24 days in Italy, Croatia & Greece Itinerary

24 days in Italy, Croatia & Greece Itinerary

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Route & dates

24 days in Italy, Croatia & Greece Itinerary

Start: Vancouver, Canada
Fly:  15​h 45​min
1
Bologna, Italy
— 2 nights
train:  45​min
2
Florence, Italy
— 2 nights
bus:  1​h 15​min
3
Lucca, Italy
— 2 nights
Drive + ferry:  2​h 30​min
4
Portoferraio, Italy
— 2 nights
Drive:  3​h 15​min
5
Siena, Italy
— 2 nights
Drive:  4​h 15​min
6
Naples, Italy
— 3 nights
Drive:  1​h 15​min
7
Ravello, Italy
— 1 night
+2
bus + train + Fly:  8​h 45​min
8
Dubrovnik, Croatia
— 3 nights
Fly:  5​h 15​min
9
Mykonos Town, Greece
— 2 nights
ferry:  2​h 15​min
10
Fira, Greece
— 2 nights
Fly:  17​h 45​min
End: Vancouver, Canada

2
nights
Bologna, Italy

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Kick off your visit on the 11th (Mon): steep yourself in history at Palazzo Re Enzo, see the interesting displays at Oratorio Di Santa Cecilia, see the interesting displays at La Macchina del Tempo, then contemplate in the serene atmosphere at Basilica - Santuario di Santo Stefano, then take in the spiritual surroundings of Basilica di San Domenico, and finally contemplate in the serene atmosphere at Chiesa di Santa Maria della Vita. Get ready for a full day of sightseeing on the 12th (Tue): contemplate in the serene atmosphere at Basilica San Francesco, examine the collection at Museo Ducati, then do a tasting at Acetaia Villa San Donnino, then examine the collection at Acetaia Giuseppe Giusti, and finally contemplate the long history of Torre Prendiparte.

To see traveler tips, ratings, and more tourist information, read our Bologna holiday planner.

Vancouver, Canada to Bologna is an approximately 16-hour flight. You can also do a combination of flight and train. The time zone difference moving from Pacific Standard Time (PST) to Central European Time (CET) is 9 hours. Traveling from Vancouver in May, you will find days in Bologna are a bit warmer (27°C), and nights are about the same (14°C). Wrap up your sightseeing on the 13th (Wed) to allow time to take a train to Florence.

Things to do in Bologna

Historic Sites Museums Outdoors

Side Trips

Modena, Museo Ducati
Find places to stay May 11 — 13:
Highlights from your plan
Basilica - Santuario di Santo Stefano ©
Museo Ducati ©
Museo Ducati
Chiesa di Santa Maria della Vita ©
Chiesa di Santa Maria della Vita

2
nights
Florence, Italy

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Do some cultural sightseeing at Gallerie Degli Uffizi and Cathedral of Santa Maria del Fiore. Eschew the tourist crowds and head to Pitti Palace and Loggia dei Lanzi. When in Florence, make a side trip to see Duomo San Donato in Arezzo, approximately 1h 05 min away. And it doesn't end there: get great views at Piazzale Michelangelo, get the adrenaline pumping with an extreme tour, appreciate the extensive heritage of Piazza del Duomo, and contemplate in the serene atmosphere at Basilica San Miniato al Monte.

To see traveler tips, maps, where to stay, and other tourist information, refer to the Florence trip planner .

Take a train from Bologna to Florence in an hour. Alternatively, you can take a bus; or drive. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Wrap up your sightseeing by early afternoon on the 15th (Fri) to allow time for the bus ride to Lucca.

Things to do in Florence

Museums Historic Sites Outdoors

Side Trip

Duomo San Donato
Find places to stay May 13 — 15:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Cathedral of Santa Maria del Fiore ©

2
nights
Lucca, Italy

Lucca ©
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
On the 15th (Fri), see the interesting displays at Puccini Museum - Casa Natale. On the 16th (Sat), you'll have a packed day of sightseeing: contemplate the long history of St Martin Cathedral, examine the collection at Chiesa e Battistero di San Giovanni e Santa Reparata, then make a trip to Torre delle Ore, then steep yourself in history at Palazzo Pfanner, and finally see the interesting displays at Domus Romana.

To see traveler tips, reviews, where to stay, and other tourist information, go to the Lucca route planner .

Traveling by bus from Florence to Lucca takes 1.5 hours. Alternatively, you can drive; or take a train. In May, plan for daily highs up to 25°C, and evening lows to 13°C. On the 17th (Sun), you'll have the morning to explore before heading off to Portoferraio.

