Private only

Greek Odyssey Yacht + Bike Tour

Sail the Turquoise Waters of the Dodecanese Islands

8 days / 7 nights Level: 3Price From: $9,995Collection: Classic, Cycle + SailNon-Rider Options

Tour Highlights

  • Sail aboard a private yacht to the neo-classical town of Symi, medieval port of Rhodes, and lesser-known islands in between
  • Discover ancient sites with a lasting impact on modern society, from the Panormitis monastery to the 4th-century acropolis in Nisiros
  • Dine on Mediterranean fare prepared by your private chef, including vine-ripened vegetables, handmade cheese, local honey, and fresh-caught seafood
  • Experience a spectrum of natural beauty in a single day, biking to the lip of an active volcano before swimming in the Aegean Sea


Mediterranean mezes like stuffed calamari, hearty moussaka, feta with aromatic oregano and olives, colorful salads, and the daily catch grilled to perfection


Unexpected wines of Greece and Turkey including Mandilaria, a red varietal grown on the island of Rhodes

As featured in:
Print Itinerary
  • Pre-tour

    Athens Pre-Tour Package

    Begin in Athens, the beating heart of ancient Greece. We’ll meet you at the airport and whisk you to your home base at the Electra Palace hotel. After a night’s rest, explore the city’s classical heritage on foot with our local guide. Marvel at the staggering columns of the Parthenon and the Ancient Agora flanked by storied temples and rocky outcroppings, then lunch on your own at one of the Plaka’s restaurants. We’ll then board a flight to the island of Kos to meet the rest of our group.

    Accommodations: Electra Palace Athens

    Price Per Person: $800

    To reserve call +1 888 396 5383

  • Day 1

    Kos Island

    Meet our guides at the Kos airport and depart for the marina to get settled aboard our private yacht. Toast to adventure with a welcome drink served by the five-person sailing crew. We’ll begin our discovery of the Dodecanese isles in the town of Kos, birthplace of Hippocrates and early hub of medicine and healing, before returning to the gulet for a sunset dinner and our first night on deck.

    Meals: Dinner
    Destinations: Kos
    Accommodations: Mezcal II

  • Day 2

    Pserimos and Kalymnos

    Savor a leisurely breakfast as we make a brief visit to Turgutreis to process maritime paperwork, then sail on to uninhabited Pserimos island and swim in its azure waters. This afternoon, we drop anchor in Kalymnos where you’ll get fitted to your bike and set off for Emporios Bay. Challenge yourself with a gradual climb to the island’s highest pass and soak in impressive vistas of the Aegean Sea before descending to the island’s northern end where the boat awaits us. Cool off with a refreshing dip or sip a Greek coffee. You have the option to sit back for a scenic cruise or continue riding back to the western coast of Kalymnos.

    Meals: Breakfast / Lunch / Dinner
    Destination: Pserimos, Kalymnos
    Accomplished: 19 miles / 28 km, elevation gain: 732 meters
    Accommodations: Mezcal II

  • Day 3


    Today we chart an early course back to the Island of Kos. In the morning, bike the island from north to south through central hills dotted with picturesque villages. Pause in the mountain village of Zia for a scenic look at Kalymnos Island and a quick snack, then continue to the ruins of the ancient healing temple of Asclepion where the Hippocratic Oath was formulated. Return to sea level and arrive on the northern shore to meet our ship in the harbor for lunch. Pass the rest of the day swimming in the Aegean Sea or getting lost in the laneways of Old Town.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Zia, Kos
    Accomplished: 22 miles / 35 km, elevation gain: 608 meters
    Accommodations: Mezcal II

  • Day 4

    Nisiros and Symi

    Greet the day over breakfast at sea en route to the Island of Nisiros. Once on land, a climb to the top of Nisiros offers infinite views of the Aegean Sea, Greek Islands, and Turkey’s imposing coastline. Arrive in Nikia, the island’s highest village, and peer into the mouth of an active volcano down below. We’ll stop by the well-preserved 4th-century acropolis in Mandraki and make our way through the city’s whitewashed amphitheater of flat-roofed homes and pumice stone streets before breaking for lunch in a friendly taverna. Back on the boat, it’s time for a siesta or cocktails as we chase the sunset towards Symi. Dinner is on your own at a restaurant tucked between neo-classic houses and late 19th-century churches.

