What to Do in Santorini

The trail from Fira to Oia follows the edge of Santorini’s volcanic caldera and is widely regarded as one of the island’s best ways to experience its dramatic landscapes. The path winds through Firostefani and Imerovigli, offering different perspectives of the cliffs, caldera, and the Aegean Sea below. Along the way, you’ll encounter stone-paved paths, traditional whitewashed houses, and small churches tucked into the cliffs. The full hike takes around three to five hours, depending on stops, and while some sections are steep, every turn offers a new, breathtaking vista.

One of Santorini’s must-do experiences is a sunset sailing cruise, ending with the island’s famous sunset viewed from the water (and without the crowds). Before the sun dips below the Aegean, you’ll cruise along the dramatic caldera cliffs, taking in the rugged coastline and charming villages along the way. Most tours include stops at both Red Beach and White Beach, giving you the chance to swim in crystal-clear waters or relax on the volcanic sand.

Santorini’s inland villages reveal a more authentic side of the island. Emborio’s medieval castle and narrow streets hint at its defensive past, while Pyrgos sits at the island’s highest point, offering panoramic views of the caldera and surrounding islands. Megalochori charms with its quiet squares, bell towers, and historic mansions. Walking these streets, you’ll encounter centuries-old architecture, local bakeries, and small tavernas, providing a glimpse into everyday life on the island away from the caldera crowds.

A short boat ride from the caldera takes you to Thirasia, once part of Santorini before the volcanic eruption reshaped the region. Life here moves at a slower pace, with small villages, terraced vineyards, and few cars. The village of Manolas perches on the cliff above the port, offering sweeping views back across the caldera to Santorini. It’s a quiet escape where you can hike, taste local wine, and experience the Cyclades without the crowds. Pure bliss.

A guided tour is the most efficient way to explore Santorini’s highlights and hidden gems. Local guides can explain the history, culture, and volcanic geology better than a guidebook ever could, all while navigating the island’s narrow roads and paths. Many tours combine sightseeing with winery visits or tastings, giving you a full picture of the island’s culinary, historical, and scenic offerings. Insight from a local can turn a simple visit into a richer, more meaningful experience – and you might just make a new friend.