Santorini is by far the most beautiful of the Greek Isles, but also the most crowded and filled with instagrammers taking hundreds of epic photos of themselves (see above). Don’t let the thousands of aspiring instagram models deter you though. You absolutely must see and experience Santorini at least once in your life. The level of natural beauty is simply off the charts. And, let’s be honest, over the top instagrammers provide some seriously fun people watching. If you enjoy laughing at people who go way above and beyond to get their perfect instagram pose as much as we do, please check out our friends on instagram at @iamsosessy

Ah…that’s more like it…

Now onto the advice….First things first: Check out the map below. You’ll notice that Santorini looks like maybe it used to be a complete circle that has been flooded by the sea. You’re not crazy! Santorini was formed millions of years ago when a giant volcano erupted through the Mediterranean Sea. This is what forms the stunning shear cliffs that make all your photos look like something out of a movie.

The moon shaped semi-circle on the right is the main island of Santorini and the volcanic caldera exists, mostly submerged, at the center of this semi-circle.

There are three main towns on the main island which run along the interior edge of this caldera. They are called Oia, Imerovigli and Thera (Fira) in order from north to south. You will most likely be picking between these three towns when deciding where to stay.

Oia

Oia (pronounced ee-aa), pictured above is probably the most photogenic. They’re all stunningly gorgeous, but Oia is the instagrammers paradise. As such, expect there to be times, particularly when the big cruise ships land at port, when the small cliffside maze of pathways and stairs in Oia are absolutely clogged with tourists. When we went to Santorini, we stayed in Oia, but, for the reasons discussed above, we probably would pick one of the other towns to stay in if we go back again.

If you decide to brave the crowds, don’t fret, Oia is still well worth your stay. But, take advantage of the reason you want to stay there in the first place. Get a cliffside room overlooking that beautiful caldera view with your own patio. If you’re looking for a relatively reasonably priced place to stay, check out VIP suites and book one of the honeymoon cave rooms.

Imerovigli

While we absolutely loved Oia, Imerovigli would be our top choice for a place to stay for when we plan our return trip. Imerovigli’s view, while not as nice as the other two towns, it’s still absolutely stunning. The real draw with Imerovigli is that besides a handful of restaurants and bars it’s all residential. And, because Oia and Thera have the most instagrammable views, Imerovigli ends up being the least overrun by tourists. It’s a much more relaxing and laid back place to call home while you use the simple and abundant local bus system to ride between Oia and Fira.

Thera (Fira)

Fira is by far the most bustling and happening town on Santorini. It is chock full of bars, restaurants, theaters and things to do. No matter where you stay you will have to take a trip to Thera for a show and dinner at least once.

Things to Do in Oia

– Obviously you can’t leave Santorini without spending a full day exploring the paths, alleys and stairways of Oia. It’s surprisingly easy to navigate as everything besides the main paths are cordoned off as private property. Don’t be the guy or girl that jumps the fences to bother people in their private hotel balconies to get your perfect photos. There’s plenty of good photos to be had without interrupting other’s vacation.

– Watch at least one sunset from the Oia Castle at the northernmost tip of the town. Get there early as the crowds will push into the small area on top of the castle for the sunset. By far the best sunset on the island is from Thera (Fira) though because you get to watch the sunset with Oia and the Caldera in the foreground. From the Oia Castle you’re really just watching the sun set over the ocean.

– Go to Oia Vineyart. It’s an incredibly cool wine bar with great Greek Meze plates, incredible wine tastings, live music and hands down the coolest and nicest staff you can imagine.

– Up the street from Oia Vineyart is an adorable boutique shop owned by some seriously nice people, featuring some incredibly unique, handmade purses. Definitely stop in here.

– Ride donkeys from Ammoudi Port up to Oia. Is there anything more Greek you could do than this. The tour companies offering this experience are easy to find.

– Get Ice Cream at Lolita’s Gelateria for some of the best gelato in Greece.

– Swim at Ammoudi Bay: One of the best swimming spots on Santorini is down the cliff from Oia at a spot just south of the Ammoudi port. Walk or drive to Ammoudi Bay then take the path that leads south from the restaurants in the port (can’t miss it, there’s only one way to go). It’s a 5 minute walk to a small island (Agios Nikolaos) that you can swim out to. Then jump from the ledge (if you want).

– Stop by Atlantis Books and get a $5 hand drawn map. It’s also a great spot for photos.

– Walk towards the east part of Oia and check out Saint George Church.

