Half-Day Hiking & Sailing Adventure with Lunch, Milos

This half-day Milos adventure begins when you meet your expert guide and set off in a 4WD Jeep, heading for the furthest accessible point on the island's remote, western side. When you near the 16th-century monastery of Agios Ioannis Siderianos, it's time to lace up your hiking shoes and set off on an hour-long trek, covering about 2 miles (3 km) of volcanic terrain. Along the way, your guide will point out some of the island's unique plants, herbs, and wildflowers, and explain how this Natura 2000-protected area is home to rare birdlife and the Mediterranean monk seal.

Although the route isn't too challenging, be prepared for some steeper stretches, and make sure to wear comfortable footwear (no sandals!). As you near the coast, you'll be rewarded with panoramic Aegean views and catch your first glimpses of Kleftiko. Nestled at Milos' southwestern tip, this collection of three small bays is ringed with dramatic limestone cliffs, caves, and rock formations, formed by thousands of years of natural erosion. The area is only accessible by boat or on foot, and its hidden setting once made it the favorite haunt of pirates (and gave the area its name; kleftiko is the Greek word for "thief").

Make your way down the hiking trail to where smooth, flat rocks lead right into the crystal-clear waters, and cool off with some swimming and snorkeling in the sheltered coves. Explore the rock formations and paddle into a wonderland of sea caves, arches, and tunnels (legend has it that the pirates hid their treasure in one of these caves, still waiting to be discovered). If the waters are calm, you can see all the way to the bottom, and if you're feeling brave enough, this is a popular spot to try some cliff diving.

Next, it's time for the second leg of your adventure, when a small dinghy whisks you from the shore to your waiting sailing vessel. Climb aboard, meet your expert crew, and chart a course either westward to Adamas or southeastward back to Pollonia (depending on the day's conditions). As you sail, the crew will prepare a homemade lunch, and you'll refuel with a delicious, family-style meal on deck. Admire the island's dramatic coastline, learn some sailing techniques, and maybe even try your hand at steering, then say your goodbyes as you cruise into port, where your driver will be waiting to take you back to your hotel.