Greece map with route

Greece: Cyclades and Rhodes

This will be my fifth trip to Greece — it’s my favorite place to travel! — and our second trip together. I’ve been to Rhodes and think we’ll love it, so we have that at the beginning of our trip, our favorite beach town (so far) at the end of our trip, and some of the less commonly visited Cyclades Islands in between. That should give us the mix of old buildings, charming villages, beaches, and walking that we enjoy.

Day 1: Athens

Planned Activities

  •  None

Actual Activities

  •  

The Plan: Our flight from the US will arrive here. We’ll spend the afternoon in the Athens area then board an overnight ferry for Rhodes. (We were going to spend the night in a hotel and fly the next day, but this is a little cheaper. And we haven’t been on an overnight ferry.) 

Fly from home

Stay on board

We're taking an overnight ferry from
Athens to Rhodes

Get around by walking

Days 2-4: Lindos, Rhodes

Planned Activities

  • Explore the village, beach, and ruins.

Actual Activities

  •  

The Plan: I made a day trip here the first time I visited Rhodes and thought the village would be a good place to spend a few nights. So we’re going to spend the first three nights here and gradually ease out of our jet lag while still doing something enjoyable. 

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Fly from Athens

Stay at Electra

In Lindos village

Get around by walking

Days 5-8: Rhodes Old Town

Planned Activities

  • Explore the old town
  • Rent a car for a day or two and tour the rest of the island

Actual Activities

  •  

The Plan: We stayed in Rhodes Town the first time I came here. We were in the new town then. We want to stay in the old town this time, right in the midst of the atmosphere. I see a lot of narrow cobblestone ways and tracking down old buildings. Maybe some beach time, though I don’t recall the beach near town being that great. Perhaps when we have the car?

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Bus from Lindos

Stay at Mango Rooms

In Rhodes Old Town

Get around by walking

We also plan to rent a car for a day or two to explore the rest of the island

Days 9-12: Amorgos

Planned Activities

  • Hike to villages from Aegiali
  • Drive from Aegiali to Chora
  • Hit the beach near Aegiali

Actual Activities

  •  

The Plan: We’d like to do some hiking on this trip and Amorgos sounded like a good island for hiking. We also want to hit some of the less-visited Cyclades islands. Not too out there. Just a bit off the beaten path. 

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Ferry from Rhodes

Fingers crossed the Blue Star ferry continues to run on Saturday between the two islands!

Stay at Studios Akrogiali

In the beach town of Aegiali

Get around by walking

We also plan to rent a car for a day or two to explore the island

Days 13-18: Milos

Planned Activities

  • Hike to Klima
  • Hike to Sarakiniko
  • Hike to Kleftiko
  • Take a boat tour to places unreachable by road
  • Beach time

Actual Activities

  •  

The Plan: We flew over this island on our flight from Crete to Athens on our last trip and it looked so fascinating from the air I put it on the short list for a future trip. The photos we’ve seen of rock formations and colorful fishermen’s huts look enticing. And it has lots of beaches!

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Ferry from Amorgos

Via Seajets

Stay at Vivere A Plakes

On the outskirts of a village, so maybe a little but of country for some variation.

Get around by walking

We also plan to rent a car for a day or two to explore the island

Days 19-22: Folegandros

Planned Activities

  • Hike to Angali beach
  • Hike from Ano Meria to Chora
  • Hike from Chora to Agios Nikolaos

Actual Activities

  •  

The Plan: On our last trip we really enjoyed the old town on Naxos, and Folegandros is reputed to have one of the nicer villages in the Cyclades. And like Amorgos it’s a little off the beaten path. 

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Ferry from Milos

Via Seajets

Stay at Meltemi

In Chora village

Get around by walking

We also plan to rent a car for a day or two to explore the island

Days 23-29: Thira (Santorini)

Planned Activities

  • Hike from Fira to Oia
  • Hike from Perissa to Ancient Thira
  • Explore caldera villages
  • Boat tour?
  • Beach time

Actual Activities

  •  

The Plan: We came here on our last visit to Greece. Yes, we know Santorini is the very definition of on the beaten path, but Perissa is our favorite beach town to date so we’re coming back. For a week this time. We plan to re-do the Thira to Oia hike and be better prepared this time! We also didn’t see much of the caldera villages so we may carve out some time away from the beach for that.  

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Ferry from Folegandros

Via Seajets

Stay at Stelios Place

We stayed here our first time. So looking forward to going back!

Get around by walking

We may take the bus to other villages

Day 30: Athens

Planned Activities

  • One last day at the beach?

Actual Activities

  •  

The Plan: We have a morning flight home so we plan to return to Athens the day before. We’re going to stay near the beach near the airport. 

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Fly from Santorini

Or take a ferry if it's cheaper

Stay at Hotel Avra

Get around by walking

Resources

Greece book cover
  • We used Lonely Planet Greece (Kindle format) as our main resource
  • Greek Travel Pages has a ferry search tool that allows you to enter an origin or destination and see how you can get from/to there. Great for researching possible ferry connections without having to know exact end points or dates. 
  • Matt Barrett’s Greece Guides has been around forever and is an encyclopedic resource to travel in Greece.