Santorini (officially Thira) is one of the Cyclades islands in the southern Aegean Sea about 120 miles southeast of Greece’s mainland. An enormous volcanic eruption destroyed a formally single island and created a giant caldera containing several smaller islands including Santorini. The island offers massive steep cliffs, diverse volcanic rock beaches, and stunning white-washed architecture. Follow these do’s and don’ts to get the most out of your holiday in paradise.
Going to Mykonos as well? Check out our Guide to Surviving Mykonos in your 30s.
Do: Rent a car so that you can get the full island exploration experience.
There is one major road that runs the length of Santorini and most of the beaches and towns are fairly easily accessible. There are also many free public lots so parking is rarely an issue.
Spend your first day exploring the north end of the island; head to the village of Oia at sunrise, then to Ammoudi Bay for the freshest grilled seafood at Dimitris Ammoudi Taverna and get an adrenaline rush cliff-jumping at a popular spot just around the bend. Finish out your day with dinner, sunset cocktails, and late night souvenir shopping in Fira.
Spend day two on the south end of the island; have a quick stop at Red Sand Beach for the views and then take the boat taxi to White Beach, and finally spend your afternoon snacking and lounging on Perissa Beach. Stop at the port to make plans for a fishing trip for your third day on the island. Enjoy amazing sunset views, delicious local wines, and appetizers at Santos Winery.
Spend day three enjoying the views of Santorini from the sea.
Don’t: Underestimate how difficult it is to maneuver the narrow roads and tour bus traffic.
Mopeds, 4-wheelers, and gigantic tour buses seem to dominate the roadways of Santorini. Take it slow and expect everyone to pass. If you find yourself head-on with a tour bus, pull as far off to the side as you can, tuck in your sideview mirrors, and trust that the bus drivers know what they’re doing.
Do: Grab a beach chair and spend the day lounging on Perissa Beach.
Perissa Beach is a black sand beach and the longest beach in Santorini. The beach is sandy, the water calm and clear, and it is not overly crowded as there is so much beach to go around. Most of the restaurants offer free lounge chairs if you purchase lunch or drinks and you’ll have a waiter checking on you regularly. Enjoy mixed plate and house wine while relaxing on your cushioned, shaded lounge chair at Pepito.
Don’t: Plan on spending too much time on Red Sand Beach.
The view of Red Beach from the hike down is impressive but the actual beach is small, crowded, and the sand and water are full of seaweed debris. Also, “red sand” is an overstatement. It’s worth checking out but don’t plan on spending the day there. There is a small area of lounge chairs with umbrellas but most of the beach is a crowded free-for-all.
Do: Head to Santos Winery around 7pm (reservation recommended) for generous wine tastes and the best sunset views on the island.
Santos Winery is positioned high on a hill in Pyrgos with views of the sea and scattered islands. They offer delicious wines from a variety of Greek wineries and you can order tastings as small as 6 and as large as 18. Arrive a few hours before sunset to guarantee a front table (or even better, make a reservation ahead of time); sip on a range of wines that suit any palette and munch on a charcuterie plate until closing time.
Don’t: Attempt to drive to or from Oia around sunset time.
The traffic in Oia is challenging to say the least no matter what time of day you attempt to visit. The streets are narrow and it is a popular tour bus destination. If you attempt the drive close to sunset time you will end up enjoying the views from your car in bumper-to-bumper traffic. If you don’t want to miss an Oia sunset, arrive early and plan on hanging out late.
Do: Hire Captain Nick to take you on an awesome fishing excursion.
Head down to Vlichada port and ask around for Captain Nick’s fishing boat. For 600 euros you’ll have a large fishing boat, a captain, a deckhand, and an English-speaking steward all to yourself for a 6-hour morning or evening cruise around the island. The sunset trip departs at 3pm and you’ll get amazing views of the cliffs and the beaches on your way out to pick up the nets they dropped hours before to see what you’ve caught for dinner. The steward is incredibly attentive and your wine glass will never be empty for long. You’ll have a swim while they prepare a delicious dinner of fresh fish, Greek salad, fava bean dip, fried tomatoes, rice pilaf, and fried bread. On the way back you’ll enjoy amazing sunset views while 2 fishing poles troll for “second dinner” which can be prepared back at the restaurant on the dock.
Don’t: Be a sardine on a catamaran booze cruise.
While catamaran cruises are generally a good time, make your Santorini adventure more memorable by actually catching your own dinner!
Do: Have a sunrise stroll through the alleyways of Oia and enjoy a cup of joe with amazing views.
If you want unobstructed views of the white-washed buildings and blue-roofed churches of Oia before the crowds and the heat make it unbearable, head to the small town at sunrise. Meander down the maze of alleyways on the hillside that often lead to amazing views and occasionally dead end. Admire the gorgeous views of the city on the hill and be sure to catch the famous church that is a popular place for wedding photoshoots. Other photographers and a few tourists will be out as well but it’s the best time to get unobstructed photos of the idyllic town setting. But don’t just stick to the main church spot, every little alleyway has something special to offer!
Don’t: Stroll Oia after 10am when the tour buses descend and the sun is unrelenting.
Oia is absolutely stunning but it is also the most popular tourist destination on the island and the low white-washed restaurants and shops offer minimal shade. If you find yourself in the thick of it at midday you’ll need to dart between small shady spots or duck into an air conditioned cafe or shop or end up sunburned and sweat-drenched.
Do: Soak in the sunset from V Lounge and then enjoy an evening shopping session in Fira.
The little town of Fira comes alive around dawn when tourists put on their fancy vacation outfits and search for the best spot to watch as the sky turns a hazy shade of pink. Head to V Lounge for generous wine pours, great music, attentive service, and the best views of the city below. After sunset move on to the alleyway shops that stay open late to pick up a few souvenirs.
Don’t: Miss a sunset in Santorini. Ever.
No matter where you are on the island the sunsets are spectacular. You’ll enjoy it more if you are high on a hill with a cold glass of white wine in hand.
Do: Learn a few words in Greek and use them.
“Ef-car-ees-toe” is “thank you”, “ee-ya-sis” is “hello” and/or “goodbye”, “yamas!” is “cheers!”, and “pa-la-ca-lore” is “please”. Most locals either speak fluent English or can find someone who can act as a translator but as they’ll appreciate if you try (and they’ll be entertained by your effort).
Don’t: Be an inconsiderate tourist and assume that everyone speaks English.
Because a lot of people don’t.
Do: Check out White Beach via taxi boat from Red Beach.
Inexpensive boat taxis come by every 30 minutes or so and drive back and forth between the two beaches. Leave your car in the parking lot and hop on the boat to check out the small, elusive white sand beach.
Don’t: Attempt the bumpy dirt road to White Beach in a rental car.
The advice from the rental car company was to drive pretty much everywhere on the island except here. Rather than spending your day enjoying the beach, you’ll have to track down a tow truck.
Do: Splurge on an amazing hotel with a pool and a view.
Gonia Residences is an absolutely stunning house with 3 large bedrooms, 2 full bathrooms, a stocked kitchen, a large living room area, a beautiful patio with stunning views of Pyrgos, and a private plunge pool. The only downside is that you may never want to leave…