36 days in Italy Itinerary
Created using Inspirock Italy route planner
Start: Tampa
Fly
1
Rome
— 5 nights
Drive
2
Assisi
— 4 nights
Drive
3
Siena
— 3 nights
Drive
4
Florence
— 4 nights
Train
5
Verona
— 4 nights
Fly
6
Lampedusa
— 1 night
Fly
7
Taormina, Sicily
— 2 nights
Fly
8
Alghero, Sardinia
— 2 nights
Drive
9
San Teodoro, Sardinia
— 3 nights
Fly
10
Ravello
— 2 nights
Fly
11
Venice
— 5 nights
Fly
End: Tampa
Mon, Sep 18 - Mon, Oct 23
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Rome — 5 nights

Eternal City
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.Visit Colosseum and Piazza Navona for their historical value. Pantheon and Arcibasilica di San Giovanni in Laterano are good opportunities to explore the local culture. Take a break from Rome with a short trip to Parco Archeologico di Ostia Antica in Ostia Antica, about 42 minutes away. There's lots more to do: admire the masterpieces at Vatican Museums, take in the architecture and atmosphere at St. Peter's Basilica, appreciate the extensive heritage of Centro Storico Associazione Centro Storico, and don't miss a visit to Cupola di San Pietro.
To see traveler tips, reviews, ratings, and other tourist information, read Rome itinerary builder site.
Tampa, USA to Rome is an approximately 14.5-hour flight. The time zone difference moving from Eastern Standard Time (EST) to Central European Standard Time (CET) is 6 hours. Prepare for little chillier weather when traveling from Tampa in September: high temperatures in Rome hover around 81°F and lows are around 60°F. Finish your sightseeing early on the 23rd (Sat) so you can drive to Assisi.
Side Trips
Find places to stay Sep 18 — 23:
Highlights from your trip
Assisi — 4 nights

City of Peace
Rich in culture and religious tradition, Assisi is known as the birthplace of St.Explore hidden gems such as Cascata delle Marmore and Pozzo di San Patrizio. Your cultural itinerary includes sights like Duomo di Orvieto and Cattedrale di Santa Maria Assunta Spoleto. Explore the numerous day-trip ideas around Assisi: Orvieto Underground (in Orvieto), Rocca Paolina (in Perugia) and Basilica of Saint Ubaldo (in Gubbio). There's much more to do: contemplate the long history of Eremo delle Carceri, pause for some serene contemplation at San Damiano, do a tasting at Tili Vini Societa Agricola, and take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola.
To find reviews, ratings, other places to visit, and tourist information, go to the Assisi online trip builder.
Traveling by car from Rome to Assisi takes 2.5 hours. Alternatively, you can take a train; or take a bus. September in Assisi sees daily highs of 78°F and lows of 57°F at night. Finish your sightseeing early on the 27th (Wed) so you can drive to Siena.
Side Trips
Orvieto, Rocca Paolina, Cascata delle Marmore, Castello Monte Vibiano Vecchio, Cattedrale di Santa Maria Assunta Spoleto
Find places to stay Sep 23 — 27:
Highlights from your trip
Siena — 3 nights

