundings by going to Cascata delle Marmore (in Marmore), Pozzo di San Patrizio (in Orvieto) and Cattedrale di Santa Maria Assunta Spoleto (in Spoleto). There's still lots to do: step into the grandiose world of Rocca Maggiore, see the interesting displays at Museo della Porziuncola, make a trip to Eremo delle Carceri, and take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi.

To find other places to visit, where to stay, ratings, and more tourist information, you can read our Assisi online tour planner.

You can drive from Florence to Assisi in 2.5 hours. Another option is to take a train. In September, plan for daily highs up to 78°F, and evening lows to 57°F. Finish up your sightseeing early on the 5th (Mon) so you can travel to Portoferraio.
Historic Sites · Museums · Nature · Parks
Side Trips
Find places to stay Sep 1 — 5:

Portoferraio, Elba Island — 3 nights

Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Discover out-of-the-way places like Spiaggia Di Sansone and Spiaggia delle Ghiaie. Get outdoors at Spiaggia di Cavoli and Spiaggia Della Biodola. Take a break from Portoferraio with a short trip to Dolphin & Whale Watching in Marina di Campo, about 32 minutes away. The adventure continues: kick back and relax at Spiaggia di Capo Bianco.

To see more things to do, reviews, where to stay, and more tourist information, you can read our Portoferraio online trip planner.

Traveling by combination of car and ferry from Assisi to Portoferraio takes 5 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus, train, and ferry. In September, daily temperatures in Portoferraio can reach 75°F, while at night they dip to 62°F. Wrap up your sightseeing on the 8th (Thu) early enough to travel to San Vito lo Capo.
Outdoors · Beaches · Parks · Tours
Side Trips
Find places to stay Sep 5 — 8:

San Vito lo Capo, Sicily — 4 nights

A vacation in San Vito lo Capo offers a chance to enjoy a sheltered bay and a town with distinctive Arab-Norman architecture.
Step off the beaten path and head to SEI - Saline Ettore E Infersa and Spiaggia di Macari. Get outdoors at Spiaggia di San Vito lo Capo and Spiaggia Isuledda. Step out of San Vito lo Capo with an excursion to Riserva Naturale Saline Di Trapani E Paceco in Trapani--about 54 minutes away. There's more to do: kick back and relax at Calette Santa Margherita and get a new perspective on things with Boat Tours & Water Sports.

For ratings, where to stay, more things to do, and more tourist information, go to the San Vito lo Capo journey builder.

You can do a combination of ferry and flight from Portoferraio to San Vito lo Capo in 5 hours. Other options are to do a combination of ferry, train, and bus; or do a combination of ferry, train, and taxi. Traveling from Portoferraio in September, expect somewhat warmer with lows of 70°F in San Vito lo Capo. Finish up your sightseeing early on the 12th (Mon) so you can catch the flight to Otranto.
Parks · Outdoors · Beaches · Wildlife
Side Trips
Find places to stay Sep 8 — 12:

Otranto — 3 nights

Otranto is a town and comune in the province of Lecce (Apulia, Italy), in a fertile region once famous for its breed of horses.It is located on the east coast of the Salento peninsula. Relax by the water at Channel Ciolo and Spiaggia Alimini. Discover out-of-the-way places like Centro Storico Otranto and Scuba & Snorkeling. Step out of Otranto with an excursion to Grotta della Poesia in Roca Vecchia--about 30 minutes away. Next up on the itinerary: head outdoors with Circolo Ippico Malepezza.

To find more things to do, reviews, ratings, and tourist information, read our Otranto trip itinerary maker.

Fly from San Vito lo Capo to Otranto in 3 hours. Alternatively, you can do a combination of car and ferry; or take a bus. Traveling from San Vito lo Capo in September, Otranto is little chillier at night with lows of 62°F. Wrap up your sightseeing on the 15th (Thu) early enough to fly to Rome.
Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Sep 12 — 15:

Rome — 5 nights

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Eschew the tourist crowds and head to Villa Borghese and Villa Adriana. You'll visit kid-friendly attractions like Colosseum and Pantheon. Next up on the itinerary: explore the world behind art at Vatican Museums, take in the architecture and atmosphere at St. Clement Basilica, steep yourself in history at Palatine Hill, and make a trip to Roman Forum.

To see photos, reviews, other places to visit, and tourist information, refer to the Rome road trip planning app.

Traveling by flight from Otranto to Rome takes 3 hours. Alternatively, you can drive; or do a combination of bus and train. In September, plan for daily highs up to 81°F, and evening lows to 60°F. Finish up your sightseeing early on the 20th (Tue) so you can catch the flight back home.
Historic Sites · Museums · Neighborhoods
Side Trips
Find places to stay Sep 15 — 20:

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.