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Greece, a love story

 

Cycle Cyclades

  • Mykonos, clean picturesque beaches

  • Hot mud in Santorini's caldera

  • Waterfront tavernas and Byzantine churches in Paros

  • A 6th century BC kouros in Naxos

  • Venetian dovecotes in Tinos

Cycle Cyclades is our best tour! Apart from cycling amidst the most gorgeous islands in the Aegean, each one a veritable honeymoon haven, the trip is enhanced by two very special guests. Cyclist Brady Kiesling, a former US diplomat stationed in Athens with a Master's in archaeology, entertains us with enlightening Greek history "seminars" delivered with his characteristic keen wit during Happy Hour. Gastronomy expert Regina Tassitano enriches our dining experience with her skilled menu choices of the local healthy Mediterranean cuisine. We promise an abundance of fun!

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.

The May 26 - June 2 tour is a Featured Tour because it has a diplomat/archaeologist and local culinary specialist. For those wanting to cycle and nothing more, select the August 18-25 tour.

Dates Rating Average
km/day
Total
Distance
Cost per person
in euros


Featured Tour

May 26 -
June 2

 

Moderate or Challenging

30 miles
48 km

215 miles 346 km

8 Days
2480

Santorini Add-on
1880

Single 500 

Single 340


August
18-25

 

Moderate or Challenging

30 miles
48 km

215 miles 346 km

8 Days
2030

Santorini Add-on
1880

Single 500 

Single
340

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

Our Bikes

Inclusions

Tour FAQs

 

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 in Athens at 9:00 am to fit the bikes and cycle the Attika coast. Afternoon boat to Tinos. 8 Day cycling tour ends in Naxos where you can catch boats to Piraeus or a flight to Athens. The Santorini Add-On tour includes morning return flight to Athens in tour cost.

Note
Brady Kiesling and Regina Tassitano are present ONLY on the May 26 to June 2 tour. They are NOT present on the August 18-25 tour.

Itinerary

Day 1: Tinos
Welcome to sunny Greece! Our cycling debut ride hugs the Attika coastline to its tip at Sounion where the magnificent Temple of Poseidon overlooks the Aegean Sea. By ferry we arrive to Tinos to encounter the serenity of Greece's most spiritual island. Pilgrims come from all over Greece to pay homage to a local icon.
Brady's Seminar: A Sweeping History of Ancient Greece

Day 2: Tinos
Today's ride into Tinos' countryside takes us past a series of small villages, all of which you must dismount to enter as they are car-free. Adorable villages where you encounter a folk art museum, aquaduct, streets with low arched vault ceilings, grotto-like water fountains and traditional basket weavers working by hand.  
Brady's Seminar: Early Cycladic Culture and its Modern Echoes

Day 3: Mykonos
Early morning cycling in Tinos on a back road that has no towns, gas stations, nothing but raw nature with vivid views of the sea. The quick boat to Mykonos brings us one of Greece's most popular islands, famous for its beaches which is precisely where we spend the day.
Brady's Seminar: Delos, the Sacred/Political Center of Greece

Day 4: Paros
We take a short boat ride to Delos island for a guided tour at one of the most sacred sites in all ancient Greece.  Afternoon boat to Paros docks right in front of the island’s signature windmill at Parikia. A short flat cycling route on a quiet back road takes us to the charming little fishing village of Naoussa now popular with chic Athenians.
Brady's Seminar: Foreign Fleets in the Aegean

Day 5: Paros
A long cycling day with lots to see. Climb to Valley of the Butterflies and be rewarded by the beauty of green moths that inhabit this shaded retreat.   A short ferry ride to the tiny island of Antiparos whose mammoth cave once held 300 people for midnight mass. Tranquil Antiparos makes Paros feel practically like a frenzied metropolis.
Brady's Seminar: Island Life in the Byzantine Years

Day 6: Naxos
A quick ascent to Lefkes, Paros’ highest village, and then the short ferry ride to Naxos.  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.  
Brady's Seminar: The Cyclades in Modern Greek Life

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.
Brady's Seminar: The Portara and Kouros of Naxos

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
(non-cycling)
June 2-6, August 25-29
Cost and Inclusions

Highlights
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. At dusk you will have your first opportunity to witness the incomparable Santorini sunsets, with a glass of local Santorini wine in hand.

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 you indulge in the fruits of your labor with 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 ride to the center of the caldera where one can scoop up soft warm mud to slather on your body standing in the sea.  A mule ride takes you up to the top of the cliffs. Later in the day, in the cool of the afternoon, a hike along the ridge path to Oia, the chic-est town on Santorini. 2-3 hours walk

Day 12 Departure 
daily flights to Athens

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

Day 1 Attika 33 miles, 54 km, 2-3 hours ride, highest ascent sea level to 230 feet

Day 2 Tinos 25 miles, 40 km, 3 hours, highest ascent 1400 feet, one steep section lasting 3 miles/6 km

Day 3 Tinos 15 miles, 25 km, 1-1½ hours, flat and downhill, highest ascent 650 feet

Mykonos 17 miles, 26 km, 2 hours, highest ascent 650 ft, 2-3 very short steep ascents

Day 4 Paros 7 miles, 11 km, ½ hour, flat easy ride to seaside hotel

Day 5 Paros & Antiparos 36 miles, 58km, 4 hours, two 3km climbs

Day 6 Paros 21 miles, 34 km, 1½ hours, one minor ascent of 700 feet
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