5 Days in Santorini: The Ultimate Santorini Itinerary

Santorini 5 day itinerary
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The most iconic of the Greek islands, Santorini, and its sea of dazzling white Cycladic buildings, is recognizable worldwide. The volcanic shores and unbeatable sunsets on this crescent-shaped island promise endless beauty. But if you’re stumped on how to spend fives days in the Aegean, you’re in the right place. 

Santorini is a small group of islands located in the southernmost part of the Greek Cyclades. Formed after a massive volcanic eruption hundreds of years ago, the Caldera provides unrivaled sea and sunset vistas that draw in flocks of tourists every summer. 

Our ultimate Santorini 5 day itinerary covers all bases and then some. From the black sand beaches and quaint market towns to the panoramic bars and the island’s best party spots. Whatever’s drawn you to Santorini, it won’t disappoint, and our guide will make sure you see it all. Swap out the days as you wish, but make sure these sights are at the top of your Santorini agenda. 

Day 1 – Touring Oia 

Santorini 5 day itinerary
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Oia is the most famous of all Santorini’s villages. This charming, scenic town is located on the island’s northwest side and extends just two kilometers. Oia is the most popular area in Santorini, known for its unique architecture and sunsets, and should be the first stop on your Santorini 5 day itinerary.  

If your budget can stretch for it, Oia is one of the best places to stay. Bagging a night or two in one of the iconic cliff face cave-houses is a bucket-list-worthy experience. Still, the nearby village of Imerovigli is a great place to lodge, and you can easily hike from the quieter and cheaper town to Oia’s bustling streets.

For your first morning in Santorini, whether you’ve started with a scenic hike or an equally picturesque breakfast on your hotel terrace, Oia’s main street should be first on the agenda. This long road is one of the widest in the village and easily identifiable by its adornments of colorful flowers and street cats. 

The main street is signposted all over town and crosses along the top of a cliff. You can access it from any of the various branching passageways but getting lost along your way is all part of the enjoyment. 

Aside from the quaint arts and crafts shops, built into the ancient caves, the main street is perfect for stumbling upon viewpoints where you’ll find unspoiled sights of Santorini’s iconic blue domes stretching down to the sea. Morning on the main street promises the least crowds and cooler temperatures so that you can peruse freely. But the cool white buildings also provide shade and relief from Santorini’s beating summer sun. 

After a few hours traversing the uneven streets of Oia’s center, you’ll have built up an appetite. And what better way to kick-start your afternoon than with an iconic Greek lunch? Check out PitoGyros, a traditional grill house right in the center of Oia with some of the town’s best gyros at reasonable prices. This lunch spot is also great for vegetarians, be sure to try the halloumi pitta and tzatziki while you soak up the restaurant’s friendly atmosphere.  

Next up, consider visiting Oia Castle, just a 10-minute walk from PitoGyros and Oia’s main street. One of the best viewpoints on the island, the castle used to be a lookout to protect Santorini from pirates. Its ancient remnants provide a great taste of ancient Greek history for visitors. There’s no entrance fee to see the ruins, but avoid the peak hours of sunset and sunrise if you don’t want your view spoiled by crowds of tourists.

If you’ve got the energy, spend the rest of the day venturing down to the alluring waters of Amoudi Bay. The cove is just a five-minute walk from Oia castle, but make sure you’re wearing comfortable footwear for the 300 steep steps. Once there, take in the picturesque blue waters and enjoy a coffee at one of the many waterfront bars. You can even take a dip to cool off after your adventurous day and spend the rest of the afternoon soaking up the Aegean sun. 

Head back up to Oia in time for sunset to watch this world-famous spectacle from any of the viewpoints. Hundreds of tourists line the white walls of Oia in the summer months, but this creates a vibrant atmosphere to enjoy the golden skies. It’s not uncommon for visitors to applaud and cheer as the sun disappears below the horizon. If that’s not a testament to its unique beauty, we don’t know what is. Finish the evening with a light dinner and hit the hay early in preparation for your busy second day in Santorini.

It’s one of the most expensive spots in Santorini, but one night in Oia is worth the splurge. Check out these great spots to stay in Oia, whatever your budget:

Pelagos Hotel ($) – Set just outside the town center and 200 m from the beach, the Pelagos offers great access to Oia but is removed from the tourist crowds. Surrounded by vineyards, soak up the sun by the pool and enjoy the clean white aesthetics.

