41 days in Italy Itinerary

41 days in Italy Itinerary

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Route & dates

41 days in Italy Itinerary

Start: Jacksonville, Florida
Bus + Fly:  16 h 45 min
1
Venice
— 3 nights
Fly + Bus:  4 h 15 min
2
San Teodoro, Sardinia
— 3 nights
Bus + Fly:  5 h 45 min
3
Lampedusa
— 2 nights
Fly:  4 h 45 min
4
Bari
— 4 nights
Drive:  3 h
5
Naples
— 4 nights
Train:  1 h 15 min
6
Rome
— 4 nights
Train:  1 h
7
Orvieto
— 3 nights
Drive:  1 h 30 min
8
Assisi
— 3 nights
Drive:  3 h
9
Pisa
— 4 nights
Drive:  2 h 45 min
10
Ravenna
— 2 nights
Drive:  1 h 15 min
11
Bologna
— 7 nights
Fly:  17 h 15 min
End: Jacksonville, Florida

3
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.
Your cultural itinerary includes sights like Castello Scaligero and San Giorgio Maggiore. Explore hidden gems such as Scrovegni Chapel and Basilica di Santa Maria Gloriosa dei Frari. Venture out of the city with trips to Centro Storico Sirmione (in Sirmione), Brescia Castle (in Brescia) and Basilica di Sant’Antonio (in Padua). And it doesn't end there: admire the striking features of Scuola Grande di San Rocco, visit Campo del Ghetto, don't miss a visit to Piazza Bra, and enjoy breathtaking views from Torre dei Lamberti.

For photos, more things to do, and tourist information, go to the Venice trip itinerary maker.

Jacksonville, USA to Venice is an approximately 17-hour combination of bus and flight. You can also do a combination of train and flight; or do a combination of bus, flight, and train. The time zone difference when traveling from Jacksonville to Venice is 6 hours. In November, Venice is a bit cooler than Jacksonville - with highs of 56°F and lows of 43°F. Finish your sightseeing early on the 9th (Mon) so you can travel to San Teodoro.

Things to do in Venice

Historic Sites Neighborhoods

Side Trips

Verona, Sirmione, Padua, Brescia Castle
Highlights from your plan
Scrovegni Chapel ©
Scrovegni Chapel
Campo del Ghetto ©
Campo del Ghetto
Brescia Castle ©
Brescia Castle

3
nights
San Teodoro, Sardinia

San Teodoro ©
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 Lu Impostu Beach. You'll enjoy a bit of beach vacationing at Oasi Biderosa and Spiaggia Isuledda. Change things up with a short trip to Spiaggia Berchida in Siniscola (about 48 minutes away). The adventure continues: tour the pleasant surroundings at Spiaggia Capo Coda Cavallo, kick back and relax at Cala Brandinchi, and step into the grandiose world of Castello della Fava.

To see reviews, more things to do, other places to visit, and other tourist information, read San Teodoro day trip planning app .

You can fly from Venice to San Teodoro in 4.5 hours. Other options are to do a combination of train and flight; or do a combination of car and ferry. Expect a bit warmer temperatures when traveling from Venice in November; daily highs in San Teodoro reach 66°F and lows reach 49°F. Finish up your sightseeing early on the 12th (Thu) so you can travel to Lampedusa.

Things to do in San Teodoro

Beaches Outdoors Parks

Side Trips

Oasi Biderosa, Castello della Fava, Spiaggia Isuledda, Spiaggia Berchida, Cala Brandinchi
Highlights from your plan
Spiaggia Berchida ©
Spiaggia Berchida
Spiaggia Isuledda ©
Spiaggia Isuledda
Castello della Fava ©
Castello della Fava

2
nights
Lampedusa

Lampedusa ©
Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.
Start off your visit on the 13th (Fri): look for all kinds of wild species at Centro di Recupero Tartarughe e Fauna Selvatica WWF and then get a new perspective on things with Boat Tours & Water Sports. On the 14th (Sat), you'll have a packed day of sightseeing: kick back and relax at Spiaggia dei Conigli, kick back and relax at Cala Pulcino, then stop by Il Veliero di Lampedusa, then tour the pleasant surroundings at Cala Croce Beach, and finally visit a coastal fixture at Faro di Capo Grecale.

