Top Cyclades Islands Walking Tours

Capture your visit to one of Europe’s most photogenic places with a private walking tour and photo shoot in Santorini. Stroll though the island’s picturesque villages while a professional photographer snaps photos of you and your friends or family against a backdrop of white-washed homes, blue roofs, and striking caldera views. Within 48 hours, receive shareable digital images in an online gallery.

See Santorini’s highlights quickly on this tour from Fira. See the charming village of Oia, with its white houses and scenic terraces set on the cliffside over the blue waters of the caldera, along with the picturesque towns of Pyrgos and Megalochori. First-time visitors can get an overview of the island, including a wine tasting, and because it’s a small-group tour, receive plenty of personal attention.

Many visitors to Santorini stick to the main island and never make it to the impressive volcano jutting out from across the caldera - but a much greater number of in-the-know visitors make the journey during peak season, meaning that seats on cruises often sell out weeks or months ahead of time. There are no water taxis or ferries to the volcano, either, so a tour is really the only way to visit. Don’t miss out on your chance to sail into the caldera, walk along the volcano ridge, and learn all about the volcano’s history and geology.

Discover the beautiful Cyclades Islands the way they were meant to be seen—from the water! On this full-day yacht cruise from Mykonos, sail across the turquoise Aegean to the uninhabited islands of Rhenia and Delos, stopping to swim and snorkel at a pristine beach cove. Customize your day at sea with either a guided visit to the UNESCO-listed archaeological site at Delos or an extra swimming stop, and savor the good life with a light Greek lunch and refreshing drinks onboard.

Experience several sides of Santorini during one tour with this half-day excursion. Get picked up at your hotel and set out on a tour that includes beaches, villages, and sunset views. Combine a coach sightseeing trip with a walking tour during this itinerary that visits Red Beach, the Perissa black sand beach, and the whitewashed village of Megalochori. Complete the tour with watching the sunset in Oia.

This half-day tour takes you to several Santorini neighborhoods including Firostefani, Finikia, Imerovigli, and Oia. Visit popular sightseeing and photo destinations like the Blue Dome, Skaros Rock, the Santorini caldera, and Oia Castle, which is considered one of the best places on the island to view the sunset. Along the way, learn about island life and history from your local guide.

This tour provides a stress-free overview of Santorini’s natural and historic beauty, making it ideal for first-time visitors and travelers with limited time. Board your traditional Greek Caique boat and venture out to the volcano of Santorini. Climb to the top and take in the views before sailing to the warm, sulfuric waters where you can have a dip. Visit Thirassia and enjoy free time to explore before heading back to Santorini,

With this full day tour, you won’t need a crystal ball (or a guidebook) to find Santorini’s historical and cultural highlights. Skip the crowded tour buses and strangers getting in your postcard-perfect photos; explore the island in a small group, getting around in an air-conditioned minivan. Visit remarkable Venetian castles in Emporio and Akrotiri, marvel at the ocean views from Firostefani and Skaros Rock, and watch the sunset over the picturesque village of Oia.

Indulge in the ultimate day of fun in the sun on this all-inclusive, full-day sailing trip to ancient Delos island, a UNESCO World Heritage Site. You also stop in scenic Rhenia Island for a refreshing swim and snorkeling session in sparkling, sun-dappled waters. A freshly prepared BBQ lunch is included, and you can upgrade to include door-to-door hotel transfers.

Enjoy a day of discovery on Santorini island on this tour from Fira. With an itinerary that covers all the must-see sights, the tour lets you find your own favorite spots on the island. Visit the volcanic Red Beach, Akrotiri Archaeological Site, a winery, the Prophet Elias Monastery, and then finish on a high note as you watch the sun slip into the sea from Oia village. A tasting of Santorini’s distinctive wine is included.

Sip on Santorini wine during this small-group tour of the island and three of its wine estates. As you explore, learn about wine production in the area, and hear about the local varieties such as assyrtiko. Explore a vineyard with a guide and walk around wine cellars. If you want to make the tour extra-special, upgrade to enjoy an evening excursion. The option includes a visit to a hilltop winery, local tapas, and sunset views to complement your wine. Numbers are limited to eight people.

Exploring classical Delos without a guide could leave you just guessing at what it is you see and missing hidden highlights. Get the best from the island’s relics and hear the full stories behind the temples, sanctuaries, and artifacts on this half-day tour from Mykonos.

Combine a visit to Santorini's caldera and hot springs with a trip out to the island of Thirasia with this cruise. You'll start at Nea Kameni, a volcanic island, where you'll have time to walk around the island and swim in its hot springs. You'll the cruise on to Thirasia, where you'll have enough time to have lunch and explore before sailing back to Santorini.

