Santorini is an intensely beautiful Greek island that draws visitors from around the world every summer to experience the iconic caldera, legendary sunsets, charming whitewashed villages with blue domes, and a culture that celebrates great food and wine. But the crowds can be intense, especially around sunset, in the capital city of Fira and the cliff-hugging picturesque town of Oia (“eee-ah”).
The high-season crowds can overwhelm local infrastructure, with narrow streets quickly becoming packed, taxis being in high demand, and movement generally taking longer. This popularity drives up the cost of food and accommodations and often reduces quality.
While avoiding travel in June, July, and August may be the best way to ensure a less-stressful experience, these tips can make Santorini sightseeing more enjoyable and relaxing.
Stay in a smaller town
Skip the bustling tourist centers of Fira and Oia, in favor of a quieter stay in a smaller town like Imerovigli, Firostefani, or Megalochori. Often, the accommodations are more luxurious, offer more space, and feature amenities that aren’t practical in more crowded parts of the island.
Vedema, a newly expanded hotel with spacious suites and private villas, acts as an extension of the quaint 17th century village of Megalochori, where you can explore free caves, dine in local tavernas, admire and shop for unique finds in this artist community, and find better prices than the rest of the island. Dine at Vedema’s restaurant Alati before 8pm and you might have the whole rooftop terrace to yourself for sunset.
Don’t miss the new Symposium Cultural Center, off a quaint white washed street filled with colorful little doors. This former winery offers an enchanting courtyard to sip wine, admire the rotating art gallery inside, learn about their collection of vintage Greek instruments, or become part of an interactive workshop reviving Greek mythology with music.
Taste wine all over the island
Santorini is known for low-growing vines that look like baskets, manipulated in this way to protect the grapes from wind and sun while also trapping moisture. Witness these volcanic-loving vines all over the island.
Appreciate the most beloved grapes at a 400-year-old wine cave at Vedema, a good place to start, as the refreshing mineral-forward dry white Assyrtiko is not found in the US. Sample Vinsanto, another sweet dessert pleasure made from Santorini’s sundried grapes. There are many old and modern wineries around the island to wine taste, some with views and some where a lunch elevates any day. Try a wine and food pairing at Cellar Door, Anhydrous Winery located in Kontochori, a village in Fira.
Find a lounge chair on a sandy beach
Unwind by taking a short drive to one of the nearby black sand pebble beaches formed from the island’s volcanic activity. Kamari and Perissa/Parivolos are the two main resort areas, separated by the rocky hill of Mesa Vuono, and both offer a variety of restaurants, shopping, and beach activities. Parivolos in particular is the quintessential laid-back beachfront experience without the crushing crowds.
Stay on the sand at twelve-suite Istoria Design Hotel, with beach chair royalty including food and drink service. No need to rent a lounge chair with umbrella, as you’ll have your own slice of the beach. Between ocean dips, cocktails can arrive with grilled octopus atop yellow fava spread with Santorini “Greek” Salad. This yellow split pea has been grown on the island for over 3,500 years. The famous peas that make fava dip and puree thrives in Santorini’s volcanic soil, receiving moisture from the sea fog, giving them a distinctive earthy and slightly sweet taste.
Book a dinner reservation after sunset
As the sun begins to drop, every restaurant on the caldera comes alive and fills with visitors hoping to catch a view of the sunset while enjoying an evening meal. Often this is a compromise, where neither the sunset view or the dinner service are at their peak. Instead, savor the sunset in a less-crowded cliffside spot and saunter off to dinner after the earlier sunset crowds have cleared out.
Seafood lovers will want to book a reservation right on the water’s edge at Ammoudi Fish Tavern in Ammoudi Bay, renowned for its fresh seafood and unparalleled Greek ambiance. An 8 PM reservation seems like the sweet spot in summer. Ogle the large catch of the day and hanging sun dried octopus as the catamarans come in and out. Hugged by red volcanic cliffs, a higher seat is the best option at this multilevel restaurant to watch the sunset over the Aegean. If you sit down below, near the water’s edge, watch out for waves that can overtake the whole dining area, as we watched the new largest cruise ship, Icon of the Seas, take off at night creating a large wake, overtaking the outdoor bottom floor.
