The Perfect Itinerary for Two Days in Santorini

Spending only two days in Santorini is going to fly by!

From the moment you arrive, you’ll be captivated by the island’s beauty and charm. Wander through the narrow streets of Oia, with its iconic blue-domed churches and whitewashed buildings perched on the cliffs. Take in the breathtaking views of the caldera and the shimmering Aegean Sea as you explore the picturesque villages and boutique shops.

Indulge in the delectable local cuisine, savoring traditional Greek dishes and sipping on refreshing local wines. Don’t forget to immerse yourself in the island’s rich history and culture by visiting ancient sites like Akrotiri or exploring the fascinating museums. As the sun begins to set, find a cozy spot to witness the famous Santorini sunset, painting the sky with hues of gold, pink, and orange.

Two days in Santorini is better than one day, buts its still not enough. I would recommend at least three to four days.

And remember, the below itinerary is just a suggestion. You can customize it based on your preferences and the time you have available. Santorini offers a multitude of experiences, from exploring its ancient history to indulging in its culinary delights and enjoying its stunning natural beauty.

To help you make the most of your two days in Santorini, Greece, this itinerary will not only help you navigate the island’s highlights, but also soak up it’s wonderful beaches, from Red Beach to Black Sand Beach!

Start your Morning Cruising the Caldera

Climb aboard the 74-foot Ocean Voyager or the 80-foot Tahiti catamaran for a 5-hour cruise around Santorini in the Aegean Sea. Set off on a journey of discovery that will first take you to the hot springs, then the Red Beach, and finally the White Beach. Swim and snorkel and tuck into a delicious meal onboard.

Start your adventure with a comfortable hotel pickup and set sail for beautiful Red Beach (picture below) to swim and snorkel.

Continue to a secluded White Beach, only accessible from the sea, for more swimming and snorkeling in the shadow of the towering white cliffs. Onboard the catamaran, savor a barbecue supper of salads and grilled meat and veggie options.

Buy a ticket in advance to make sure that you have a ticket for the specific day you want to go.

Hike to Skaros Rock

Embark on an unforgettable hiking adventure to Skaros Rock in Santorini. Your hike to the Skaros rock starts in Imerovigli and the church of Agios Georgios (Saint George). The church is the perfect place for preparation and relaxation before the hiking.

This iconic landmark perched atop a dramatic cliff offers breathtaking panoramic views of the Aegean Sea and the island’s picturesque caldera. As you navigate the winding path (see picture below), you’ll be immersed in the island’s natural beauty, passing by charming villages and vineyards along the way.

The reward at the end of the trail is truly awe-inspiring, with the opportunity to witness a magical sunset or simply soak in the awe-inspiring vistas.

How to Get to Skaros Rock

The Skaros Rock hike is really pretty straightforward, with one way down and back.

The path is clearly marked and begins in Imerovigli, on the stairs that lead down from the Grace Hotel (I can guarantee you’ll be staring at their pool enviously as you make the sweaty return journey back up the stairs to Imerovigli!).

Alternatively, if you’re completing the Fira to Oia hike, you can follow the path left from Blue Note Restaurant.

How Long is the Skaros Rock Hike?

The hike takes about 45 minutes one way from the edge of Imerovigli to the outcrop, but shouldn’t be underestimated; it’s mostly up and down, and absolutely should be avoided in the middle of the day when the heat is searing (we know this because we made this mistake so you don’t have to).

You could also do the Skaros Rock hike as part of your longer Fira to Oia hike (guide coming soon!) – just add another 1-1.5 hours to your total itinerary.

Hiking to Skaros Rock is not just an exploration of nature, but also a journey into the history and charm of Santorini. So lace up your hiking boots (or gym shoes), breathe in the fresh island air, and get ready for an adventure that will leave you with lasting memories.

Best of all, the hike is FREE but make sure to bring plenty of water! Try to avoid hiking this in the middle of the day (I learned the hard way) and please wear proper sun protection!

