How Santorini Can be Your Next Vacay

Who hasn’t seen the Instagram photos of the ivory white and cobalt blue Cyclade homes spilling over a cliff? Santorini has a personality unlike any other place in the universe and just about anyone who’s ever seen a photo of this magical European island has dreamed of going there someday. 

Church at Oia Photo: Bill Wiatrak

You could book it today. 

Maybe that seems a little soon, but there’s no reason you can’t visit this little piece of paradise in the near future. Prices are reasonable and none of us are getting any younger. 

How to book your flight 

Here’s how simple it is. Go to Skyscanner or your favorite booking app and purchase  a round trip ticket to Athens. At the time of writing, Houston, NYC and Miami are the cheapest departure cities with tickets ranging from $575-$625. Sometimes changing your date can lower the price. From Athens you can take a ferry, fly or book a cruise that stops in Santorini. A cruise gives you very limited time unfortunately, so I don’t recommend it if you’d like to get to know the island. You can fly round trip to Santorini for as little as $35 on a discount airline such as Ryan .So, for less than $700, you can be at one of the world’s most beautiful spots. 

Now that the sticker shock is out of the way, let’s get to the nuts and bolts of how to make this a wonderful trip. 

Perissa Beach Photo: Bill Wiatrak

Athens and the Mainland 

Getting to Santorini from most major cities in Europe is pretty straightforward, but Athens is a great hub to visit some of the other islands or see the mainland. Meteora, Olympia, Delphi, Monemvasia, Nafplion and Thessaloniki are all popular cities that can be combined with your island visit. Car rental is an easy option, but trains are also available if you’re not a DIY type of traveler. Athens has several major sites including the Agora and the iconic acropolis. The nearby port of Piraeus is where you can catch ferries to most anywhere and is a nice location to spend a night. We found a very unique hotel called XCite there as well as reasonably priced Michelin starred restaurant  called Varoulko right on the water. 

Map of the Greek Islands

There’s no such thing as an island hopper pass for planes or ferries, but Greece has a ridiculous number of beautiful islands to visit and some are more convenient to visit using a ferry, than flying back to Athens to catch a flight to a different island.

Where to Stay

The two towns perched above the cauldron are the main hot spots of Santorini. Fira is a little less expensive than Oia, and are both beautiful places to wake-up to. If you’re looking for something a lot less expensive, there’s deals on the east coast at Perissa and Kamari beaches. These areas are good options for beach lovers as well, since the west coast is a cliff drop-off. If time permits, try a few places around the island to change things up a bit. If you think that you can’t afford Santorini, you’d be wrong. Although there’s beautiful hotels in the $500 range, there’s also plenty under $100 with a few starting at $28. You won’t find that in America.

Sunset at Santo Winery Photo: Bill Wiatrak


The restaurants in Oia and Fira offer the most dramatic views of the island, however there’s great establishments on the beach side of the island as well as the possibility of renting a thatched umbrella and enjoying the fresh seafood and traditional Greek dishes. One of our favorites is Almira on the shore at Kamari. For an astounding sunset show, head to Santo winery on the central west coast. Santo offers some great wine tasting options as well as unusual and delicious appetizer trays. Prices at higher end restaurants will be more expensive than other places in Greece, but mid-range restaurants are cheaper than US prices. For an authentic tourist experience, find a restaurant that hosts a plate smashing evening. Restaurants such as Naoussa offer this traditional Greek custom as well as great food.

Windmill at Oia Photo: Bill Wiatrak

Getting Around

A majority of travelers take the bus which circles the island. Parking can be a little challenging in Oia, but the rest of the island is not nearly as congested. To see the whole island, getting a rental car for a couple days is recommended. There’s several options at the airport. There’s a popular hike from Oia to Fira that follows the rim of the cauldron for 6.5 miles. In earlier times, tourists would use donkeys as transport from the port to the top of the hill and between cities. There’s now a cable car that ferries cruise ship passengers and other adventurous travelers. A donkey company still exists, but they are rated very poorly for their treatment of their animals and are not recommended by the majority of travelers who have used them.

What else?

The island of Santorini has plenty to offer besides the cauldron towns and beaches. The ancient city of Thira is fantastic if it’s open (the hours are very inconsistent) and the trip to the top of the hill is some of the best scenery on the island. There are boat trips available that explore nearby islands, and the ruins of Akrotiri (nicknamed Santorini’s Pompeii) is a wonderful stop to learn more about the island’s history. Oenophiles will enjoy the unique method wine grapes are grown on a winery tour.

Santorini also has a love of bakeries and once you’ve tried Greek pastries, you will too. There’s 8 choices on the island and they’re all open 24 hours!