A Long Weekend in Santorini

Santorini is a dream. The island received its name from the Venetians in the 13th century in honor of Saint Irene, but is known as Thira in Greek. Santorini is full of stunning caldera and Aegean views, delicious seafood and local delicacies, and amazing (albeit windy!) weather from spring through fall. Get lost in the windy stone streets, pop into little boutiques and enjoy the endless views around the island. Santorini is the perfect stop for a long weekend or on a tour of the other Greek islands.

We recommend traveling to Santorini in the shoulder season from April to early June, or September. The island is small and can get very crowded in high season.

Some European airports, including London Gatwick, have direct flights into Santorini National Airport. Otherwise, we recommend flying through Athens or taking a ferry from Athens or a nearby island. It is possible to take the ferry from Naxos to Santorini in two hours.

From the airport, there are a few options for getting to accommodation around the island. Most hotels will provide a pick-up/drop-off service for around €40. Alternatively, take a taxi from the airport for a similar price, but you will need cash. It is possible to take the local bus from the airport to Fira for €1.80, and then onwards to wherever you are staying from there.

Getting around the island is somewhat of a challenge, as the different villages are spread out. There is a public bus service to most major villages that begins and starts from Fira Central Bus Station. Most bus trips range from €1.80 to €2. Tickets are purchased on the bus and it is reliable, though can get quite crowded. For those who want the flexibility to explore at their leisure, we recommend renting a car (Vazeos is a reputable local brand), moped or ATV.

While the island is small, there is so much to do that we recommend planning at least three to five days to explore, or a long weekend in Santorini.

EAT

Argo Mediterranean and Greek taverna in Fira.

Dimitris Fresh seafood caught daily at Ammoudi Bay. Dimitris is the farthest restaurant on the walkway to the left and has the best sunset views. Make a booking and make sure to try the saganaki mussels or shrimp.

Fino Cocktail Bar & Restaurant Nice cocktails and tasty bites in Oià. The tuna tartare and eggplant souffle come highly recommended.

Karma Traditional Greek food in a cozy atmosphere in Oia.

Pito Gyros The best gyros in Oià and a great place for lunch or a casual dinner.

The Athenian House Local, romantic seafood restaurant featuring great views in Imerovigli.

DRINK

Coffee lovers! Substitute your go-to cappuccino for the Greek freddo cappuccino.

Marykay’s Bar Fun, cozy spot in Oià that is also open late.

Meteor This tiny bar in Oià is an oasis away from the sunset crowds and chill winds in spring. Stop in for a drink before heading to dinner.

Tango Great cocktails and tunes in Fira. Start start out the evening here.

Tropical Bar Casual, local dive with a great sunset view in Fira.

Wine! Wine has been produced in Santorini since the ancient times and there are several varieties indigenous to the island that are highly prized, including the white Assyrtiko grape. Today, the island is dotted with wineries. Make time to visit a few, either organizing a tour with a guide or DIY. We have listed some of our favorite wineries below. Note that Gavalas, Santo and Venetsanos are all within walking distance of one another and bus stops in Megalochori or Pyrgos.

Domaine Sigalas Just 15 minutes from Oià, this winery has a lovely patio with elevated Aegean views.

Gavalas This fourth generation, family-owned winery has won international awards. Their tasting room in the Megalochori village is tiny but worth a visit for a €14 tasting. We loved their Aidani white.

Santos A cooperative owned by over 1000 grape farmers, Santos is situated just west of Pyrgos and high on the cliffs overlooking the caldera. Enjoy a tasting on their large patio. Table for two? We recommend splitting a flight of 10.

Venetsanos Just a 12 minute walk from Santos, Venetsanos is smaller and a bit more intimate. It has an equally as stunning view but has a smaller patio. Book in advance.

PLAY

Ancient Thera The ruins of Santorini’s ancient city feature breathtaking views of the island, caldera and Aegean. Hike to the top (not for the faint of heart!) or drive.

Boat Tour There are a tons of options. We recommend one that takes you to the volcano, hot springs and some of the beaches. There are also sunset cruise options.

Firà to Oià or Oià to Firà hike This 10km hike has amazing caldera views. Take the bus back from either ending point. 

Kamari This coastal village on the Aegean features a long, rocky beach, beach-side tavernas and a bit of nightlife. It has long been popular with the tourist set.

Megalochori This adorable and picturesque village in the island’s center is worth a stop on its own. Known for its stunning bell tower, it is also home to Gavalas Winery.

Perissa Black Sand Beach Another coastal, resort village on the Aegean, albeit a bit further south than Kamari.

Pyrgos Visit this medieval village in the center of the island for its castle and quaint shops. It is a mile walk from the square to Santos Winery.

Red Beach The most beloved beach on the island is celebrated for its rocky red beach and the dramatic red cliff sheltering it. The beach is a short hike from the parking lot and gets crowded in summer.

Skaros Rock A little trek to some amazing views in Imerovigli.

Watch the sunset Oià is the best place on the island to catch the setting sun, or by boat.

STAY

It depends! If you are looking for luxurious and romantic accommodations, or for something special for a honeymoon, we recommend staying in either Oià or Imerovigli. Both have tavernas and restaurants nearby for dinner and drinks, but turn quieter after the sun goes down.

In Oià check out Art Maisons, which has two luxury boutique hotels, Onar Villas or Solstice Luxury Suites. All feature cave rooms, and either private hot tubs or cave pools.

In Imerovigli try Cocoon Suites, modern, luxury suites with private plunge pools.

If you want to be near nightlife, and have the flexibility to get around the island on public transportation, stay in Fira. We loved Enigma Suites Santorini and still dream of the views and delicious breakfast delivered to our suite each morning.

For a more casual experience, or proximity to the beach, stay on the Aegean Sea side of the island. Both Kamari and Perissa have nice beaches with enough going on to keep you fed and relaxed.

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