Santorini, Greece – home of the white-washed buildings and the blue rooftops. This island, in the middle of the Aegean sea, is a romantic place filled with adventure. The setting is absolutely gorgeous, with cities perched atop steep cliffs, and sweeping views of the central caldera. You can sample world-class wines, hike along the coastline, get lost among the winding laneways, take a sailing tour to the caldera, swim at a black sand beach, and watch incredible sunsets. Come along as we show you all of the above, and more!

In this article, we will share our experiences on the island of Santorini and give you 13 tips to make your stay unforgettable.

1. Flights from Europe are Cheap

Getting to a remote island, like Santorini, can seem tricky. We came up empty when we searched for award flights to the island. However, we learned that if we could get to a nearby city, like Athens or Rome, roundtrip flights are very cheap. You can use points/miles to get to the major airport, and then grab a quick flight to Santorini.

We flew from ATH to JRT on RyanAir ($51), and we returned on Volotea ($52). The flights were only 45 minutes from Athens. Unfortunately, budget airlines like these are not generally bookable with Chase UR points.

2. Stay in Firostefani

It can be tricky to pick a place to stay on Santorini, especially if you have never been there. Every picture looks beautiful, so it seems hard to go wrong. We looked at 50+ different hotels and villas before deciding to book the Alta Visa Villas in Firostefani. I am very glad that we picked this location, because it is centrally-located on the caldera, and it has relatively low foot traffic. We were able to easily take day trips to either end of the island from our base in Firostefani. Dining options here are nice, with a slightly lower price point than other places on the island.

The cities of Fira and Oia are popular spots, but we would not recommend that you stay in either place. Fira is where the cruise ships dock, unleashing thousands of passengers directly into the tiny streets. With the constant arrival of tourists, many cheesy trinket shops and high-priced cafes have set up in Fira. Oia is absolutely beautiful, but it sits at the far end of the island. This makes day trips to the black sand beach or wineries a long journey. Additionally, at sunset, Oia becomes the most popular place on the island. You literally cannot move through the narrow laneways, because so many people flock to Oia in the evening.

3. Book Your Hotel with Chase Ultimate Rewards

We found virtually no chain hotels on Santorini. Many of the hotels/villas are quite small and locally owned. This made it a challenge to book accomodations with award points. Fortunately, the Chase Ultimate Rewards portal offers a wide selection of lodging options. You can even sort by location and price. Since we have the Chase Sapphire Reserve card, our UR points are worth 1.5 cents each toward travel!

Learn about this card, as well as other travel rewards credit cards here.

We found the Alta Vista Suites in Firostefani for 18,761 points per night. The hotel was very small, with only 5 rooms. Each morning, they served a full Greek breakfast, with omelets, bacon, yogurt, fruits, honey, croissants, coffee, and juice! The pool area sits on a ledge, with an incredible 180-degree view of the caldera and both ends of the island.

4. Rent a Four Wheeler

You have a few options to get around Santorini. A public bus runs back and forth along the length of the island. The bus is the most economical option, but we wanted a more flexible mode of transportation.

Many vendors offer small cars, scooters, and four wheelers of various sizes. Prices vary widely, and most seem to be a bit flexible. We rented a 200cc four wheeler for 25 euros per day at a random shop in Firostefani. This is the minimum size that I would recommend for two people. Four wheelers offer maximum flexibility for getting around and are very easy to park in tight spaces. It takes only a minute to get used to the controls, and then you’re off to explore. Be sure to wear your helmet and be mindful of the cars and busses along the road.

5. Oia for Sunset

Sunsets are magnificient in Santorini. You will get a great view of the sunset from almost anywhere on the island, but Oia offers the best option. We recommend planning a day trip to Oia, with plans to stay for sunset.

A few places in Oia offer optimal views. One option is the fort at the far end of the island. You can simply walk onto the tower and have an unabated view of the water and the city of Oia. If you want a spot along the outer wall, you will need to arrive a couple hours before sunset.

Another option is to have dinner or drinks at a restaurant or cafe in Oia. We found a cafe and claimed our spot an hour before sunset. We ordered a pitcher of sangria and some light snacks while we waited. The sunset is so magnificient here that people actually clap once the sun slips below the horizon.

Be sure to pack long sleeves, because the temperature drops sharply once the sun is gone. Also, don’t be in a hurry to leave, because the narrow streets will be crammed full of people trying to get out of the city. It took nearly an hour to get from the cafe back to the edge of town, where we parked.

