The first thing you notice is not the view. Not exactly. It’s the light. It’s a quality of light that feels different, ancient, almost liquid. It pours over the landscape, clarifying the impossible white of the villages and deepening the Aegean blue to a shade you’ve only ever seen in paintings. Then comes the air—dry, warm, scented with salt, wild thyme, and the faint, mineral tang of volcanic earth.
You have arrived. You are standing on the rim of a legend, a crescent-moon island cradling the ghost of a volcano. The view, when you finally let your eyes settle on it, is everything you were promised, and yet, infinitely more. It’s a sight that can, and should, stop your heart for a moment.
Welcome to Santorini.
Your first day here is precious. It’s a delicate balance between the magnetic pull of the iconic and the quiet whisper of the authentic. It’s easy to get it wrong—to rush, to follow the crowds, to end up feeling like you’ve merely observed the island from behind a velvet rope. But it’s just as easy, with a little intention and strategy, to get it profoundly right.
This is not an itinerary designed to help you “see it all.” That is a fool’s errand. This is a narrative guide to your first 24 hours, a curated experience designed to connect you to the island’s rhythm, to build your day towards a crescendo of beauty, and to leave you at the end of it feeling not exhausted, but utterly, incandescently alive. We will walk the path of a pilgrimage, from the awakening capital to the legendary sunset point, and we will do it with the soul of a storyteller, not the haste of a tourist.
Contents
Your First 24 Hours
Before we take a single step, we must establish the philosophy of our day. Great travel is not about what you do, but how you do it. These principles will be our compass.
Rule of Day 1 – Don’t Rush the Sunset
This is the single most important piece of advice I can offer. The number one mistake travelers make in Santorini is treating the day as a frantic preamble to the Oia sunset. They rush through meals, tick off sights, and arrive in Oia frazzled and stressed, only to battle a wall of people for a glimpse of the main event.
We will not do this.
Our day is a slow burn. It is a symphony in three movements, and the sunset is the final, glorious chord, not the entire piece. We will earn our sunset. We will build towards it, arriving in Oia with a sense of accomplishment and wonder, ready to receive its beauty not with anxiety, but with grace.
Where You Wake Up Matters
Your first day’s rhythm will be influenced by where you wake up. This itinerary is designed to be adaptable, but it’s helpful to know your starting point.
- If you’re in Fira or Firostefani, You are perfectly positioned. Our journey begins at your doorstep.
- If you’re in Imerovigli: You are in the middle of our main path, giving you the luxury of a slightly later start.
- If you’re in Oia: You will live the day in reverse, starting with the quiet magic of an Oia morning and perhaps journeying towards Fira.
- If you’re in Megalochori, Pyrgos, or the southern beaches: Your day will involve a bit more travel, but it will reward you with a deeper appreciation for the island’s diversity as you journey towards the caldera’s edge.
What to Pack for the Day
You will leave your hotel in the morning and may not return until long after dark. Prepare accordingly. This is your essential day-pack:
- The Right Shoes: This is non-negotiable. You will be walking on ancient stone paths, uneven stairs, and cobblestones. Wear the most comfortable, broken-in walking shoes or supportive sandals you own. Leave the heels at the hotel.
- Sun Protection: The Aegean sun is glorious but unforgiving. High-SPF sunscreen, a wide-brimmed hat, and quality sunglasses are your essential armor.
- Water, and More Water: Stay hydrated. Carry a reusable water bottle and refill it whenever you can. You will drink more than you think.
- Cash (Euros): While most restaurants and shops accept cards, many smaller bakeries, local tavernas, and market stalls are cash-only. It’s also essential for buses and tips.
- A Portable Charger: Between navigating with maps and taking hundreds of photos, your phone battery will drain faster than you expect. A power bank is a lifesaver.
- A Light Layer: Even after a warm day, the wind can pick up on the caldera once the sun goes down. A light sweater, scarf, or jacket will be a welcome comfort.
Getting Around
For this specific itinerary, we will be relying primarily on our own two feet. However, understanding your transport options is key.
- On Foot: The caldera path between Fira and Oia is one of the world’s great walks. This will be the centrepiece of our day.
