Travel around Santorini with Bobby
Day 1Touching Down in Paradise – Sunset Dreams in Oia
As soon as I landed in Santorini, the island’s warmth and charm enveloped me. I checked into my hotel in Fira, a beautiful boutique spot perched right on the caldera’s edge. The view from my balcony was jaw-dropping—whitewashed buildings cascading down the cliffside, and the Aegean Sea stretching endlessly in the distance. After settling in, I decided to spend my first afternoon in Oia, the famous village known for its unbeatable sunsets.
I wandered through Oia’s narrow streets, lined with art galleries, charming cafes, and blue-domed churches that looked like they belonged on a postcard. Every corner of Oia felt magical. As the sun began to sink, I found a cozy spot at a cliffside restaurant to watch the legendary sunset, with a glass of local Assyrtiko wine in hand. It didn’t disappoint—seeing the sky turn shades of pink and orange over the caldera was one of the most breathtaking moments I’ve ever experienced.
Santorini’s sunsets are truly spectacular, but they also draw large crowds. To avoid the rush, arrive early to claim a good spot, or better yet, book a sunset dinner at a cliffside restaurant in Oia.
Day 2Exploring the Caldera – A Volcanic Adventure
The second day was all about diving into Santorini’s volcanic history, and what better way to do that than by taking a boat tour around the caldera? I hopped onto a traditional wooden boat, setting off to explore the islands formed by the ancient volcanic eruptions. Our first stop was Nea Kameni, an active volcanic island where I hiked to the top of the crater. It was surreal walking across the rugged black terrain, with steam still rising from cracks in the ground.
Afterward, we sailed to the hot springs of Palea Kameni. The water here was warm and rich with minerals, a perfect natural spa experience. We finished the tour with a stop at the island of Thirassia, a quieter spot away from the main tourist crowds. Here, I enjoyed a simple yet delicious lunch of freshly grilled seafood at a taverna overlooking the sea.
That evening, back in Fira, I decided to explore the town’s nightlife. I found a lively bar with traditional Greek music and friendly locals—Santorini’s nightlife may not be wild, but it has an authentic charm that’s hard to beat.
Lunch on Thirassia was simple yet delicious—freshly grilled seafood with a traditional Greek salad. The small island offered a more authentic dining experience away from the tourist crowds.
Food
Returning to my hotel in Fira after a day of adventure felt comforting. The staff was welcoming, and the view from the balcony continued to amaze, especially with the night lights.
Accomodation
The caldera tour, with stops at the volcano and hot springs, was thrilling. Hiking the volcanic terrain was both challenging and rewarding, and the hot springs provided a soothing end to the adventure.
Activity
If you’re into history or just love a good adventure, a caldera tour is a must! Just remember to bring sturdy shoes for the volcano hike and enjoy the slower pace of Thirassia for a more laid-back experience.
Day 3Black Sand and Ancient Wonders – A Day of Discovery
On my third day, I ventured to the other side of the island to see Santorini’s famous black sand beaches. Kamari Beach, with its unique volcanic sand and crystal-clear waters, was my first stop. It was unlike any beach I’d seen before, and I couldn’t resist spending a few hours lounging under the sun, with a refreshing dip in the sea to cool off. The beachside cafes here are great for grabbing a quick snack, so I enjoyed a light Greek salad and a cold frappe.
In the afternoon, I headed inland to one of Santorini’s hidden gems: the ancient ruins of Akrotiri. This archaeological site is often compared to Pompeii, as the city was preserved by volcanic ash after a catastrophic eruption thousands of years ago. Walking through the remains of the ancient city, I could almost feel the history beneath my feet—this place is a fascinating glimpse into the island’s past.
That night, I dined at a lovely restaurant in Fira, where I tried moussaka, a hearty Greek dish made of layers of eggplant, minced meat, and béchamel sauce. It was the perfect way to end a day full of exploration and history.
A light Greek salad and cold frappe at Kamari Beach made for a perfect beachside lunch. The beachfront cafes offer fresh, affordable options, ideal for a day in the sun.
Food
After a day at the beach and exploring the ruins, my hotel provided the perfect escape. The evening was quiet, and the room’s comforts were a welcome relief after a full day.
Accomodation
Visiting Akrotiri’s ancient ruins was a cultural highlight. The historical significance of the site combined with its preservation made it one of the most fascinating places on the island.
Activity
Santorini’s beaches are beautiful, but don’t skip out on the island’s rich history. Akrotiri is a must-see for anyone interested in ancient civilizations—it’s a humbling experience to walk through a city that has been frozen in time.
Day 4Wine, Waves, and Farewell – Savoring the Island’s Spirit
For my final day in Santorini, I wanted to take it easy and soak in the island’s famous wine culture. I booked a wine-tasting tour that took me to several vineyards across the island. Santorini’s volcanic soil creates some of the best wines in Greece, and I loved learning about the unique process behind their production. The highlight was tasting Vinsanto, a sweet dessert wine that’s famous on the island.
After the wine tour, I headed to Perissa Beach for a more relaxed afternoon. This black sand beach was quieter than Kamari, and the calm waves were perfect for a lazy swim. I spent the rest of the day simply enjoying the peaceful atmosphere, letting the beauty of the island sink in one last time.
That evening, I made my way back to Oia for one final sunset. This time, I wandered down to Ammoudi Bay, where I found a charming seafood restaurant right on the water. As I enjoyed my last meal in Santorini—fresh calamari and a chilled glass of wine—I reflected on the incredible experiences the island had offered me.
The seafood dinner at Ammoudi Bay was a highlight, with fresh calamari and perfectly paired local wine. The ambiance right by the water added to the experience.
Food
My last night in Santorini felt like a dream. The calming environment of the hotel, combined with the breathtaking views of the caldera, made it hard to leave.
Accomodation
The vineyard tour was a unique experience, offering insights into the island’s wine-making process and a chance to taste some incredible wines. It was the perfect way to wrap up my time on Santorini.
Activity
If you’re a wine lover, make sure to take a vineyard tour in Santorini. The wines are truly unique, and the experience gives you a deeper appreciation for the island’s volcanic landscape. Perissa Beach is also a great spot to unwind away from the crowds.
Summary of My Trip
Through Bobby's eyes
My experiences
Santorini offers a well-rounded experience that combines stunning natural beauty with rich cultural and historical depth. From its iconic attractions like Oia’s sunsets to its traditional Greek cuisine, the island delivers on every front. It’s an ideal destination for those seeking relaxation, exploration, and a taste of authentic Greek life.
I started my culinary journey with a glass of local Assyrtiko wine paired with fresh seafood while watching the sunset in Oia. The flavors were vibrant and matched the stunning scenery perfectly. The freshness of the ingredients stood out immediately.
Food
My hotel in Fira was a boutique gem, offering a breathtaking caldera view from the balcony. The room was cozy, and the location was perfect for exploring the town. However, it could’ve been a bit more spacious.
Accomodation
Watching the sunset in Oia was magical, but the experience was slightly crowded due to its popularity. Still, the beauty of the scene made up for it, and the atmosphere was unforgettable.
Activity