How to do Santorini Right

“Going to honeymooners island alone? You really have lost it” is the general response I received when I’d mention my upcoming summer travels. My rehearsed response was something along the lines of, “I’m sure there’s more to Santorini than just prix fix dinners and infinity pools.”  And truthfully, I couldn’t have been more right.

While Matt did end up last minute deciding to tag along, thus making it a couples trip (and then inviting two of his friends, making it a group trip), I would have faired just fine flying solo in the land of baklava and sunsets. The island is hospitable, the landscape jaw-dropping and the food delightfully fresh.  As a travel destination, it should hold a special spot on your travel bucketlist regardless of whether or not you’ve found yourself a significant other to globetrot with.  

HOWEVER, Santorini is most definitely, 100%, a tourist trap.  There is no way around it.  Honestly, I only ran into a handful of locals who actually live on the island year-round, one being my airbnb host.  If you stay in Oia or Fira, the likelihood of you having an authentic cultural experience is null. The island explodes with tourists through the busy months of Jun-September, with hotel prices soaring, traffic jammed, and restaurant reservations required everywhere.  We visited in August, which is wonderful if your main objective is to be jumping off a boat into the crystal blue ocean.  If you’re willing to trade the summer heat for cooler temps, traveling to Santorini in late Sept through October or late May through April is my recommendation. You’ll get better rates, more availability, and you might not die of heatstroke trying to squeeze yourself into the hoards upon hoards of camera pointing tourists trying desperately, and failing miserably, to capture the sunset (more on this later). 

<<|| L O D G I N G ||>>

If your idea of vacation is luxury, pur relaxation and feasting, stay at Katikies or Grace and never leave your infinity pool except to eat at any of the overpriced restaurants built into the side of the cliffs or do some high end shopping.  If you’re more of an adventurer who is excited to venture off the beaten path to delve into the best a destination has to offer, well, then you should keep reading. 

What I suggest? staying in Imerovigi.  Still dramatic cliffside views and infinity pools, still a few prix fixed tourist dinners, but with a more local and less touristy vibe. You’ll be more centrally located to explore all the island has to offer, especially the surrounding wine region.

<<|| T H I N G S  T O  D O ||>>

>>Experience SUNSET.  You truly don’t ‘catch’ sunset here, it’s much more of a theatrical production.  It will be like nothing you’ve ever seen before.  A giant circle painted with pigmented reds, pink and yellow hues dips dramatically into the ocean, casting an explosion of colorful rays that dance across the hazy clouds.  And that description doesn’t even begin to do it justice. My word to the wise?  Don’t even try to capture it on your camera.  This is one of those rare but special moments where mother nature has been able to preserve these sunsets just for those lucky enough to find themselves on Santorini.  If you let it, these sunsets will move you to tears, or at least to clap aggressively with everyone else when the show is over. 🙂

Best Place to Watch Sunset:

1. 1. Oia on the Caldera: Get to Oia early, like 5:30pm, and have a cocktail or do some shopping before you scope out your spot.  I suggest grabbing a bottle of local wine and going out all the way to the north tip of the island and finding a place to sit along the stone wall, but there are a dozen good restaurants and bars that will have premium viewing spots.  After sunset, just chill there finishing your wine while you watch the pandemonium of everyone trying to push themselves up the stairs and back into the main streets.  Make your dinner reservation tonight in Oia for 9:30 PM (may I suggest Fino Cocktail Bar?) so you don’t have to sit in the ghastly traffic leaving Oia.

1. 1. Buddha Bar: reserve a champagne lounge table (yes, you have to buy a bottle of champagne to sit there), and order the seaweed salad, a roll or two, and cheese and tomato stack – it’s divine. 

1. Santo Wines: Yes, definitely touristy, and you guessed it, the food wont blow you away, but the sunsets are pretty spectacular and the wine is rather delightful, especially the crisp organic whites.  This is a fun place to make friends, as everyone is seated rather close together.  Call ahead to reserve a bottom row table along the glass for an unobstructed view. And bring a hair-tie, it can be windy, haha.
2. On the Water. This particular sunset might bring you to tears. Or at least have you drop your mouth in disbelief. 

