Greece
Santorini
The home of whitewashed shops and churches with blue domes, Santorini is at the top of most honeymooners’ travel list. You’ll find plenty of newlyweds meandering the winding sidewalks—but there’s more to this island than couple’s massages and candlelit dinners.
The island is made up of several distinct villages, with Oia the most quintessential Santorini aesthetic. The whitewashed cliffside community and spectacular sunset views make this one of the most expensive choices for accommodation on the island. Nearby Imerovigli matches Santorini’s iconic architecture with fewer crowds and amenities. Fira, the capital of this small island, provides plenty of nightlife, shops, and sightseeing opportunities. This larger village is the first stop for cruise ship daytrippers, rivaling Oia’s bustling crowds but without the same charm.
The entire island is a popular stop for cruise ships, so there is a marked difference between midday and early morning/late night on the island. It’s also worth noting that this is not the island to visit if you want to spend plenty of time on the beach. Perissa, a coastal village known for its volcanic black sand beach, is located on the southeastern edge of the island, a 40-minute Uber from Oia.
Santorini Highlight #1
Hike from Oia to Fira
If you start the hike early enough, this might be the longest you go without seeing other tourists—a near-impossible feat anywhere else on the island. We set out at 5:45 am and had Oia to ourselves, just in time to catch the sun creeping over the blue domes. The path along the caldera is not well signposted, so we followed a blog that clearly outlined the markers to look for (one is a sign on the side of an industrial building). The entire trek will take between 2 and 5 hours, depending on how many stops you take for photos. There’s also an option to deviate slightly off course to visit Skagos Rock, a 13th-century fortress. While we took the long, winding stairs down to observe the rock closer, we did not attempt to fully climb it—there are plenty of signs warning tourists to avoid this area altogether, and the steep cliffside drop into the water was enough to encourage me back onto the main path.
There are few opportunities for water or snacks, so come prepared with anything you’ll want for the hours-long trek. Imerovigli is the first village you’ll encounter, about two-thirds of the way through the hike, though the majority of their restaurants were not yet open for early-morning hikers. We bought pastries outside of Fira, about two hours into our hike, and later enjoyed a well-deserved gyro (Lucky’s Souvlaki is a must-try!) when we reached the island’s capital.
Santorini Highlight #2
Sip wine at the island’s clifftop vineyards
If you begin researching your trip to Santorini early enough, one vineyard will come up time and time again. Santo Winery has reigned as the go-to destination amongst Santorini’s vineyards, but it’s far from the only jaw-dropping vineyard in the area. We stumbled upon the nearby Venetsanos Winery as we waited for our reservation at Santos, and this cliffside location is well worth the trip in its own right. The winery boasts prime caldera views (that’s Fira to the right and Oia in the far distance in the photo) and is located directly above the ferry port, where eager travelers arrive from other Greek islands. We enjoyed wine flights and a cheese platter as we awaited our dinner at the neighboring Santo Winery.
Note: We combined these 2 activities, setting out from our Airbnb in Oia at 5:45 am, arriving in Fira in time for lunch, then taking a bus south to Megacholori. The buses that reach the southern part of the island will require a transfer in Fira, or you can take a pricier car option that can cost around 50 euros. We decided to pack our nicer clothes and change at the vineyards, to enjoy some well-deserved glasses of wine after a physically intense morning.
Santorini Highlight #3
Explore the caldera by catamaran
There are a number of tour operators to choose from, but we selected the sunset cruise offered by Sunset Oia. The company offers morning or evening excursions for small groups of up to 20 people, or you can opt to charter your own boat for a truly personalized experience. The tickets aren’t inexpensive, we paid over 100 euros per person for a 4-hour outing that included dinner, unlimited drinks, a tour around the interior of the caldera, and a few opportunities to get out of the boat and swim.
Note: We ventured out on a particularly choppy day, and conditions were so rough at times that we experienced some seasickness. This is a large operation, and 15 boats returned to the pier at the same time—unfortunately, we were last in line. We circled the dock for around 45 minutes, leaving everyone to regret their last drink.
Restaurant Highlights
Ammoudi Fish Tavern (Oia)
Ammoudi Bay is a must-visit waterfront neighborhood within Oia. The walk down from the town center is not a short journey (250+ steps!)—and the return trip is a full workout. You’ll find a number of restaurants lining this narrow strip of land between the cliffs and the Aegean Sea, mostly with similar offerings, though we were referred to Ammoudi Fish Tavern by friends and thoroughly enjoyed our meal. You can walk inside the restaurant and select your catch of the day, ensuring your seafood is as fresh as it comes.
Lucky’s Souvlaki (Fira)
One of the most popular gyro shops on the island, there is extremely limited seating in this quick-eats operation. Be sure to pay at the register before joining the line—you’ll need to have a ticket receipt to hand to the employees behind the grill.
Candouni (Oia)
This local hotspot fills up quickly, but don’t let that discourage you—we were able to walk in with little wait time. The restaurant itself feels like an intimate family home, where the waiters masterfully offer complementary bites as you select your entree from a selection of local dishes. The food itself was delicious and authentic, and the side-street location gave it a locals-only feel.
Santo Wines (Pyrgos)
This is one of the most recommended restaurants on the island for a reason. From the jaw-dropping sunset views to the incredible wine flights and beautifully presented dishes, we were blown away by our experience. Time your dinner to the sunset and book well in advance—this is a large restaurant but tables can be hard to come by. We arrived early for a winery tour, where we were walked around the property and learned how they produce the volcanic wines. We were lucky enough to get the best seat in the house—scroll through the photos above to see our spectacular sunset view.
What to Know Before You Go
Getting around:
Cabs and Ubers are the most convenient way to get around the island, but due to the limited number of cars, it comes at a price. Our most expensive Uber was around 50 euros to cross the island. There are buses connecting the various cities, but these are not entirely straightforward. A journey from Oia to the southern part of the island requires a bus transfer in Fira. ATV rentals are plentiful, but the roads are winding; we witnessed a couple return their ATV straight from the hospital, so consider your skill and comfort level before choosing this method of transportation.
Where to stay:
When most people picture Santorini, they picture Oia. The blue domes and sunset views are picture-perfect in this northern town, where the whitewashed hotels and Airbnbs are built into the cliffside. The price of accommodations varies greatly—from the exclusive Canaves Oia resort to the rustic cliffside Airbnb where we stayed. Prices are more reasonable in Fira, the capital city, while nearby Imerovigli offers the aesthetics of blue domes but little else in the way of amenities. Further south, you’ll find the beach town of Perissa, where sand and surf-loving families base themselves for quick access to the island’s black sand shores.
What to eat:
The plentiful, fresh seafood options across the island make this cuisine a favorite amongst tourists. The island is also known for its volcanic wine, so be sure to visit a vineyard in the south of the island.
When to visit:
June through September is peak season across the island. Expect large crowds, particularly when a cruise ship disembarks, and book your accommodations and a few choice restaurants well in advance. Some seasonal excursions, including catamaran tours, are only available from late March until late October. Much of the island shuts down in the cooler months, so check before planning to visit Santorini during the shoulder season.