37 days in Italy Itinerary

37 days in Italy Itinerary

Created using Inspirock Italy journey planner
Make it your trip
Fly
1
Venice
— 4 nights
Drive
2
Padua
— 3 nights
Drive
3
Portofino
— 2 nights
Drive
4
Cinque Terre
— 3 nights
Drive
5
La Spezia
— 2 nights
Drive
6
Naples
— 3 nights
Drive
7
Pompeii
— 5 nights
Drive
8
Positano
— 5 nights
Ferry
9
Capri
— 2 nights
Unknown

S M T W T F S
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Venice — 4 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.
Get out of town with these interesting Venice side-trips: Verona (Piazza delle Erbe, Arena di Verona, &more). There's much more to do: examine the collection at Doge's Palace, take in the architecture and atmosphere at San Giorgio Maggiore, admire the landmark architecture of Basilica di San Marco, and explore the activities along Canal Grande.

For other places to visit, reviews, ratings, and other tourist information, read our Venice trip maker.

Newark, USA to Venice is an approximately 11.5-hour flight. Traveling from Newark to Venice, you'll lose 6 hours due to the time zone difference. In May, plan for daily highs up to 72°F, and evening lows to 55°F. Wrap up your sightseeing on the 5th (Fri) to allow time to take a shuttle to Padua.
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Historic Sites · Museums · Tours · Parks
Side Trip

Padua — 3 nights

Holy City

Padua is a picturesque city with a dense network of arcaded streets opening into large communal piazze (squares).
Venture out of the city with trips to Ferrara (Ferrara Cathedral, Palazzo Schifanoia (Palazzo della Gioia) - World Heritage Site, &more) and Sacrario di Cima Grappa (in Borso del Grappa). There's much more to do: take in the architecture and atmosphere at Scrovegni Chapel, see the interesting displays at Museo del Precinema, contemplate in the serene atmosphere at Chiesa degli Eremitani - World Heritage Site, and indulge your taste buds at Food & Drink.

For traveler tips, ratings, more things to do, and tourist information, read Padua day trip planner.

You can take a shuttle from Venice to Padua in an hour. Alternatively, you can drive; or take a train. In May, daily temperatures in Padua can reach 70°F, while at night they dip to 59°F. Finish up your sightseeing early on the 8th (Mon) so you can go by car to Portofino.
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Historic Sites · Tours · Wineries · Parks
Side Trips

Portofino — 2 nights

Portofino is an Italian fishing village and holiday resort famous for its picturesque harbour and historical association with celebrity and artistic visitors. On the 9th (Tue), don't miss a visit to Piazza Martiri Dell'Olivetta, then take in the spiritual surroundings of Church of San Giorgio, then step into the grandiose world of Castello Brown, and finally take in the waterfront activity at Marina di Portofino. Get ready for a full day of sightseeing on the 10th (Wed): enjoy the sea views from Faro Di Portofino, identify plant and animal life at Area Marina Protetta Portofino, then admire the masterpieces at Museo Del Parco, and finally take a tour by water with Boat Tours & Water Sports.

To see ratings, reviews, more things to do, and tourist information, you can read our Portofino trip planner.

You can drive from Padua to Portofino in 4 hours. Alternatively, you can take a train; or fly. Expect a daytime high around 69°F in May, and nighttime lows around 58°F. Finish your sightseeing early on the 10th (Wed) to allow enough time to take a train to Cinque Terre.
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Historic Sites · Parks · Wildlife · Outdoors

Cinque Terre — 3 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Explore Cinque Terre's surroundings by going to San Pietro Church (in Porto Venere) and Levanto (Pista Ciclopedonale Levanto - Framura & Levanto to Monterosso Trail). The adventure continues: look for all kinds of wild species at Enjoy Cinqueterre Boat Tours, pause for some serene contemplation at Convento dei Cappuccini e Chiesa di San Francesco, trek along Cinque Terre footpaths, and head outdoors with Cinque Terre Trails.

For traveler tips, reviews, more things to do, and more tourist information, you can read our Cinque Terre online tour planner.

Traveling by train from Portofino to Cinque Terre takes 1.5 hours. Alternatively, you can drive. Traveling from Portofino in May, Cinque Terre is little chillier at night with lows of 52°F. Finish your sightseeing early on the 14th (Sun) to allow enough time to drive to La Spezia.
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Parks · Outdoors · Trails · Historic Sites
Side Trips

La Spezia — 2 nights

La Spezia, at the head of the Gulf of La Spezia in the Liguria region of Northern Italy, is the capital city of the province of La Spezia.In terms of population, La Spezia is the second city in the Liguria region, preceded just by Genoa. Start off your visit on the 15th (Mon): learn about all things military at Museo Tecnico Navale della Spezia, walk around Parco Naturale Regionale di Porto Venere, then visit Portovenere, and finally look for gifts at La Bottega Di Rena. Here are some ideas for day two: take in the spiritual surroundings of Chiesa di Nostra Signora della Neve, then do a tasting at Enoteca la Civilta del Bere e Altro, and then take a tour by water with Boat Tours & Water Sports.

