27 days in Greek Isles Itinerary

27 days in Greek Isles Itinerary

Created using Inspirock Greek Isles trip planner

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Route & dates

27 days in Greek Isles Itinerary

Start: Johannesburg
Fly + Shuttle:  16​h 30​min
1
Chania Town, Crete
— 5 nights
Taxi + Ferry:  4​h
2
Fira, Santorini
— 5 nights
Fly:  4​h
3
Skiathos
— 5 nights
Fly:  4​h 15​min
4
Rhodes Town, Rhodes
— 6 nights
Fly:  3​h 45​min
5
Karpathos
— 3 nights
Fly:  20​h 15​min
End: Johannesburg

5
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.
Discover out-of-the-way places like Seitan Limania Beach and Agii Apostoli Beach. We've included these beaches for you: Kedrodasos Beach and Damnoni Beach. Change things up with these side-trips from Chania Town: Skinaria Beach (in Plakias), Holy Trinity Monastery (Agia Triada) (in Akrotiri) and Elafonisi Viewpoint (in Elafonissi). There's still lots to do: enjoy the sand and surf at Karavostasi Beach, take in nature's colorful creations at Botanical Park & Gardens Of Crete, explore the different monuments and memorials at German War Cemetery, and brush up on your military savvy at Maritime Museum of Crete.

To see photos, other places to visit, maps, and tourist information, read our Chania Town road trip app .

Johannesburg, South Africa to Chania Town is an approximately 16.5-hour combination of flight and shuttle. You can also fly. Traveling from Johannesburg in September, Chania Town is somewhat warmer at night with lows of 23°C. Wrap up your sightseeing on the 12th (Sat) early enough to travel to Fira.

Things to do in Chania Town

Parks Outdoors Beaches

Side Trips

Plakias, Akrotiri, German War Cemetery, Kedrodasos Beach, Frangokastello Beach
Highlights from your plan
Damnoni Beach ©
Damnoni Beach
Skinaria Beach ©
Skinaria Beach
Kedrodasos Beach ©
Kedrodasos Beach

5
nights
Fira, Santorini

Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.
You'll get in some beach time at Perivolos and Vlychada Beach. You'll explore the less-touristy side of things at Helicopter Tours and Skaros Rock. Next up on the itinerary: relax and rejuvenate at some of the best spas, pause for some serene contemplation at Cathedral of Saint John the Baptist, examine the collection at Wine Museum Koutsogiannopoulos, and do a tasting at Domaine Sigalas.

Plan my day in Fira using traveler tips and tourist information provided by Inspirock.

Traveling by combination of taxi and ferry from Chania Town to Fira takes 4 hours. Alternatively, you can fly; or do a combination of bus and ferry. In September, daytime highs in Fira are 32°C, while nighttime lows are 24°C. Finish your sightseeing early on the 17th (Thu) to allow enough time to travel to Skiathos.

Things to do in Fira

Outdoors Tours Parks

Side Trips

Oia, Megalochori - Traditional Village, Vlychada Beach, Scuba & Snorkeling, Akrotiri LightHouse
Highlights from your plan
Helicopter Tours
Perivolos ©
Perivolos
Vlychada Beach ©
Vlychada Beach

5
nights
Skiathos

Skiathos ©
Boasting some of Greece's finest beaches, Skiathos swells with vacationers from colder European countries at the height of the tourist season.
Step off the beaten path and head to Lalaria Beach and Troulos Beach. You'll enjoy a bit of beach vacationing at Mandraki Beach and Maratha Beach. Next up on the itinerary: enjoy the sand and surf at Megalos Aselinos Beach, stroll the grounds of Skiathos Cemetery, enjoy breathtaking views from Agios Nikolaos Church and Clock Tower, and explore the ancient world of Kastro Ke Medieval Ekklisia.

To find more things to do, ratings, where to stay, and tourist information, you can read our Skiathos online trip itinerary builder .

Traveling by flight from Fira to Skiathos takes 4 hours. Alternatively, you can do a combination of ferry, taxi, and flight; or do a combination of ferry and bus. In September, plan for daily highs up to 30°C, and evening lows to 24°C. Finish your sightseeing early on the 22nd (Tue) so you can travel to Rhodes Town.

Things to do in Skiathos

Beaches Outdoors Parks
Highlights from your plan
Lalaria Beach ©
Lalaria Beach
Mandraki Beach ©
Mandraki Beach
Maratha Beach ©
Maratha Beach

6
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.
Step off the beaten path and head to Agathi Beach and Plakia Beach. We've included these beaches for you: Stegna Beach and Gennadi Beach. Change things up with these side-trips from Rhodes Town: Pefkos Beach (in Pefkos), Monastery Tsambika (in Kolimbia) and Ancient Kamiros (in Kalavarda). There's still lots to do: make a trip to Traganou Beach, kick back and relax at Oasis Beach, test your problem-solving skills at popular escape rooms, and steep yourself in history at Street of the Knights.

To see photos, where to stay, other places to visit, and other tourist information, refer to the Rhodes Town trip planner .

You can fly from Skiathos to Rhodes Town in 4.5 hours. Alternatively, you can ride a ferry; or do a combination of ferry and car. In September, plan for daily highs up to 33°C, and evening lows to 26°C. Finish your sightseeing early on the 28th (Mon) so you can travel to Karpathos.

Things to do in Rhodes Town

Outdoors Beaches Parks

Side Trips

Rhodes, Pefkos, Gennadi Beach, Agathi Beach, Stegna Beach
Highlights from your plan
Agathi Beach ©
Agathi Beach
Stegna Beach ©
Stegna Beach
Traganou Beach ©
Traganou Beach

3
nights
Karpathos

Karpathos ©
Known largely for its secluded coves and untamed mountains, rugged Karpathos reputedly remains one of the last truly authentic Greek islands.
You'll get in some beach time at Apella Beach and Diakoftis Beach. Eschew the tourist crowds and head to Amoopi Beach and Cave Church of St. Luke. There's lots more to do: enjoy the sand and surf at Damatria Beach, stroll through Lefkos Beach, and look for gifts at Bonendis Art Center.

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

Traveling by flight from Rhodes Town to Karpathos takes 4 hours. Alternatively, you can ride a ferry. In September in Karpathos, expect temperatures between 32°C during the day and 26°C at night. Wrap up your sightseeing on the 1st (Thu) to allow time to travel back home.

Things to do in Karpathos

Parks Beaches Outdoors
Highlights from your plan
Diakoftis Beach ©
Diakoftis Beach
Bonendis Art Center ©
Bonendis Art Center

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