Get off Santorini’s main island and explore the volcanic islets around it, which are home to unique volcanic landscapes. Visit two islets accessible only by boat. Sail to Nea Kameni to hike up to the crater of the active volcano (own expense) and to Palea Kameni, where you can soak in naturally-heated pools.

Explore Santorini while getting fresh Mediterranean air and exercise on an e-bike tour. Get away from the crowds and big buses while pedaling along the coast, past windmills, and through old villages for a glimpse at traditional island life. Ride through volcanic vineyards and stop for wine tasting at an historic winery or Greek coffee at a local cafe. The battery-powered bike makes it easy to climb any hills and cover plenty of distance without breaking a sweat.

Experience the Cyclades’ natural beauty and history on this luxury cruise to Rhenia and Delos islands. After a convenient hotel pickup, board a 112-foot (34-meter) yacht and sail for the picturesque, uninhabited island of Rhenia. Go snorkeling with complimentary gear and enjoy a delicious lunch with wine and beer—they’re included in the tour—before heading to the sacred ruins of Delos for a guided tour.

Experience the best of Mykonos during this combination walking and driving trip. Along with a small group, enjoy the scenic drive to Mykonos hotspots like Kalafatis Beach and the charming village of Ano Mera. Then, take a walking tour to explore the white-washed buildings of Mykonos Town.

Succumb to Santorini’s charms on a private tour to see its highlights. Traveling by luxury, air-conditioned vehicle with a guide, learn about Santorini’s history and culture as you explore. Stop at Red Beach, view the Minoan ruins at Akrotiri independently, see Oia, visit the village of Megalochori, and more. An optional winery visit is also possible.

Learn how to prepare traditional Greek dishes, and enjoy a convivial, homey setting in a traditional Cave House: this Santorini cooking class offers a delicious immersion into local culinary traditions. Make your own way to the facilities, and enjoy appetizers and wine upon arrival. With your guide’s hands-on instructions, learn how to prepare several Greek dishes. At the end of class, enjoy your meal on the lovely terrace, with wine, desserts, and Greek coffee to go with.

Santorini is famous for its whitewashed houses and beautiful sunset, but the island is also home to a number of historical landmarks. Embark on a bus tour of the Greek island and see traditional villages, the Akrotiri excavations, and a notable monastery. You also stop at the Red Beach and black-sand Perivolos Beach, where you can participate in a wine tasting.

Experience Santorini’s beauty, hot springs and beaches on a catamaran cruise. Select a daytime or sunset cruise, and sail around the island and caldera (flooded volcanic crater) on a deluxe catamaran. Stop to bathe in the Nea Kameni springs; swim, snorkel or unwind at beaches; and enjoy complimentary Santorini wine and Greek beer, plus a Greek meal prepared on board. On the evening cruise, be treated to awe-inspiring sunset views. A cruise is essential when you visit Santorini, and with numbers limited to 20, this offers a small-group experience. The catamaran vessel that is used on this tour is both motor-powered and wind-powered(sails). Its sails might or might not be used/opened, subject to weather conditions and captain’s judgement. This is a gentle note for guests that are opting for a pure sailing experience on board a non-motorized sailing boat.

Cruise around Santorini on this half-day catamaran tour departing from Vlihada Marina. Observe famed sights such as the Venetian Lighthouse, the Indian Rocks, the Red Beach and the village of Akrotiri as you glide atop clear blue water. Go ashore at the White Beach and enjoy a swimming and snorkeling excursion, then take in panoramic views of the Aegean Sea and the neighboring Cyclades Islands during the return trip. During the trip indulge in a buffet-style meal and sip drinks from the open bar on board.

Spend the day sailing around beautiful Santorini on a catamaran. Imbibe unlimited amounts of white wine, soft drinks, and water and indulge in a delicious barbecue prepared onboard the catamaran as you sail in the gorgeous blue waters of the sea off the shore of Santorini.

Learn about some of Santorini’s best wines on this comprehensive day tour. Save hours researching where to find the best wineries, and instead, have an insider’s guide to three of the island’s most acclaimed estates. Travel in a comfortable vehicle between dispersed wineries, and sample a variety of different regional wines with olives, salami, and gourmet cheese to satisfy your hunger on this half-day adventure.

Savor an epic Santorini sunset accompanied by local wine and tapas during this 4-hour island tasting tour. Learn about wine production as you sample local Greek varietals like ‘Nykteri’ and ‘Assyrtiko’ at a pair of traditional Santorini wineries, capping off the day with a tasting at dusk hosted at Venetsanos Winery on the caldera cliffs. Nine wine samples, local cheese pairings, and a sunset tapas plate are included.