29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy sightseeing planner

Make it your trip
Fly
1
Rome
— 4 nights
Train
2
Florence
— 4 nights
Drive to Piombino, Ferry to Portoferraio
3
Portoferraio, Elba Island
— 2 nights
Ferry to Piombino, Drive to Assisi
4
Assisi
— 4 nights
Train to Rome, Fly to Lampedusa
5
Lampedusa
— 2 nights
Fly
6
San Vito lo Capo, Sicily
— 3 nights
Fly
7
San Teodoro, Sardinia
— 3 nights
Drive
8
Baunei, Sardinia
— 1 night
Drive
9
Villasimius, Sardinia
— 1 night
Fly
10
Venice
— 3 nights
Fly

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Rome

— 4 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Bring the kids along to Colosseum and Piazza Navona. Step off the beaten path and head to Centro Storico Associazione Centro Storico and Basilica di Santa Maria degli Angeli e dei Martiri. There's much more to do: pause for some serene contemplation at Basilica Papale San Paolo fuori le Mura, have fun and explore at Welcome to Rome, delve into the distant past at Pantheon, and make a trip to Cupola di San Pietro.

To find traveler tips, photos, other places to visit, and more tourist information, go to the Rome attractions planner.

Winnipeg, Canada to Rome is an approximately 17.5-hour flight. The time zone difference when traveling from Winnipeg to Rome is 7 hours. Traveling from Winnipeg in August, things will get a bit warmer in Rome: highs are around 38°C and lows about 24°C. Finish up your sightseeing early on the 9th (Mon) so you can catch the train to Florence.

Things to do in Rome

Historic Sites · Museums · Childrens Museums

Side Trip

Florence

— 4 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Museum-lovers will appreciate Florence Academy of Fine Arts and Stibbert Museum. Family-friendly places like Cathedral of Santa Maria del Fiore and Centro Storico di Siena will thrill your kids. Change things up with these side-trips from Florence: San Gimignano 1300 (in San Gimignano), Siena (Palazzo Pubblico and Museo Civico, Duomo di Siena, &more) and Monteriggioni (Walls of Monteriggioni & Castello di Monteriggioni). Next up on the itinerary: contemplate in the serene atmosphere at Duomo di Pisa, admire the landmark architecture of Basilica San Miniato al Monte, explore the world behind art at Pitti Palace, and make a trip to Leaning Tower of Pisa.

To see ratings, photos, where to stay, and other tourist information, read Florence trip builder app.

Getting from Rome to Florence by train takes about 2.5 hours. Other options: drive; or fly. Plan for a bit cooler nights when traveling from Rome in August since evenings lows in Florence dip to 20°C. Cap off your sightseeing on the 13th (Fri) early enough to travel to Portoferraio.

Things to do in Florence

Historic Sites · Museums

Side Trips

Portoferraio, Elba Island

— 2 nights
Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Start off your visit on the 14th (Sat): get outside with Spiaggia di Spartaia, trek along Walking trail to Spiaggia della Biodola, enjoy the sand and surf at Spiaggia Della Biodola, stroll through Spiaggia di Seccione, then enjoy the sand and surf at Spiaggia Di Sansone, and finally tour the pleasant surroundings at Spiaggia La Sorgente. On the 15th (Sun), you'll have a packed day of sightseeing: head outdoors with Spiaggia di Lido di Capoliveri all Isola d'Elba, see some colorful creatures with a scuba or snorkeling tour, explore the historical opulence of Castello del Volterraio, then kick back and relax at Spiaggia Di Sottobomba, and finally stop by Gelateria Zero Gradi.

To see traveler tips, photos, other places to visit, and other tourist information, use the Portoferraio driving holiday planner.

Do a combination of car and ferry from Florence to Portoferraio in 4 hours. Alternatively, you can do a combination of car and ferry; or do a combination of train and ferry. In August, plan for daily highs up to 33°C, and evening lows to 23°C. Finish your sightseeing early on the 15th (Sun) so you can travel to Assisi.

