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
Call to book 1 888 396 5383
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.
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.
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.
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.
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.
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
Accomplished: 16 miles / 26 km, elevation gain: 152 meters
Longer Option: 32 miles / 52 km, elevation gain: 785 meters
Accommodations: Mezcal 2 or Dolce Mare
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.
DuVine itineraries may be subject to slight route changes, hotels substitutions, and other modifications.
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.
Airport City: Kos, Greece
Pick-Up Location: Until 5:20pm at the Kos Airport
Airport City: Rhodes, Greece
Drop-Off Location: 9:00am departure from boat in Rhodes
- 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 wines with every meal
- 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
- 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
- Open bar onboard
Have more questions?
See our FAQs page for answers to common questions.See FAQs