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Greece—the cradle of European civilization, the land of delectable 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 through 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.

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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


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.

  • Thalassa and Erato boats are both on offer every date of the tour. If one of those yachts particularly caught your eye, you can inquire whether it’s still available and we’ll do our best to accommodate you.

    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.

    Thalassa boat
  • Depending on which boat will be your home for the week, Thalassa or Erato, make your way to the Marina Zeas in Piraeus (Thalassa) or Marina Alimos in Palaio Faliro (Erato). 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
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Meet your guides

Dionysios Chaikalis
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
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
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.
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.
5.00 (5 reviews)
Luli Cox (source: Facebook)

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!

Sarah Styles (source: Facebook)

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

Arnold Maier (source: Google reviews)

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.

Toni Todoric (source: Google reviews)

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

Ralph J. Schiel (source: Google reviews)

Great trips with even better people

Things to know

  • What you get on this adventure:

      • English-speaking professional, experienced guides
      • 8-day sailing & cycling tour of the Cyclades and Saronic Islands
      • Most meals — 2x full board & 5x half board
      • Bottled water onboard and during all activities ashore
      • Accommodation on a deluxe yacht with crew (7 nights)
      • Bed linen and towels
      • Overview maps for the daily tours

    Mountain bike and helmet rentals are available for an added fee of $90-$220.

    What’s not included:

      • Transportation to and from Athens
      • Accommodations before and after the tour
      • Airport transfers — from Athens Airport to the boat is 70 euros/person for 1 private car, same price for return trip
      • 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
      • Beach towel for ashore use (if needed)
      • Guide and crew gratuities — optional
      • Travel insurance

    Additional optional services:

      • Erato or Thalassa Boat options
        • Shared twin cabin — no surcharge, on request
        • Double cabin for single use — $880
      • Rental bike with Ortlieb pannier (if bicycle has a rack) + insurance
        • E-bike — $220 for the whole trip + $25 insurance
        • Hybrid bike — $90 for the whole trip + $10 insurance
      • Group airport transfers (on embarkation and disembarkation days only) — price on request
      • Private airport transfers — price on request
      • Additional nights in good hotels in Athens — price on request
      • 3-day extension in Athens — includes transfers between airport-hotel, hotel-boat, 2 nights in 3* or 4* hotels, entrance to Athens Archeological Park (including the Acropolis), one evening meal in To Kafeneion excl. drinks, one guided tour of choice (Athens by e-bike, Athens foodies tour, mythological walk) — price on request
      • 4-day extension in Santorini — includes transfers between Santorini airport or ferry port to hotel, 3 nights in a 3* boutique hotel, one tour of choice (sea kayak tour, sunset wine tour, culinary caldera walk) — price on request
      • 4-day extension on Mykonos — includes transfers between Mykonos airport or ferry port to hotel, 3 nights in 3* or 4* boutique hotel, one tour of choice (Rhenia-Delos-Cruise, jeep safari, culinary farm experience) — price on request
  • Your home of the sailing and cycling adventure in the Cyclades and Saronic Islands will either be the Thalassa or Erato deluxe yacht.

    The Thalassa is a 38-meter (125-foot) yacht with 10 cabins. It features a spacious and wonderfully decorated saloon, and it is here where the crew serves culinary delights (should the weather prevent you from eating outdoors on deck). The large sundeck provides plenty of sun mats to lie on, and the covered stern provides comfortable upholstered areas to relax in.

    The Erato is an elegant motor sailer, offering all the comfort and luxury you could desire during your adventure. The bordeaux-red yacht is an instant eye-catcher! The outdoor area boasts plenty of comfortable seating and space for you to relax under the sky. The friendly and attentive crew have spent most of their lives on the water and are fully dedicated to fulfill your holiday dreams.

    Thalassa boat

    You will have a private chef onboard, preparing the breakfast and one or two warm meals a day. The catering begins with dinner on the arrival day and breakfast on the departure day.

    A free WiFi connection is available on both boats. On the open sea, reception cannot be guaranteed at all times. Should you need a stable Internet connection during your stay, it’s recommended you go to a café or bar at the port—free WiFi is offered almost everywhere, if you order something there, you can use their WiFi.

    Thalassa boat saloon

  • These deluxe yachts offer comfortable and equipped cabins below deck with functional fine wood furnishings, offering a warm and cozy atmosphere. Each cabin has individually regulated air-conditioning and an ensuite bathroom with shower, wash bin, hair dryer and toilet. There are cabins with a double bed (140 x 200 cm) and with two single beds (200 x 80 cm).