Take a Sunset Winery Tour

Are you ready for some relaxation after your busy day?

How about learning about the history of winemaking in Santorini and what makes it so famous all over the world?

Visit both traditional and modern wineries and have the chance to witness how Santorinian winemaking has grown over time. Taste unique signature wines at each location.

Immerse yourself in Koutsoyannopoulos, which hosts important artwork by Greek and foreign artists in its old winery dating back to 1861. Discover the fascinating grounds, including a modern winery offering renowned products of high quality. 

Admire incredible views over the Caldera and volcanic islands from Venetsanos winery. First built in 1947, take the chance to discover the history and traditions as well as new winemaking techniques. Finally, visit Roussos, one of the most traditional wineries in Santorini.

Enjoy an Evening Stroll

You’ve had an extremely long day by now and it’s time to wind down.

Take in the last views of the caldera or grab a traditional Greek dish on the balcony of the many restaurants above the Aegean Sea. Look for crowded restaurants (worth the wait) or highly rated restaurants using Google Maps or Apple Maps before you even step foot into a restaurant. 

You don’t want to get stuck with an incredible view and a less than desirable palette of food. 

Traveler Tip: The restaurants overlooking the caldera will be much more expensive than those inland.

Start your Next Day…

Saddle up and embark on a breathtaking journey through the enchanting landscapes of Santorini on horseback. Feel the wind in your hair as you trot along the winding paths that lead you to hidden treasures and panoramic views.

Ride along the shores of Vlichada on horseback and take in the views of this volcanic beach. Stop for photos and enjoy the support of an on-hand guide.

Begin your horse riding adventure by having an expert show you the basics with all the necessary equipment. After starting your journey at the magical dunes of Caldera Beach, head to the Santorini fields to admire the unblemished beauty of nature, taking in panoramic views of the Aegean Sea.

Next, your path will lead you to the black beach of Vlichada, where you’ll ride along the shoreline dipping in and out of the water’s edge.

Here you’ll have the chance to stop and take photos of the surrounding landscape and appreciate the picturesque sand dunes all around. Finally, you’ll continue along a route that takes you back to your stable, finishing your journey where you began but enriched with memories that will last a lifetime.

Book your tour in advance for the specific day you want to go.

Lunch & Cliff Jump at Amoudi Bay

Amoudi Bay is the hidden jewel of Santorini. And, while finding it can be a little challenging, it’s well worth the effort. This harbor has great seaside taverns and also one of the best places to swim in Santorini.

Did I mention that cliff jumping and swimming are FREE?!

You may want to book an afternoon lunch at one of the seaside restaurants at least a week in advance because it’s very busy in the high season (June – September).

Below is a map of how to find the secret swimming spot and where to cliff jump.

Take a Cooking Class

After swimming and catching rays by the seashore, you will be ready for your next traditional Greek meal.

And that’s why I recommend taking a traditional Greek cooking class.

I try to book a cooking class in every country that I visit. If you know, you know!

I have loved cooking classes in Greece, Spain, Thailand and Italy. In fact, there hasn’t been a cooking class I have not enjoyed!

Cook a 4-course meal with a chef, based on the Cycladic and Mediterranean cuisine in Santorini. Wander in the brewery and then feast on a full meal with a craft beer while enjoying the scenery.

Just make sure to bring an appetite!

In Conclusion

If you’re lucky enough to have more than two days in Santorini, consider checking out the Top 10 Things to Do in Santorini.

Like, visit the ancient site of Akrotiri and the Akrotiri Lighthouse for sunset!

Relax on the unique black sand beaches of Perissa or Kamari.

Take a wine tour and visit local vineyards to sample Santorini’s famous wines and so much more!

For more information, check out this super detailed Santorini Travel Guide I wrote that includes more things to do, costs, safety tips, transportation advice, and ways to save money

Book Your Trip Now!

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For companies, check out my favorite travel companies section that includes even more of my favorite travel companies that will help you value travel!

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