Visiting the cliffside village of Oia has been #1 on my bucket list for some time. I have literally been dreaming about traveling to Greece with my guy for years. Needless to say, my expectations were super high and I was not disappointed. Not one bit. The white-washed buildings, blue domes and brightly colored bougainvillea vines perfectly compliment the Aegean Sea. I loved the simplistic romance of this place and couldn’t have dreamt up a better setting to celebrate our Anniversary. Around every corner there’s another view to get lost in together. It’s seriously a paradise and photographer’s dream. Traveling to the Mediterranean can be costly, but Santorini is one of those places you just HAVE to see. The panoramic views are breathtaking, the sunsets unrivaled and no where in the world will you find another place like it.

Getting there: Traveling to the island of Santorini is easy. You can arrive by ferry or plane. Flying Aegean/Olympic Air from Athens is just a 45 minute flight and under $200. Taking a ferry is a more economical choice (as low as $30), but depending on what boat you choose, can take anywhere from 5-10 hours. 

When to travel: The warmest (and busiest) months of travel are July-Aug. Accordingly to locals, the island pretty much shuts down during the winter months which leaves the shoulder seasons of April-June and Sept-Oct as the most desirable times to travel. We stayed in Santorini the last week of May. Jackets were preferred in the evening, but it was warm during the day. We had a few cloudy days where the views of the caldera were not as clear, but a break in heat and sunshine wasn’t the worst thing - especially when hiking! 

Where to stay: Oia (pronounced E-YA) is considered the most charming and romantic village: great little boutiques, winding stone paths, home to Ammoudi bay and the best sunset views on the island. It’s also the most well-known area so if tourists turn you off, consider staying in one of the lesser known villages such as Firostefani or Imerovigli (more on this later). Caldera views in Oia come at a premium, but it is worth it, at least for your first stay on the island. Hotels are plentiful, but we chose to stay in a traditional cave house instead. Not only are they more budget-friendly and private, it really adds to the overall experience. The property owner Maria took care of everything for us from arranging airport pick-up, handling our bags, booking tours and making helpful recommendations. It was like having a personal concierge service and allowed us to skip all the hassle and confusion we saw other tourists experience. If a traditional cave house interests you, Maria has multiple properties in Oia ranging from $100-700/night. The only thing we wish we had splurged on was a property with a hot tub, especially for those cooler nights! 

Fira is also an option, although we did not find it to be as picturesque. This is where the cruise ships port. Fira offers plenty of restaurants, less touristy shops and the closest thing to nightlife you’ll find on the island. I think it’s clearly a personal choice, but we were happy with Oia being our home on the island. 

After spending some time in the lesser known village of Imerovigli, we weren’t opposed to the idea of staying there for a second trip. The hotels are less expensive and the view of Skaros rock is sensational. Renting transportation is fairly inexpensive, so getting to and from Oia (about 20 minutes by ATV) wouldn’t be a problem. We found it very easy to relax there and again … the views! But if you are visiting Santorini for the first time, I would suggest Oia over Imerovigli. Here’s a few photos of our home away from home for the week – and the gorgeous patio view! 

What to do: The island is small and easily navigable. We spent five days there and it was the perfect amount of time to both explore and relax. Here are the top five things I recommend doing in Santorini!

#1 Explore the island by ATV: The number one activity I would recommend is renting an ATV to explore the island. You can also rent motorcycles (requires proof of license) or a car, but ATVs are widely used and totally safe on the roads. If I recall, it was $50-70 for a day rental and worth every penny. Go explore the other towns and backroads for spectacular views. Traveler tip: We booked a dinner reservation that evening at Ammoudi bay and avoided the 300 stairs trek back to town on full stomachs. You’ll thank me!

#2 Hike Skaros Rock: The best panoramic views I’ve ever witnessed came from hiking Skaros Rock in the village of Imerovigli. This was our favorite activity of the trip and a memory I’ll hold on to forever. We had great weather that day which I think could make or break the experience for someone. The hike has many stairs but with good weather (not too hot) it was bearable, even enjoyable at a leisurely pace. You don’t have to be experienced to do the hike, but you do need comfortable shoes. At the very end of the hike, if you want to climb on top of the rock it does takes some level of athleticism and I would not recommend it for someone with fear of heights … or falling off a cliff. It’s not an actual trail at that point as much as it is rock climbing. There were plenty of people who ended the hike once they reached the rock though. The views are out of this world and worth every step! 

A more notable hike is the path from Fira to Oia. From what I’ve read, the hike takes around 3 hours one-way, 4-5 hours at a very leisurely pace. The trail will lead you from Fira through the sister villages of Firostefani, Imerovigli and finally to Oia. The hike offers great caldera views and affords you the opportunity to see the lesser known villages along the way. If starting in Oia, you can find the trail head past a big yellow church on the square near the parking lot. There is a clearly marked sign on a rock wall that will get you on your way! 

