22 days in Greece Itinerary
Created using Inspirock Greece trip planner
Start: Montreal
Fly to Santorini, Bus to Oia
1
Oia
— 4 nights
Taxi to Santorini, Ferry to Ios
2
Ios
— 1 night
Ferry
3
Paros
— 2 nights
Ferry
4
Mykonos Town
— 4 nights
Fly
5
Faliraki
— 4 nights
Fly
6
Athens
— 5 nights
Fly
End: Montreal
Fri, May 10 - Fri, May 31
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View full calendar
Oia — 4 nights
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Every day hundreds of visitors come to Oia just to experience its sunsets.You'll get in some beach time at Kamari Beach and Red Beach. Shop till you drop at Aquamarine Jewelry and Eduart Gjopalaj Workshop. Get out of town with these interesting Oia side-trips: Perissa Black Sand Beach (in Perissa) and Akrotiri (Caldera Beach, Experience Horse Riding, &more). Next up on the itinerary: trek along Ekklisia Theoskepasti hiking trail, take in the exciting artwork at Mnemossyne Gallery, browse the exhibits of Art Space, and take in the dramatic natural features at Skaros Rock.
To see ratings, maps, more things to do, and tourist information, read Oia driving holiday planner.
Montreal, Canada to Oia is an approximately 15-hour combination of flight and bus. The time zone difference moving from Eastern Standard Time (EST) to Eastern European Standard Time (EET) is 7 hours. Traveling from Montreal in May, things will get a bit warmer in Oia: highs are around 28°C and lows about 20°C. Finish up your sightseeing early on the 15th (Wed) so you can travel to Ios.
Side Trips
Find places to stay May 11 — 15:
Highlights from your trip
Ios — 1 night
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Halfway between Naxos and Santorini lies tiny Ios, famous worldwide as one of the Aegean's liveliest nightlife hubs.On the 16th (Thu), kick back and relax at Manganari Beach and then enjoy the sand and surf at Kolitsani Beach.
For ratings, traveler tips, more things to do, and other tourist information, read Ios trip builder app.
Getting from Oia to Ios by combination of taxi and ferry takes about 1.5 hours. In May in Ios, expect temperatures between 27°C during the day and 19°C at night. Wrap up your sightseeing on the 16th (Thu) to allow time to ride a ferry to Paros.
Find places to stay May 15 — 16:
Highlights from your trip
Paros — 2 nights
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Poor Man's Mykonos
Long ignored by tourists because of its reputation as a plain ferry hub, Paros today serves as one of the Aegean's major holiday destinations, luring travelers with its fashionable resort towns and quaint mountain villages.Kick off your visit on the 17th (Fri): head off the coast to Parikia Town, browse the exhibits of Yria Ceramic Studio, then pause for some serene contemplation at Panagia Ekatondapiliani, then look for gifts at ONEIPA Concept Store, and finally kick back and relax at Piso Aliki Beach. Get ready for a full day of sightseeing on the 18th (Sat): contemplate the long history of Lefkes and then enjoy the sand and surf at Voutakos Beach.
To see traveler tips, more things to do, and other tourist information, you can read our Paros vacation planner.
Traveling by ferry from Ios to Paros takes 3 hours. Expect a daytime high around 27°C in May, and nighttime lows around 19°C. Finish your sightseeing early on the 18th (Sat) to allow enough time to ride a ferry to Mykonos Town.
Find places to stay May 16 — 18:
Highlights from your trip
Mykonos Town — 4 nights
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Chora Mykonos
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.You'll get in some beach time at Panormos Beach and Paradise Beach. Give yourself a bit of retail therapy at Savvas Mykonos and Minima Gallery. There's lots more to do: wander the streets of Little Venice, kick back and relax at Elia Beach, explore the galleries of Dio Horia, and view the masterpieces at The Big White Gallery.
To see photos, other places to visit, ratings, and other tourist information, refer to the Mykonos Town online route planner.
Getting from Paros to Mykonos Town by ferry takes about 2 hours. In May, plan for daily highs up to 26°C, and evening lows to 20°C. Finish your sightseeing early on the 22nd (Wed) to allow enough time to fly to Faliraki.
Side Trips
Find places to stay May 18 — 22:
Highlights from your trip
Faliraki — 4 nights
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Famed for its sandy beaches, Faliraki serves as a major destination on the island of Rhodes.Get outdoors at Faliraki Beach and Tsambika Beach. Shop till you drop at Kallithea Springs and Artistic Village Contemporary Art - Art gallery & Museum of Ceramic Art. You'll find plenty of places to visit near Faliraki: Lindos (Lindos Beach, Acropolis of Lindos, &more), Valley of the Butterflies (in Petaloudes) and Agathi Beach (in Haraki).
To find more things to do, maps, where to stay, and more tourist information, you can read our Faliraki trip itinerary planner.
Traveling by flight from Mykonos Town to Faliraki takes 5 hours. Alternatively, you can do a combination of ferry and taxi; or do a combination of ferry and bus. May in Faliraki sees daily highs of 27°C and lows of 20°C at night. Finish your sightseeing early on the 26th (Sun) so you can fly to Athens.
Side Trips
Find places to stay May 22 — 26:
Highlights from your trip
Athens — 5 nights
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The Birthplace of Democracy
One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.Head to Ermou Street and Eleni Marneri Galeriefor plenty of shopping. And it doesn't end there: take a stroll through Plaka, stop by Monastiraki, kick back and relax at Glyfada Beach, and view the masterpieces at Pandora Art Gallery.
To see maps, ratings, where to stay, and other tourist information, read Athens road trip app.
Traveling by flight from Faliraki to Athens takes 2.5 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus and ferry. In May, daytime highs in Athens are 29°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 31st (Fri) early enough to fly back home.
Side Trips
Find places to stay May 26 — 31:
Highlights from your trip
Greece travel guide
Few places manage to capture the world's imagination quite like Greece, a land of sun-kissed coastlines, tranquil whitewashed villages, lively seaside towns, and well-preserved ancient sites. One of the world's top tourist destinations since ancient times, the country draws nearly 20 million visitors each year. Athens, the birthplace of Western civilization, continues to attract the biggest crowds and serves as a base for exploring the country and its 227 inhabited islands. Away from its cities, Greece features a picturesque countryside of olive groves, vineyards, and tiny settlements nestled against rolling hills and rugged mountain ranges. Explore the old mainland on foot and discover the islands on a guided boat or ferry tour.
Mykonos travel guide
Island of the Winds
Local tradition claims that Mykonos, the trendiest of the Cyclades group of islands, came into existence from the petrified bodies of giants killed by the mythological hero Hercules. Named after the grandson of the god Apollo, this cosmopolitan "Ibiza of Greece" offers modern tourists a blend of glamour and simplicity. Be prepared for hip and loud dance clubs along the coastline and quieter areas farther from the water. Avoid cruise ship crowds thronging the narrow streets by exploring the small villages located in the center of the island. The easiest way to discover the island's golden beaches is by guided boat tour, private car, or motorcycle.
Rhodes travel guide
Island of the Knights
An island of green hills, fertile valleys, and golden beaches, Rhodes blends cosmopolitan and traditional cultures, exemplified by its traditional taverns, upscale hotels, and archaeological sites. Nicknamed the "Island of Roses," this island offers visitors a chance to discover lively tourist resorts in the north and tranquil rural areas in the south. The island's slow pace seems utterly unaffected by the challenges of mass tourism, its permanent residents stubbornly clinging to their age-old traditions and relaxed lifestyle. As you explore the areas farther away from the busy coastline, take time to meet the garrulous locals in their natural environment, the village tavern.
