Santorini is the glittering gem of the Cyclades. You'll spend five days exploring this iconic Greek island from top to bottom with beach time, volcano tours, and sunsets that'll take your breath away. Then ferry to neighboring Folegandros to relax on a smaller and lesser-visited (but no less beautiful) island, discovering empty coastline and medieval architecture before returning to Santorini for your departure.


  • Get to know Santorini's scenic walking routes and waterfront tavernas
  • Sail across the island's caldera (flooded crater) and visit a volcano with hot springs
  • Explore the many small beaches in Folegandros, reachable by foot or fishing boat
  • Pack a picnic and hike up a zigzag path to Panagia Church for sunset

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Santorini Santorini
Day 2 Perissa Beach & Oia Sunset Tour Santorini
Day 3 Explore the Volcano Santorini
Day 4 Relax in Kamari Coastal Village Santorini
Day 5 Santorini to Folegandros Folegandros
Day 6 Guided Walking Tour in Folegandros Folegandros
Day 7 Explore Folegandros Chora Folegandros
Day 8 Transfer to Santorini, Depart  

Day 1: Arrive in Santorini

No shortage of lounge chairs on Kamari beach
No shortage of lounge chairs on Kamari beach

Welcome to Greece! Your private transfer will be waiting once you step off the plane at Santorini airport to take you to your lodging. There are many villages around the island with their own unique charms including Fira, Oia, Kamari, Imerovigli, and Firostafani—all of which have plenty of accommodations to choose from.   

There's nothing like catching your first glimpse over Santorini's iconic cliffside architecture. While you're at it, look for your first views of the island's central caldera—the site of one of the largest volcanic eruptions in history—rising up in a crescent. 

In fact, the island's volcanic history has led to the formation of some of the more unique beaches in the Greek Islands, like Kamari, with a stretch of black sand against the clear blue water. The beach is backed by the town of its namesake, a popular area with hotels, restaurants, beachside bars, and shops. Spend the rest of the day either relaxing at a beach or catching some exercise (and more views!) from one of Santorini’s more than 12 scenic walking routes, ranging between two to eight miles each.

In the evening, watch the sunset and then make your way to one of the island's numerous restaurants or tavernas for dinner, especially along the waterfront. 

Day 2: Perissa Beach & Oia Sunset Tour

Sunset over Oia
Sunset over Oia

Wake up with a fresh Greek breakfast before making your way to Perissa beach, known for its distinctive black sands. Extending for more than four miles down the southeastern side of the island, Perissa boasts crystalline waters and distinct rock features. The towering Mesa Vouno is recognizable down the beach and in the surrounding area, and you can climb up to its top if you're feeling particularly active.

Once you've enjoyed sufficient sunbathing, meet in the late afternoon for a group tour to Oia. The furthest town along the rim of the caldera, Oia's arty streets are the perfect spot for sunset views. Stake out your viewing platform over the panorama, then stick around to wander the alleys and linger in the town's tavernas into the evening.

Day 3: Explore the Volcano

A view of Santorini from the center of the volcano
A view of Santorini from the center of the volcano

No trip to Santorini is complete without an exploration of its iconic caldera. The island is shaped by the volcanic eruptions of its past. The most intense is known as the Minoan eruption in the mid 2nd millennium BC, which created the island's current geography and was felt around the ancient world. 

After breakfast, you'll head to the port and take a boat to the volcano, either on a private trip or together with a larger group. Hike down into the basin toward two small black lava islets in its center. These are the youngest of their kind in the eastern Mediterranean, only forming about 50 years ago. Hike around their rocky red soil before hopping in the hot spring at Nea Kameni. These yellow-tinted waters are high in sulfur and renowned for their potential therapeutic benefits.

Plan your trip to Greece
Chat with a local specialist who can help organize your trip.

Day 4: Relax in Kamari Coastal Village

Kamari Beach and Mesa Vouna mountain
Kamari Beach and Mesa Vouna mountain

After yesterday's activities, take a day to just relax in your temporary neighborhood. If staying in Kamari, for instance, this cosmopolitan beach area is worth savoring. The peak of Mesa Vouna, which you spotted previously from Perissa beach, also overlooks this long stretch of black sand, running into crystal blue waters. A stone promenade runs the length of the crescent-shaped bay and is closed to traffic during the summer, making it ideal for a casual stroll.

Wander past a wide spread of cafes, bars, shops, and even supermarkets to complement your sun session, or just recline on a sun lounger and order drinks. As the sun goes down, the beach swings into nightlife mode just waiting for you to dance until dawn. Romantics, on the other hand, can skip the party crowds and take an evening stroll. 

Day 5: Santorini to Folegandros

Waterfront dining in Santorini
Waterfront dining in Santorini

This morning, you'll take a brief post-breakfast ferry to the neighboring island, Folegandros. At 12 square miles, this smaller, lesser-known summer destination (with fewer than 1,000 residents), is the antithesis of Santorini's hustle and bustle. It also boasts one of the most striking main towns in Greece on its quiet shores, which have been mostly untouched by the tourist industry so prevalent on the neighboring islands.

Spend your day discovering this new island. Head to some quiet beaches by foot, bus, or fishing boat, or explore the main town of Chora, particularly the Kastro, a medieval district made up of joined wall-to-wall white houses. Both colorful door frames and the local children playing in the afternoon brighten up the district, where you'll feel right at home.

As the sun begins to set, continue your wander through this clifftop town to a taverna and sample truly authentic cuisine. Pounda and Nicolas Taverna are both popular spots to meet both the locals and local dishes.

Day 6: Guided Walking Tour in Folegandros

Explore the island's interior on foot
Explore the island's interior on foot

Load up on breakfast today, as you're in for some hiking. Take your pick between guided walking routes across the island, which our specialists can customize for you based on your interests and physical activity levels. If you don't know where to begin, there are two classic routes to try out. 

The route from Ano Meria (Agios Andreas) to Agios Sostis and Agios Georgios and back is roughly 90 minutes on foot, though it can be broken up by some of the island's best scenery and stops at the beach. Views across the sea to many of your Cycladic neighbors complement the meandering path before you descend for a dip at the Agios Georgios beach.

Going from Chora to Deftera Parousia to Agios Nikolaos will take you less time. This stonier landscape will lead you to your ultimate destination of the small church of Agios Nikolaos. Though the church is no longer in use, it provides a picturesque endpoint for you to relax amid the olive trees.

Your guide can help you choose your path for the day, as well as recommend some of the best stops along the way for shade and snacking.

Day 7: Explore Folegandros Chora

Fewer tourists in Folegandros
Fewer tourists in Folegandros

Today is a chance to become better acquainted with the island's main town. A good place to start is by taking a seat in a cozy square where locals go about their daily life. Take shade in the shadows of the plane trees as you sample a slew of local delicacies, either at one taverna for the afternoon or stopping at many during your wander. Don't miss the handmade matsata pasta (frequently served with rooster), karavoli (snails), orange pies, and amygdalota almond sweets. 

If you need to walk off some of your indulgences, head up to the Panagia church. The uphill 15-minute walk from Pounta Square can be challenging but the views reward your effort. It's also one of the most popular spots for sunset-watching so pack a picnic or come back later in the evening. Once you've had your fill of the scenery, end your trip in style with fine seafood dining at Blue Cuisine.

Day 8: Transfer to Santorini, Depart

Ferry back to Santorini
Ferry back to Santorini

It's time to say goodbye to Greece! Linger over one last breakfast before catching the ferry back to Santorini for your return flight home.


Map of Santorini & Folegandros - 8 Days
Map of Santorini & Folegandros - 8 Days