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Sailing & Cycling in the Greek Cyclades and Saronic Islands

Greece—the cradle of European civilization, the land of mouth-drooling delicacies and pristine blue seas. Hop on a deluxe yacht and tour its Cyclades and Saronic Islands under the Greek sun, islands bursting with authenticity, lush nature, and historic remnants! This 8-day island-hopping tour will have you exploring the fusion of antiquity and modernity on Kythnos, Serifos, Syros, Kea, Poros, and Aegina by pedaling your way along their quiet roads. Flower-adorned cobblestone streets, delicious Greek cuisine, golden sandy beaches, an Acropolis-lookalike temple, typical white houses with turquoise blue shutters… All of it combined results in a Mediterranean holiday for your mind, your body, and all your senses.

Adventure highlights

  • Set sail on a deluxe yacht
    Beautiful and spacious yacht is your home for the week, allowing you to explore multiple islands
  • Island hopping in Greece
    Nothing better than immersing yourself in the atmosphere of the Cyclades and Saronic Islands
  • Historic remnants and tranquil landscapes
    Byzantine monastery & antiquity temple fused with turquoise seas & fragrant pine forests

Available itineraries

Sailing & Cycling in the Greek Cyclades and Saronic Islands — Thalassa Boat

By choosing this itinerary, you will stay aboard the Thalassa boat. The daily itinerary remains the same.

Experience the symbiosis of antiquity and modern times on this island hopping tour in Greece. By sailing and cycling the Cyclades and Saronic Islands over the course of 8 days, you get to experience Greek culture, history, and spectacular nature. Your home for the week is Erato or Thalassa, both of them deluxe yachts with spacious cabins and a vast sun deck, perfect for soaking up that Greek sun which will be your fuel for months to come. Daily cycling tours around Kythnos, Serifos, Syros, Kea, Poros, and Aegina take you to the islands’ highlights, but you’re always welcome to chill on the yacht and re-energize yourself by swimming in the Aegean Sea.

  • The Cyclades can have stronger winds, which can result in minor modifications of the tour route. However, should the wind be too strong, the route might markedly differ from the planned route. It would take you through the Saronic Gulf for the entire week, one of the most historic regions of Greece. In that case, you would cross between the Greek mainland and the Peloponnese, discovering the islands of Aegina, Poros, Hydra, Spetses, and the Methana peninsula. A highlight of the substitute journey would be a visit to the ancient Epidaurus, home to the best-preserved theater in Greece!

    Regarding the daily tours and cycling, you can always skip a day tour and hang out on your boat, swimming in the azure sea or basking in the sun on its spacious sun deck.

  • Make your way to the Marina Zeas in Piraeus, which is where your Talassa boat will be waiting for you. Check-in on the ship is possible from 2 pm onwards. Settle into your comfy cabin, get some rest, and meet your team and your guide over a dinner on board. Overnight stay in Athens.

    Lunch aboard Thalassa
  • Early in the morning, set sail towards Kythnos Island, famous for its delicious cheese and honey since classical antiquity. Begin your first cycling tour in the harbor of Merichas and head towards the island’s capital, Chora. Along the way, enjoy wonderful scenic views of the coastline. Chora is a lovely town, perched highly up on a plateau, featuring recognizable white facades with blue windows and cobblestone streets. Continue onto the bucolic Driopida before returning to Merichas, where you can spend the evening in one of its cozy tavernas.

    Distance: 15 miles / 25 km

    Chora cobblestone street
  • The boat takes you to Serifos in the morning, a small island off the beaten tourist track. The island is characterized by countless bays and hidden coves, deep valleys, and many sandy beaches. From the harbor town of Livadi, cycle along a serpentine road to the island’s main town of Serifos, whose cube-shaped white houses stretch along the mountain ridge high above the sea. From there, continue on through pristine landscape to the Byzantine monastery of the Archangel Michael. Return to Livadi along a panoramic road, where you’ll board the boat and head to Syros. Stroll through the breathtaking old town and end the day in one of the numerous dainty cafes on the lovely harbor promenade.

    Distance: 17 miles / 28 km

    Serifos houses
  • Ermoupolis on Syros is the capital town of the Cyclades and offers an incredible view upon arrival. This unique town is built on two hills, and its pastel-colored facades make it different from the other towns. Cycle along the coast of Syros, which is full of bays and coves along the entire southern half of the island, all the way to the beach of Galissas, and past the convent of Saint Barbara. Come back to Ermoupolis in the afternoon and continue by boat to the island of Kea.

