You’ve seen pictures of Santorini with its blue church domes and white-washed buildings. It is one of the Greek Cyclades islands in the Aegean Sea, and to me, the whole island looks like it’s right out of a painting.

After a packed full day in Athens, we took a quick night flight to Santorini to relax and explore what some say is the most beautiful Greek island. We took advantage of low season rates in October when the prices drop dramatically on the islands. Most visitors try to see a few islands, but we only had five full days in Greece and didn’t want to jump around.

While we typically lay out full day by day itineraries on TBP, for this post, I’m going to share my top 10 experiences because truly the best part about Santorini is moving slowly and setting your own pace. You can be as relaxing or active as you’d like spending your days lying on the beach or your hotel pool or hiking from town to town. Or maybe it’s a combination of both…everything in moderation right (well, except for the feta)? Either way, I have no doubt you’ll fall in love with Santorini just as I did.

xx M

QUICK LINKS

1. TBP's Top 10 Experiences

2. Where to Stay

3. Eats

4. TBP Insider Tips

TBP’s Top 10 Experiences on Santorini

1. Take a Cruise Around the Island

Spend 5 hours on a beautiful catamaran cruising around the island. There are a number of providers that offer similar excursions. We went with Sunset Oia’s semi-private tour on our hotel’s recommendation. You can opt for the Day or Sunset cruise. We took the Day cruise, so it would be warmer, but I would highly suggest Sunset if you’re there during the summer. You’ll swim in the hot springs and at the Red and White sand beaches. And don't forget about the endless supply of Santorini wine and ouzo. Plus, the views sailing in or out of Ammoudi Bay are spectacular!

2. Watch the Sunrise and Sunset in Oia

People come to Santorini for Oia's sunset. I know the sunset is on everyone's list, but most people don't tell you to watch the sunrise! I am NOT an early riser, but supposedly the sunrises in Oia are not to be missed. I say “supposedly” because of course it was cloudy the one morning we woke up early to catch it. It was still beautiful, but not what I was expecting. That being said, there was a photographer near us that morning who said the previous couple of mornings were outrageous. Please go and capture it for me! For the sunset, make sure to secure your spot early because it can get quite crowded. You can also simply have dinner and watch the sunset from Ammoudi Bay (see next point).

The sun finally came out from the clouds!

3. Have Dinner During Sunset at Dimitris in Ammoudi Bay

Call ahead for a reservation and request a table on the water to catch the sunset. Order any of the fresh fish! They offer donkey rides back up to Oia (not my thing), you can cab, or work off your dinner and hike up (our preferred method). Get ice cream at Lolita's as a treat back up in Oia.

4. Cliff Jump at Ammoudi Bay

Test your fear of heights jumping off cliffs into the Aegean. We were there in October and only had two really great swimming days, one at our hotel and the other on the cruise. If we had a third, swimming at Ammoudi Bay would be our top choice. We asked around at Dimitris and our waiter pointed out the path towards the cliffs. Basically continue around the bend until you reach the end. If you go, report back!

5. Have a Lazy Day at Your Hotel

Don’t underestimate the power of a relaxing day…or 2. Splurge to stay in Oia and you may never want to leave your hotel.

6. Get Lost in the Winding Streets of Oia

The town is a photographer’s paradise! Spend a few hours getting lost among the narrow streets. Make your way to the tip of the island to see the old windmills and gorgeous caldera views. Oia is also a great area for shopping!

7. Road Trip!

Everyone knows about Greece's ouzo, but how about their great wine and beer? We rented a car for a day and visited Santorini Brewing Company, the small town of Pyrgos, and Santo Winery. This road trip around the island is a great option if the weather isn’t great (we had two very windy and cooler days). Do not miss the chance to visit the brewery just for a quick tasting. The beers are excellent. We also wine tasted at Santo Winery, but honestly didn’t think the wines were anything major to write home about. The views were incredible though!

Meeting a new blogger friend at Santorini Brewing Company. Check out Jasmine at Signature Coast.

