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Sunsets, Cobblestones, and All the Feta You Can Eat - All you need to know about Santorini
Summer is coming and so are you to Santorini, are you prepared? No? "Not yet" I say as I compose this Santorini guide for you.
Jorden Daffer
10 min read

Decoding the Whereabouts of Sleep

Santorini doesn't just offer a backdrop for your dream vacation; it also comes with a multitude of accommodation options tailored to every fantasy. Now, if you're a first-timer, Fira might be your best bet. Situated as the island's capital, it's like the Times Square of Santorini—buzzing with life and neon lights, minus the neon. The location is as central as you can get, with easy access to public transportation, making it a hub for exploring the island’s other picturesque locales. Oia, on the other hand, is the place you've probably seen on Instagram a thousand times. It's perfect for those romantic getaways where every sunset feels like a renewal of vows. However, it's a bit like dining at a fancy restaurant: stunning but comes at a premium price. Now, if you're more of a beach bum and your vacation mantra is 'sun, sea, and sand,' then you'll likely find your Eden in Kamari or Perissa. These coastal towns provide plenty of opportunities to splash around, with the convenience of beachside cafes and bars that promise not to judge your sandy feet.


Photo by Matt Artz on Unsplash

Sightseeing with a Strategy

So you've unpacked your bags and are itching to explore—where should you go first? If your entourage includes tiny tots, you might want to make a beeline for Kamari Beach. With its sandy stretches and myriad water activities, it's an ideal playground for both young and old. The beach is well-organized and offers plenty of loungers, parasols, and even a cinema—yes, a cinema. Another family-friendly option is Fira, where you get a taste of the quintessential Santorini without rubbing shoulders with the entire population of tourists. For the honeymooners, anniversary celebrators, or simply the romantically inclined, Oia is your endgame. Stroll through its labyrinthine streets, pop into artisan shops, and play hide-and-seek with the sun as it sets over the Caldera. If it's the road less traveled you're after, then Pyrgos is your unsung hero. This charming village offers narrow, winding paths that guide you through its historical charm, along with fewer crowds and more authentic local experiences.


Photo by Link Hoang on Unsplash

Deals, Deals, Deals!

We all know that a great vacation deal can make the difference between a good trip and a great one. In Santorini, there are several ways to bag that bargain. Booking websites like and Airbnb have essentially become the modern traveler's best friend, offering a range of options from luxurious villas to cozy bed and breakfasts. But here's a pro tip: sometimes, going old-school and reaching out to the hotel directly can work in your favor. Why? Well, they often save their best rates for direct bookings. If your travel dates are flexible, consider swinging by during the shoulder seasons of May or late September. The weather is almost as generous as the summer months, but without the summer crowds, which means you could even score that ocean-view room without having to auction off a kidney.

When Not to Go

Timing isn't just crucial in comedy; it's also key in travel. For Santorini, there are times when it's better to admire its beauty from afar—on a postcard. Take August, for example. If your idea of a vacation doesn't include getting to know hundreds of tourists on a very intimate level, then steer clear of this month. It’s also when the Mediterranean sun seems to be on a relentless mission to melt everything in its path. Conversely, if you're not a fan of brisk, chilly winds that can sweep you off your feet—literally—avoid the winter months of January and February. Santorini is at its best when you can comfortably explore its outdoor beauty without rushing back to your room for an extra layer or a blast of A/C.

Timing Your Stay and Bookings

You've probably heard the saying, "Good things come to those who wait." But when it comes to booking your Santorini vacation, good things actually come to those who act early. A four-to-five-day stay generally hits the sweet spot, giving you ample time to absorb the island's iconic beauty and still leave room for some delightful detours. This length of stay allows you to take those Insta-worthy photos in Oia, relax on the beaches of Kamari, discover the historical layers in Akrotiri, and even sneak in a wine-tasting session. Now, if you're wondering when to click that 'Book Now' button, the ideal window is around 3 to 6 months before your intended visit. It's that magic period where availability and affordability dance in a perfect tango. But let's say you're not a planner. Let's say you're spontaneous—reckless even—and you decide to book a last-minute trip. No worries! Santorini is full of pleasant surprises, and you can still find hidden gems in less touristy areas like Pyrgos or Akrotiri, which often have last-minute availability.


Photo by Andreas M on Unsplash

Tricks to Beat the Crowds

For those of you who'd like to experience Santorini without the side order of crowds, there are tricks to escape the throngs of sun-hungry tourists. In Oia, the sunset is a public affair, akin to a daily festival where everyone gathers to celebrate the sun's swan song. However, you can circumvent this by reserving a spot at a restaurant with a panoramic view. Pair your sunset with a delightful dinner, and you've got yourself a two-for-one deal. Another alternative is to explore the sea by boat. Many companies offer private or semi-private tours that not only give you an exclusive experience but also provide a unique vantage point for those famous Santorini sunsets. And if you're really looking to dodge the crowds, consider visiting off-the-beaten-path attractions during peak hours and saving the popular spots for early morning or late afternoon visits.