Things to do in Lucca

Historic Sites Museums Parks
Find places to stay May 15 — 17:
Highlights from your plan
Puccini Museum - Casa Natale ©
Puccini Museum - Casa Natale
Palazzo Pfanner ©
Palazzo Pfanner
St Martin Cathedral ©
St Martin Cathedral

2
nights
Portoferraio, Italy

Portoferraio ©
Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Explore hidden gems such as Spiaggia Di Sansone and Spiaggia delle Ghiaie. Get some historical perspective at Sant'Andrea LI and Forte Stella. Change things up with these side-trips from Portoferraio: Spiaggia di Fetovaia (in Campo nell'Elba) and Spiaggia di Cavoli (in Seccheto). There's lots more to do: kick back and relax at Spiaggia di Capo Bianco, tour the pleasant surroundings at Spiaggia di Seccione, and get engrossed in the history at Napoleonic Mills House.

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

Traveling by combination of car and ferry from Lucca to Portoferraio takes 2.5 hours. Alternatively, you can do a combination of train and ferry; or do a combination of bus and ferry. In May, daily temperatures in Portoferraio can reach 23°C, while at night they dip to 15°C. Cap off your sightseeing on the 19th (Tue) early enough to go by car to Siena.

Things to do in Portoferraio

Outdoors Beaches Parks

Side Trips

Spiaggia di Cavoli, Sant'Andrea LI, Spiaggia di Fetovaia
Find places to stay May 17 — 19:
Highlights from your plan
Spiaggia di Cavoli ©
Spiaggia di Cavoli
Spiaggia Di Sansone ©
Spiaggia Di Sansone
Spiaggia di Fetovaia ©
Spiaggia di Fetovaia

2
nights
Siena, Italy

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 20th (Wed): steep yourself in history at Loggia della Mercanzia, pause for some serene contemplation at Basilica di San Clemente in Santa Maria dei Servi, take in panoramic vistas at Torre del Mangia, take in the spiritual surroundings of Cappella di Piazza, then get a sense of history and politics at Palazzo Pubblico and Museo Civico, and finally contemplate in the serene atmosphere at San Francesco.

For maps, traveler tips, reviews, and more tourist information, go to the Siena travel planning tool .

You can drive from Portoferraio to Siena in 3.5 hours. Traveling from Portoferraio in May, you will find days in Siena are a bit warmer (27°C), and nights are about the same (13°C). Cap off your sightseeing on the 21st (Thu) early enough to go by car to Naples.

Things to do in Siena

Historic Sites Museums

Side Trip

Abazzia di Torri
Find places to stay May 19 — 21:
Highlights from your plan
Loggia della Mercanzia ©
Loggia della Mercanzia
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico
Torre del Mangia ©
Torre del Mangia

3
nights
Naples, Italy

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Do some cultural sightseeing at Catacombe di San Gaudioso and Forum. You'll explore the less-touristy side of things at Parco Archeologico Pausilypon and Teatro Grande. Venture out of the city with trips to Santa Maria Capua Vetere (Anfiteatro Campano e Museo dei Gladiatori & Mitreo) and Odeon - Teatro Piccolo (in Pompeii). Next up on the itinerary: see the interesting displays at Museo Nazionale Ferroviario di Pietrarsa, contemplate in the serene atmosphere at Museo Cappella Sansevero, steep yourself in history at Acquaquiglia del Pozzaro, and take in the architecture and atmosphere at Cloister of Santa Chiara.

To see reviews, photos, and tourist information, use the Naples trip itinerary maker site .

Traveling by car from Siena to Naples takes 4.5 hours. Alternatively, you can take a train; or take a bus. In May in Naples, expect temperatures between 27°C during the day and 17°C at night. Finish up your sightseeing early on the 24th (Sun) so you can go by car to Ravello.

Things to do in Naples

Historic Sites Museums Childrens Museums

Side Trips

Pompeii, Santa Maria Capua Vetere
Find places to stay May 21 — 24:
Highlights from your plan
Catacombe di San Gaudioso ©
Catacombe di San Gaudioso
Forum ©
Forum

1
night
Ravello, Italy

Ravello ©
Start off your visit on the 25th (Mon): view the masterpieces at Ceramiche Cosmolena di Margherita di Palma, take in the architecture and atmosphere at Cappella Sant'Angelo all'Ospedale, contemplate in the serene atmosphere at Cloister del Paradiso, then take in the spiritual surroundings of Duomo di Sant'Andrea, then admire the striking features of Villa Rufolo, and finally contemplate in the serene atmosphere at Duomo di Ravello.