For where to stay, more things to do, traveler tips, and other tourist information, go to the La Spezia trip itinerary planner.

Traveling by car from Cinque Terre to La Spezia takes an hour. Alternatively, you can take a train; or ride a ferry. Expect a daytime high around 71°F in May, and nighttime lows around 52°F. Wrap up your sightseeing on the 16th (Tue) early enough to fly to Naples.
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Outdoors · Tours · Neighborhoods · Parks
Side Trip

Naples — 3 nights

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. You'll find plenty of places to visit near Naples: Reggia di Caserta (in Caserta) and Vesuvio National Park (in Ottaviano). The adventure continues: see the interesting displays at Museo Archeologico Nazionale di Napoli, get engrossed in the history at Museo e Real Bosco di Capodimonte, engage your brain at MUSA - Museo Universitario delle Scienze e delle Arti, and explore the ancient world of Parco Acheologico di Ercolano.

To see more things to do, where to stay, traveler tips, and tourist information, read our Naples holiday planner.

Traveling by flight from La Spezia to Naples takes 3 hours. Alternatively, you can take a train; or drive. Expect a bit warmer evenings in Naples when traveling from La Spezia in May, with lows around 58°F. Finish up your sightseeing early on the 20th (Sat) so you can go by car to Pompeii.
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Historic Sites · Museums · Parks · Nature
Side Trips

Pompeii — 5 nights

Underground City

Pompeii has been a tourist destination for more than 250 years.
Get out of town with these interesting Pompeii side-trips: Palazzo Mezzacapo (in Maiori), Paestum (Archaeological Park of Paestum & Parrocchia Ss. Annunziata) and Salerno (Bossa, Promenade Trieste, &more). There's still lots to do: explore the ancient world of Pompeii Archaeological Park, don't miss a visit to Terme del Foro, trek along Ravello - Atrani Walk, and admire the landmark architecture of Villa dei Misteri.

To find traveler tips, other places to visit, maps, and more tourist information, go to the Pompeii travel website.

Pompeii is just a stone's throw from Naples. Expect a daytime high around 74°F in May, and nighttime lows around 58°F. Finish your sightseeing early on the 25th (Thu) to allow enough time to drive to Positano.
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Historic Sites · Tours · Parks · Trails
Side Trips

Positano — 5 nights

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.
Get out of town with these interesting Positano side-trips: Sorrento (St Francis Church and Convent, Piazza Tasso, &more), Ravello (Ceramiche Cosmolena di Margherita di Palma, Villa Cimbrone Gardens, &more) and Amalfi (Valle delle Ferriere, Museo della Carta, &more). There's lots more to do: take some stellar pictures from Il Sentiero Degli Dei, enjoy the sand and surf at Fornillo, Head underground at Cave of Smeraldo, and take a memorable drive along Amalfi Coast.

To see where to stay, more things to do, reviews, and tourist information, go to the Positano itinerary planning tool.

You can drive from Pompeii to Positano in 1.5 hours. Another option is to take a bus. Expect a daytime high around 74°F in May, and nighttime lows around 60°F. Finish your sightseeing early on the 30th (Tue) so you can ride a ferry to Capri.
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Historic Sites · Parks · Outdoors · Tours
Side Trips

Capri — 2 nights

The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Kick off your visit on the 31st (Wed): tour the pleasant surroundings at Giardini di Augusto, take in the dramatic natural features at I Faraglioni, take a memorable drive along Via Krupp, then trek along Fortini Coastal Walk, then explore the fascinating underground world of Blue Grotto, and finally take an in-depth tour of Villa San Michele. Keep things going the next day: appreciate the history behind Natural Arch, make a trip to Piazza Umberto I, then make a trip to Via Camerelle, then take a tour by water with Boat Tours & Water Sports, and finally take some stellar pictures from Belvedere Cannone.

To find ratings, more things to do, where to stay, and more tourist information, you can read our Capri trip itinerary website.

You can ride a ferry from Positano to Capri in 1.5 hours. Other options are to do a combination of taxi and ferry; or do a combination of bus and ferry. In May in Capri, expect temperatures between 74°F during the day and 60°F at night. Cap off your sightseeing on the 1st (Thu) early enough to travel back home.
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Outdoors · Parks · Trails · Tours
Side Trip

Italy travel guide

4.6
Landmarks · Ruins · Beaches
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.
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