- Local Bus (KTEL): The public bus system is efficient and incredibly affordable (usually under €2 per trip). It’s a fantastic way to travel between the main villages if you choose not to do the full hike. The main bus depot is in Fira.
- ATV/Quad Bike: Renting an ATV is a popular way to explore the island, offering freedom and a sense of adventure. However, for this specific Day 1 itinerary focused on the caldera path, it’s less necessary. It’s a better option for Day 2 or 3 when you explore the beaches and wineries.
- Rental Car: A small rental car offers comfort and air conditioning but can be a liability in the narrow, congested streets of the villages. Parking is notoriously difficult.
- Taxis & Pre-booked Transfers: Taxis are available but are few in number and can be very expensive. Pre-booking a transfer, especially for your return journey from Oia after sunset, is a wise and stress-saving strategy.
The Classic Caldera Itinerary
This path is designed for the first-time visitor, the traveler who wants to experience the quintessential, heart-stopping beauty of the caldera. It is a journey of about 10 kilometers (6 miles) on foot, but more importantly, it is a journey through the very soul of Santorini.
Morning (8:00 AM – 12:00 PM): Fira – The Awakening Capital
We begin our day in Fira, the island’s bustling capital. In the early morning, before the cruise ship crowds arrive, the village has a different energy—a local, authentic hum.
8:00 AM: The Perfect Greek Breakfast Your first mission is to bypass the overpriced caldera-front cafes with their generic “continental breakfast” signs. Instead, we seek out a local fournos, a traditional bakery. Follow the scent of freshly baked bread and pastries. Here, you will find the fuel for your day. Order a spanakopita (spinach pie) or a tiropita (cheese pie), its flaky phyllo pastry shattering at the first bite. It’s warm, savory, and deeply satisfying. Pair it with a strong Greek coffee—a freddo espresso if you want it iced and invigorating. Find a small bench away from the main path, and eat your breakfast as you watch the village come to life. This is not just a meal; it is your first act of local immersion.
9:00 AM: A Walk Through Fira’s Heart Now, we explore. With the sun still low in the sky, we dive into the labyrinthine alleys of Fira. The goal is to get intentionally lost. Wander away from the main caldera path, deeper into the residential warren. Here, the world of souvenir shops gives way to quiet courtyards, pots of vibrant bougainvillea spilling over whitewashed walls, and the occasional blue-domed chapel hiding around a corner.Make your way to the Three Bells of Fira (the iconic blue-domed church in Firostefani, a short walk from Fira). This is one of the most photographed spots on the island, and by visiting in the morning, you will experience it with a fraction of the afternoon crowds. Frame your photo, but then put the camera down. Absorb the silence, the panoramic view, the sheer, impossible beauty of it all.
11:00 AM: The Cable Car & The Old Port From the center of Fira, we will take a journey down the cliff face. You have two options: the cable car or the winding steps. We will take the cable car down. The five-minute ride is a spectacle in itself, offering a dizzying, cinematic perspective of the volcanic cliffs.You will arrive at the Old Port of Gialos. This was once the island’s main commercial hub. Today, it’s a charming collection of waterside tavernas and small shops. This is a good place for a mid-morning refreshment. Sit at a cafe, feel the sea breeze, and watch the small boats bob in the impossibly clear water.For the journey back up, you have three choices: the cable car, the steps, or the donkeys. I urge you to choose the cable car or the steps. The welfare of the donkeys and mules used for tourist transport is a significant and troubling issue. Choosing not to ride is a small but powerful act of responsible tourism. The walk up the 588 steps is strenuous but rewarding, a zigzagging journey through the history of the island.
Midday (12:00 PM – 4:00 PM): The Legendary Fira to Oia Hike
This is the heart of our day. This is where we earn our sunset. The hike from Fira to Oia is not just a walk; it is a pilgrimage along the rim of the volcano. It is one of the most beautiful coastal walks in the world.
The Decision Point: This hike takes between 3 to 5 hours, depending on your pace and how often you stop for photos (which will be often). It requires a moderate level of fitness. If the sun is too intense, or if you are not prepared for a long walk, there is an excellent alternative: take the bus from Fira to Imerovigli. Explore Imerovigli and the path around Skaros Rock, and then take another bus from Imerovigli to Oia. This allows you to experience the most beautiful section of the hike without committing to the full distance.