    Distance: 20 miles / 34 km

    Ermoupolis, Syros
  • The starting point of exploring this Cycladic island is the harbor of Korissia. From there, climb up to the island’s capital Ioulis before continuing onto the whitesand Otzias Beach, where you can take a dip and get refreshed. Cycle back to Korissia, and then sail to Poros in the Saronic gulf in the afternoon. The harbor town of Poros is a spectacular sight with its iconic clock tower soaring high above the town. Poros is the perfect place to have a nice, relaxing evening and soak in the authentic Greek island atmosphere.

    Distance: 15 miles / 25 km

    Greek streets of Cyclades
  • Today you will almost completely circle the entire island of Poros. In ancient times, the island was dedicated to Poseidon, the sea god. Shortly before the end of the cycling tour, arrive at Russian Bay, a sandy beach with turquoise waters, presenting a perfect spot to swim. Once back in Poros, board the boat and enjoy a delicious lunch on your way to Aegina.

    Distance: 14 miles / 23 km

    Poros island in Greece
  • The island of Aegina is known far beyond the Greek borders of its delicious pistachio nuts! Start pedaling up towards the Temple of Aphaia (think of it as a mini Acropolis), towering high above the blue seas. The location of this incredibly well-preserved temple is the only point on the island where the Aegean Sea can be seen on both sides. On your way back to the boat, cycle across the middle of the island, past the monastery of Nektarios, and all the way to the town of Aegina. Board the boat and enjoy your last cruise back to Athens. The last evening onboard ends with a group dinner and last get-together in a cozy atmosphere with the crew, fellow travelers, and tour guides.

    Distance: 22 miles / 35 km

    Temple of Aegina, Greece
  • After breakfast, it’s time to disembark the boat. Say your goodbyes and head home. Alternatively, you can extend your stay in Greece—just ask your guides for some recommendations, they’re happy to arrange a wonderful stay for you!

    Harbor dinner in Greece
Sailing & Cycling in the Greek Cyclades and Saronic Islands — Erato Boat

By choosing this itinerary, you will stay aboard the Erato boat. The daily itinerary remains the same.

Experience the symbiosis of antiquity and modern times on this island hopping tour in Greece. By sailing and cycling the Cyclades and Saronic Islands over the course of 8 days, you get to experience Greek culture, history, and spectacular nature. Your home for the week is Erato or Thalassa, both of them deluxe yachts with spacious cabins and a vast sun deck, perfect for soaking up that Greek sun which will be your fuel for months to come. Daily cycling tours around Kythnos, Serifos, Syros, Kea, Poros, and Aegina take you to the islands’ highlights, but you’re always welcome to chill on the yacht and re-energize yourself by swimming in the Aegean Sea.

  • The Cyclades can have stronger winds, which can result in minor modifications of the tour route. However, should the wind be too strong, the route might markedly differ from the planned route. It would take you through the Saronic Gulf for the entire week, one of the most historic regions of Greece. In that case, you would cross between the Greek mainland and the Peloponnese, discovering the islands of Aegina, Poros, Hydra, Spetses, and the Methana peninsula. A highlight of the substitute journey would be a visit to the ancient Epidaurus, home to the best-preserved theater in Greece!

    Regarding the daily tours and cycling, you can always skip a day tour and hang out on your boat, swimming in the azure sea or basking in the sun on its spacious sun deck.

  • Make your way to Marina Alimos in Palaio Faliro, which is where your boat will be waiting for you. Check-in on the ship is possible from 2 pm onwards. Settle into your comfy cabin, get some rest, and meet your team and your guide over a dinner on board. Overnight stay in Athens.

  • Early in the morning, set sail towards Kythnos Island, famous for its delicious cheese and honey since classical antiquity. Begin your first cycling tour in the harbor of Merichas and head towards the island’s capital, Chora. Along the way, enjoy wonderful scenic views of the coastline. Chora is a lovely town, perched highly up on a plateau, featuring recognizable white facades with blue windows and cobblestone streets. Continue onto the bucolic Driopida before returning to Merichas, where you can spend the evening in one of its cozy tavernas.

    Distance: 15 miles / 25 km

    Chora cobblestone street
  • The boat takes you to Serifos in the morning, a small island off the beaten tourist track. The island is characterized by countless bays and hidden coves, deep valleys, and many sandy beaches. From the harbor town of Livadi, cycle along a serpentine road to the island’s main town of Serifos, whose cube-shaped white houses stretch along the mountain ridge high above the sea. From there, continue on through pristine landscape to the Byzantine monastery of the Archangel Michael. Return to Livadi along a panoramic road, where you’ll board the boat and head to Syros. Stroll through the breathtaking old town and end the day in one of the numerous dainty cafes on the lovely harbor promenade.