Freebies and Views

Everyone loves a freebie, and in Santorini, nature generously offers some of the best. Sure, you can't take home the sunset, but you can certainly relish it at zero cost. And if you're a wanderlust-infused soul, strolling around Fira is your best bet for a free experience. The architecture itself is an art form, and the buzzing atmosphere won't cost you a dime. But let's say you're itching for a different angle—a bird's eye view, perhaps? Skaros Rock in Imerovigli is your spot. It’s far less crowded than the famous Oia lookout but offers a panoramic view that could easily be a Windows desktop background. Here, the experience is free, yet priceless—just like the best things in life.

skaros rock santorini, mountain, lake

Culture and Payments

As for culture, Santorini offers a rich tapestry that extends beyond its picturesque landscapes. This is an island that invites you to dig deep—both into its ancient history and its culinary delights. From the unique volcanic wines that echo the island's turbulent geological past to the blue-domed churches that seem to sprout like charming mushrooms, there's a bit of culture around every corner. Now, you might be wondering about the practicalities of payments during your stay. Credit cards are widely accepted, especially in the more touristy areas, but it's always good to keep a stash of cash. Small tavernas and the occasional bus ride might not accept cards, and you wouldn't want to miss out on a delicious gyro or a scenic route because you’re strapped for cash.


Photo by Markus Spiske on Unsplash

Getting Around

Moving around in Santorini can be both an adventure and a strategic challenge, much like an exciting round of chess with Mother Nature. The island's local bus system is highly efficient, but during peak season, you may find yourself standing a little too close for comfort with your fellow passengers. Taxis are another option, particularly useful for those late-night returns or when you're laden with shopping bags from Fira. However, if you're not careful, taxi fares can quickly accumulate, making a significant dent in your budget. Walking is the ideal mode of transport for shorter distances and offers you the luxury of taking your sweet time to soak in the surroundings. The cobblestone streets add a rustic touch to your journey, reminding you at every step that you're far from the urban chaos. For the adrenaline junkies, renting a bike or an ATV can turn the island into your playground, giving you the freedom to explore those hidden corners that buses and taxis can't reach.


Photo by Devon Divine on Unsplash

Hidden Treasures and Fine Dining

Not all of Santorini's gems are in plain sight; some require a bit of treasure hunting. The Akrotiri Archaeological Site, for example, is a time capsule that takes you back to the prehistoric city destroyed by a volcanic eruption. Vlychada Beach, with its lunar-like landscape, offers a unique beach experience that's worlds apart from the more popular beaches. As for your culinary adventures, Santorini doesn't disappoint. If you're on a budget but still want to taste the essence of the island, Lucky's Souvlakis in Fira is your go-to for mouthwatering street food. However, if you're willing to splurge, Ambrosia in Oia offers an unparalleled dining experience. Imagine savoring gourmet Greek cuisine as you overlook the Caldera, the sea sparkling below as if applauding your excellent choice in restaurants.


Photo by Chris Curry on Unsplash

The Little Things

Let's not forget the little things, those tiny but important details that can make or break your vacation. First, Santorini has its own 'windy season,' usually in July and August, when the meltemi winds swoop down on the island. So ladies, you might want to think twice before wearing that flowy summer dress unless you're aiming for a Marilyn Monroe moment. As for footwear, those charming cobblestone streets can quickly turn into ankle-breakers if you're sporting high heels or flimsy flip-flops. A sturdy pair of walking shoes will be your best companion. And finally, the electrical plugs in Greece are of the Type C and Type F variety. If your devices use a different plug type, an adapter will be your lifeline. These might seem like tiny details, but trust me, they can make a world of difference in the quality of your trip.


Photo by Karen Gillman on Unsplash

Santorini FAQs

Best Time to Visit: Late spring to early fall.

Is Santorini Expensive: It can be. Especially in Oia, you might feel like you're living a billionaire's life, minus the billions.

Getting Around: Local buses are your most economical bet, but taxis, rentals, and even your own two feet are excellent alternatives.

Tipping: Not mandatory but appreciated. A 5-10% tip can go a long way in showing your appreciation for good service.

So there you have it, an all-inclusive guide to Santorini. Pack your bags, book your flights, and get ready to live your Greek dream. Because as anyone who’s been there will tell you, Santorini isn't just a destination; it's an experience that stays with you long after you've shaken the last grain of sand from your shoes.

Jorden Daffer
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