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 + Sail

Tour Highlights

  • Sail aboard a private yacht with your friends and family, pampered by your own dedicated and professional crew
  • Let your personal chef prepare special meals suited to your tastes—try Mediterranean fare, vine-ripened vegetables, handmade cheese, local honey, and fresh-caught seafood
  • Discover ancient sites with a lasting impact on modern society, from the Panormitis monastery to the 4th-century acropolis in Nisiros
  • 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 or Istanbul Pre-Tour Packages

    Begin in Athens, the beating heart of ancient Greece. We’ll meet you at the airport and whisk you to 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. The rest of today is yours to explore this intriguing city. The next day, board a flight to Kos where you will be greeted by your DuVine guide. We’ll have lunch at a local taverna, visit the island’s archeological museum, and spend some free time in the charming harbor. Then, board a ferry to Bodrum to meet the rest of our group and embark on the Kaya Guneri Plus.

    Accommodations: Electra Palace Athens

    Price Per Person: $1400

    To reserve call +1 888 396 5383

    Begin in Istanbul, the cultural capital of modern Turkey that converges on two continents. From the airport, we’ll transfer you to the Four Seasons Sultanahmet for your first restful evening. On our second day in Istanbul, explore the city’s heritage on foot with our local guide: marvel at the Hagia Sophia, the Hippodrome, mesmerizing Byzantine monuments, and an opulent underground cistern. After lunch in a local restaurant, we’ll weave through the stalls of the labyrinthine Grand Bazaar and tour the iconic Blue Mosque. Then it’s time for our flight to Bodrum—we’ll meet our boat and the rest of the group.

    Accommodations: Four Seasons Sultanahmet

    Price Per Person: $800

    To reserve call +1 888 396 5383

  • Day 1

    Welcome to the Greek Isles

    Meet our guides at the Kos airport and transfer to the harbor, or arrive in Bodrum for a bit of free time before your tour. After a ferry ride to Turgutreis, get settled aboard our private yacht. Toast to adventure with a welcome drink served by the five-person sailing crew as we enjoy a sunset dinner aboard the gulet and our first night on deck.

    Meals: Dinner
    Destinations: Kos, Bodrum, Turgutreis
    Accommodations: Mezcal II

  • Day 2

    Kalymnos and Pserimos

    Savor a leisurely breakfast before we clear customs and cruise to Kalymnos Island, dropping anchor in the harbor and getting fitted to our bikes before today’s ride to Argoninta 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 western shores. Refuel with a Greek coffee in a local taverna, then pedal back to meet the boat, completing a full circle around the island. Lunch is served on board, followed by an afternoon of exploring the port town on your own. This evening, sail on to the almost uninhabited Pserimos Island, perhaps seizing the opportunity for a refreshing swim before dinner on the gulet.

    Meals: Breakfast / Lunch / Dinner
    Destination: Kalymnos, Pserimos
    Accomplished: 25 miles / 40 km, elevation gain: 2,723 feet / 830 meters
    Accommodations: Mezcal II

  • Day 3

    Kos to Kefalos

    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 at the ruins of the ancient healing temple of Asclepion where the Hippocratic Oath was formulated, then continue climbing to the mountain village of Zia for a scenic look at Kalymnos Island and a light lunch. Return to sea level, arriving in Zipari Village for a tasting of local wine with our friends, the Triantafyllopoulos family. This afternoon, choose to cycle along the southern coastline of Kos or head straight back to the boat. Our next stop is Kefalos, with a cocktail hour and dinner served en route.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Kos, Zia, Zipari, Kefalos
    Accomplished: 15 miles / 25 km, elevation gain: 1,903 feet / 580 meters
    Longer Option: 26 miles / 42 km, elevation gain: 2,461 feet / 750 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: 2,831 feet / 863 meters
    Accommodations: 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. 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 after your guided tour of the medieval town you are free to explore and dine in one of the many local restaurants.

    Meals: Breakfast / Lunch
    Destinations: Symi, Rhodes
    Accomplished: 15 miles / 24 km, elevation gain: 2,116 feet / 645 meters
    Accommodations: Mezcal II

  • Day 6

    Kolympia and Lindos

    Rise early for breakfast onboard as we cruise to Kolympia. Today, we’ll ride toward the island’s center through the towns of Archipoli and Eleousa and arrive in the village of Apollona. After lunch in a family-run taverna, we’ll breeze downhill through the island’s valleys into verdant forests, finally reaching sea level in Lindos. Off the bike, spend the afternoon discovering the labyrinthine streets and climb to the Acropolis for a breathtaking view. Return to the boat in Lindos Bay for a quick dip in the Mediterranean and dinner prepared by the boat’s private chef.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Rhodes, Kolympia, Lindos
    Accomplished: 38 miles / 61 km, elevation gain: 2,999 feet / 914 meters
    Accommodations: Mezcal II

  • Day 7

    Anthony Quinn Beach to Marmaris

    Breakfast is served on the gulet as we cruise to our first destination, a stunning beach named for actor Anthony Quinn. Today, we cycle Rhodes from east to west. A gradual climb brings us to Psinthos: pause for a coffee, then pedal the rest of the way down to a well-deserved lunch at a local micro-winery. A short transfer takes us back to the boat in Rhodes harbor. After clearing Greek customs, we part the Mediterranean to reach Marmaris—our berth for the night. There’s another opportunity to swim in the spectacular turquoise waters, then wind down with a beautiful onboard dinner.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Rhodes, Marmaris
    Accomplished: 20 miles / 33 km, elevation gain: 2,067 feet / 630 meters
    Longer Option: 33 miles / 52 km, elevation gain: 2,559 feet / 780 meters
    Accommodations: Mezcal II

  • Day 8

    Goodbye, Greece!

    A final breakfast on our gulet is followed by goodbyes with your guides before they see you off.

    Meals: Breakfast
    Destinations: Marmaris

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

Arrival Details

Airport City: Kos, Greece or Bodrum, Turkey Pick-Up Location: Kos or Bodrum Airport Pick-Up Time: Kos until 4:15 pm or Bodrum any time
Departure Details

Airport City: Dalaman, Turkey Drop-Off Location: Marmaris ferry terminal or Dalaman airport Drop-Off Time: 9:00 am for both
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.

Please note that a travel visa is required for this destination. Each traveler is responsible for securing their own visa. Further information can be found here.

Weather by Month
Average Temperature + Precipitation

Average Temperature + Precipitation

High (°F)
Low (°F)
Rain (in)


  • 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
  • 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
  • One complimentary laundry service onboard

See our FAQs page for answers to common questions.

See FAQs

Cyclo Cross 500

Manufacturer: Merida

Type: Cross

Square Cross 6

Manufacturer: Ghost

Type: Hybrid


Manufacturer: Merida

Type: Hybrid

Electric Assist

Type: E-Bike