To see traveler tips, maps, ratings, and more tourist information, read our Lampedusa trip planner.

Getting from San Teodoro to Lampedusa by flight takes about 6 hours. Other options: do a combination of ferry, train, and bus; or do a combination of train, ferry, and bus. Traveling from San Teodoro in November, you can expect nighttime temperatures to be somewhat warmer in Lampedusa, with lows of 64°F. Cap off your sightseeing on the 14th (Sat) early enough to travel to Bari.

Things to do in Lampedusa

Outdoors Parks Beaches
Highlights from your plan
Cala Croce Beach ©
Cala Croce Beach
Cala Pulcino ©
Cala Pulcino
Faro di Capo Grecale ©
Faro di Capo Grecale

4
nights
Bari

Bari ©
Puglia's capital city, Bari, is a growing metropolis of industry and one of the country's most important commercial ports.
Explore hidden gems such as Basilica San Nicola and Basilica di Santa Croce. Get a sense of the local culture at Castel del Monte and Cattedrale di Trani. You'll find plenty of places to visit near Bari: Lecce (Piazza del Duomo & Duomo di Lecce), Chiesa San Francesco (in Andria) and Castello Aragonese (in Taranto). There's still lots to do: get to know the fascinating history of Centro Storico, pause for some serene contemplation at Parrocchia Spirito Santo, and make a trip to Centro Storico di Polignano a Mare.

To find reviews, photos, other places to visit, and tourist information, refer to the Bari online tour itinerary builder .

Fly from Lampedusa to Bari in 5 hours. Alternatively, you can do a combination of flight and train; or do a combination of ferry and car. Traveling from Lampedusa in November, expect slightly colder with lows of 49°F in Bari. Cap off your sightseeing on the 18th (Wed) early enough to go by car to Naples.

Things to do in Bari

Historic Sites

Side Trips

Lecce, Andria, Castello Aragonese, Centro Storico di Polignano a Mare, Parrocchia Spirito Santo
Highlights from your plan
Basilica San Nicola ©
Basilica San Nicola
Centro Storico ©
Centro Storico
Basilica di Santa Croce ©
Basilica di Santa Croce

4
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Satisfy your inner culture vulture at Parco Acheologico di Ercolano and Castello Aragonese d'Ischia. Explore hidden gems such as Galleria Borbonica and Paestum Ruins. You'll find plenty of places to visit near Naples: Chiesa di Santa Maria di Costantinopoli (in Ischia), Anacapri (Eureka & Villa San Michele) and Duomo di Salerno (in Salerno). There's still lots to do: explore the different monuments and memorials at Catacombe di San Gennaro, appreciate the extensive heritage of Via Caracciolo e Lungomare di Napoli, don't miss a visit to Via San Gregorio Armeno, and take in nature's colorful creations at Giardini di Augusto.

For where to stay, maps, ratings, and more tourist information, use the Naples trip planner.

Traveling by car from Bari to Naples takes 3 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 66°F in November, and nighttime lows around 50°F. Cap off your sightseeing on the 22nd (Sun) early enough to catch the train to Rome.

Things to do in Naples

Historic Sites Museums Shopping

Side Trips

Anacapri, Ischia, Capri, Parco Acheologico di Ercolano, Duomo di Salerno
Highlights from your plan
Castello Aragonese d'Ischia ©
Castello Aragonese d'Ischia
Villa San Michele ©
Villa San Michele
Galleria Borbonica ©
Galleria Borbonica

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.
Deepen your sense of the past at sights like Arcibasilica di San Giovanni in Laterano and Parco Archeologico di Ostia Antica. Centro Storico Associazione Centro Storico and Abbey of St. Paul Outside the Walls are good opportunities to explore the local culture. Explore Rome's surroundings by going to Monastero Di S.Benedetto (in Subiaco) and Villa d'Este (in Tivoli). There's lots more to do: don't miss a visit to Villa Borghese, take in the spiritual surroundings of Chiesa di Sant'Ignazio di Loyola, appreciate the extensive heritage of Piazza Venezia, and pause for some serene contemplation at Church of St. Louis of the French.