Indulge in red shrimp carpaccio and move into a shared seafood platter of shrimp, calamari, octopus, and whole sea bream, deboned and drizzled with olive oil. When in Greece, find room for the handmade loukoumades (deep fried dough balls with honey and walnuts) and galaktoboureko, a traditional Greek dessert with custard but modernized here topped off with crunchy phyllo dough cracked in front of you and drizzled with syrup and a scoop of vanilla ice cream with cinnamon.
Explore Oia after the cruise ships leave
Since you are on a crescent shaped volcano in the Aegean Sea, dining on Santorini’s caldera multiple times is a must! Visit the iconic village of Oia after the cruise ships have sailed. Wander the alleyways of this famous whitewashed town at sunset while the tourists are gathered on the caldera’s edge, peruse the shops without the cruise ship crowds, and book a reservation of Aegean epicurean elegance at one of the boutique restaurants overlooking the moonlit caldera.
Lure Restaurant at Mystique Hotel rolls out a Symphony of Flavors – sometimes with a guest chef, like Chef Luca Piscazzi from the Four Seasons Athens when we were there – bringing mind-blowing flavor surprises with each course. Fanciful bites – like a peeled tomato ball stuffed with sun dried tomato cream and caviar, or cured shrimp saganaki floating in ouzo and oregano oil – are amplified with a pairing of local Gaia Wines; sips of Assyrtiko with Sauvignon Blanc, pink skinned Moschofilero and a Greek port accent the experience.
This cliff-hanging table setting overlooking the magical Oia coastline might be one of the most memorable places in the world to dine, where the land evolves at dusk into many personalities, appearing to float like 3D Cubist jeweled clouds in the liquid darkness.
Walk the caldera north from Fira
Just north of Fira is a cliffside village bursting with charm and picturesque views. Firostefani is a short walk from the bustling city center, and a peaceful scenic alternative. Settle into one of Firostefani’s charming restaurants for a morning coffee or a leisurely lunch, and combine incredible views with delicious local food, for a perfect cliffside setting to relax and appreciate Santorini’s authentic allure.
Once an island of tomato factories, light crisp deep-fried tomato fritters called domatokeftedes are a Santorini specialty made with tomatoes, spring onions and herbs. Found on most menus, we devoured the largest ones at cliffside Vanilia Restaurant atop the caldera, along with plates of taramasalata and marinated anchovies, washed down with the island’s beloved Assyrtiko (white wine) and Santorini Blue Monkey beer. This idyllic cliff-hugging restaurant, housed in a refurbished 1872 stone windmill, is the best place to hang over the deep blue Aegean and rest your weary legs after admiring artifacts at the new Archeological Museum of Santorini and bargaining with the local merchants in Fira’s street markets.
Hike the caldera between Imerovigli and Oia
For adventurous travelers, a breathtaking and rewarding 5-mile hike (each way) atop the caldera, between the towns of Imerovigli and Oia, is one to start early to avoid midday heat. While you’ll see other people on the trail, it’s not crowded and is the best way to gain a more serene bird’s eye view of Santorini as you come upon villages, churches, and blue domes. Reward yourself with a stop at Lolita’s Gelato in Oia with a handmade creamy gelato or fresh sorbet that comes in authentic flavors like Sicilian pistachio and strawberry.
Stay midway between the cities in quiet accommodations – like Amaze Suites on the caldera’s edge in Imerovigli, where affordable rates will get you an adorable pool terrace and classic simple rooms with private jacuzzi – complete with dreamy sunset views. Take your complimentary breakfast outside next to the pool to sample numerous Greek delights. In the town of Imerovigli, dine at local favorite Mama Lena.
Sail around the island
Perhaps the most extraordinary way to experience Santorini is a day on a catamaran with your closest friends or family, to admire the dramatic scenery. Santorini Sailing Center offers private boat charters on the Daiquiri, which leaves Ammoudi Bay around 2 PM and sails until sunset – including swimming at several stops like Thirassia Island and Sulfer Springs volcanic waters. Stand in awe of grandiose volcanic rock bays, white towering rock faces, and red sand beaches. The mesmerizing sail includes unlimited wine and drinks served right to you and an incredible Greek meal cooked by the captain, on the grills off the back of the boat.