Theodora $$ – Slightly on the pricier side, Theodora offers classic Oia architecture and authentic Santorini cave accommodation just minutes from the main street. 

Esperas $$$ – For true luxury, the Esperas does Santorini elegance like no other. One of the village’s first cave hotels, the studio accommodation and lavish pool are carved into the rock face. Enjoy the sunset views in solitude from your private suite and wake up to a world-class continental breakfast served on your terrace overlooking the dazzling bay below.   

Day 2 – Fira

Santorini 5 day itinerary
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Whether you’re staying in Oia or Imerovigli, starting your second morning in Santorini with a hike to Fira along the Caldera promises stunning scenes and a fun adventure. Start early when the sun is still low in the sky, and bring water and snacks to keep you going. If you’re an early bird, you can even consider a sunrise hike for the most magical views of the island. There is also a public bus that runs between the towns that takes just 20 minutes and costs less than two euros.

Once in Fira, dip in and out of the shops and enjoy the colorful and crooked buildings that differ from Oia’s iconic architecture. Make sure you visit the Old Gialos Port when you’re there too. Fira is Santorini’s capital, and the small harbor is steeped in the island’s maritime history. 

Grab lunch at Lombranos for authentic Greek food and hospitality, then make your way back up to Fira by Cable Car. This transfer option runs every day between the center and the harbor and costs just five euros. Sit back and soak up the aerial views of Fira from one of the oldest and safest transports systems on the island. 

Finish the afternoon at the Museum of Prehistoric Thira, where you can view living documentation of the Minoan Civilisation in their wall carvings that still survive today. These people resided in Fira almost 4000 years ago before being killed off by earthquakes and volcanic eruptions. The Three Bells of Fira and the Cathedral of Saint John the Baptist continue the history lesson. These monuments dominate Fira’s architectural skyline and are the town’s key historic religious buildings. 

By this point in the evening, the sun will have set, and you’ll have plenty of time to enjoy a casual dinner at MeRaki’s, a quaint terrace restaurant, before grabbing the last bus out of Fira at 10 pm.

Day 3 – Chartering the Seas

Santorini 5 day itinerary
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One of the best ways to see Santorini and the nearby islands is by doing a boat tour. If you can, spending your third day in Santorini at sea will be an exhilarating experience. There are tons of companies you can organize through, many of which you can find online or ask your hotel for help booking. Whether you want a rustic group trip or a private luxury experience, there’s something to suit every budget. 

Starting in either Oia or Fira, your tour is likely to set off in the morning for the Santorini Volcano and hot springs. Just 30 minutes around the coast from Fira, you can only access the volcano in the port of Erina by boat and with an organized group and tour guide. Once there, brave the summit and trek to the hot springs where you can take a dip and venture back to your boat before setting sail to one of the nearby islands of Thirassia or Nea Kameni for snorkeling in the afternoon

The water around Santorini is warm and rich in minerals that are great for your skin. Depending on your tour, soak up the sun on board, enjoy refreshments and lunch or have a bite to eat on Thirassia. Some trips even include a sunset package, where you can take in the golden hour from the best seat in the house—at sea.  

Check out these different boat tours for different budgets: 

Volcano Boat Tour $ – This large pirate ship is a fun, social, and inexpensive way to explore Santorini’s waters. Visit the volcano, hot springs, and Thirassia island, snorkeling equipment included, with a big group of like-minded strangers. 

Private Motor Yacht $$ The perfect way to take in Santorini’s cliffs and seaside villages in privacy. Choose where your captain takes you and bring your own food and drinks onto the moat for a slow day of snorkeling and exploring. 

Private Catamaran Cruise $$$ – The true luxury experience at sea, ideal for birthdays, honeymoons, and party groups. Get pampered for five hours by attentive staff with all meals included and unlimited alcoholic beverages. Finish the day in Oia harbor, watching the sunset from the most exclusive spot. 