Things to do in Thera (Fira)

– Buy tickets and go to The Greek Wedding Show in Fira at the White Door Theatro. Seriously…DO NOT leave Santorini without seeing this show. It is our #1 thing to do in Santorini. It is a live action play where the audience is part of the show. The show takes place at an event venue and is based around a wedding in the 1940s. You will enter the theatre and be greeted by the cast with hugs and kisses like you are long lost family members arriving at their wedding. You will sing, dance, drink endless amounts of Greek wine and be served a large plate of Greek Mezze while being regaled by songs, dance, music and a charming love story. End your night while smashing plates as everyone does traditional dances around you. Check them out here: https://www.whitedoorsantorini.com/

– Do not leave Santorini without watching a sunset from Thera (Fira)

– Hike the caldera path between Fira and Oia. The hike takes 2-5 hours depending on speed and stops. Start in Fira and move north through Firostefani and then Imerovigli and then from there to Oia, when in doubt stay left/west. Start before 8am in July and August as it gets way too hot in mid afternoon.

– Take the cable car from Old Port to Fira. Walk down stairs to the Old Port, grab a drink, then take the Cable Car back up. It runs every 20 min.

Things to do Elsewhere in Santorini

– Take a wave runner tour of the caldera. All of these Jetski/Waverunner tours leave from Perivolos, a town in the far south of the island. Public transportation on the bus may or may not get you there when you need to. You will most likely need to reserve a taxi the day before to get you there on time. Email info@wavesports.gr to reserve your tour. They have three tours: The South Tour is the shortest tour (90min) and includes stops at both Red Beach and White Beach. The Volcano Tour (140min) goes all the way into caldera and stops for a swim in hot springs. The Grand Tour (200min) includes a volcano tour plus Thirassia Island and Ammoudi Bay. These are relatively expensive tours, but we did the Volcano Tour and absolutely loved it. One of the best things we did on our trip.

– Take a boat tour of the caldera

Private Catamaran Cruise by Spiridako

– $1,151.26

– 10am or 3pm departure

– Volcano, swim in hot springs, White beach, BBQ with local wine, Red Beach

Small Group Catamaran Cruise by Oia

– $191 per person

– 5 hours, starts at 3:30pm

– cruise around volcano, caldera, swim hot springs, snorkeling, huge dinner, sunset below Oia

Small Group Cruise by Spiridakos

– $174.43

– 5 Hours

– Volcano, caldera, snorkeling, BBQ

Santorini Wineries and Vineyards

An absolute must do on Santorini is to spend a day or two or three exploring their many wineries and vineyards. The wine in Santorini is fantastic. It’s easy to order a taxi and have them drop you off at your first winery and then have them call for your next cab before you finish your tasting.

Wineries with the best caldera views are Santo and Venetsanos. Venetsanos has much better wines and is a lot nicer, but requires a reservation made in advance. Santo has decent wines, but is much more touristy, of slightly lower quality and crowded. You can walk in at any time and the views are well worth the trip. But, if you’re going for the wine make the reservation at Venetsanos.

The best wine varieties to try are Assyrtiko (white) and Mavrotragano (Red). We will cover these in more detail on our Wines of Santorini page.

Below is a list of the best Wineries and Vineyards to visit on your trip:

Santo Winery (Pyrgos)

– Fantastic views of the cliffs and caldera with

– most comprehensive cellar tour

– Huge selection and shop

– Wine tastings = 3, 6, or 12 glasses

– Awesome Deli Shop

– Very Touristy

Venetsanos Winery (Megalochori)

– Similar views as Sanos Winery but a bit smaller with a little more charm

– built into the side of a cliff

– make reservations in advance: hospitality@venetsanoswinery.com

– Sunset terrace for glasses of wine and snacks opens Mon-Sat 6pm-10pm

Gavalas (Megalochori)

– small, intimate winery

– hard to find if driving by yourself

Estate Argyros Winery

– top 100 wineries in the world for many years

– Bare bones but amazing wines

– Winery for real wine-lovers, not a tourist attraction with instagrammable views

– Wine tasting is free

Art Space Santorini (Exo Gonia)

– Mix of wine, caves and art. The owner guides you around the property and explains its history with a thick Greek accent.

Domaine Sigalas (Oia)

– Small winery thats only a 10min walk from a bus stop on the Fira-Oia bus route

– Gorgeous for outside sitting in romantic terrace

– Amazing food

– During summer, there is a bus every half an hour that connects Fira with Oia. In order ot come to the winery it would be better to make a stop at Foinikia village. When you get out of the bus there is a sign that says “Streets of Wine Domaine Sigalas”. You turn right. The road goes down, it has a great view and the distance is about 10 minutes walk.

– Has wine tastings with appetizers from March to November

Koutsoyannopoulos Wine Museum (Vothonas)

– 300 meter long cellar with wine museum

Hadjidakis Winery

– 100% Organic

– Must try Assyrtiko de Mylos

Artemis Karamolegos Winery

– Most award winning wines on Santorini

– Has an amazing restaurant called “Aroma Avlis”

– Gorgeous views of the Monolithos Beach

Canava Roussos Winery

– Lovely wine tasting terrace