27 days in Greece Itinerary

27 days in Greece Itinerary

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Route & dates

27 days in Greece Itinerary

Start: Calgary
Fly + Drive:  15 h 30 min
1
Rafina
— 1 night
ferry:  4 h
2
Tinos
— 2 nights
ferry:  1 h
3
Mykonos Town, Mykonos
— 2 nights
ferry:  1 h
4
Paros
— 2 nights
ferry:  1 h
5
Naxos Town
— 2 nights
ferry:  2 h
6
Fira, Santorini
— 2 nights
Drive:  1 h
7
Oia, Santorini
— 2 nights
Drive:  2 h
8
Milos
— 3 nights
Fly + Subway:  2 h
9
Athens
— 4 nights
Bus:  4 h
10
Kalambaka
— 2 nights
Bus:  3 h
11
Delphi
— 2 nights
Bus:  2 h 30 min
12
Athens
— 1 night
Subway + Fly:  17 h 30 min
End: Calgary

1
night
Rafina

Rafina
Rafina is a town located on the eastern coast of Attica in Greece. For other places to visit and more tourist information, you can read our Rafina trip itinerary planning site.

Calgary, Canada to Rafina is an approximately 19.5- hour combination of flight and car. The time zone difference when traveling from Calgary to Rafina is 9 hours. Expect a bit warmer temperatures when traveling from Calgary in May; daily highs in Rafina reach 29°C and lows reach 16°C. You will have some time to spend on the 5th (Tue) before leaving for Tinos.

Things to do in Rafina

Nightlife Tours Museums

2
nights
Tinos

Tinos ©
Tinos is a Greek island situated in the Aegean Sea. Your day-by-day itinerary now includes Kolimvithra Beach, Monastery Agias Pelagias, Taxiarchon Cathedral, and other attractions you added. Start off your visit on the 5th (Tue): take in the architecture and atmosphere at Taxiarchon Cathedral, browse the exhibits of Panayia Evanyelistria Cathedral and Museums, and then examine the collection at Oursoulinon Church. Get ready for a full day of sightseeing on the 6th (Wed): kick back and relax at Agios Romanos Beach, tour the pleasant surroundings at Apigania Beach, see the interesting displays at Museum of Marble Crafts, tour the pleasant surroundings at Kolimvithra Beach, then don't miss a visit to Monastery Agias Pelagias, and finally tour the pleasant surroundings at Livada Beach.

To see more things to do, maps, other places to visit, and other tourist information, go to the Tinos day trip planning app.

You can drive from Rafina to Tinos in 3 hours. Traveling from Rafina in May, plan for a bit warmer nights in Tinos, with lows around 20°C. You'll have a few hours on the 7th (Thu) to wrap things up before traveling to Mykonos Town.

Things to do in Tinos

Outdoors Beaches Parks
Highlights from your plan
Pachia Ammos Beach ©
Pachia Ammos Beach
Museum of Marble Crafts ©
Museum of Marble Crafts

2
nights
Mykonos Town, Mykonos

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.
Your day-by-day itinerary now includes White, Agios Nikolakis Church, Paraportiani Church, and other attractions you added. On the 7th (Thu), stop by White, pause for some serene contemplation at Agios Nikolakis Church, take in the spiritual surroundings of Paraportiani Church, wander the streets of Little Venice, then pause for some serene contemplation at Virgin of St. Rosary, and finally don't miss a visit to The Windmills (Kato Milli). Keep things going the next day: kick back and relax at Paradise Beach, then kick back and relax at Panormos Beach, then kick back and relax at Elia Beach, and finally enjoy the sand and surf at Mirsini Beach.

For more things to do, traveler tips, photos, and more tourist information, refer to the Mykonos Town trip itinerary maker app.

You can drive from Tinos to Mykonos Town in 2.5 hours. In May, daily temperatures in Mykonos Town can reach 26°C, while at night they dip to 20°C. You'll have a few hours on the 9th (Sat) to wrap things up before traveling to Paros.

Things to do in Mykonos Town

Outdoors Beaches Parks

Side Trips

Panormos Beach, Elia Beach, Paradise Beach
Highlights from your plan
Elia Beach ©
Elia Beach
Little Venice ©
Little Venice
The Windmills (Kato Milli) ©
The Windmills (Kato Milli)

2
nights
Paros

Paros ©
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.
You've added Livadia Beach, Lolantonis Beach, Tripiti Βeach, and other attractions to your itinerary. On the 9th (Sat), take in the architecture and atmosphere at Panagia Ekatondapiliani, then step into the grandiose world of Frankish Castle, then step off the mainland to explore Parikia Town, and finally kick back and relax at Livadia Beach. On your second day here, pause for some serene contemplation at Logovarda Monastery, enjoy the sand and surf at Kolymbithres Beach, take in the waterfront activity at Old Port of Naoussa, then enjoy the sand and surf at Lageri beach, then enjoy the sand and surf at Damouli Beach, and finally steep yourself in history at Lefkes.

