Explore Greece’s Gorgeous Dodecanese Islands On A Bike-And-Boat Tour

Cycling in Greece’s Dodecanese Islands offers splendid seaside views.

Andrea Garreffa, ExperiencePlus!

Last holiday season, my 11 year-old announced that his New Year’s resolution was to visit Greece. He wanted an up-close look at the storied land that inspired his favorite Percy Jackson novels. I was thrilled that, one, my son dreamed big, and two, his bucket-list destination lined up with mine.

Although it was easy to say yes to Greece as the location for our first-ever, mother-son vacation, it took several months to agree on an itinerary. Talon wanted a Greek adventure that was active, avoided big cities and allowed for beach time. I wanted one that included good food, cultural history and plenty of warm sun.

E-Bikes Make Cycling In Greece A Cinch

After lots of research, I found a week-long bike and boat trip through the Dodecanese Islands that seemed to fit the bill. As the southernmost islands in Greece, the Dodecanese archipelago is only a stone’s throw from western Turkey’s Turquoise Coast. Its islands include the more popular Rhodes and Kos, as well as little-known gems full of ancient ruins and stunning scenery, like Nisyros and Tilos.

Talon and I perused photos of the Dodecanese Islands. We saw cerulean seas plied by wooden sailboats, olive-laden trees dotting blond hills, quaint coffee shops on cobblestone roads, and 1,000-year-old castles framed against blue skies. We were sold.

The only hitch? Neither me nor Talon are road bikers. We were a little intimidated by the idea of cycling 20 to 30 miles each day up and over the islands’ rugged mountains.

“Being really flexible is the first key when bike touring with kids, and taking lots of breaks for playtime and enjoyment,” said Jessica Zephyrs, vice president of marketing and communications for Adventure Cycling, a nonprofit organization that inspires, empowers and connects bicycle travelers.

Zephyrs told me that some families consider using e-bikes for tours, especially if the child is a competent rider who is comfortable handling a heavier, faster bike. “We see e-bikes increasing people’s accessibility and reach on both sides of the age spectrum.”

Fortunately, the US-based cycling tour company ExperiencePlus! offered e-bikes as an option for its Dodecanese trip. Their staff recommended we both use a hybrid step-through e-bike since it would fit Talon’s shorter frame. Plus, the battery boost would help us sail through routes that required upwards of 2,000 feet of elevation gain.

Biking up rugged hills in Greece’s Dodecanese Islands was a cinch with an e-bike like this hybrid step-through model.

Andrea Garreffa, ExperiencePlus!

Bodrum, Turkey Is Brimming With Ancient History

The tour began in Bodrum, Turkey, a cosmopolitan seaside city brimming with Byzantine and Ottoman history. We gave ourselves a couple of days beforehand to explore the city before the cycling started.

I snapped photos of Talon’s wonderstruck face as he climbed the steps of an amphitheater built by ancient Greeks, ran laps through the centuries-old Bodrum Castle, and touched marble columns at the Mausoleum of Halicarnassus, one of the Seven Wonders of the Ancient World.

On the first day of our bike and boat tour, we boarded the Aegean Clipper, 135-foot sailing gulet, along with eight other Americans. All of them were veteran European cyclers, happy to share their wisdom with us. We also met our two trip leaders, one Greek and one Italian, and the five Turkish crew members.

The captain, Ergun Malatyali, gave us a tour of the boat, which he had designed and built himself. Although it had two towering masts, he described it as “more like a small cruise ship than a sailboat”.

Malatyali let Talon take the helm as we crossed from Bodrum to Kalymnos, our first stop in the Dodecanese Islands. The light glinting off the golden wheel was almost as blinding as my son’s smile.

Talon takes a turn at the helm of the Turkish sailing gulet that was home base for the Dodecanese bike and boat tour.

