Greece Bike Tour

Meet your guides in Kalamata this morning and transfer to a sleepy beach town to start our ride. This is the beginning of the Mani peninsula: one of Greece’s best-kept secrets, defined clear bays and stately stone towers against the backdrop of the Taygetus Mountains. We’ll warm up our legs on a coastal bike path before our first climb through the olive groves, which takes us high above the sea—the endless horizon views are a welcome reward. Stop for lunch at a waterfront taverna in the picturesque port of Limeni and tuck into some freshly grilled seafood. After lunch, choose between longer and shorter ride options to reach our first hotel of the trip: a piece of Mediterranean paradise on the southernmost tip of mainland Europe. Tonight it’s another meal with a view as we settle into the rhythms of relaxation and catch our first sunset at a table on the terrace.

Meals: Lunch / Dinner
Destinations: Stoupa, Limeni
Accomplished: 24 miles / 38 km, elevation gain: 2,312 feet / 705 meters
Longer Option: 39 miles / 63 km, elevation gain: 3,979 feet / 1,213 meters
Accommodations: Aria Estate or Bassa Maina Villa & Suites

This morning we’re headed into the Deep Mani, the wildest part of the Peloponnese peninsula. Our route passes clusters of stone towers and the rugged, rocky shores of Cape Tainaron. There’s something otherworldly about this place—according to Greek mythology it’s where Orpheus entered the cave into Hades, land of the dead, to rescue his wife Eurydice. Thankfully, our own odyssey has much lower stakes: we’ll be sampling local honey, stopping at frescoed churches, and cycling a stretch of seaside road that snakes all the way around the peninsula’s eastern side. In the historic port of Gerolimenas, we’ll pause for lunch and listen to the waves lapping against the village’s stone walls. Spend the afternoon enjoying the hotel before we make our way to dinner at an impossibly charming seaside taverna.

Meals: Breakfast / Lunch / Dinner
Destinations: Cape Tainaron, Lagia, Areopolis
Accomplished: 37 miles / 59 km, elevation gain: 4,454 feet / 1,358 meters
Longer Option: 54 miles / 87 km, elevation gain: 5,805 feet / 1,770 meters
Accommodations: Aria Estate or Bassa Maina Villa & Suites

Today we ride in pursuit of culinary spoils: first, our route crosses the heart of the Mani to reach the little village of Kotronas, where we’ll sip rich and frothy Greek coffee with locals. A lovely stretch of coastal road follows, full of sweeping vistas and sapphire-blue bays. On the other end is our friend Vasilis’ restaurant, where we’re received with xenia—a long-held Greek concept of showing hospitality to strangers. This evening we’ll make our way to nearby Areopolis, where a 19th-century revolt against Ottoman rule helped spark the creation of the modern Greek state. To round out this delicious day, you’re free to dine on your own admist cobbled streets of the historic center—your guides are happy to suggest their favorite local restaurants.

Meals: Breakfast / Lunch
Destinations: Kotronas, Skoutari, Drosopigi
Accomplished: 24 miles / 39 km, elevation gain: 2,362 feet / 720 meters
Longer Option: 39 miles / 63 km, elevation gain: 4,123 feet / 1,257 meters
Accommodations: Aria Estate or Bassa Maina Villa & Suites

Begin the day with an hourlong transfer to the Malea, the easternmost finger of the Peloponnese. From Plitra, we’ll pedal along the western coast before climbing inland to a high point in the heart of the peninsula. Continue cycling on a stunning stretch of coastal road, where sweeping views reach all the way to the island fortress of Monemvasia. A picnic lunch awaits amidst the olive trees at the luxurious Kinsterna hotel, where we’ll have the chance to taste local Athinolia olive oil made using a stone mill. Spend the afternoon settling in and relaxing before heading into Monemvasia in the evening. The town is reminiscent of Gibraltar, with topography that made it a strategic stronghold over centuries of political turmoil between the Byzantines, Venetians, and Ottomans. Explore the unusual warren of tiny alleyways, fortifications, and cascade of red-tiled roofs before dinner at our favorite taverna.

Meals: Breakfast / Lunch / Dinner
Destinations: Plitra, Agios Georgios, Monemvasia
Accomplished: 32 miles / 52 km, elevation gain: 3,359 feet / 1,024 meters
Accommodations: Kinsterna Hotel

It’s our last day of riding—we’re going to make it count. We start our epic loop along the coast before turning inland and watching as Monemvasia recedes. A series of switchbacks take us high above the plains, gaining elevation until one last bend in the road brings us to the summit. But what goes up must come down: revel in the long descent into Gerakas, a fishing village that’s home to Europe’s southernmost natural fjord. After lunch at a taverna owned by a family of fishermen, you may choose to complete the loop or take a ride in the van right back to the hotel. Tonight, we raise our glasses to a spectacular Greek week.

Meals: Breakfast / Lunch / Dinner
Destinations: Agios Ioannis, Metamorfosi, Gerakas
Accomplished: 38 miles / 61 km, elevation gain: 3,844 feet / 1,172 meters
Longer Option: 56 miles / 90 km, elevation gain: 5,133 feet / 1,565 meters
Accommodations: Kinsterna Hotel

Catch one last sunrise over Monemvasia, sip a coffee on the terrace, or take your time heading to breakfast this morning. Your guides will transfer you to Athens or back to Kalamata and see you off to your next destination.

Meals: Breakfast
Destinations: Athens or Kalamata