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

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 nearby Areopolis for dinner with a side of Greek history—the revolt against Ottoman rule took place here in the 19th century set in motion the creation of the modern Greek state.

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

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. To round out our delicious day, this evening finds us at a taverna, or small Greek café, that specializes in locally sourced seafood served Mediterranean style.

Meals: Breakfast / Lunch / Dinner
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

Begin with an hourlong transfer to the Malea, the easternmost finger of the Peloponnese. Our ride starts in a sea of olive trees and ascends to the heights of Finiki as we make our way across the peninsula. After a detour to taste olive oil on an ancient farm, we reach the island fortress of Monemvasia. It’s reminiscent of Gibraltar, with topography that made it a strategic stronghold over centuries of political turmoil between the Byzantines, Venetians, and Ottomans. We’ll have lunch in the town to appreciate the unusual warren of tiny alleyways and cascade of red-tiled roofs, then check into our final hotel of the week. You’re free to dine on your own this evening, either back in the old city or at the hotel for a laid-back dinner al fresco.

Meals: Breakfast / Lunch
Destinations: Elea, Finiki, Monemvasia
Accomplished: 25 miles / 41 km, elevation gain: 1,952 feet / 595 meters
Longer Option: 32 miles / 51 km, elevation gain: 2,398 feet / 731 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