    Distance: 17 miles / 28 km

    Serifos houses
  • Ermoupolis on Syros is the capital town of the Cyclades and offers an incredible view upon arrival. This unique town is built on two hills, and its pastel-colored facades make it different from the other towns. Cycle along the coast of Syros, which is full of bays and coves along the entire southern half of the island, all the way to the beach of Galissas, and past the convent of Saint Barbara. Come back to Ermoupolis in the afternoon and continue by boat to the island of Kea.

    Distance: 20 miles / 34 km

    Ermoupolis, Syros
  • The starting point of exploring this Cycladic island is the harbor of Korissia. From there, climb up to the island’s capital Ioulis before continuing onto the whitesand Otzias Beach, where you can take a dip and get refreshed. Cycle back to Korissia, and then sail to Poros in the Saronic gulf in the afternoon. The harbor town of Poros is a spectacular sight with its iconic clock tower soaring high above the town. Poros is the perfect place to have a nice, relaxing evening and soak in the authentic Greek island atmosphere.

    Distance: 15 miles / 25 km

    Greek streets of Cyclades
  • Today you will almost completely circle the entire island of Poros. In ancient times, the island was dedicated to Poseidon, the sea god. Shortly before the end of the cycling tour, arrive at Russian Bay, a sandy beach with turquoise waters, presenting a perfect spot to swim. Once back in Poros, board the boat and enjoy a delicious lunch on your way to Aegina.

    Distance: 14 miles / 23 km

    Poros island in Greece
  • The island of Aegina is known far beyond the Greek borders of its delicious pistachio nuts! Start pedaling up towards the Temple of Aphaia (think of it as a mini Acropolis), towering high above the blue seas. The location of this incredibly well-preserved temple is the only point on the island where the Aegean Sea can be seen on both sides. On your way back to the boat, cycle across the middle of the island, past the monastery of Nektarios, and all the way to the town of Aegina. Board the boat and enjoy your last cruise back to Athens. The last evening onboard ends with a group dinner and last get-together in a cozy atmosphere with the crew, fellow travelers, and tour guides.

    Distance: 22 miles / 35 km

    Temple of Aegina, Greece
  • After breakfast, it’s time to disembark the boat. Say your goodbyes and head home. Alternatively, you can extend your stay in Greece—just ask your guides for some recommendations, they’re happy to arrange a wonderful stay for you!

    Harbor dinner in Greece
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Meet your guides

Dionysios Chaikalis
5.00
Dionysios Chaikalis
Raised and born in Greece, Dionysios loves giving his guests an insight into the Greek lifestyle, showing them places that he loves, and being able to share the history of his country with them. When he’s not sailing and cycling around Greece, he enjoys hiking, playing football, and sports in general. Dionysios speaks English and German.
Dionysios Katsiopis
5.00
Dionysios Katsiopis
Tour Guide Greece
Dionysios has been a tour guide for Islandhopping since 2018. He gave up on his lawyer profession to pursue something he truly enjoys—meeting people from all over the world and helping them discover new places.    
Marylu Tsiouma
5.00
Marylu Tsiouma
Tour Guide Greece
Marylu has been a tour guide for Islandhopping since April 2023. Her favorite destination is Ionian Islands, because of the unique beauty. When she's not guiding, she travels and keeps up with her life interests and goals. Her favorite activities aside from cycling include walking through nature, yoga and any holistic approach to wellbeing.
Islandhopping
5.00
Islandhopping
Founded in 1998, Islandhopping is your top choice for biking, mountain biking, road biking, e-biking, and multi adventures aboard a boat. What started out as two bicycle tours in Croatia has grown into 300 tours a year with over 7,000 guests from all around the world. They guide travelers all over the Mediterranean, Central & Northern Europe, in Vietnam, South Africa, and Patagonia. Islandhopping’s tour guides are incredibly knowledgeable, multilingual, and educated in first aid, cultural presentations, and bike repairs. They’ll liven up the tour experience and make sure guests create lasting memories for a lifetime.