Cultural Heart of Tuscany
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.Get some cultural insight at Historic Centre of San Gimignano and Wine Tours & Tastings. Your inner history buff will appreciate Abbazia di San Galgano and Palazzo Pubblico and Museo Civico. Get out of town with these interesting Siena side-trips: San Gimignano (Torre e Casa Campatelli, Duomo di San Gimignano, &more). There's lots more to do: enjoy breathtaking views from Torre del Mangia, pause for some serene contemplation at Duomo di Siena, step into the grandiose world of Castello di Monteriggioni, and admire the masterpieces at Museo dell'Opera Metropolitana.
For photos, other places to visit, more things to do, and tourist information, read Siena driving holiday planner.
Drive from Assisi to Siena in 2 hours. Alternatively, you can take a bus; or take a train. In September in Siena, expect temperatures between 81°F during the day and 61°F at night. Finish your sightseeing early on the 30th (Sat) to allow enough time to drive to Florence.
Side Trips
Find places to stay Sep 27 — 30:
Highlights from your 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.Your inner history buff will appreciate Cathedral of Santa Maria del Fiore and Basilica San Miniato al Monte. Piazzale Michelangelo and Duomo di Pisa are good opportunities to explore the local culture. Change things up with these side-trips from Florence: Montecatini Alto (in Montecatini Alto) and Pisa (Camposanto, Battistero di San Giovanni, &more). Next up on the itinerary: contemplate in the serene atmosphere at The Baptistery of St. John, steep yourself in history at Basilica of Santa Croce, get to know the fascinating history of Centro Storico, and admire the masterpieces at Pitti Palace.
For reviews, more things to do, ratings, and other tourist information, refer to the Florence journey planner.
You can drive from Siena to Florence in 1.5 hours. Alternatively, you can take a bus; or take a train. September in Florence sees daily highs of 78°F and lows of 59°F at night. Wrap up your sightseeing on the 4th (Wed) to allow time to take a train to Verona.
Side Trips
Find places to stay Sep 30 — Oct 4:
Verona — 4 nights
City of Romeo and Juliet
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.Visiting Mountbaldo and Lago di Garda will get you outdoors. You'll discover tucked-away gems like Spa Termale Aquaria and Palazzo Te. Change things up with these side-trips from Verona: Santuario di San Romedio (in Coredo), Castel Thun (in Ton) and Borghetto sul Mincio (in Valeggio Sul Mincio). There's lots more to do: contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, kick back and relax at Jamaica Beach, explore the historical opulence of Castello Scaligero, and wander the streets of Piazza delle Erbe.
To find maps, where to stay, ratings, and more tourist information, read our Verona tour planner.
Traveling by train from Florence to Verona takes 2.5 hours. Alternatively, you can drive. When traveling from Florence in October, plan for slightly colder days in Verona, with highs around 66°F, while nights are about the same with lows around 50°F. Wrap up your sightseeing on the 8th (Sun) early enough to fly to Lampedusa.
Side Trips
Find places to stay Oct 4 — 8:
Highlights from your trip
Lampedusa — 1 night

Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.On the 9th (Mon), see the vivid underwater world at Capo Ponente, stroll through Cala Pulcino, then kick back and relax at Spiaggia dei Conigli, and finally tour the pleasant surroundings at Cala Croce Beach.
To see reviews, traveler tips, maps, and other tourist information, you can read our Lampedusa trip maker tool.
Getting from Verona to Lampedusa by flight takes about 3.5 hours. Other options: do a combination of train, ferry, and bus; or do a combination of train, bus, and ferry. While traveling from Verona, expect a bit warmer days and much warmer nights in Lampedusa, ranging from highs of 77°F to lows of 71°F. Finish up your sightseeing early on the 9th (Mon) so you can catch the flight to Taormina.
Find places to stay Oct 8 — 9:
Highlights from your trip
Taormina, Sicily — 2 nights