To see maps, ratings, photos, and other tourist information, refer to the Rome journey tool .

You can take a train from Naples to Rome in 1.5 hours. Other options are to drive; or take a bus. In November, daytime highs in Rome are 63°F, while nighttime lows are 47°F. Cap off your sightseeing on the 26th (Thu) early enough to catch the train to Orvieto.

Things to do in Rome

Historic Sites Museums Parks

Side Trips

Vatican City, Monastero Di S.Benedetto, Villa d'Este, Parco Archeologico di Ostia Antica
Highlights from your plan
St. Peter's Square ©
St. Peter's Square
Abbey of St. Paul Outside the Walls ©
Parco Archeologico di Ostia Antica ©
Parco Archeologico di Ostia Antica

3
nights
Orvieto

Orvieto ©
The striking town of Orvieto, perched on a volcanic cliff overlooking the Umbrian countryside, is known as the Green Heart of Italy.
Explore hidden gems such as Duomo di Orvieto and Civita di Bagnoregio. Satisfy your inner culture vulture at Pitigliano Centro Storico and San Quirico d'Orcia. Get out of town with these interesting Orvieto side-trips: Cascate del Mulino (in Saturnia), Santuario della Madonna delle Grazie (in Pitigliano) and Castello di Monteriggioni (in Monteriggioni). The adventure continues: take in the architecture and atmosphere at Abbazia di Sant'Antimo, steep yourself in history at Pozzo di San Patrizio, explore the fascinating underground world of Orvieto Underground, and enjoy breathtaking views from Fortezza di Montalcino.

For photos, ratings, other places to visit, and more tourist information, read our Orvieto tour planner.

Traveling by train from Rome to Orvieto takes an hour. Alternatively, you can take a bus; or drive. Expect a daytime high around 59°F in November, and nighttime lows around 45°F. Finish your sightseeing early on the 29th (Sun) to allow enough time to drive to Assisi.

Things to do in Orvieto

Historic Sites Nature Parks

Side Trips

Pitigliano, Montalcino, San Quirico d'Orcia, Cascate del Mulino, Civita di Bagnoregio
Highlights from your plan
Pitigliano Centro Storico ©
Pitigliano Centro Storico
San Quirico d'Orcia ©
San Quirico d'Orcia
San Donato Church ©
San Donato Church

3
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Deepen your sense of the past at sights like Basilica di Santa Maria degli Angeli - Porziuncola and Cattedrale di Santa Maria Assunta Spoleto. Your cultural itinerary includes sights like Basilica di Santa Chiara and San Damiano. Explore the numerous day-trip ideas around Assisi: Spoleto (Ponte delle Torri & Piazza del Duomo), Rocca Paolina (in Perugia) and Eremo Le Celle (in Cortona). There's still lots to do: take in the spiritual surroundings of Eremo delle Carceri, see the interesting displays at Museo della Porziuncola, and take in the architecture and atmosphere at Cattedrale di San Rufino.

For traveler tips, reviews, more things to do, and more tourist information, read our Assisi trip itinerary maker.

Getting from Orvieto to Assisi by car takes about 1.5 hours. Other options: take a train; or take a bus. In November, plan for daily highs up to 58°F, and evening lows to 44°F. Finish up your sightseeing early on the 2nd (Wed) so you can go by car to Pisa.

Things to do in Assisi

Historic Sites Museums

Side Trips

Spoleto, Arezzo, Rocca Paolina, Eremo Le Celle
Highlights from your plan
Cattedrale di San Rufino ©
Cattedrale di San Rufino
San Damiano ©
San Damiano
Eremo Le Celle ©
Eremo Le Celle

4
nights
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Get some cultural insight at Historic Centre of San Gimignano and Abbazia di San Galgano. Step off the beaten path and head to Duomo di Pisa and Centro Storico di Siena. Explore Pisa's surroundings by going to Torre del Mangia (in Siena) and Florence (Museo Nazionale del Bargello, Basilica San Miniato al Monte, &more). The adventure continues: contemplate in the serene atmosphere at Baptistery of St. John and contemplate the long history of Camposanto.