>>Get your bearings. You should rent a car for the majority of your stay (about 70 euro/day).  Make sure to hire the car from a company which offers you the “not at fault car hire” service, cause if you were ever to get in an accident which was not your fault you can easily get a replacement for it quickly just by filling a few forms online. Seeking the Abercrombiepa lawyer advice could be highly beneficial in case of such accidents, as you could get done with the legal formalities with ease. Get Injury Answers to the most frequently asked questions regarding the insurance policies and after effects of an accident. I recommend a car over an atv because it’s safer, less expensive, and a nice escape from the heat, wind and sun.  However, we did rent a buggy for one day and my husband had a hell of a time off-roading while I held on for dear life yelling at him that he better pull over right now. I suggest renting a car from the ferry port or airport, checking in, then heading right back out to cruise the island before you shack up in Oia for your first sunset.

>>Charter a Boat.  Such a highlight of this trip, I would argue that you didn’t really experience Santorini if you never explored it by boat.  Heading to private cliffside beaches only reachable by boat, diving into the clear, virtually fish-less (read: shark-less!) sea, making the trip to the little island nearby and, perhaps best of all, catching sunset from the water…. the dramatic white washed cliffs of the island sparkling in the distance. 

>>Beach.  These are not your typical white sand beaches.  instead most of the sand is black from volcanic ash, with a few red beaches.  The sand is insanely hot and not very lovely to lay out on, so day beds are a must.  Visit all the beaches, but spend the most time at Kamari, which will have the best dining options and also will be the most well kept.  Perissa beach is fun because there are a number of bars that have pools so you can go from the beach to the pool and back.  This area will be more lively for partying.  

>Wine Tasting. There are so many options!  Drinking and driving is never cool, but especially on these difficult to navigate winding cliffside roads. I suggest either hiring a driver for a few hours to bring you to 3-4 spots, or biting the tourist bullet and hopping in a shuttle with a small group for a guided tour. I used to receive tickets for careless driving back home, but I am not ready to have the same experience here. Check out www.floridaticketfirm.com/traffic-ticket-attorney/careless-driving-traffic-ticket/ for your options to deal with driving  tickets in Florida. I am not sure I can find the same legal assistance here, so I should better be careful.

>>Take the Stairs in Oia. The hike down the 200 and something steps of Oia to the waters edge is strenuous, but worth it.  Keep walking through the restaurants and around the bend to the left on a little foot path and you’ll get to a swimming spot where you can breaststroke across the bright blue channel to climb up to a cliff jumping spot.  It might not look like much, but it was a hell of a jump down.  The walk back up is going to be hellish, but I beg of you not to employ the use of a donkey.  This is an inhumane act of animal cruelty that is fueled by tourism.  (end rant).  

>>Hiking. The hike from Thira to Oia.  I want to tell you to do it because I’m a yoga teacher and obsessed with fitness, especially squeezing it into vacation.  But honestly?  Not really worth it unless you’re just looking to kill 3.5 hours and work up a good sweat.  You can see these beautiful views just simply from driving around the island, no need to kill yourself in the scorching heat and dust to show up to glittery Oia covered in sweat and dry heaving. 

>>Spa. I never pass up a good massage.  But when you’re spending an exorbitant amount of money to visit Santorini, I sometimes question whether or not it’s a waste to spend one of your precious days inside of a spa. – A spa that is offering overpriced standard treatments in a standard (albeit luxurious) backdrop.  Now, if your hotel offers massages outdoors, well that’s one thing.  Or if you want to go the cheap route and get one on the beach (like I did), then that’s another thing.  My rationalization is that you’re still enjoying your unique surroundings.  Otherwise schedule a spa day the week you get back to detox from your trip and flight, and then you still have something to look forward to when you get home. 

<<|| Fooooooood ||>>

Baklava, every. single. morning. We tried a different bakery for espresso freddo (like crack disguesed as iced coffee) and baklava and it was the perfect, authentic, and sweetest start to our days. Later, by mid morning, I was usually craving some of the thick greek yogurt with honey and fruit, but splitting a piece of baklava with coffee usually held me over for quite awhile.