Brianna Randall

Finding Cycling Confidence On Kalymnos

I was nervous as we set out the first morning on e-bikes. Mostly, I worried about how my son would fare riding in European traffic and whether his energy would flag going uphill. Our Greek trip leader, Panos Paraskevopoulos, put us at ease. “I have a son who is your age,” Paraskevopoulos told Talon. “You remind me of him. Both of you are adventurous and strong.”

Boosted by that affirmation, as well as an expert bike fitting from our other trip leader, Andrea Garreffa, Talon and I cycled around Kalymnos without a hitch. We took selfies with goats on the deserted road and admired the white-washed walls along orchards.

Part of my newfound cycling confidence stemmed from the fact that ExperiencePlus! made it easy to navigate in foreign territory. One of the trip leaders set out early each morning to mark the day’s route with chalk arrows. They even chalked “lunch stop”, “swim”, or “coffee” on the road so we could take frequent breaks at the best spots on each island.

A bike and boat tour through the Dodecanese Islands is full of cultural stops, like this ancient Greek amphitheater.

Brianna Randall

Biking To The World’s First Hospital On Kos

We quickly settled into the rhythm of daily rides in the Greek Isles. Talon loved careening down the uncrowded, winding roads and trying new flavors of gelato at each island. I loved the expansive views and colorful villages.

The daily routes also included plenty of cultural and scenic stops (or “booty breaks”, as Talon called the welcome respites from sitting on the bike seat).

My favorite historical stop was biking up to the Asklepieion on Kos, one of Greece’s longest standing archeological sites. Its terraces are the world’s first known hospital, where Hippocrates taught medicine in the 4th century BCE.

As for scenery, Symi’s verdant forests, calm beaches and colorful seaside buildings were a crowd pleasers all around.

Talon’s favorite day was riding down into the crater of an active volcano on Nisyros. We hiked next to steaming vents on sandy ground, then drank well-earned icy beverages afterward.

Barbara Hulsizer has been on more than 20 bike tours, most of them in Europe.

Brianna Randall

A European Bike Touring Veteran

One afternoon I rode beside Barbara Hulsizer, a 79 year-old cyclist from Lexington, Massachusetts, who was on a hybrid step-through e-bike, like me.

Hulsizer recounted stories from a few of her previous trips, including an expedition-style bike tour through Italy from Palermo to Turin. “One day we rode 140 kilometers, 8,000 feet up and 9,000 feet down—and I didn’t have an e-bike back then,” she said.

Hulsizer has taken more than 20 bike trips with ExperiencePlus! since 1996 with her partner Scott Chamberlain, most of them in France. “I like that the company is family owned. You just get to know everybody,” she said.

The current owners, Monica and Maria Elena Malpezzi-Price, are the daughters of ExperiencePlus! founders, Rick and Paola Malpezzi-Price. The sisters grew up riding along on tours. “They started a lot younger than your son,” Hulsizer told me, as Talon zoomed past us.

The Dodecanese tour was Hulsizer’s first time biking from a boat. While she enjoyed the novelty of sailing to our destinations and the delicious food aboard, she prefers riding to different hotels each night. “I’m not really a water person. It’s kind of like flying—you just don’t want to think about having to go overboard,” she joked.

The author and her son take in the Asclepieion on the island of Kos, the ancient site where Hippocrates taught medicine.

Brianna Randall

Cycling In Greece With Kids Is A Magical Experience

Talon, however, was definitely a water person. He inspired many of the adults to jump overboard with him to swim in the Aegean Sea, where we cooled off after long days on the pedals. He also regaled us with tales of Greek heroes during the family-style dinners served onboard each evening.

Although Talon was the youngest aboard by a few decades, everyone seemed thrilled to have his youthful energy on the trip—including me. For his part, he learned physical stamina as well as all sorts of interesting history as we rode beside ancient landmarks.

Biking through the Dodecanese Islands with my son was a magical experience, and cycling may be my new favorite way to travel around Europe. I can’t wait to hear Talon’s 2026 New Year’s resolution.