Things to do in Portoferraio

Outdoors · Parks · Beaches · Trails

Side Trips

Assisi

— 4 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Appreciate the collections at Studio Moretti Caselli and House Museum Palazzo Sorbello. Discover out-of-the-way places like Eremo delle Carceri and Cattedrale di San Rufino. Change things up with these side-trips from Assisi: Foligno (Abbazia di Sassovivo, Cattedrale di San Feliciano, &more), Spoleto (Chiesa di San Ponziano & Piazza del Duomo) and Centro Storico (in Montefalco). And it doesn't end there: step into the grandiose world of Rocca Maggiore, don't miss a visit to City Centre, explore the ancient world of Roman Forum and Archaeological Museum, and get to know the fascinating history of Centro Storico di Assisi.

For ratings, where to stay, traveler tips, and more tourist information, read our Assisi trip planning app.

You can do a combination of ferry and car from Portoferraio to Assisi in 5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and train; or do a combination of ferry, train, and bus. Traveling from Portoferraio in August, plan for little chillier nights in Assisi, with lows around 20°C. Cap off your sightseeing on the 19th (Thu) early enough to travel to Lampedusa.

Things to do in Assisi

Historic Sites · Museums · Neighborhoods

Side Trips

Lampedusa

— 2 nights
Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.
Kick off your visit on the 20th (Fri): tour the pleasant surroundings at Cala Croce Beach, don't miss a visit to Archivio Storico Lampedusa, get outside with Mare Morto, visit a coastal fixture at Faro di Capo Grecale, then make a trip to Cala Calandra, and finally look for all kinds of wild species at Centro di Recupero Tartarughe e Fauna Selvatica WWF. On your second day here, kick back and relax at Spiaggia di Portu Ntoni, look for all kinds of wild species at Centro Recupero Tartarughe Marine, then make a trip to Cala Guitgia, and finally stop by Il Pescato Di Lampedusa S.A.S. Di Costa Antonino & C..

For photos, more things to do, other places to visit, and tourist information, refer to the Lampedusa online travel route builder.

Traveling by combination of train and flight from Assisi to Lampedusa takes 6.5 hours. Alternatively, you can fly; or do a combination of train, ferry, and bus. Traveling from Assisi in August, you can expect nighttime temperatures to be somewhat warmer in Lampedusa, with lows of 29°C. Finish up your sightseeing early on the 21st (Sat) so you can travel to San Vito lo Capo.

Things to do in Lampedusa

Parks · Outdoors · Beaches · Wildlife

Side Trip

San Vito lo Capo, Sicily

— 3 nights
A vacation in San Vito lo Capo offers a chance to enjoy a sheltered bay and a town with distinctive Arab-Norman architecture.
You'll explore the less-touristy side of things at Selinunte Archaeological Park and Chiesa della Santissima Trinita di Delia. Bring the kids along to Chiesa Madre and Museum Of Optical Illusions. Explore the numerous day-trip ideas around San Vito lo Capo: Trapani (Cattedrale di San Lorenzo, Corso Vittorio Emanuele di Trapani, &more). There's much more to do: pause for some serene contemplation at Chiesa di San Domenico, tour the pleasant surroundings at Stabilimento Balneare Al Sabbione, appreciate the extensive heritage of Borgo Storico Erice, and enjoy the sand and surf at Cala Tonnarella dell'Uzzo.

To find more things to do, photos, and more tourist information, go to the San Vito lo Capo road trip planning tool.

Fly from Lampedusa to San Vito lo Capo in 5.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, bus, train, and taxi. In August, daily temperatures in San Vito lo Capo can reach 34°C, while at night they dip to 26°C. Finish up your sightseeing early on the 24th (Tue) so you can travel to San Teodoro.