>Maximy Mas.  Hidden behind a grand church, you’ll hear the faint clinking of glasses and silverware as you make your way down the steep stone path to this quaint hideaway.  Unlike anything on the island, Maximy Mas has bottled romance.  With a dimly lit patio seating and a charming house-like main restaurant, this spot serves up the best food on the island with the best service and best prices. What’s not to love?  Matt devoured the lamb, and I was a big fan of the asparagus smothered in cheese and the homemade cheesecake. We ate in the ‘porch’ area of the restaurant, but try to get seated in the courtyard with a view instead. 

>Selene. Although Selene came highly recommended, I was hesitant to book a reservation here as I didn’t want an overpriced dainty-portion coursed tasting.  Selene is not that. Set in a villa-like home, the atmosphere is romantic and sophisticated.  The menu is thoughtfully crafted with local ingredients, and the food was absolutely delightful.   It would be a shame to come to Santorini and miss this experience.

>>Psorias.  Far from fancy, this cliffside spot in the Southern part of the island is a locals hidden gem.  Get the tuna and the ceviche, they’re both the best I’ve ever had.  Seriously. Service will be slow, but prices are more than affordable and you get the opportunity to watch dingys take the uber rich out to their mega yachts down at the port below, which is also exciting. 

>Seaside by Noto. Great fish and tableside tzaiki steps from the sandy black beach, Seaside is a great posh spot serving up modern Greek cuisine.   Felt a little L.A. to us, but the sceney atmosphere is fun and lively.

>Fino Cocktail Bar. Not necessarily traditional Greek food, but the vibe of this low key cocktail bar tucked off of the busy streets of Oia has pretty exceptional food.  We couldn’t recommend the lobster roll apps more.

>Buddha Bar. Breathtaking place to watch the sunset. Creative and fun cocktail menu and a variety of sushi rolls and sashimi. I forget what this cheese appetizer was called, but just show this photo to the waiter and order 5, it was heaven.

<Passagio. Creative healthy spot offering greek yogurt bowls, smoothies, fresh juice, and a variety of salads and sandwiches.  Eat upstairs on the rooftop for a beautiful view.  Service is painful, so expect to wait. 

<Pelekanos. Nice little lunch spot with a gorgeous view.  I wouldn’t go out of my way to eat here, but it’s worth popping into if you’re looking for some R&R mid Oia tourist shuffle. Get the watermelon salad, so refreshing. 

<<|| I T I N E R A R Y ||>>

Day 1: Rent car, check in, sunset in Oia. Then you can eat at whichever touristy restaurant you’ve been researching to get it out of your system.  Get the whole fish fileted tableside and a huge greek salad.  Can’t go wrong with either of those anywhere.  

Day 2: Espresso freddo + baklava.  Stroll through streets of Oia for daytime pictures, shopping and frozen greek yogurt.  Make the trek down the stairs in Oia and take the little walking path to cliff dive. Reward yourself with a cocktail with a view.  Order the Greek Salad & the watermelon salad from Pelekanos. Back to the place to freshen up and swim. Sunset, dinner @ Maximy Mas.

Day 3: Espresso freddo + baklava. Boat Day.  Dinner @ Psorias because you’ll already be dirty from the boat and your boat docks right below the restaurant. Home to shower after dinner, and out for drinks in Thira. Start at Tango Bar with an aperol spritz. It’s the best nightlife spot on the island.

Day 4: Espresso freddo + baklava. Dune Buggy AM to different beaches and explore the island. Opt for lunch and daybeds at Kamari, by far my favorite beach.   Go off roading in your dune buggy before freshening up for dinner @ Selene.

Day 5: Espresso freddo + baklava. Exploring Thira by daylight, Wine Tasting, ending at Santos Winery for sunset, dinner @ Seaside by Notos.

<< T R A V E L  T I P S >>

-Don’t swim in the ‘hot springs’.  The water isn’t warm enough to kill bacteria, just a few degrees hotter than the ocean.  Which means you’re basically just dunking in a cest pool

-Don’t bring heels.  Petite wedges, if you must, but heels of any sort – even chunky ones – are a liability here and not worth the trip to the hospital.

-There’s no such thing as too much baklava.

-There is such a think as too much ouzo.

-Don’t ride the donkeys, it’s animal abuse.

-Do get an international drivers license before you go. It  costs $35 at AAA.

Shop my look: The blue button down shirt dress is from Koy Resorts, all sandals are from Malvados.