Santorini in 48 Hours: A First-Time Itinerary for Oia, Views, and Sunset Spots

This post is part of my Greece travel series. Browse all my Greece travel guides in one place.

Santorini is one of the most photographed islands in the world, yet visiting in person still feels surreal.

This was my third time visiting Greece and one of my favorite stops during our Cyclades itinerary. While Santorini is often associated with honeymoons and luxury resorts, the island can absolutely be experienced in just 48 hours if you plan your stay strategically.

For first-time visitors, two days is enough time to experience:

• Oia’s cliffside views
• Caldera sunsets
• Boutique hotels
• Rooftop dining
• Walking paths along the sea
• Quiet mornings before the crowds arrive

Here is exactly how I would spend 48 hours in Santorini, Greece.

Is 48 Hours in Santorini Enough?

Yes, especially if this is your first visit.

Santorini is relatively small, and most visitors spend the majority of their time around:

• Oia
• Fira
• Imerovigli

While you could easily stay longer, two days gives you enough time to enjoy the atmosphere without feeling rushed.

The key is staying in the right location and slowing down rather than trying to check off every attraction on the island.

Where to Stay

For first-time visitors, I recommend staying in Oia.

Oia is known for its whitewashed buildings, blue domes, luxury cave hotels, and famous caldera sunsets. It is also one of the most walkable and visually stunning areas on the island.

During my stay, I focused primarily on Oia because it offers the best balance of:

• Views
• Restaurants
• Boutique hotels
• Walkability
• Sunset access

If possible, book a hotel with:

• A caldera view
• Outdoor terrace
• Small plunge pool or hot tub
• Breakfast included

Santorini is one of those destinations where the hotel experience becomes part of the trip itself.

We recommend staying at the Andronis Boutique Hotel, which sits right on the caldera edge in Oia. The suites are carved into the cliffside in traditional Cycladic style, all white-washed curves, natural stone, and organic-shaped walls. Minimalist without being cold. The private jacuzzi on the terrace faces the Aegean, and the infinity pool dissolves into the same view.

Best Things to Do in Santorini in 48 Hours

Book a Private Airport Transfer in Santorini

Santorini Airport may be small, but arrivals can feel surprisingly hectic depending on the time of day and number of incoming flights. Booking a private airport transfer made the entire arrival experience far smoother, especially after a long travel day through Greece.

Instead of waiting for shared shuttles or searching for taxis outside the airport, we had a private driver waiting upon arrival and were on our way to Oia within minutes.

For first-time visitors staying in Oia or along the caldera, private transfers are one of the easiest ways to start your Santorini itinerary stress-free.

Take a Private Santorini Wine and Village Tour

One of my biggest recommendations for first-time visitors to Santorini is booking a private island tour, especially if you only have 48 hours on the island.

Santorini’s roads are narrow, parking is limited, and moving efficiently between villages, wineries, and viewpoints requires local knowledge. Going private made the experience significantly more relaxed and allowed us to explore the island at our own pace without dealing with navigation or crowded group tours.

A private Santorini tour also gives you flexibility throughout the day. You can linger longer at wineries you enjoy, skip overcrowded areas, and discover smaller villages many visitors miss entirely.

For a shorter Santorini itinerary, it is one of the best ways to maximize your time.

What I Wore

Every outfit you see in these photos was chosen specifically for this trip, from what to wear on the plane to dinner on the last night. Shop my travel wardrobe and similar looks by destination on ShopMy.

Flying Dress Photo Shoot in Santorini

One of the most memorable experiences from our time in Santorini was doing a flying dress photo shoot with Alex at Sokolove Photographer in Oia. If you have ever dreamed of capturing those iconic Santorini cliffside photos with flowing dresses against the caldera backdrop, this is absolutely worth adding to your itinerary.

We booked a 30-minute session and enough time to capture multiple stunning shots around Oia without taking up half the day. Alex made the experience feel relaxed and natural, even during the busy morning crowds. The final images honestly looked like editorial travel photos and are the kind of keepsake photos you will actually want to print and hang on your wall.

For couples, solo travelers, best friend trips, or milestone celebrations, this is one of those unique Santorini experiences that feels touristy in the best possible way. Tell Alex I sent you!

Explore Imerovigli for Caldera Views

Imerovigli quickly became one of my favorite villages in Santorini.

Located at the highest point of the caldera rim, the village offers some of the best panoramic views on the island. Compared to Oia, Imerovigli feels quieter, slower, and slightly more residential.

The shopping also felt more curated and local.

We found:

• Handmade ceramics
• Hand-painted tiles
• Small food shops
• Local capers and fava products
• Boutique artisan stores

Imerovigli is ideal if you want beautiful Santorini views without the heavier crowds found in Oia during sunset hours.

Visit Megalochori Village in Santorini

Megalochori was one of the most underrated stops of the trip.

Many visitors skip the village because it is not known for sunsets, but it ended up being one of the most authentic-feeling places we visited in Santorini.

The village is filled with:

• Narrow Cycladic alleyways
• Traditional whitewashed homes
• Historic wine cellars
• Quiet courtyards
• Small local boutiques

Megalochori feels slower and far less commercialized compared to Oia and Fira.

We originally planned for a short stop but stayed much longer exploring the village and browsing local shops. It was one of the few places on the island that still felt calm and residential despite Santorini’s popularity.