Accommodation

4.86(7 reviews)
R
Roger B.
|October 2024
Crew, staff, good, boat was perfect. It was very clean and comfortable except at night when we were on docks without electricity we were hot. We loved our time swimming and kayaking. It was disappointing that the SUPs on board were broken.
R
Robert M.
|September 2024
The boat crew were outstanding. Each of them skilled and engaging.
L
Luli Cox

Love the guides, the boat, service and the bikes are really amazing! Boat and bikes are the best combination! The experience is fantastic and unforgettable .
Thanks Guys!

Show all reviews
4.86(7 reviews)
R
Roger B.
|October 2024
Crew, staff, good, boat was perfect. It was very clean and comfortable except at night when we were on docks without electricity we were hot. We loved our time swimming and kayaking. It was disappointing that the SUPs on board were broken.
R
Robert M.
|September 2024
The boat crew were outstanding. Each of them skilled and engaging.
L
Luli Cox

Love the guides, the boat, service and the bikes are really amazing! Boat and bikes are the best combination! The experience is fantastic and unforgettable .
Thanks Guys!

S
Sarah Styles

Brilliant idea. Cycling, swimming and island hopping in one package . And teenagers up before 8!

A
Arnold Maier

It is really very difficult to put into words what we were able to experience. It was by far the best trip of my life, I can’t put it any other way. The ship, the crew, the guides, the tours, the food and and and everything was just perfect. Thank you so much for letting me experience that.

T
Toni Todoric

If you’re looking for a great bike & boat experience, look no further- you found it!

R
Ralph J. Schiel

Great trips with even better people

Things to know

  • Included:

      • An experienced, English-speaking cycling guide with extensive knowledge of the area
      • 8-day sailing & cycling tour of the Cyclades and Saronic Islands
      • Most meals — 2x full board & 5x half board
      • Accommodation aboard the Erato or Thalassa yacht with crew for 7 nights
      • Drinking water onboard
      • Bed linen and towels
      • Overview maps for the daily tours
      • Plus-tour specials
      • SGR Insolvency Protection (5 euros)

    Add-ons:

      • Single supplement — 50% of the tour base price (this depends on availability and season), let us know prior to booking if interested
      • E-bike rental — $260
      • Limited liability protection for e-bike rentals (theft and damage covered, grossly negligent damage not) — $30
      • Shared transfer from Athens Airport to the boat — $50 per person
      • Shared transfer from hotel in Athens to the boat — $25 per person
      • Additional nights in Athens — let us know if interested prior to booking
      • 4-day Santorini extension or 3-day Athens extension — let us know if interested prior to booking
      • Special dietary requirements — $75, to be paid on board

    Not included:

      • Flights to Athens
      • Meals not listed in the itinerary & snacks
      • Beverages on board (tally sheet; to be paid to the captain)
      • Meals and beverages ashore
      • Entrance fee for sights not included in the tour price
      • Guide and crew gratuities — optional
      • Travel and medical insurance
  • This sailing and e-bike holiday in Croatia’s south coast is suitable for cyclists with a good basic level of fitness. The tours and elevation gain are very manageable with an e-bike. You can expect between 23-35 km (14-22 miles) with 350-700 m (1,150-2,300 ft) of elevation gain per day.

    The roads are mostly asphalted. Keep in mind that you’re free to set aside a half or full day to swim or spend on board the boat instead of taking a planned cycle tour.

    If you’d like to give other activities a shot in the Greek Cyclades, check out this island hopping & hiking tour in the Cyclades and sailing and kitesurfing in Greece.

  • Due to safety regulations on the ship, it is not allowed to bring your own e-bike. By renting it with your guides, you will get high-quality, fully serviced rental bikes perfect for the terrain of this tour. You can bring your own bike seat and pedals, guides will be happy to assist you in attaching these to your rental bikes.

    Helmet wearing is mandatory and it’s recommended you bring your own, well-fitted helmet. Rental helmets are available, but in a limited capacity, so reservation is required should you need it.

    Your guide’s rental e-bikes are high quality pedelecs, most of which are fitted with Bosch motors with extra battery range. They are characterized by their relatively light weight and great components. Some of the fleet is equipped with other motor systems. These e-bikes are a true set of wings for anyone who needs a little ‘tail wind’ to make their ride that little bit more enjoyable.

  • Here’s what you’ll need:

      • Comfortable riding or athletic clothing, preferably moisture wicking or synthetic material
      • Helmet (mandatory to wear) — please bring your own, well-fitted helmet, rental ones are limited (reservation required)
      • Padded cycling shorts — recommended
      • Week’s worth of relaxed leisure clothing
      • Swimming gear
      • Long-sleeved sweater or sweatshirt
      • Waterproof jacket
      • Sneakers or sport shoes
      • Sunglasses
      • Plenty of water, water bottle or hydration bladder
      • Daypack with snacks
      • Biking gloves are optional but recommended
      • Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.)

    Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

  • Group sizes and prices:

      • For this sailing & cycling tour in the Cyclades, the usual client-to-guide ratio is 8:1. Depending on the number of people, there can be between 1 and 3 professional guides per trip.
      • It takes a minimum of 14 people for this tour to operate. The maximum group size is set at 18 participants.
      • While solo travelers are welcome, please note that a single supplement is mandatory (50% of the tour price, and this depends on availability and season). It’s not possible to join as a solo traveller and share a cabin with another guest. If interested in joining solo, please let us know before booking!
      • If not enough participants sign up, your guides reserve the right to cancel the reservation. Your guides will let you know as soon as possible, at least three weeks prior to the start of the trip.

    Sailing and cycling in the Cyclades and Saronic Islands can be arranged for bigger groups. Contact us prior to booking.

    Min. age requirements:

      • If you are older than 18, you’re good to go.
      • Minors older than 10 may be permitted to join the boat and bike tour in Greece on a case-by-case basis, but must be in the presence of a parent or legal guardian.
      • Children up to the age of 16 are eligible for a 200-euro discount (double occupancy). None of these are combinable with other discounts. As there’s limited availability, please let us know if you’re interested prior to booking and we’ll get back to you!

    If your group has riders under the age of 18, contact us prior to booking to make arrangements.

  • Depending on which yacht you’re boarding, the starting point is either in Piraeus (Marina Zeas) for the Thalassa boat or Palaio Faliro (Marina Alimos) for the Erato boat. To get there, most people fly into Athens International Airport (ATH).

    From there, it will take you up to 45 minutes to reach the starting points by car or up to 1.5 by using public transportation. To make your journey hassle-free, please reach out to us before booking and we’ll make arrangements.

    Check-in on the ship is possible from 2pm onwards.

  • We highly recommend that you cover all your bases with both medical and travel protection. To make your booking and traveling experience as carefree as possible, simply choose Redpoint—the official 57hours insurance partner!

    Redpoint tailors their protection packages for adventure travel, offering a comprehensive travel program, even in remote locations. Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

    Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s protection. If you need any help or require more information, let us know and we will be happy to help!

    The price of the tour includes the 5 euro SGR Insolvency Protection. This is mandatory consumer contribution called the SGR insolvency protection guarantee scheme.

  • Deposits

    Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.

    Cancellations

    Booking fees are non-refundable after a 48-hour grace period. During checkout, however, you can choose one of 57hours’ flexibility options—Basic, Flexible, or Super Flexible. Depending on which one you choose, a different cancellation policy will apply to your booking.

    Basic

      • If canceled within 48 hours of booking, a full refund will be issued.
      • If canceled 90 or more days before departure, a 70% refund of the total trip price will be issued.
      • If canceled within 89 days of departure, no refund will be issued.

    Flexible

      • If canceled within 48 hours of booking, a full refund will be issued.
      • If canceled 90 or more days before departure, a full refund of the total trip price will be issued.
      • If canceled 60-89 days before departure, a 50% refund of the total trip price will be issued.
      • If canceled within 59 days of departure, no refund will be issued.

    Super Flexible

      • If canceled within 48 hours of booking, a full refund will be issued.
      • If canceled 60 or more days before departure, a full refund of the total trip price will be issued.
      • If canceled within 59 days of departure, a 50% refund of the total trip price will be issued.

     

    Early Bird booking

    Want to be the first one to know when we publish new dates or secure your spot well in advance? Select a future month that suits you best and lock in your Early Bird spot in time with just a 10% deposit. 

    As soon as our guides publish new tour dates, you’ll be the first one to know. We’ll hold your spot for 2 weeks until you choose the date that suits you best. 

    More about how Early Bird bookings work below:

      • Only a 10% non-refundable deposit must be paid upon booking, but this deposit can be transferred to any other 57hours adventure in case the dates don’t end up working for you.
      • Once our guides publish new tour dates, we’ll reach out to you so you’ll be the first one to choose from newly released dates.
      • When you pick your date, you’ll confirm your booking by paying another 20% of the total trip amount (amounting to the standard 30% deposit). 
      • Once the trip has been confirmed, the regular cancellation policy (found above) applies.
      • The remaining balance is due 90 days before the trip.
Have more questions? Read our FAQ, or Talk with us
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