15 days in Greek Isles Itinerary

15 days in Greek Isles Itinerary

Created using Inspirock Greek Isles itinerary planner

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Route & dates

15 days in Greek Isles Itinerary

Start: Montreal, Quebec
Fly:  15 h 15 min
1
Fira, Santorini
— 5 nights
Ferry + Taxi:  3 h
2
Rethymnon, Crete
— 2 nights
Bus:  1 h 15 min
3
Chania Town, Crete
— 3 nights
Shuttle + Fly:  4 h 30 min
4
Rhodes Town, Rhodes
— 3 nights
Fly:  14 h 15 min
End: Montreal, Quebec

5
nights
Fira, Santorini

Fira ©
Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
Give yourself a bit of retail therapy at Atlantis Books and Asimis Kolaitou Art Gallery Santorini. You'll explore the less-touristy side of things at Skaros Rock and Wine Museum Koutsogiannopoulos. Get out of town with these interesting Fira side-trips: SYMPOSION by La Ponta (in Akrotiri) and Perivolos (in Perivolos). Next up on the itinerary: see the interesting displays at Museum of Prehistoric Thira, delve into the distant past at Akrotiri, enjoy the sand and surf at Kamari Beach, and pause for some serene contemplation at Cathedral of Saint John the Baptist.

To find reviews, photos, other places to visit, and more tourist information, you can read our Fira online road trip planner .

Montreal, Canada to Fira is an approximately 15.5-hour flight. You can also do a combination of flight, taxi, and ferry; or do a combination of flight and ferry. Due to the time zone difference, you'll lose 7 hours traveling from Montreal to Fira. Plan for a bit warmer temperatures traveling from Montreal in May, with highs in Fira at 28°C and lows at 20°C. Wrap up your sightseeing on the 21st (Thu) to allow time to travel to Rethymnon.

Things to do in Fira

Parks Outdoors Historic Sites

Side Trips

Oia, Akrotiri, Perissa, Kamari Beach, Venetsanos Winery
Find places to stay May 16 — 21:
Highlights from your plan
Akrotiri LightHouse ©
Akrotiri LightHouse
Perivolos ©
Perivolos
Skaros Rock ©
Skaros Rock

2
nights
Rethymnon, Crete

Rethymnon combines the old-fashioned charm of a small town with proximity to long sandy beaches with all the modern conveniences usually found in big tourist resorts.
On the 22nd (Fri), enjoy the sand and surf at Karavostasi Beach, experience rural life at Paraschakis Olive Oil - Crete, and then see Off-Road Tours. Here are some ideas for day two: visit Rethymnon Old Town, then look for gifts at Cloclo's Art Handmade Creations, then kick back and relax at Damnoni Beach, and finally enjoy the sand and surf at Skinaria Beach.

Take the guesswork out of planning a Rethymnon vacation by using our trip itinerary maker.

Traveling by combination of ferry and taxi from Fira to Rethymnon takes 3 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of flight and shuttle. In May, daytime highs in Rethymnon are 29°C, while nighttime lows are 19°C. Finish up your sightseeing early on the 23rd (Sat) so you can catch the bus to Chania Town.

Things to do in Rethymnon

Outdoors Beaches Parks

Side Trips

Plakias, Karavostasi Beach
Find places to stay May 21 — 23:
Highlights from your plan
Off-Road Tours
Skinaria Beach ©
Skinaria Beach
Damnoni Beach ©
Damnoni Beach

3
nights
Chania Town, Crete

Chania Town ©
The place where Cretan and Venetian cultures merged in the 13th century, Chania Town attracts throngs of tourists with its well-preserved medieval harbor.
Visit Chania Venetian Lighthouse and Kastro Gramvoussas for their historical value. Get in touch with nature at Balos Lagoon and Agii Apostoli Beach. The adventure continues: stroll the grounds of Souda Bay War Cemetery, take in nature's colorful creations at Botanical Park & Gardens Of Crete, brush up on your military savvy at Maritime Museum of Crete, and examine the collection at Greek National Football Museum.

Take the guesswork out of planning a Chania Town vacation by using our trip itinerary maker.

You can take a bus from Rethymnon to Chania Town in 1.5 hours. Another option is to drive. Expect a daytime high around 29°C in May, and nighttime lows around 19°C. Cap off your sightseeing on the 26th (Tue) early enough to travel to Rhodes Town.

Things to do in Chania Town

Parks Beaches Outdoors

Side Trips

Souda, Balos Lagoon, German War Cemetery, Botanical Park & Gardens Of Crete, Manousakis Winery
Find places to stay May 23 — 26:
Highlights from your plan
Kastro Gramvoussas ©
Kastro Gramvoussas
Agii Apostoli Beach ©
Agii Apostoli Beach
Manousakis Winery ©
Manousakis Winery

3
nights
Rhodes Town, Rhodes

Rhodes Town ©
A conglomeration of many distinct architectural styles, Rhodes Town is the biggest urban center of the eponymous Greek island known for its golden beaches and relaxed way of life.
Acropolis of Lindos and Mandraki Harbour are good opportunities to explore the local culture. Your inner history buff will appreciate Filerimos Monastery and Street of the Knights. Explore Rhodes Town's surroundings by going to Agathi Beach (in Haraki) and The Church of the Panagia (in Lindos). Next up on the itinerary: get engrossed in the history at Kahal Kadosh Shalom Synagogue, pause for some serene contemplation at Church of Our Lady of Filerimos, explore the historical opulence of Palace of the Grand Master of the Knights of Rhodes, and expand your understanding of the military at Fort of St. Nicholas.

To plan Rhodes Town vacation without wasting time, ask Inspirock to design an itinerary.

Getting from Chania Town to Rhodes Town by combination of shuttle and flight takes about 4.5 hours. Other options: do a combination of car and ferry; or do a combination of bus and ferry. May in Rhodes Town sees daily highs of 27°C and lows of 20°C at night. Finish your sightseeing early on the 29th (Fri) to allow enough time to travel back home.

Things to do in Rhodes Town

Historic Sites Beaches Outdoors

Side Trips

Lindos, Filerimos, Agathi Beach
Find places to stay May 26 — 29:
Highlights from your plan
The Church of the Panagia ©
The Church of the Panagia
Agathi Beach ©
Agathi Beach
Street of the Knights ©
Street of the Knights

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