To see more things to do, where to stay, photos, and tourist information, read Pisa online holiday planner .

Getting from Assisi to Pisa by car takes about 3 hours. Other options: take a train; or take a bus. In December, daily temperatures in Pisa can reach 55°F, while at night they dip to 39°F. Wrap up your sightseeing on the 6th (Sun) to allow time to drive to Ravenna.

Things to do in Pisa

Historic Sites Museums

Side Trips

Florence, Siena, Historic Centre of San Gimignano, Abbazia di San Galgano
Highlights from your plan
Historic Centre of San Gimignano ©
Historic Centre of San Gimignano
Camposanto ©
Camposanto
Abbazia di San Galgano ©
Abbazia di San Galgano

2
nights
Ravenna

Ravenna ©
Famous for its wealth of original mosaics, Ravenna is a hub of artistic and cultural heritage.
Start off your visit on the 7th (Mon): take in the architecture and atmosphere at Basilica di San Francesco, Ravenna, contemplate in the serene atmosphere at Basilica di Sant'Apollinare in Classe, steep yourself in history at Battistero Neoniano (Battistero degli Ortodossi), then contemplate in the serene atmosphere at Battistero degli Ariani, then take in the spiritual surroundings of Basilica San Vitale, and finally don't miss a visit to Mausoleo di Galla Placidia. On the 8th (Tue), you'll have a packed day of sightseeing: see the interesting displays at Musei San Domenico, then don't miss a visit to Porto Turistico Cesenatico, then examine the collection at Archiepiscopal Museum, and finally take in the spiritual surroundings of Basilica di Sant'Apollinare Nuovo.

To see other places to visit, photos, more things to do, and other tourist information, go to the Ravenna trip builder app .

Drive from Pisa to Ravenna in 3 hours. Alternatively, you can take a train; or take a bus. Expect little chillier weather when traveling from Pisa in December: highs in Ravenna hover around 48°F, while lows dip to 35°F. Finish up your sightseeing early on the 8th (Tue) so you can go by car to Bologna.

Things to do in Ravenna

Historic Sites Museums

Side Trips

Porto Turistico Cesenatico, Musei San Domenico, Basilica di Sant'Apollinare in Classe
Highlights from your plan
Basilica di San Francesco, Ravenna ©
Basilica di San Francesco, Ravenna
Basilica di Sant'Apollinare in Classe ©
Battistero degli Ariani ©
Battistero degli Ariani

7
nights
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Do some cultural sightseeing at Basilica - Santuario di Santo Stefano and Palazzo Te. You'll get in some beach time at Playa del Sol and Altamarea Beach Village. Explore the numerous day-trip ideas around Bologna: Modena (Duomo di Modena, MEF-Museo Enzo Ferrari, &more), Cathedral of Cremona (in Cremona) and Ferrara (Palazzo dei Diamanti, Castello Estense, &more). There's lots more to do: take in the architecture and atmosphere at Santuario di Madonna di San Luca, admire the landmark architecture of Rocca Sanvitale di Fontanellato, examine the collection at Museo Ferrari, and explore the historical opulence of Castello di Torrechiara.

To find where to stay and other tourist information, refer to the Bologna itinerary planner.

You can drive from Ravenna to Bologna in 1.5 hours. Another option is to take a train. In December, plan for daily highs up to 47°F, and evening lows to 34°F. Wrap up your sightseeing by early afternoon on the 15th (Tue) to allow enough time to travel back home.

Things to do in Bologna

Historic Sites Museums Outdoors

Side Trips

Mantua, Ferrara, Modena, Maranello, Battistero di Parma
Highlights from your plan
Rocca Sanvitale di Fontanellato ©
Rocca Sanvitale di Fontanellato
Castello di Torrechiara ©
Castello di Torrechiara
Rotonda di San Lorenzo ©
Rotonda di San Lorenzo

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