To see photos, where to stay, reviews, and more tourist information, you can read our Ravello trip itinerary builder app .

You can drive from Naples to Ravello in 1.5 hours. Other options are to do a combination of subway and taxi; or take a bus. Traveling from Naples in May, expect a bit warmer with lows of 21°C in Ravello. Finish your sightseeing early on the 25th (Mon) to allow enough time to travel to Dubrovnik.

Things to do in Ravello

Historic Sites Shopping Museums

Side Trip

Amalfi
Find places to stay May 24 — 25:
Highlights from your plan
Duomo di Ravello ©
Duomo di Ravello
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea

3
nights
Dubrovnik, Croatia

Dubrovnik ©
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.
You'll explore the less-touristy side of things at Cavtat Old Town and Upper Corner Tower Foundry Museum. Your cultural itinerary includes sights like Dubrovnik City Walls and Old Town. Next up on the itinerary: examine the collection at War Photo Limited, enjoy the sand and surf at Sveti Jakov Beach, contemplate in the serene atmosphere at Dominican Monastery, and pause for some serene contemplation at Church of Saint Blaise.

To see ratings, reviews, maps, and tourist information, read our Dubrovnik trip builder site .

Traveling by combination of bus, train, and flight from Ravello to Dubrovnik takes 9 hours. Alternatively, you can do a combination of bus and flight; or do a combination of car and ferry. Traveling from Ravello in May, plan for a bit cooler nights in Dubrovnik, with lows around 16°C. Wrap up your sightseeing on the 29th (Fri) early enough to travel to Mykonos Town.

Things to do in Dubrovnik

Neighborhoods Historic Sites Parks

Side Trip

Cavtat Old Town
Find places to stay May 25 — 29:
Highlights from your plan
Old Town ©
Old Town
Dubrovnik City Walls ©
Dubrovnik City Walls
Cavtat Old Town ©
Cavtat Old Town

2
nights
Mykonos Town, Greece

Mykonos Town ©
A holiday in Mykonos Town offers a chance to relax on picturesque beaches and explore a labyrinth of charming streets lined with traditional white houses.
Kick off your visit on the 30th (Sat): take in the waterfront activity at Old Port, take in the exciting artwork at Dio Horia, pause for some photo ops at Manto Mavrogenous Square, then relax and rejuvenate at some of the best spas, then enjoy the sand and surf at Paradise Beach, and finally pause for some serene contemplation at Church of Saint George. Keep things going the next day: stop by 100% Mykonos, then make a trip to The Windmills (Kato Milli), then don't miss a visit to Rarity Gallery, and finally learn about winemaking at Mykonos Vioma Organic Farm.

For more things to do, reviews, maps, and more tourist information, refer to the Mykonos Town trip itinerary website .

Getting from Dubrovnik to Mykonos Town by flight takes about 5.5 hours. Other options: do a combination of car and ferry; or do a combination of bus and ferry. The time zone difference when traveling from Dubrovnik to Mykonos Town is 1 hour. Expect a bit warmer evenings in Mykonos Town when traveling from Dubrovnik in May, with lows around 20°C. Wrap up your sightseeing on the 31st (Sun) early enough to ride a ferry to Fira.

Things to do in Mykonos Town

Parks Wineries Spas

Side Trips

Mykonos Vioma Organic Farm, Paradise Beach
Find places to stay May 29 — 31:
Highlights from your plan
Old Port ©
Old Port
Paradise Beach ©
Paradise Beach
Mykonos Vioma Organic Farm ©
Mykonos Vioma Organic Farm

2
nights
Fira, Greece

Fira ©
Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Start off your visit on the 31st (Sun): stop by the White, Santorini. Here are some ideas for day two: explore the historical opulence of Castelli of Pyrgos, examine the collection at Cultural Village, then learn about winemaking at Venetsanos Winery, and finally see the interesting displays at Wine Museum Koutsogiannopoulos.

To find photos, ratings, maps, and more tourist information, read our Fira road trip planning website .

Getting from Mykonos Town to Fira by ferry takes about 2.5 hours. Other options: fly. Expect a daytime high around 28°C in May, and nighttime lows around 20°C. Finish up your sightseeing early on the 2nd (Tue) so you can travel back home.

Things to do in Fira

Museums Shopping Historic Sites

Side Trips

Pyrgos, Venetsanos Winery, Wine Museum Koutsogiannopoulos
Find places to stay May 31 — Jun 2:
Highlights from your plan
Venetsanos Winery ©
Venetsanos Winery
Wine Museum Koutsogiannopoulos ©
Wine Museum Koutsogiannopoulos
Spas

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