8. Have Dinner at Metaxy Mas

Hands down the best restaurant on the island, and the locals agree! It’s best to go the day you rent a car because it’s on the opposite side of the island from Oia and in the middle of nowhere near Pyrgos. You must get the Feta with honey and baked eggplants to start.

9. Beach Day

If you’re there during the summer, it’s a no brainer. Our hotel recommended the following: Perivolos and Kamari. Just remember to bring your own towel and watch out because the black sand can get very hot!

10. Hike from Oia to Fira

See Santorini by foot! We opted to drive because of the wind, but most visitors complete the hike from Oia to Fira. It takes about 2.5 hours and offers some of the most dramatic views of the caldera. If you’re there during the summer, try to go earlier or later in the day to avoid the high heat.

Where to Stay

I highly recommend staying in Oia, the town famous for its sunsets at the northernmost point of the island. While some say it’s mostly for honeymooners, I think it’s the nicer part of the island and allows you the chance to explore this quaint area more in depth. Plus, there are great restaurants! If you’re looking for luxury, stay at Canaves Oia. Just spectacular with breakfast overlooking the caldera. If you stay in the suites, they all have plunge Jacuzzi pools. This hotel is worth the splurge. Airbnb is another great option in this area. Check out Santorini Dave for his hotel recommendations.

Eats

I covered most of the must-try Greek foods in my Athens post. Here are a few more plus a few restaurant recommendations. The number 1 take away: EAT AT METAXY MAS.

What to Eat and Drink

> Eggplant - Santorini white eggplants specifically. OMG from Metaxy Mas baked with feta and fresh tomatoes.

> Rusks - a hard dry biscuit. Great with olives to start.

> White wine - nice and sweet

Where to Go

> Candouni - a very romantic spot in Oia right out of The Sisterhood of the Traveling Pants. Go for the meze plates. Get a bunch and share. They were better than the main entrées in my opinion. Make sure to get the capers. Did you know you can eat caper leaves?

> Metaxy Mas - clearly a local hangout. Food was amazing. You start with a bottle of rika, olives, and rusks on the house. Make sure to get the feta baked with honey and the baked eggplant. You'll finish with a dessert on the house!

> Dimitris - a traditional Greek tavern on Ammoudi Bay. Go at sunset for fresh fish. Make sure to make a reservation for a waterfront table with a view.

> Argo - a great option in Fira. Was recommended by friends, but was closed in late October.

> Melenio Cafe - great spot for an afternoon snack. Amazing pastries. Make sure to go upstairs and sit outside on the terrace.

> Lolita’s – for great gelato.

TBP Insider Tips

> Santorini is an expensive island – food, activities, and lodging. Go during the shoulder season (April-mid June and end of September-October) to take advantage of cooler temperatures, fewer tourists, and lower prices. It’s the only way we were ever going to stay at Canaves. Just be aware that if you are looking for a beach vacation only, the weather can be hit or miss by the third week of October. I'd suggest going end of May-early June or September-first 2 weeks of October.

> Many people rent ATVs for a day to get around the island. It can be very windy and we didn’t love this idea, so we rented a convertible SMART car. Great decision and highly recommend. Costs around 60 euro per day. Ask if you can leave the car at the airport if you can time it correctly to save yourself the transfer fee. We used Vazeos Car Rental in Oia.

> You must make reservations for dinner at all restaurants!

> In case you’re confused like I was, a caldera is a large depression that can form during volcanic eruptions. The whole Santorini island group, including a few surrounding small islands, form the caldera and are the only visible points above the water. The specific view to which people refer is the large body of water looking out to the small volcanic islands in the center.

> Go to the windmills at the end of the island in Oia to watch the sunset. Most people will stop at the sunset viewpoint, but continue a bit further to avoid the crowds.

> If you're going in the hot springs, make sure to wear a dark bathing suit because the sulfur can stain.

> If you’re already on the islands, you most likely will have to ferry to Santorini. If you’re in Athens, you should fly. It’s so easy and inexpensive. Save yourself the sea sickness.

> Although I haven’t been to the other islands, I wouldn’t recommend anything less than 3 days and in my opinion, you need 4.

> Make sure you pair your trip with a day in Athens...you’re likely flying through there anyway. Here’s how to fit it all in.