With its warm island weather and cliffside location overlooking the Ionion Sea, Taormina has been one of Sicily's most popular getaway destinations since the early 19th century.On the 10th (Tue), see some colorful creatures with a scuba or snorkeling tour, then take in the pleasant sights at Piazza IX Aprile, then don't miss a visit to Corso Umberto, and finally stroll around Villa Comunale. Here are some ideas for day two: take in the architecture and atmosphere at Duomo di Taormina, delve into the distant past at Ancient Theatre of Taormina, then do a tasting at Gambino Vini, and finally step off the mainland to explore Isola Bella.
For reviews, other places to visit, maps, and tourist information, read Taormina trip planner.
Traveling by flight from Lampedusa to Taormina takes 3 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Traveling from Lampedusa in October, Taormina is a bit cooler at night with lows of 64°F. Finish up your sightseeing early on the 11th (Wed) so you can catch the flight to Alghero.
Side Trips
Find places to stay Oct 9 — 11:
Highlights from your trip
Alghero, Sardinia — 2 nights
©
Little Barcelona
Built surrounding a 16th-century fortified port, Alghero remains one of Sardinia's most visited sites, rich in cultural and historical heritage.Kick off your visit on the 12th (Thu): get a new perspective on things with Boat Tours & Water Sports, enjoy the sand and surf at Spiaggia di Maria Pia, and then do a tasting at Azienda Agricola Leda' d'Ittiri. Keep things going the next day: Head underground at Frecce delle Grotte di Antonio Piccinnu, then explore the striking landscape at Capo Caccia, then explore the fascinating underground world of Neptune's Grotto, and finally enjoy the sand and surf at Spiaggia Mugoni.
Ask Inspirock to suggest an itinerary and make planning a trip to Alghero fast, fun, and easy.
Traveling by flight from Taormina to Alghero takes 3 hours. Alternatively, you can do a combination of train, ferry, and bus; or do a combination of train and ferry. Traveling from Taormina in October, Alghero is a bit cooler at night with lows of 56°F. Cap off your sightseeing on the 13th (Fri) early enough to go by car to San Teodoro.
Find places to stay Oct 11 — 13:
Highlights from your trip
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.Step out of the city life by going to Spiaggia La Cinta and Cala Brandinchi. Step off the beaten path and head to Lu Impostu Beach and Spiaggia Berchida. Change things up with these side-trips from San Teodoro: Grotta del Bue Marino (in Cala Gonone) and Golfo Aranci (Dolphin & Whale Watching & Spiaggia Bianca). It doesn't end there: stroll through Porto Taverna Beach and enjoy the sand and surf at Spiaggia Capo Coda Cavallo.
For where to stay, other places to visit, ratings, and more tourist information, use the San Teodoro tour planning site.
You can drive from Alghero to San Teodoro in 2.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. October in San Teodoro sees daily highs of 76°F and lows of 56°F at night. Wrap up your sightseeing on the 16th (Mon) early enough to fly to Ravello.
Side Trips
Find places to stay Oct 13 — 16:
Highlights from your trip
Ravello — 2 nights

Best known for its celebrated terraced gardens, Ravello is a hidden gem of Italy's Amalfi Coast.On the 17th (Tue), take advantage of the amenities at Fornillo, take a tour by water with Boat Tours & Water Sports, then take in the architecture and atmosphere at Chiesa di San Pancrazio Martire, then shop like a local with Ceramiche Cosmolena di Margherita di Palma, and finally contemplate the long history of Duomo di Ravello. On the 18th (Wed), you'll have a packed day of sightseeing: admire the landmark architecture of Villa Rufolo, tour the pleasant surroundings at Villa Cimbrone Gardens, steep yourself in history at Ruderi della Basilica di Sant'Eustachio, then examine the collection at Museo della Carta, then contemplate in the serene atmosphere at Duomo di Sant'Andrea, and finally take in the spiritual surroundings of Cloister del Paradiso.
To find maps, traveler tips, other places to visit, and tourist information, you can read our Ravello visit planning tool.
You can fly from San Teodoro to Ravello in 3 hours. Other options are to do a combination of bus, ferry, train, and taxi; or do a combination of bus, ferry, and train. Traveling from San Teodoro in October, expect a bit warmer with lows of 63°F in Ravello. Wrap up your sightseeing on the 18th (Wed) to allow time to fly to Venice.
Side Trips
Find places to stay Oct 16 — 18:
Highlights from your trip
Venice — 5 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 explore and learn at Doge's Palace and Peggy Guggenheim Collection. Step off the beaten path and head to Centro Storico di Venezia and Basilica of St. Anthony. Explore Venice's surroundings by going to Padua (Chiesa degli Eremitani - World Heritage Site & Scrovegni Chapel) and Castello Estense (in Ferrara). The adventure continues: contemplate in the serene atmosphere at Scuola Grande di San Rocco, contemplate the waterfront views at Canal Grande, don't miss a visit to Basilica di San Marco, and take in the views from Ponte di Rialto.
To find maps, reviews, ratings, and tourist information, use the Venice online trip planner.
You can fly from Ravello to Venice in 3 hours. Other options are to do a combination of taxi and train; or drive. In October, Venice is a bit cooler than Ravello - with highs of 66°F and lows of 51°F. Wrap up your sightseeing on the 23rd (Mon) early enough to fly back home.
Side Trips
Find places to stay Oct 18 — 23:
Highlights from your trip
Italy travel guide
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.