The Trail, Chapter by Chapter:
- Chapter 1: Fira to Firostefani. This first section is a gentle, paved path that winds through the village of Firostefani. The views are constant and spectacular.
- Chapter 2: Firostefani to Imerovigli. The path continues, leading you to Imerovigli, known as the “Balcony of the Aegean.” This is the highest point of the caldera, and the panoramic views are simply breathtaking. This is a perfect place to pause. If you have the energy, consider the short detour to Skaros Rock, a dramatic headland that was once the site of a Venetian castle.
- Chapter 3: The Wilderness. After Imerovigli, the paved path gives way to a more rugged, natural trail. This is where you leave the villages behind. The silence here is profound, broken only by the wind and the crunch of volcanic scree under your feet. You will pass solitary chapels, their white walls a stark contrast to the red earth and blue sea. This section feels ancient and wild. It is the spiritual core of the hike.
- The Experience: This walk is a meditation. It’s a chance to feel the scale of the caldera, to understand the island not as a collection of villages, but as a single, magnificent geological entity. You will feel the sun on your skin, the wind in your hair, and a growing sense of awe with every step.
Late Afternoon (4:00 PM – Sunset): Oia – The Prelude to Gold
You will likely arrive in Oia tired, dusty, and thirsty. Your first view of the village from the hiking trail—a cascade of white buildings tumbling down the cliffside—is a moment of pure triumph.
4:00 PM: Arrival & Rejuvenation Your first stop in Oia is not for a photo. It’s for a reward. Find a small cafe or a gelateria. Order the most refreshing drink you can imagine—a freshly squeezed orange juice, a cold beer, or a scoop of artisanal gelato. Find a shaded spot, sit down, and simply breathe. You’ve made it. You are here. Let the beauty of the village wash over you before you dive into its streets.
4:30 PM: Exploring Oia’s Labyrinth Now, we explore Oia, but we do it strategically. The main marble path will be starting to fill with people making their way to the sunset spot. We will turn away from them. Duck into the narrow side alleys. Discover the hidden staircases that lead to nowhere and everywhere.Seek out the famous Atlantis Books, a charming, cave-like bookstore that is a haven for literature lovers. Find the iconic three blue domes, but try to photograph them from a unique angle. The real magic of Oia is found in these quiet moments of discovery, away from the main thoroughfare.
The Strategic Sunset Choice: As sunset approaches, the crowds in Oia swell to a fever pitch. Choosing where to watch it from will define your experience.
- Option A: The Byzantine Castle Ruins (The Classic, Crowded Choice). This is the most famous viewpoint in Santorini. It offers the iconic, postcard view of the windmills and the village bathed in golden light. The downside? It is incredibly crowded. To get a good spot, you will need to claim your territory at least 90 minutes before sunset. It’s an experience, but it can be intense.
- Option B: A Sunset Bar (The Comfortable Choice). Many bars and restaurants in Oia have terraces perfectly positioned for the sunset. This is a more comfortable, civilized option, but it comes at a price. You will need to book a table far in advance and be prepared for a minimum spend.
- Option C: The Path Back (The Hiker’s Choice). My personal recommendation. Instead of crowding into the castle, walk a little way back on the hiking trail you just arrived on. Find a quiet ledge or a spot by a small chapel. Here, you will have a more panoramic, peaceful, and personal view. You will see the sun dip into the sea, and you will see the golden light illuminate the entire village of Oia from a distance. It is, in my opinion, a far more profound experience.
Evening (Sunset Onward): The Afterglow & Dinner
The moment the sun disappears below the horizon, a strange and beautiful thing happens in Oia: people applaud. Then, there is a mass exodus. This is your cue to stay.
The Post-Sunset Moment: The Blue Hour The 30 minutes after the sun has set is known as the “blue hour.” The sky glows with soft hues of pink, purple, and deep blue, and the lights of the village begin to twinkle on. It is a time of pure magic, and with the crowds dispersing, you will have space to breathe it all in. This is the time to take a slow walk back through the now-enchanted streets of Oia.
Dinner: Oia vs. Ammoudi Bay You have two excellent choices for your celebratory dinner.