    Meals: Breakfast / Lunch
     Nisiros, Symi
    : 26 miles / 42 km, elevation gain: 863 meters
    Mezcal II

  • Day 5

    Symi and Rhodes

    We return to our bikes first thing in the morning and ascend to a scenic ridge perched above the sea. Nearing the water once again, our epic ride ends with a visit to a remote monastery in Panormitis for an illuminating glimpse of Greek Orthodox monastic life. Here you can choose the extra ride back to town or transfer by van. Our next stop is a secluded cove only accessible by boat for an idyllic lunch on board and swimming in secret waters. Then it’s onto the island of Rhodes where you are free to explore the lively town and dine in one of the many local restaurants.

    Meals: Breakfast / Lunch
    Destinations: Symi, Rhodes
    Accomplished: 14 miles / 21 km, elevation gain: 585 meters
    Accommodations: Mezcal II

  • Day 6


    After breakfast we’ll be cycling the island of Rhodes from its northern tip, starting with a flat run-up to a Greek micro-winery. Meet the proprietress in her vineyard and select a few wines to drink later with lunch. Now begins the ascent towards Butterfly Valley where a magical walk reveals an oasis filled with flitting butterflies and waterfalls. Reach Psinthos after two more uphill miles for a well-deserved lunch, then breeze down the rest of the way across the island. A shorter ride retreats to the van right from the winery and heads to the stunning beach named for actor Anthony Quinn – our berth for the night.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Rhodes
    Accomplished: 16 miles / 26 km, elevation gain: 152 meters
    Longer Option: 32 miles / 52 km, elevation gain: 785 meters
    Accommodations: Mezcal II

  • Day 7

    Lindos and Kolympia, Rhodes

    Our gulet cruises down the eastern edge of Rhodes and delivers you to Lindos for a serious day of riding in the island’s center. Pedal past the coastal towns of Pefki and uphill to Laerma, arriving in Apollona via the region’s hills and valleys. Hop off among the olive trees for a satisfying lunch in a local taverna before cruising downhill through evergreen forests and hidden lakes. Tonight is a very special farewell dinner on-board capped off with a stroll through Rhodes’ medieval streets.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Rhodes
    Accomplished: 38 miles / 61 km, elevation gain: 914 meters
    Accommodations: Mezcal II

  • Day 8


    A final breakfast on-board is followed by goodbyes with the gracious crew before your guides see you off to the airport in Rhodes.

    Meals: Breakfast
    Destinations: Rhodes
    Accommodations: Mezcal II

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Kos, Greece Pick-Up Location: Kos Airport Pick-Up Time: Until 4:15 pm
Departure Details

Airport City: Rhodes, Greece Drop-Off Location: Rhodes Drop-Off Time: 9:00 am
Travelers Take Note

Because this tour relies on calm sailing conditions, weather and winds may dictate itinerary changes or prevent sailing at certain times, at the discretion of the captain and Tour Guides.


  • Thoughtfully selected accommodations that reveal the true character of the region
  • Luggage transfers


  • Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
  • 5 gourmet dinners at our favorite local restaurants and renowned culinary establishments
  • Carefully selected local wine, beer, or spirits with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line bicycle selection and bike helmet
  • Complimentary DuVine gear, including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
  • GPS in most destinations


  • Expert bilingual guides with extensive local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Daily bike maintenance to ensure optimal performance

Additional Inclusions

  • Open bar onboard

See our FAQs page for answers to common questions.

See FAQs

Electric Assist

Type: E-Bike

Cyclo Cross 500

Manufacturer: Merida

Type: Cross

Square Cross 6

Manufacturer: Ghost

Type: Hybrid


Manufacturer: Merida

Type: Hybrid