#3 Cliff jumping at Ammoudi Bay: I love Ammoudi bay. The water is a gorgeous turquoise blue, the seafood is amazing and it’s home to one of the best swimming spots I’ve ever seen. If you’re looking for a little added adventure, you can swim out to a 20 ft cliff and cross jumping into the Mediterranean off your bucket list. In full disclosure, my husband did the cliff jumping, I did the sunbathing. But I absolutely loved swimming in the bay. It was an incredible experience! To get there, we decided to walk the 300 steps down from Oia to the port. There are no signs directing you to the place, but it’s an easy 5 minute walk. Just turn left from the bottom of the stairs and you’ll find your way! On the way back up, I considered briefly riding a donkey but felt too guilty. So instead, I suffered my way up the 300 stairs and regret it only partially :-) Here’s a few photos of our adventure! 

#4 Relax at the public pool: You’re not as likely to find this recommendation on another travel blog but it was one of the best surprises of our trip. Our property owner Maria gave us the in on this and I’m so glad she did. If you choose to stay in a hotel, you’ll likely have access to a pool. For those of you who choose a traditional cave house, this is the perfect and free option to lounge! If you search Lioyerma Lounge Cafe Pool bar on Trip Advisor you’ll see some pictures and have the address to locate it. The pool itself is free, and you can order drinks and food from the bar. The pool area wasn’t too crowded which is how I know this is a well kept secret. Traveler tip: arrive later in the afternoon and stay to watch an unobstructed view of the sunset in comfy lounge chairs. As far as I’m concerned, hitting the public pool should be on everyone’s list! 

#5 Sunset Boat Tour: The smell of the ocean and wind on my face is one of my favorite feelings in the world, so there’s no surprise I recommend taking a boat tour. Catamarans are pretty much synonymous with a good time and a must-do on this island. We chose to set sail with Sunset Oia and booked the sunset tour. Maria handled the booking and took care of transportation to and from the bay. The tour itself includes beach hoping and a stop at the infamous hot springs (which are more like warm springs at this point). Overall, we had a great experience. The boat was clean, the food good and the drinks plentiful. At the end of the evening, all the boats line up at the bay and chase the sun. It’s such a romantic setting and the perfect way to catch a world famous sunset. 

Where to eat: I was a little nervous in anticipation for this trip and trying traditional Greek food. I’m not proud to admit my palate is less than sophisticated, but that’s the honest truth. Between my husband and I though, we didn’t have a single dish we didn’t like. I pretty much lived on bread with tzatziki, olives, seafood and pasta. I found the menus had plenty of variety and can’t imagine anyone having a problem finding something they like. There are many restaurant options, both authentic and a little less traditional. We tried a bit of everything! 

Sweets: If you have a sweet tooth there is a great little gelato place called Lolita’s. It’s right by a small market where we got milk, bread, cereal, fruit and other essentials for the house. It’s right off the main street and very easy to find. It’s a hot place so if you’d like to skip the crowd, head to Skiza cafe for some of the best cheesecake I’ve ever had. So light and fluffy! Seriously divine. You can dine in or grab your dessert to-go.

Best seafood: For the best seafood, head down to Ammoudi bay. We made reservations for Ammoudi Fish Tavern as it came highly recommended. Other recommendations are Sunset Ammoudi Taverna and Dimitris Ammoudi Taverna. The view of the bay at sunset is truly spectacular. I ordered the Seafood Linguine and my hunky date enjoyed the largest grilled Tuna Steak I’ve ever seen. Hands down one of the best meals we had in Greece. 

Best cafe: If you are anything like us, you’ll be looking for excuses to just sit and take in the views. We frequented Vitrin Cafe Creperie because they had delicious cafe drinks and crepes. We would sip on our coffee and sing along to the American tunes playing. Maybe we were just homesick, but I swear he had a great playlist going.  

Best restaurants: I usually follow Trip Advisor like it’s the law but they have it wrong on this gem of a restaurant. Attentive staff, breathtaking views, great atmosphere and really, really good food. Apsithia is currently ranked #66 of 70 restaurants in Oia but only has three reviews (all five stars). Maybe it’s a new establishment or took new ownership – I’m not sure, but it was perfection. My other recommendation is Terpsi. The service was a bit slower here, but they offer breakfast, lunch and dinner. Great views and amazing food. The fresh squeezed orange juice was my love affair while on the island! 

My final recommendation? Run, don’t walk to Greece. Experience the magic of Santorini for yourself. One of my favorite traveling quotes is it’s better to see something for yourself than to hear about it a thousand times. There’s great truth in that. We all see things through a different lens and what one experiences may be completely different than your own. Personally, my favorite thing about Santorini was never escaping the views. It doesn’t matter where you are, there’s endless beauty in sight. Greece was truly the perfect way to end our Anniversary trip. Thank you for reading along and following our journey. Until next time!