Where to Eat in Santorini

Best Affordable Gyros in Oia: Souvlaki n’ Wrap

Souvlaki n’ Wrap, Oia, Santorini 847 02, Phone: +30 2286 072448

Santorini is known for caldera-view restaurants and luxury dining, but sometimes the best meals are the simplest ones.

Located in Oia, Souvlaki n’ Wrap became one of our favorite casual lunch spots during our Santorini itinerary. While many restaurants in Oia focus heavily on views and upscale pricing, this spot delivers fresh gyros, kebabs, falafel, and wraps at surprisingly affordable prices by Santorini standards.

Everything is made to order, portions are generous, and most dishes are under 10 euros.

We stopped here between exploring Oia’s cliffside streets, and it ended up being one of the best quick meals of the trip. It felt far more local and relaxed compared to the crowded caldera restaurants nearby.

If you are looking for:

• Affordable food in Oia
• Quick lunch spots in Santorini
• Casual Greek street food
• Fresh gyros in Santorini

this is absolutely worth visiting.

Best Thai Restaurant in Oia: Paradox Thai Food and Bar

Paradox Thai Food and Bar, Oia, Santorini 847 02, Phone: +30 2286 071675, Hours: Daily 1pm to 11pm

Paradox Thai Food and Bar was one of the biggest surprises of our Santorini trip.

Located near the Oia bus stop and slightly away from the main tourist pathways, the restaurant offers Thai and Asian dishes that feel like a welcome reset after several days of Greek food.

The atmosphere is casual, the staff was friendly, and the prices felt reasonable compared to many restaurants in Oia.

After days of seafood, Greek salads, and grilled meats, having a flavorful curry or plate of pad thai honestly hit differently.

For visitors spending multiple days island hopping through Greece, this is a great alternative dining option in Santorini when you want something outside the traditional Greek restaurant scene.

Sunset Dinner in Oia: Mia’s Restaurant

Mia’s Restaurant, Fira-Oia Regional Road, Oia, Santorini 847 02. Phone: +30 2286 072072, Hours: Monday 5:30pm to midnight, Tuesday to Sunday 12:30pm to midnight

Mia’s Restaurant was our sunset dinner reservation in Oia and one of the more elevated dining experiences of the trip.

Located along the caldera edge inside a traditional Cycladic-style residence, the restaurant focuses on modern Greek cuisine using fresh seafood, local cheeses, and vegetables sourced from farms throughout the Cyclades.

The setting feels elegant without becoming overly formal or staged.

We booked dinner around sunset, which I highly recommend if you want caldera views while dining. The upstairs terrace can become windy depending on the evening, although indoor seating is also beautifully done.

The cocktails were excellent and easily some of the best we had in Santorini.

While I was underwhelmed by the bread service, the overall experience, atmosphere, and sunset setting still made this one of the standout dinners of the trip.

Reservations are highly recommended during peak season.

Seafood Lunch by the Black Sand Beach: Savvas Popeye

Savvas Popeye, Agios Georgios Beach, Perivolos, Santorini 847 03, Phone: +30 2286 081332, Hours: Noon to 11 pm daily, early May through mid-October

Savvas Popeye offered a completely different side of Santorini compared to the polished caldera restaurants in Oia.

Located across from Agios Georgios Beach near Perivolos, this longtime seafood restaurant has been serving visitors since 1956. The atmosphere feels relaxed, local, and tied closely to the island’s fishing culture.

Fresh fish arrives daily from the family’s own fishing boat. Guests can choose directly from the fresh catch display before it is grilled simply and traditionally.

This ended up being one of my favorite meals in Santorini because it felt slower, more local, and less curated for tourism.

Do not skip:

• Santorini tomato fritters
• Grilled octopus
• Greek salad with local capers
• House white wine
• Fresh seafood plates

The tomato fritters in particular are one of the signature dishes of Santorini because of the island’s naturally sweet cherry tomatoes grown in volcanic soil.

Lunch here felt completely different from Oia. Sitting near the black sand beach with seafood and wine made Santorini feel less polished and more authentic in the best possible way.

That contrast is part of what makes the island worth experiencing beyond just the famous sunset views.

Best Time to Visit Santorini

I visited Santorini in May, and it was one of the best times to go.

The weather was warm enough for outdoor dining and walking, yet the island still felt manageable before peak summer crowds fully arrived.

For the best experience, visit:

• May
• Early June
• September
• Early October

July and August are significantly busier and hotter.

What to Wear in Santorini

Santorini is extremely photogenic, so lightweight and neutral outfits work especially well against the white architecture and blue water.

For this trip, I packed:

• Lightweight dresses
• Linen pieces
• Flat sandals
• Neutral layers
• Sunglasses
• A carry-on only wardrobe

Comfortable shoes are important because Santorini involves more walking and stairs than many people expect. See my outfit recommendations for Greece here and what to pack in your carry-on here.

Is Santorini Worth Visiting?

Absolutely.

Even after multiple trips to Greece, Santorini still feels visually striking every time I return. The island combines dramatic landscapes, architecture, boutique hospitality, and sunsets in a way that genuinely feels unique.

Yes, Santorini is popular. However, if you stay in the right area, wake up early, and slow your pace down, the island still feels incredibly special.

For first-time visitors to Greece, Santorini remains one of the most iconic stops in the Cyclades.

Plan Your Trip

If you are thinking about putting together a Santorini itinerary, Nomoon Travel can take care of it from transfers to day tours to hotel bookings.