Things to do in San Vito lo Capo

Historic Sites · Beaches · Outdoors · Parks

Side Trips

San Teodoro, Sardinia

— 3 nights
A chance to sip cocktails at swanky beach bars by day and experience the vibrant club scene by night makes San Tedoro vacations extremely popular.
Explore hidden gems such as Spiaggia La Cinta and Spiaggia Capo Coda Cavallo. Appreciate the collections at Museo Deleddiano - Casa natale di Grazia Deledda and Man Museum of Art Province of Nuoro. Change things up with these side-trips from San Teodoro: Golfo Aranci (Sos Aranzos Beach, Cala Sassari, &more), Olbia (Pozzo Sacro Sa Testa & L'Area Naturale Marina Protetta Tavolara - Punta Coda Cavallo) and Spiaggia del Dottore (in Murta Maria). The adventure continues: kick back and relax at Lu Impostu Beach, get outside with Nata Libera, don't miss a visit to Complesso Nuragico di Noddule, and explore the ancient world of Necropoli di San Simplicio.

To find where to stay, other places to visit, ratings, and more tourist information, use the San Teodoro online trip itinerary maker.

Traveling by flight from San Vito lo Capo to San Teodoro takes 5.5 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus, ferry, and train. Expect a bit cooler evenings in San Teodoro when traveling from San Vito lo Capo in August, with lows around 22°C. Finish your sightseeing early on the 27th (Fri) to allow enough time to drive to Baunei.

Things to do in San Teodoro

Outdoors · Parks · Beaches · Wildlife

Side Trips

Baunei, Sardinia

— 1 night
Baunei is a comune (municipality) in the Province of Nuoro in the Italian island of Sardinia.GeographyThe municipality of Baunei is located about 100km northeast of Cagliari and about 11km north of Tortolì. Start off your visit on the 28th (Sat): kick back and relax at Cala Goloritzè, kick back and relax at Piscine di Venere, tour the pleasant surroundings at Cala Mariolu, then see some colorful creatures with Diving Cala Mariolu, then take in the architecture and atmosphere at Chiesa di San Pietro al Golgo, and finally delve into the mystery of Maschera di Pietra.

For photos, reviews, traveler tips, and more tourist information, read our Baunei day trip tool.

You can drive from San Teodoro to Baunei in 2 hours. Alternatively, you can take a bus. Traveling from San Teodoro in August, Baunei is a bit warmer at night with lows of 26°C. Wrap up your sightseeing on the 28th (Sat) to allow time to drive to Villasimius.

Things to do in Baunei

Outdoors · Beaches · Parks · Wildlife

Villasimius, Sardinia

— 1 night
For ratings, other places to visit, more things to do, and more tourist information, read our Villasimius trip maker.

You can drive from Baunei to Villasimius in 2 hours. Another option is to take a bus. Traveling from Baunei in August, Villasimius is a bit cooler at night with lows of 22°C. You'll set off for Venice on the 29th (Sun).

Things to do in Villasimius

Outdoors · Parks · Tours · Beaches

Venice

— 3 nights

City of Romance

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.
You'll discover tucked-away gems like Centro Storico di Venezia and Basilica di Santa Maria Gloriosa dei Frari. Do some cultural sightseeing at Piazza San Marco and Dorsoduro. You'll find plenty of places to visit near Venice: Lido (in Lido di Venezia), Church of Santa Maria e San Donato (in Murano) and Basilica di Santa Maria Assunta e Chiesa di Santa Fosca (in Torcello). There's lots more to do: see the interesting displays at Doge's Palace, take in the architecture and atmosphere at Basilica di Santa Maria della Salute, wander the streets of Cannaregio, and admire the striking features of Basilica di San Marco.

To find ratings, traveler tips, where to stay, and tourist information, use the Venice trip itinerary maker app.

Fly from Villasimius to Venice in 6 hours. Alternatively, you can fly; or do a combination of car and ferry; or do a combination of bus, ferry, and train. Traveling from Villasimius in August, you will find days in Venice are slightly colder (34°C), and nights are about the same (22°C). You will have some time to spend on the 1st (Wed) before leaving for home.

Things to do in Venice

Historic Sites · Neighborhoods · Nature · Parks

Side Trips

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.