55 days in Dubrovnik, Trsteno & Italy Itinerary

55 days in Dubrovnik, Trsteno & Italy Itinerary

Created using Inspirock Europe trip itinerary planner
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Fly
1
Dubrovnik, Croatia
— 3 nights
Drive
2
Trsteno, Croatia
— 1 night
Drive
3
Positano, Italy
— 2 nights
Drive
4
Pompeii, Italy
— 5 nights
Train
5
Naples, Italy
— 5 nights
Train
6
Rome, Italy
— 18 nights
Train
7
Florence, Italy
— 7 nights
Train
8
Pisa, Italy
— 2 nights
Train
9
Venice, Italy
— 5 nights
Train
10
Milan, Italy
— 5 nights
Fly

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Dubrovnik, Croatia — 3 nights

Pearl of the Adriatic

Along the Dalmation Coast, the city of Dubrovnik has become famous for its pedestrian-only Old Town surrounded by fortress walls, and its historical heft has earned it World Heritage Site status.
Your list of things to see and do now includes Dominican Monastery, Speed Boats Tours, Dance Beach, and other attractions. Popular historic sites such as Prijeko street and Minceta Fortress are in your itinerary. You'll explore the less-touristy side of things at Red History Museum and Dubrovnik Beer Company. Next up on the itinerary: take in the architecture and atmosphere at Church of Saint Blaise.

To see traveler tips, reviews, photos, and other tourist information, go to the Dubrovnik road trip planner.

Chicago, USA to Dubrovnik is an approximately 15-hour flight. The time zone difference moving from Central Standard Time (CST) to Central European Standard Time (CET) is 7 hours. Expect a bit warmer temperatures when traveling from Chicago in March; daily highs in Dubrovnik reach 58°F and lows reach 45°F. Wrap up your sightseeing on the 4th (Sat) to allow time to drive to Trsteno.
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Historic Sites · Outdoors · Tours · Beaches
Find places to stay Mar 1 — 4:

Trsteno, Croatia — 1 night

Your day by day itinerary now includes Ston Old Town. Start off your visit on the 5th (Sun): make a trip to Ston Old Town.

To see reviews, ratings, traveler tips, and other tourist information, go to the Trsteno trip itinerary builder tool.

Trsteno is just a stone's throw from Dubrovnik. March in Trsteno sees daily highs of 59°F and lows of 45°F at night. Wrap up your sightseeing by early afternoon on the 6th (Mon) to allow enough time to drive to Positano.
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Historic Sites
Side Trip
Find places to stay Mar 4 — 6:
Highlights from your trip

Positano, Italy — 2 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.
Valle delle Ferriere has been added to your itinerary. On your second day here, take in the dramatic scenery at Valle delle Ferriere and then contemplate in the serene atmosphere at Church of Santa Maria Assunta.

For ratings, maps, other places to visit, and tourist information, refer to the Positano trip planner.

Drive from Trsteno to Positano in 13 hours. In March, daily temperatures in Positano can reach 61°F, while at night they dip to 50°F. Cap off your sightseeing on the 8th (Wed) early enough to go by car to Pompeii.
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Wildlife · Parks · Nature · Historic Sites
Side Trip
Find places to stay Mar 6 — 8:
Highlights from your trip

Pompeii, Italy — 5 nights

Underground City

Pompeii has been a tourist destination for more than 250 years.
Your day by day itinerary now includes Tempio di Hera II, Temple of Athena, Museo Archeologico Nazionale di Paestum, and other attractions you added. Visit Villa San Marco and House of Menander (Casa del Menandro) for their historical value. Step off the beaten path and head to Anfiteatro Romano and Casa del Poeta Tragico. There's more to do: contemplate the long history of Casa Dei Quadretti Teatrali o Casca Longus - Pompei and explore the ancient world of Termopolio di Vetuzio Placido.

To see photos, traveler tips, where to stay, and more tourist information, use the Pompeii day trip planning tool.

You can drive from Positano to Pompeii in 1.5 hours. Another option is to take a bus. In March in Pompeii, expect temperatures between 61°F during the day and 46°F at night. Wrap up your sightseeing on the 13th (Mon) early enough to drive to Naples.
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Historic Sites · Museums
Side Trips
Find places to stay Mar 8 — 13:

Naples, Italy — 5 nights

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Your list of things to see and do now includes Teatro Greco-Romano, Anfiteatro Campano e Museo dei Gladiatori, Parco Archeologico Pausilypon, and other attractions. Change things up with a short trip to Antro della Sibilla in Pozzuoli (about 42 minutes away).

