Sunsets, Sailboats & All Things Santorini – Dreamy Activities Not to Miss

Writing about my favorite stays in the Greek Islands last week still has me reminiscing about my trip to Santorini, so here is another post about that dreamy Greek island…

Catch “The World’s Most Famous Sunset”

Yep, thats right! The island of Santorini is known for having “The World’s Most Famous Sunset.” The island’s sunset has been featured in magazines, paintings, and photography around the world, but there is no better place to see it then on the island itself. During our time on the island, we stayed in the town of Oia, which is home to the infamous caldera (rocky cliffs) and blue-domed buildings. The Oia Castle is the best place in town to catch the sunset, as it offers panoramic views of the caldera and surrounding area. Be sure to head there early to grab a good spot – it can get really crowded!

Visit & Dine at Ammoudí Bay

Follow the winding steps down to Ammoudí Bay and enjoy a meal by the water. The trek to Ammoudí Bay is easily a couple hundred rocky steps, so be ready to break a sweat! As you descend down to the bay, enjoy the scenic views and adorable porches of homes built into the cliff. When you reach the bay, grab a table at one of the nearby restaurants and treat yourself to a fresh seafood meal – I had seafood pasta and calamari, and it was delicious! Don’t feel guilty about how much food you enjoy because you will work it off during your climb back up from the bay. If you are too tired and can’t make it back up, locals do offer donkeys rides for a cheap price, but the best experience is on foot!

Sail Around the Island of Santorini

Sail around the magical island of Santorini and view the caldera from afar via a catamaran cruise. Jump off the boat and swim in the Aegean Sea, admire the unique clay and shale cliffs, or simply enjoy a delicious traditional Greek lunch on the boat deck – I tried Greek olive leaves for the first time on this trip and I fell in love! Bring a speaker and your cutest bathing suit and soak up some Greek sun and an afternoon of fun! Catamaran cruises with lunch run between $100-$150 USD and can be easily booked via Viator or organized through your hotel/villa.

Enjoy a Luxury Stay on the Caldera

One of the best parts of vacationing in the Greek Islands are the luxurious stays. White-washed walls, stone bathtubs, private pools, and immaculate service, the hotels/villas, especially in Santorini, have it all! During our stay in Oia town we stayed in two places along the caldera – The Big Blue Villa, and Armenaki. My favorite was the Big Blue Villa and the pictures below don’t do it any justice! Find out more about this stay and others in the Greek Islands in my previous post.

With a friend or lover, Santorini is always dreamy, so definitely add this destination to your bucket list in 2026. You already know all the cool things you should do while there, so what are you waiting for!?