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Cycle Cyclades

  • Syros, ringed by picturesque beaches

  • Mykonos, gorgeous and cosmopolitan
  • Waterfront tavernas and Byzantine churches in Paros

  • A 6th century BC kouros in Naxos

  • Hot mud in Santorini's caldera

When travelers fantasize about Greece they usually conjure up stark whitewashed island villages surrounded by a blinding blue sea. That's the Cyclades. Blue and White, just like the Greek flag. Our bike tour uses ferries to hop from island to island. Read a day by day account of the Cycle Cyclades tour in Odyssey magazine at this PDF link.

The 4 night Santorini hiking add-on offers Cyclades in all its glory. You climb to the highest point on the island and witness the sea 360 degress. Sail into the caldera and hike a volcanic peak. Visit undiscovered Thirasia island.

Read about the fabulous meals on the Cycle Cyclades tour as described in the Food 411 blog, an award winning food directory, here and here.


Dates Rating Average
Cost per person
in euros

May 20-27

September 24- October 1


Moderate or Challenging

30 miles
48 km

215 miles 346 km

8 Days

Santorini Add-on

Single 700 

Single 500

Santorini Hiking Add-on May 27-31 and October 1-5

All tours are priced in euros, the currency of Greece.
Click here for daily exchange rates

Our Bikes


Tour FAQs


We also offer Cyclades Self-Guided

A tour needs 10 fully paid riders to run, with a maximum of 16 riders.

All tours are based on double occupancy.
An additional charge applies if you wish your own room
(known as a single supplement).

Google Maps logoTOUR MAP

Start/End Points
Meet on Day 1 at Athens' port in Piraeus -- time is subject to boat departure schedule. Day 8 cycling tour ends in Naxos where you can catch an afternoon boat to Piraeus. Naxos has an airport but not daily flights. The Santorini Hiking Add-On tour departs Day 8 from Naxos and cost includes Day 12 morning return flight to Athens.


Day 1: Syros
Welcome to sunny Greece! The capital of the Cyclades islands is Syros known for its many beaches and elegant capital, Ermoupoli which means "trading city." After settling in to our hotel, we hike up to medieval Ano Mera to visit the rebetiko museum -- a genre of music born in Syros in the 1920s and likened to the Blues. Evening engagement is a Greek cooking class at Vardakeios School which offers Greek language lessons.

Day 2: Syros
Today's ride makes a big loop in the southern half of Syros' countryside. The ride bascially goes from beautiful beach to another beautiful beach to yet another beautiful beach. If you are so inclined in the evening you can drop by the only casino in the Cyclades.  

Day 3: Paros + Mykonos
Heading south from Syros to Paros, we make a detour to Mykonos for several hours of free time on this world-class cosmopolitan island. Depending on boat schedules, you can visit sacred Delos island. By the afternoon we are on another ferry to Paros where we meet up with our bikes to cycle to our hotel in Naoussa village.

Day 4: Paros
Our main destination is adorable Antiparos island, a 10 minute boat ride from Paros. We make several pit stops en route, including Valley of the Butterflies and an ancient cemetery, continuously used from the 8th century BC to the 2nd century AD. In Antiparos we descend into the famous cave.

Day 5: Paros
Today's bike loop takes us to Lefkes, the highest town on the island and the capital of Paros during the Byzantine Empire. A very special treat en route -- the ancient Marathi marble quarries where we descend into the mines.

Day 6: Naxos
In the morning a splendid bike & hike to the lighthouse before making a quick ferry crossing to to Naxos, the largest Cyclades island.  At Naxos we linger in its harbor town, Hora. Here you find an endearing cluster of whitewashed houses, narrow winding medieval alleys, and the distinguished Apollonian Portara gateway which captures everyone’s imagination.  

Day 7: Naxos
Today is the tour’s highest cycling day, up to 1633 feet.  En route we stop at a marble kouros (ancient Greek male statue) left unfinished in its quarry.  At Halki, the owners of a kitron distillery give a demonstration and tasting of their famous liqueur made from lemon leaves.  For the more ambitious, we cycle to Aria Springs, fill up the water bottles, and take a hike up to Za Cave where Zeus was said to be born.

Day 8: morning in Naxos, afternoon in Santorini
Morning cycling to Dimitra Temple on Naxos which is a nicely reconstructed site with a meticulously laid stone walkway. The ride is quick enough to return to the hotel, shower and check-in time to catch an afternoon ferry. The cycling tour is now over. Opt for the Santorini Add-On package to reach Thira (as the Greeks call the island) in time for a sunset wine tasting overlooking the caldera.  

Four Day Santorini Add-On

Cost and Inclusions

Wine tastings & traditional Greek cooking class
Caldera sailing to hot springs with warm mud
Hikes to Ancient Thira & Oia atop caldera ridge
Swimming at Red Beach & sunset harbor dining.

Day 8: Santorini
Leaving Naxos we take a high speed ferry to Santorini, lasting about two hours. Your first glimpse of the caldera cliffs will enchant you with its "vanilla icing" on top, meaning the classic Cyclades white villages adorning the island's ridge. We take a late afternoon hike on the caldera, arriving in Oia to catch an incomparable sunset.

Day 9: Santorini
A delightful introduction to Santorini is through its cuisine. We attend a fascinating cooking class that focuses on indigenous foods of the island. Even if you never cook you will still assuredly enjoy hearing the history and origins of Santorini cooking plus learning to make four different appetizers, an entree and dessert. The class includes wine tasting and a sumptuous lunch.

Day 10: Santorini
A day full of culture. An hour hike up to the 7th century BC ruins of Ancient Thira, tour a renovated winery that is now a contemporary art gallery, visit an underground wine museum with Santorini's oldest wine press, study the finely preserved Minoan frescos in the local museum. Afternoon swimming at Red Beach.  

Day 11: Santorini
We take a boat to Thirasia island for a hike on this unpopulated, unspoilt land that seems worlds away from the cosmopolitan glamour of Santorini. A boat ride to the center of the caldera where you can swim and scoop up soft warm mud to slather on your body standing in the sea.  

Day 12 Departure 
daily flights to Athens

Support vehicle available for lifts. Additional mileage available for road warriors

Day 1 Syros -- walking 45 minutes to ascend to Ano Mera. Less than 45 minutes to descend

Day 2 Syros 22 miles, 36 km, 3 hours, highest ascent 670 feet, other small hills, lots of flat terrain too

Day 3 Mykonos -- no biking (free time). Paros 7 miles, 11 km, ½ hour, few hills, easy ride to seaside hotel

Day 4 Paros & Antiparos 36 miles, 58km, 4 hours, two 3km climbs

Day 5 Paros 21 miles, 34 km, 1½ hours, one minor ascent of 700 feet

Day 6 Paros morning cycling 9 miles + 45 minute hike. Naxos 3 miles, 5 km, flat easy ride to seaside hotel

Day 7 Naxos 43 miles, 69 km, 5-6 hours, one long ascent 1600 ft, tour’s hardest ride

Day 8 Naxos 18 miles, 30km, 2 hours roundtrip, ascend 721 ft, gentle ups and downs