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

Naples is just a short distance from Pompeii. In March, daily temperatures in Naples can reach 61°F, while at night they dip to 46°F. You'll set off for Rome on the 18th (Sat).
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Historic Sites · Museums
Side Trips
Find places to stay Mar 13 — 18:

Rome, Italy — 18 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Your day by day itinerary now includes St. Peter's Basilica, Villa dei Quintili e Santa Maria Nova, Colosseum, and other attractions you added. Explore hidden gems such as Parco Archeologico di Ostia Antica and Le Domus Romane di Palazzo Valentini. You'll explore and learn at Museo Nazionale Romano - Palazzo Massimo alle Terme and Museum and Crypt of Capuchins. Explore the numerous day-trip ideas around Rome: Tivoli (Villa Adriana, Villa d'Este, &more), Giardino di Ninfa (in Cisterna di Latina) and Sanctuary of Giove Anxur (in Terracina). Next up on the itinerary: take in the spiritual surroundings of Santa Maria Sopra Minerva, pause for some serene contemplation at Abbey of St. Paul Outside the Walls, don't miss a visit to Cupola di San Pietro, and get to know the fascinating history of Piazza Venezia.

To see maps, other places to visit, traveler tips, and tourist information, read our Rome trip planning website.

You can take a train from Naples to Rome in 2 hours. Other options are to drive; or fly. Expect a daytime high around 61°F in March, and nighttime lows around 45°F. On the 5th (Wed), you're off to Florence.
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Historic Sites · Museums · Parks · Tours
Side Trips
Find places to stay Mar 18 — Apr 5:

Florence, Italy — 7 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You've added Museo Galileo - Institute and Museum of the History of Science, Torre di Arnolfo, Museo dell'Opera di Santa Croce, and other attractions to your itinerary. Let the collections at Corridoio Vasariano and Cappella Brancacci capture your imagination. Deepen your sense of the past at sights like Battistero di San Giovanni and Basilica della Santissima Annunziata - Chiesa di Santa Maria della Scala.

For where to stay, traveler tips, other places to visit, and more tourist information, use the Florence route planner.

Take a train from Rome to Florence in 2.5 hours. Alternatively, you can fly; or drive. April in Florence sees daily highs of 67°F and lows of 50°F at night. Finish your sightseeing early on the 12th (Wed) so you can drive to Pisa.
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Historic Sites · Museums · Childrens Museums
Side Trips
Find places to stay Apr 5 — 12:

Pisa, Italy — 2 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Your list of things to see and do now includes Costiera di Calafuria, Duomo di Pisa, Battistero di San Giovanni, and other attractions. Start off your visit on the 12th (Wed): explore the different monuments and memorials at Camposanto, take in the spiritual surroundings of Duomo di Pisa, contemplate in the serene atmosphere at Battistero di San Giovanni, then explore the gorgeous colors at Costiera di Calafuria, and finally see the interesting displays at Museo Civico Giovanni Fattori. On the 13th (Thu), you'll have a packed day of sightseeing: admire the striking features of Camminamento in Quota Sulle Mura di Pisa, make a trip to San Piero a Grado, examine the collection at National Museum of Saint Mathew, then get to know the fascinating history of Piazza Martiri della Liberta, and finally take in the spiritual surroundings of Chiesa di Santa Caterina d'Alessandria.

To see other places to visit, maps, where to stay, and more tourist information, read Pisa driving holiday planning tool.

Drive from Florence to Pisa in 1.5 hours. Alternatively, you can take a bus; or take a train. In April, daytime highs in Pisa are 66°F, while nighttime lows are 47°F. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Venice.
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Historic Sites · Museums · Wildlife · Parks
Side Trip
Find places to stay Apr 12 — 14:

Venice, Italy — 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.
Your day by day itinerary now includes Torre dell'Orologio, Doge's Palace, Punta della Dogana, and other attractions you added. Deepen your sense of the past at sights like Centro Storico di Venezia and Basilica dei Santi Giovanni e Paolo (San Zanipolo). Step off the beaten path and head to Cannaregio and Dorsoduro. Next up on the itinerary: take in the spiritual surroundings of Basilica di Santa Maria Gloriosa dei Frari and admire the masterpieces at Museo Correr.

To see ratings, photos, other places to visit, and other tourist information, read our Venice road trip planner.

Traveling by car from Pisa to Venice takes 3.5 hours. Alternatively, you can take a train; or fly. In April in Venice, expect temperatures between 65°F during the day and 49°F at night. Finish your sightseeing early on the 19th (Wed) so you can drive to Milan.
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Historic Sites · Museums · Neighborhoods
Find places to stay Apr 14 — 19:

Milan, Italy — 5 nights

Fashion Capital of World

In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
Your day by day itinerary now includes Pinacoteca Castello Sforzesco, Pinacoteca di Brera, Chiesa di San Maurizio al Monastero Maggiore, and other attractions you added. Visit Chiesa di San Cristoforo sul Naviglio and Foro Buonaparte for their historical value. Let the collections at Casa Museo Boschi Di Stefano and La Sala delle Asse capture your imagination. Go for a jaunt from Milan to Varese to see Palazzo e Giardini Estensi about 1h 10 min away. The adventure continues: delve into the distant past at Teatro Romano and see the interesting displays at Triennale Milano.

To see maps, traveler tips, ratings, and other tourist information, use the Milan trip planner.

Traveling by car from Venice to Milan takes 3 hours. Alternatively, you can take a train; or take a bus. In April in Milan, expect temperatures between 66°F during the day and 46°F at night. On the 24th (Mon), you'll have the morning to explore before heading back home.
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Historic Sites · Museums · Parks
Side Trip
Find places to stay Apr 19 — 24:

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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