Search here...
TOP

Four Days of Paradise: The Perfect Santorini Itinerary for an Unforgettable Trip

Day 1: Arrival and Exploring Fira

Accommodation Options:

Santorini offers a plethora of stunning accommodation options, each with its own charm. If you can splurge a bit for a place with a caldera view and a pool—especially if you’re celebrating a special occasion—go for it. Here are two fantastic choices:

  • Aenaon Villas: One option is Aenaon Villas, where I’ve stayed and absolutely loved it. I mean you will fall in love and never want to leave. With six villas in total, each offering unique charm and breathtaking caldera views, it’s a special place. My favorite is the Elidami Villa, set in an elevated position for extra privacy and stunning vistas. It’s a bit of a splurge, but the dreamy experience makes it well worth it.

  • Dreams Luxury Suites: I’ve also stayed at Dreams Luxury Suites, which is a fantastic option if you want luxury without such a hefty price tag. The suites are stylish, many come with plunge pools, and the views are stunning. We stayed in the Armonia Suite, which was lovely.

Afternoon:

  • Lunch at Athenian House: Enjoy a delicious lunch at Athenian House in Fira, known for its modern Greek cuisine and stunning caldera views.
  • Stroll around Fira: Begin your exploration with a walk around Fira. Enjoy the charming streets, boutique shops, and panoramic views of the caldera. Spend some time shopping for local crafts, jewelry, and souvenirs in Fira’s quaint shops and boutiques. Be sure to take lots of pictures of this amazing town and the surrounding views.

Something Unique to Try: If you have a little extra time in Fira, consider getting a fish pedicure. These tiny fish gently nibble away dead skin from your feet, offering an exfoliating experience and a wonderfully ticklish sensation.

Evening:

  • Dinner at La Colline Restaurant: Enjoy dinner at La Colline Restaurant, which offers exquisite Mediterranean dishes and an lovely atmosphere.

Day 2: Boat Trip and Winery Visit

Morning:

  • Private Boat Trip: Embark on a half-day private boat tour around Santorini. Explore the caldera, swim in hot springs, and marvel at the breathtaking views of the caldera. Enjoy lunch on the boat.

Tip: I would recommend doing this in the earlier days of your itinerary in case there is a need to reschedule (we were cancelled twice due to windy conditions).

Late Afternoon:

  • Winery Visit: After returning from your boat trip, head to Santo Wines, one of Santorini’s renowned wineries. Located about a 20-minute drive from Fira, it’s best to take a taxi for a hassle-free journey. At Santo Wines, you’ll get to sample Santorini’s unique volcanic wines and learn about the island’s winemaking tradition. The beautiful views from the winery are an added bonus, making it a relaxing and interesting stop.

Fun fact: Did you know that Santorini’s grapevines are uniquely adapted to the island’s strong winds? Instead of growing tall like typical vines, the grapes are cultivated close to the ground. This technique, known as the “kouloura” method, involves training the vines into circular baskets that protect the grapes from harsh winds.

Evening:

  • Dinner at the Winery: After your wine tasting, enjoy dinner at Santos Winery.

Day 3: Island Exploration and Oia

Morning:

  • Quad Bike Adventure: Renting a quad bike is one of the most exciting ways to explore Santorini. This activity lets you experience the island’s rugged terrain and beautiful landscapes with a sense of freedom and fun. Start your adventure by cruising along the island’s coastal roads, where you can stop at hidden beaches like the secluded Red Beach or the lesser-known Vlychada Beach. These spots are perfect for a quick dip or simply soaking up the sun away from the crowds. Next, head inland to discover traditional villages such as Pyrgos and Megalochori. In Pyrgos, wander through charming narrow streets, explore local shops, and enjoy panoramic views from the old Venetian castle. Megalochori offers a glimpse into authentic village life with its picturesque square and traditional architecture.

Tip: Make sure to stop for some photos at some of Santorini’s stunning viewpoints. Places like the hills around Emporio and the clifftop paths offer breathtaking vistas of the caldera.

Late Afternoon:

  • Lunch at Karma: Head to Oia for a late lunch at Karma. This spot offers great Mediterranean dishes with a lovely view of the caldera. It’s a perfect place to enjoy a relaxed meal and take in the charming atmosphere of Oia.

  • Explore Oia: Take a leisurely stroll through Oia’s charming streets, where you’ll discover cute boutiques, cozy cafes, and those iconic blue-domed churches that are so famous. Enjoy the amazing views of the caldera and the Aegean Sea as you wander around. It’s a great place to soak up the local vibe, snap some fantastic photos, and just enjoy the beautiful scenery.

Evening:

  • Dinner at Ammoudi Fish Tavern: For a memorable dinner, enjoy fresh seafood at Ammoudi Fish Tavern, located right by the water in Ammoudi Bay. This is one of my favorite restaurants in Santorini. You can read my review here.

Day 4: Traditional Greek Wedding and Hidden Gems

Morning/Afternoon:

  • Tour with Your Greek Friend: Discover the best of Santorini on a guided day tour with Your Greek Friend. Explore both popular sights and off-the-beaten-path treasures, including charming villages and stunning viewpoints. Your guide will also help tailor the itinerary to your preferences. During the tour, we enjoyed a delightful Greek lunch at a local spot.

Evening:

  • Experience a Traditional Greek Wedding: Attend a Traditional Greek Wedding at The White Door Theatro. This immersive experience offers a taste of Greek culture, complete with music, dance, and local cuisine. You can read my review of the experience here.

Late Evening:

  • Cocktails with a View: After dinner, swing by one of the many bars and restaurants with a view and enjoy a dessert and a glass of champagne on your final night in Santorini.