- Dinner in Oia: Staying in Oia for dinner offers convenience and a wonderfully romantic atmosphere. Choose a restaurant tucked away in a side alley rather than one on the main path for a more intimate experience.
- Dinner in Ammoudi Bay (The Ultimate Reward): For a truly unforgettable meal, take the 300 steps down from Oia to the tiny, charming fishing port of Ammoudi Bay. Here, a handful of seafood tavernas sit right on the water’s edge. You will choose your fish from the day’s catch, and it will be grilled to perfection. Eating fresh seafood with the sound of the waves lapping just feet from your table, looking up at the illuminated cliffs of Oia, is the perfect end to your pilgrimage.
- Getting Home: After dinner, you will be tired. The walk back up the steps from Ammoudi Bay is daunting. There is a taxi stand at the bottom. It is wise to have pre-booked a transfer, or to be prepared to wait for a taxi. The last buses from Oia back to Fira will be very crowded.
Alternative Day 1 – The Vineyard & Soul Itinerary
If the idea of a long hike and caldera crowds doesn’t appeal, or if you are a returning visitor, this alternative Day 1 offers a deeper, more soulful immersion into the island’s interior.
- Morning: The Timeless Village of Megalochori. Start your day by getting lost in the maze-like streets of Megalochori, one of the most traditional and picturesque villages on the island. Discover its hidden squares, beautiful bell towers, and historic wine canavas.
- Midday: A Journey Through Volcanic Wine. Santorini’s wine is unique in the world, grown in volcanic soil. Visit one of the island’s renowned wineries. Choose Santo Wines for its staggering caldera views, Venetsanos Winery for its incredible architecture built into the cliffside, or Gavalas Winery for a more traditional, family-run experience. Do a tasting and learn about the crisp, mineral-rich Assyrtiko grape.
- Afternoon: Ancient History and Lunar Landscapes. Visit the incredible prehistoric ruins of Akrotiri, a Minoan Bronze Age settlement preserved in volcanic ash, often called the “Minoan Pompeii.” Afterward, drive to the nearby Red Beach and Vlychada Beach to witness the island’s dramatic, multi-colored volcanic geology.
- Evening: A Different Sunset. For a completely different and uncrowded sunset experience, drive to the Akrotiri Lighthouse on the island’s southwestern tip. Watch the sun sink into the Aegean from this wild, windswept vantage point. Follow it with a relaxed, authentic dinner at a family-run taverna in the village of Akrotiri or nearby Megalochori.
The End of the Beginning
As your first day in Santorini draws to a close, whether you are finishing a glass of wine in Ammoudi Bay or driving back from a quiet village taverna, take a moment to reflect. You did not just see the sights. You walked the earth. You felt the sun. You tasted the wine. You earned the sunset.
You have oriented yourself not just to the island’s geography, but to its soul. You have filled your senses, challenged your body, and rewarded yourself with moments of profound beauty and quiet contemplation.
This was not just Day 1. This was the beginning of your story. And the rest of the island is now waiting for you to write the next chapter.
Frequently Asked Questions (FAQ)
- Is the Fira to Oia hike difficult? It is a moderately challenging 10km (6-mile) walk with some uneven terrain and hills. It requires a good pair of shoes and a reasonable level of fitness. The main challenge is often the heat, so it’s best to avoid hiking during the peak midday hours in the summer.
- How much should I budget for my first day in Santorini? Excluding accommodation, a comfortable budget for a day following this itinerary would be €100-€150 per person. This would cover a bakery breakfast, a casual lunch or snacks, a nice dinner with wine in Ammoudi Bay, drinks, and transport (bus or a shared taxi back from Oia).
- Is it better to stay in Fira or Oia? It depends on your preference. Stay in Fira for a more central location, vibrant nightlife, and better transport links. Stay in Oia for a more romantic, luxurious, and quiet (except at sunset) atmosphere.
- Do I need to book restaurants in advance? For a casual lunch, no. For a sunset-view bar or a popular dinner restaurant in Oia or Ammoudi Bay, booking at least a day or two in advance is highly recommended, especially in the high season.
- What is the best month to visit Santorini? The shoulder seasons—May, June, and September—are often considered the best time to visit. The weather is beautiful, the sea is warm, and the crowds are more manageable than in the peak months of July and August.