Spend your evening back in Oia and enjoy a Mediterranean seafood dinner at one of the town’s best spots. Check out Mia’s Restaurant for great harbor views or Lioyerma Lounge for a vibrant atmosphere and cocktails to accompany your meal. Finish the night at Lolita’s Gelato for the best ice cream in town.

Day 4 – Kamari and Sunset Wine Tour

Kamari black sand beache
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Day four, and it’s time for a change of scenery. After three days of adventure, you deserve some downtime by the beach, and you should do so while getting a different taste of Santorini. 

Kamari is a bustling seaside town on the southeastern coast of Santorini and is an excellent alternative to Oia with lower prices and contrasting scenery. Set at the foot of the Mesa Vouno mountain, Kamari’s most unique quality is its vast black sands beaches that stretch the length of the coastal village. 

There’s no shortage of beautiful hotels and lively homestays to spend the last portion of your trip. The main beach in Kamari is perfect for swimming, lounging on the sand, and traversing the beach shops for sarongs and trinkets. Hire a sunbed in exchange for a drink or meal from one of the many beachfront restaurants, and spend the day soaking up the sun. 

A unique way to spend your fourth evening in Santorini is embarking on a sunset wine tour in the late afternoon and visiting a handful of the traditional wineries dotted all around the island. Learn about the rich Greek wine culture and taste a variety of grapes at the Venetsanoa, Roussos, and Koutsoyannopoula Wineries, all inclined in the Kamari Wine Tour. Perfect for wine lovers, history buffs, and anyone who wants to enjoy local snacks and wine while watching the sun go down.  

Finish the evening dancing the night away at any one of Kamari’s beachfront bars and clubs that come alive every weekend. Greece is notorious for its vibrant nightlife, and while Santorini is one of the quieter honeymoon islands, Kamari will not disappoint if it’s evening entertainment that you’re after. 

Check out Albatross Bar for late-night drinks and a vibrant dance floor every day of the week. Or, if partying isn’t your thing, Kamari’s picturesque outdoor cinema promises a more tranquil and romantic evening. This open-air venue is one of the best globally and plays movies in English with Greek subtitles, perfect for tourists.  

Places to stay in Kamari:

Join Us Homestay $ – For the best budget accommodation, visit the Join Us guesthouse located just 200 m from the beach, promising fun and friendly vibes. 

Ancient Thera Studios $$- With all the features you could want from a three-star hotel and more, the Ancient Thera Studios hotel offers luxury lodgings at half the price. With an authentic Santorini aesthetic and inviting azure pool, the hotel provides various room options to suit any traveler.

Santorini Loft $$$ – The perfect balance between private apartments and a four-star hotel, Santorini Lofts provide stylish and comfortable studios with large clean living spaces and a great central location. Better yet, breakfast is included in the price of every room. 

Day 5 – Island Hopping and Paros 

Paros Greek house
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Your Santorini 5 day itinerary is coming to a close, but why end your Greek adventure here? Whether you’ve got a few more days to spare in the Aegean, or even if you are flying home the following day, visiting one of the nearby islands shouldn’t go amiss.

Island hopping in Greece is a bucket-list-worthy venture and promises sun and fun for any summer vacationer. Oia is a great vantage point to the rest of the Cyclades and journeying across the ocean for the promise of more great food, stunning beaches, and unique architecture is a temptation you shouldn’t resist.  

You can arrange day trips or jump on a local ferry to the charming islands of Paros, Paxos, Anafi, and Amorgos from Santorini’s shores. You can even reach Ios, Mykonos, and Crete in just a few hours if you’re continuing with your Greek travels.

Paros is one of the closest islands, and you can soak up the best of its quaint villages and cobblestoned streets even if you only have one day. Lefkes is one of the most beautiful towns in Paros, famed for its traditional Greek houses and beautiful pink trees. Visit Naoussa Old Port before you head back to Santorini or onwards with your travels and stroll around watching the boats come in.  

Santorini is well connected and there’s an extensive ferry route between all the surrounding areas. Book your boats at any of the local ports, through your hotel, or online in advance to ensure availability.

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Esmé is an English literature graduate and freelance writer. Originally from London, Esmé is lucky enough to call Bali home. Her travels have taken her from the far corners of the East to the islands of the Caribbean. When she's not writing, you'll find her lying on a beach somewhere, lost in a crime novel.