To see more things to do, maps, reviews, and other tourist information, go to the Paros itinerary app.

Traveling by car from Mykonos Town to Paros takes 3 hours. In May, plan for daily highs up to 27°C, and evening lows to 19°C. You'll have a few hours on the 11th (Mon) to wrap things up before traveling to Naxos Town.

Things to do in Paros

Parks Outdoors Beaches
Highlights from your plan
Old Port of Naoussa ©
Old Port of Naoussa
Parikia Town ©
Parikia Town
Piso Aliki Beach ©
Piso Aliki Beach

2
nights
Naxos Town

Naxos Town ©
Naxos Town tops the itinerary of most visitors exploring the Aegean islands, drawing their attention with taverns, shops, beaches, and ancient ruins.
Your list of things to see and do now includes Agios Nikolaos Church, Mikri Vigla Beach, BAZEOS TOWER, and other attractions. Start off your visit on the 11th (Mon): pause for some serene contemplation at Panagia Myrtidiotissa, then delve into the distant past at Portara, then wander the streets of Old Town, and finally contemplate the long history of Bellonia Tower. On the 12th (Tue), you'll have a packed day of sightseeing: take in the architecture and atmosphere at Agia Kiriaki Church, delve into the distant past at Tower of Zevgolis, pause for some serene contemplation at Panagia Damniotissa, then make a trip to BAZEOS TOWER, then kick back and relax at Mikri Vigla Beach, and finally stroll through Plaka Beach.

To see traveler tips, photos, maps, and other tourist information, read Naxos Town trip planner.

Traveling by car from Paros to Naxos Town takes 2 hours. May in Naxos Town sees daily highs of 27°C and lows of 19°C at night. Wrap up your sightseeing by early afternoon on the 13th (Wed) to allow enough time to drive to Fira.

Things to do in Naxos Town

Historic Sites Outdoors Beaches

Side Trips

Naxos, Mikri Vigla Beach, Panagia Damniotissa, Tower of Zevgolis
Highlights from your plan
Portara ©
Portara
Old Town ©
Old Town
Plaka Beach ©
Plaka Beach

2
nights
Fira, Santorini

Fira ©
Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
You've added Cathedral Church Of Candlemas Of The Lord, Cathedral of Saint John the Baptist, Orthodox Metropolitan Cathedral, and other attractions to your itinerary. Kick off your visit on the 13th (Wed): take in the spiritual surroundings of Orthodox Metropolitan Cathedral, look for gifts at the White, Santorini, contemplate in the serene atmosphere at Monastery of Dominican Sisters, then pause for some serene contemplation at Cathedral of Saint John the Baptist, and finally take in the architecture and atmosphere at Cathedral Church Of Candlemas Of The Lord. Keep things going the next day: kick back and relax at Kamari Beach, then explore the ancient world of Akrotiri, and then enjoy the sand and surf at Red Beach.

For photos, ratings, where to stay, and tourist information, use the Fira trip itinerary planning app.

Traveling by car from Naxos Town to Fira takes 5 hours. Expect a daytime high around 28°C in May, and nighttime lows around 20°C. Finish your sightseeing early on the 15th (Fri) to allow enough time to drive to Oia.

Things to do in Fira

Historic Sites Outdoors Beaches

Side Trips

Akrotiri, Anastasis Church, Kamari Beach
Highlights from your plan
Akrotiri ©
Akrotiri
Red Beach ©
Red Beach
Kamari Beach ©
Kamari Beach

2
nights
Oia, Santorini

Oia ©
Every day hundreds of visitors come to Oia just to experience its sunsets.
Kick off your visit on the 15th (Fri): make a trip to Sunset in Oia. Get ready for a full day of sightseeing on the 16th (Sat): pause for some serene contemplation at Ekklisia Panagia Platsani, then take in the pleasant sights at Oia's Main Street, then step into the grandiose world of Byzantine Castle Ruins, and finally contemplate the waterfront views at Amoudi Bay.

Plan my Oia trip by asking Inpirock to come up with tips and suggestions.

Oia is just a stone's throw from Fira. In May, plan for daily highs up to 28°C, and evening lows to 20°C. Wrap up your sightseeing by early afternoon on the 17th (Sun) to allow time for the car ride to Milos.

Things to do in Oia

Historic Sites Parks Nature

Side Trip

Oia's Main Street
Highlights from your plan
Byzantine Castle Ruins ©
Byzantine Castle Ruins
Amoudi Bay ©
Amoudi Bay
Sunset in Oia ©
Sunset in Oia

3
nights
Milos

Milos ©
The result of thousands of years of volcanic activity, the island of Milos features a craggy coastline interspersed by shallow beaches.
Your day-by-day itinerary now includes Ecclesiastical Museum of Milos - Church of the Holy Trinity, Church of Agios Haralambos, Venetian Castle of Milos, and other attractions you added. Next up on the itinerary: tour the pleasant surroundings at Pollonia Beach, enjoy the sand and surf at Firiplaka Beach, and delve into the distant past at Ancient Roman Theatre - Milos.