    Twin shared cabin on Thalassa

    Cabin on the Thalassa

  • This Cyclades and Saronic bike & boat tour is suitable for both hybrid and e-bikers. You will tour between 25 and 35 km (15-22 miles) per day, with between 350 and 700 m (1,150-2,300 ft) of elevation gain.

    If you choose to ride an e-bike, you need to have a good basic level of fitness. Distances covered and elevation gains are very manageable with an e-bike.

    If you choose to join with a hybrid bike, things get a bit more challenging. There will be some longer climbs, but you’re welcome to take breaks or push your bikes if necessary. The roads are mostly asphalt. Keep in mind that this tour is adapted to e-bikers, meaning that if you’re joining with a hybrid bike, you need to have the necessary physical condition to keep up with this pace You’re always welcome to set aside a half or full day to swim or spend some time on board, instead of taking the day’s planned cycling tour.

  • 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.

    If you’re joining with a hybrid bike, you can either bring your own or rent it with the guides. If you’re bringing your own, it’s recommended you bring a bike that meets the technical requirements to keep up the pace with the higher speed of e-bikes. In addition, your bike will need to have good tires (e.g. Gravel Bike or Cyclocross Bike). Before traveling, please check the condition of brakes, gears, and tires as well as bringing repair kits and essential spare parts (e.g. inner tube). Your bike must be in top technical condition. Please keep in mind that transporting your own bike will result in additional costs when flying.

    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.

    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.

  • 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:

      • The group size for this sailing and cycling tour in the Cyclades and Saronic Islands is set at 18 people. That is the maximum number of people that can be accommodated on the yacht. Both yachts sail out on the same offered dates.
      • It takes a minimum of 14 people aboard a yacht for this tour to operate. 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.
      • Depending on the number of people, there can be 1-3 professional guides per trip.
      • The price is based on a twin-shared room, but if you’d like to stay alone in a double room, a single supplement is possible upon checkout.

    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.
      • Only children with a good physical condition, previous bicycle tour experience and a minimum age of 10 can join. Please note that the minimum height for a rental e-bike is 1.50 m (4’9”). Follow-me bikes, bike seats, and bike bungees can also be hired for accompanying children. There is also a 25% percent discount (not combined with other discounts) for children up to the age of 16. For more information about your child joining, please contact us.

    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.

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

  • We highly recommend that you cover all your bases with both emergency medical and travel insurance. With medical insurance, if you have an accident or medical emergency on or off the mountain, you’ll avoid paying out of pocket for costly expenses. This covers everything from hospital treatments to emergency air transportation and more.

    Travel insurance covers canceled flights, natural disasters and other scenarios that may interrupt your travel plans.

    We also expect you to respect local regulations and take measures to protect yourselves, your guides, and the communities you’re traveling to. For more information on travel recommendations and restrictions in Greece, please refer to Greece’s foreign travel advice.

    If you need assistance selecting the right insurance for your group, let us know and we will be happy to help!

  • Deposits

    You can secure one of the 2024 dates with a 30% deposit upon booking. The remaining 70% of the trip price is to be paid 90 days prior to departure, at the latest.

    Secure your early bird spot for 2025 with a 10% deposit! This tour gets sold out very quickly, but with early-bird booking, you will be the first one to know about any new upcoming dates. Pick your preferred dates without the risk of your bucket list adventure selling out!

      • Only 10% of the total amount should be paid as a deposit upon booking. This deposit is non-refundable, but can be transferred to another 57hours adventure any time in case the dates don’t suit you.
      • Once the dates are set, you can confirm your booking by paying another 20% of the total amount.
      • The final balance is due 3 months (90 days) prior to departure.


    Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:


      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 60 or more days before the trip, you are eligible for a 70% refund of the trip price.
      • For cancellations 0-59 days before the trip, there is no refund.


      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 60 or more days before the trip, you are eligible for a full refund of the trip price.
      • For cancellations 30-59 days before the trip, you are eligible for a 50% refund of the trip price.
      • For cancellations 0-29 days before the trip, there is no refund.

    Super Flexible

      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 30 or more days before the trip, you are eligible for a full refund of the trip price.
      • For cancellations 0-29 days before the trip, you are eligible for a 50% refund of the trip price.
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