Mamma Mia soundtrack blasting and bikinis on— it’s time for a Santorini summer. With the island’s iconic whitewashed buildings, deep blue domes, and jaw-dropping sunsets that feel too perfect to be real, every moment is a dream in Santorini. Santorini offers the perfect mix of relaxation, beauty, and adventure. For this reason, it is one of the most popular Greek islands to visit with the crowds to match. This itinerary includes all the can’t-miss moments for an unforgettable trip. From beach-hopping and catamaran cruises to lingering over long lunches with ocean views and fresh Greek food, this itinerary is your guide to experiencing Santorini in all its dreamy, delicious glory with Fira as your home base.
Where to Stay in Santorini
While planning your accommodation, you’ll quickly discover it’s popular to stay in either Fira or Oia. Both sides of the island are quite different and will give you two unique experiences.
Stay in Fira if you want to be in the center of all the action and have easy access to transportation and nightlife. On the other hand, stay in Oia if you dream of iconic views, peaceful luxury, and a quieter side of the island.
Day 1
Explore Fira Town
Fira is the island’s capital and its busiest town, packed with cliffside views, cobblestone streets, shops, and cafés. Here’s how to spend the perfect day exploring Fira:
Morning: Start your day with a Greek coffee or iced freddo cappuccino at a cliffside café—V Lounge or Galini Café have epic views.
Afternoon: Time to roam the twisty little alleys of Fira. You’ll find everything from handmade jewelry and local art to stylish beachwear and souvenirs. Pop into local boutiques like Ilias Lalaounis for gold jewelry or quirky spots selling lava rock accessories and olive oil soaps. Don’t forget to grab a scoop of gelato from Zotos to cool off.
Lunch: Refuel with lunch at a terrace taverna like Naoussa or Lucky’s Souvlakis. I was eating my weight in Greek salad this trip, so that’s personally what I’d go for.
Evening: As the sun starts to dip, head to a rooftop bar like Volkan on the Rocks for sunset cocktails. Cap off your day with dinner under the stars. Salt & Pepper is cozy with classic Greek comfort food. Nightlife in Fira is the best on the island—check out Two Brothers Bar or Koo Club if you’re feeling the party mood.
Day 2
Red Sand Beach
Start your day at Santorini’s famous Red Sand Beach. Take a taxi or bus south to Red Beach and then walk the rest of the way down to the beach. We took the local bus (which is very busy and packed) to the drop-off point and walked the rocky path down.
Formed by the island’s volcanic activity, the beach gets its “red” sand from the lava rocks surrounding it. This creates a very cool contrast against the clear blue waters of the Aegean Sea, making this beach unlike anything I’ve ever seen. While not the most traditional sandy beach, it’s a unique experience with incredible views, surrounded by cliffs.
Make sure to pick up some gyros and snacks at any one of the local shops near the beach.
Back in Fira, go for the Caldera sunset walk where you’ll walk the cliff path toward Firostefani for epic sunset views. Once the sun goes down, enjoy dinner in town and go for drinks at PK Cocktail Bar.
Day 3
Hike to Oia
This is a beautiful hike along the coast of Santorini that takes you across the entire island. The hike takes 3 to 4 hours and is moderate, as there is uneven terrain along the way.
In the summer heat, this hike is not for the faint of heart, mainly because reaching the opposite end of the island seems eternal in that Grecian heat. You can hike in either direction ( Fira to Oia or Oia to Fira). I’ll be sharing my own experience with Fira as the start.
Hike Breakdown: Starting in Fira, the trail leads you through the charming villages of Firostefani and Imerovigli, each offering its own unique viewpoints and photo-worthy spots. Imerovigli is the highest point along the hike, and a perfect place to rest and take in panoramic views.
The path continues along dirt trails and cobblestone streets, past volcanic rock formations and scenic chapels, with the sparkling sea always in sight. While the route isn’t always clearly marked, it’s well-traveled and fairly intuitive—just follow the cliff’s edge toward Oia.
As you approach Oia, you’ll see those iconic blue domes and white buildings that make this village world-famous. Reaching Oia at sunset is a magical experience, but expect crowds if you plan to stay for it.
Once you reach Oia, pick a cliffside restaurant for sunset and enjoy a post-hike drinky drink. Yes, the restaurants are crowded, and yes, they are touristy. Listen, I am none the wiser, and after that hike, I was ready to sit at the first place that sat me. I couldn’t guzzle down a Greek salad quick enough.
The best way to return to Fira is via the local bus.
Back in Fira, enjoy a laid-back dinner with a million-dollar view at Mama’s House.
Day 4
Black Sand Beach & Water Sports
It’s not every day you lie out on black sand made from lava. Perissa Beach is one of Santorini’s most beloved dramatic black sand beaches. Tucked away on the southeastern coast of the island, Perissa Beach is the perfect spot to relax, swim, tan, and grab some lunch.
If you’re craving a bit of adrenaline between tanning sessions, go to Wavesports located right on the beach, offering all the water sports you can imagine. I went parasailing and tubing with Wavesports, and their crew is so helpful and friendly. We discovered we had mutual friends with some of the crew all the way over in London— it’s a smaaalllllll world!
Have a fabulous lunch by the sea at Seaside by Notos or Tranquilo.
Later, spend the night listening to jazz music at Kira Thira Jazz Bar. This is a busy, teeny tiny bar tucked away in a side street that has live music and a cozy, dimly-lit atmosphere.
Day 5
Boat Day
No trip to Santorini is complete without spending a day out on the Aegean Sea—and trust me, a boat day is the ultimate way to see the island from a whole new angle.
We booked a catamaran cruise and, let me tell you, it was one of the most fabulous days of my life. You will spend the day sailing around the island, stopping for swimming and snorkeling, and lounging on the deck.
Most boat tours include lunch or dinner on board—usually grilled meats, Greek salads, and fresh seafood. Plus, there’s often unlimited wine, beer, and soft drinks on catamaran cruises.
Head back to Fira and enjoy a nice, long nap back at your accommodation. The sea and sunshine tend to make you deliciously tired.
Later, for your final sunset in Santorini, walk up to the town of Imerovigli to enjoy the sunset from one of the many beautiful terraces. For dinner, I recommend Ouzeri. This was one of my favorite meals of the whole trip. We loved it so much, we ate here twice! This is the perfect place to spend your last evening and say goodbye to beautiful Santorini.
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