To find where to stay, reviews, traveler tips, and tourist information, go to the Milos online day trip planner.

Traveling by car from Oia to Milos takes 5 hours. Expect a daytime high around 27°C in May, and nighttime lows around 19°C. Finish your sightseeing early on the 20th (Wed) to allow enough time to travel to Athens.

Things to do in Milos

Outdoors Beaches Parks
Highlights from your plan
Sarakiniko Beach ©
Sarakiniko Beach
Volcano Boat ©
Volcano Boat
Church of Agios Haralambos ©
Church of Agios Haralambos

4
nights
Athens

Athens ©
One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Athens is known for historic sites, museums, and nightlife. Your plan includes some of its best attractions: explore the ancient world of Acropolis of Athens, admire the masterpieces at Benaki Museum, get engrossed in the history at Acropolis Museum, and appreciate the history behind Temple of Olympian Zeus.

To see traveler tips, reviews, maps, and tourist information, read our Athens online day trip planner.

Do a combination of flight and subway from Milos to Athens in 2.5 hours. Alternatively, you can ride a ferry. Expect a daytime high around 29°C in May, and nighttime lows around 20°C. On the 24th (Sun), you'll have the morning to explore before heading off to Kalambaka.

Things to do in Athens

Museums Historic Sites Parks
Highlights from your plan
Acropolis of Athens ©
Acropolis of Athens
Acropolis Museum ©
Acropolis Museum
Plaka ©
Plaka

2
nights
Kalambaka

Kalambaka ©
The gateway to one of the largest monastery complexes in Greece, the small town of Kalambaka nestles against a landscape of imposing rock formations rising 400 m (1,300 ft) into the air. Nearly leveled during World War II, the town rebuilt and reinvented itself in the post-war period, quickly becoming one of the region's major travel destinations.
On the 24th (Sun), contemplate in the serene atmosphere at Holy Trinity Monastery (Agia Triada), then contemplate in the serene atmosphere at Agios Stefanos, then pause for some serene contemplation at Byzantine Church of the Assumption of Virgin Mary, and finally make a trip to Theopetra's Prehistoric Cave. Get ready for a full day of sightseeing on the next day: steep yourself in history at Roussanou Monastery, then take in the spiritual surroundings of Monastery of the Great Meteoron, then admire the natural beauty at Varlaam Monastery, and finally contemplate the long history of Agios Nikolaos Anapaphsas.

To find photos, ratings, traveler tips, and other tourist information, you can read our Kalambaka tour planner.

Drive from Athens to Kalambaka in 4 hours. Alternatively, you can take a train; or take a bus. Prepare for a bit cooler weather when traveling from Athens in May: high temperatures in Kalambaka hover around 26°C and lows are around 11°C. Finish your sightseeing early on the 26th (Tue) to allow enough time to drive to Delphi.

Things to do in Kalambaka

Historic Sites Parks Museums
Highlights from your plan
Meteora ©
Meteora
Monastery of the Great Meteoron ©
Monastery of the Great Meteoron
Holy Trinity Monastery (Agia Triada) ©

2
nights
Delphi

Delphi ©
Ancient Greeks revered Delphi as the center of their universe, building an impressive sanctuary to Apollo in order to mark this sacred spot.
Start off your visit on the 27th (Wed): explore the ancient world of Temple of Apollo In Delphi, explore the ancient world of Delphi, then get engrossed in the history at Delphi Archaeological Museum, and finally pause for some serene contemplation at Ieros Naos Agiou Georgiou. On the 28th (Thu), you'll have a packed day of sightseeing: take in the architecture and atmosphere at Metamorfoseos tou Sotiros Church and then take your sightseeing to a higher altitude at Parnassus.

To find maps, where to stay, ratings, and more tourist information, read Delphi online trip planner.

Getting from Kalambaka to Delphi by car takes about 3 hours. Other options: do a combination of train and taxi; or take a bus. Traveling from Kalambaka in May, Delphi is a bit warmer at night with lows of 15°C. Wrap up your sightseeing on the 28th (Thu) to allow time to drive to Athens.

Things to do in Delphi

Historic Sites Museums Parks

Side Trips

Metamorfoseos tou Sotiros Church, Ieros Naos Agiou Georgiou
Highlights from your plan
Delphi ©
Delphi
Delphi Archaeological Museum ©
Delphi Archaeological Museum
Temple of Apollo In Delphi ©
Temple of Apollo In Delphi

1
night
Athens

Athens ©
To see photos, other places to visit, traveler tips, and more tourist information, refer to the Athens trip planner.

You can drive from Delphi to Athens in 2.5 hours. Other options are to do a combination of taxi and train; or take a bus. Traveling from Delphi in May, plan for somewhat warmer nights in Athens, with lows around 20°C. On the 29th (Fri), you'll have the morning to explore before heading back home.

Things to do in Athens

Historic Sites
Highlights from your plan
Theater of Dionysus ©
Theater of Dionysus