6. Atlantis Books in Oia

Oia is home to a world-famous bookstore called Atlantis Books. This store features a well-curated selection of interesting books from around the world. It also sells rare books with very high price tags. We saw an original copy of To Kill a Mockingbird on sale for 17,500 euros. This store is definitely worth a visit while you’re in Oia.

7. Santorini Sailing

Santorini Sailing is one of the premier sail tour operators on Santorini. They offer a variety of boats and experiences, ranging from private sail tours to large party boats. All tour packages include pick up and drop off service near your villa. We booked a small group sunset tour package aboard the Horizon. This tour includes dinner and unlimited beer and wine. Woo!

Their shuttle service transported us to Ammoudi Bay at the base of Oia, where we boarded the boat with 10 other people. The boat itself felt very deluxe, with leather lounging furniture, an interior cabin, and a large sun deck. Capitain Theo and his crew welcomed us aboard and we were off to our first stop.

Cliff Diving

The first place we stopped was just outside of the port, where we had the opportunity to cliff dive into the clear blue water. We decided to jump from the 20-foot cliff, and it was AWESOME! After a bit of swimming, we grabbed some wine and headed to the next stop.

Caldera Swim

Our next stop was at the volcanic cone at the center of the caldera. Here, we could borrow snorkel gear and swim around the edge of the cone. The water here is crystal-clear, and we could see a few fish. The terrain felt like something from another planet!

Dinner Aboard

After some time snorkeling, they called us in for dinner. Captain Theo grilled some chicken and steak for us on the main deck. Other items included prawns saganaki, steamed mussels, penne Santorini, Greek salad, baked veggies, and fresh bread. We all sat around the main table on the boat, sipped wine, and enjoyed the delicious food.

Volcanic Spring

Our next stop offered the opportunity to soak in a volcanic hot spring. At a smaller island, near the middle of the caldera, minerals turn the water a rust color. This area is a quite a bit warmer than the open water areas. We only hung out here for a few minutes, before returning to the boat.

Sunset Champagne Toast

Leaving the central caldera, we cruised toward the south end of Santorini. We passed around the southern point, with a great view of the lighthouse. As the sunlight began to fade, Captain Theo pointed out the red and white sand beaches on this side of the island. These beaches are very difficult to reach on land, so you need to be on a boat for the best view. Right as the sun was setting we popped the corks on some champagne bottles for a toast. Glasses clinked while we saw the sun hit the water, bringing a great day to a close.

8. Santo Wines Tasting

Santorini is home to a few excellent wineries. Santo Wines is one of the largest and most well-known on the island. We reached the winery in 20 minutes from Firostefani. The tasting area sits high upon a cliff, with excellent caldera views. We decided to try the 12-wine sampler flight. The total volume of the sampler was roughly equal to a bottle of wine. This gives you the opportunity to taste a dozen different wines, including their famous dessert wine, Vinsanto.

9. Black Sand Beach

Passing Santo Wines, and heading south to the town of Perissa, you will find a beautiful, black sand beach. We parked the four wheeler on the edge of the sand and walked down for a swim. The water here is quite cold, but very clear. If you decide to go swimming, be aware that the bottom is a VERY slippery rock.  We had trouble standing here, because the bottom was so slick!

10. Eat Gyro Pitas

Gyro meat, tomato, onion, feta, and tzatsiki sauce, wrapped in a warm pita… mmm! You can find gyro pita options all over Santorini. We tried a couple different places and were very impressed.

The first place we tried is a popular spot in Fira called Lucky’s. The restaurant is a very narrow space, with some barstools to sit and eat. While we were there, it was absolutely packed! We also found it interesting that they add French fries to their wraps.

Another place we ate was just around the corner from our villa in Firostefani. It is called “Eat Here!” and I recommend that you do just that. Their gyro pitas are cheap and delicious. We loved it so much that we ate there a few times during our stay.

11. Skaros Rock

Skaros Rock is a large rock formation jutting out of the cliffside near Imerovigli. You can follow the coastline along, until you see signs for a trail to Skaros. The trail leads out to the rock itself, where you can climb to the top for a nice view. By the time we found the trail, we were too tired to make the trek out to Skaros Rock. I’m sure it’s worth the effort, but not for us in the summer heat.

12. Relax and Enjoy the Views

As you can see, there is plenty to do in Santorini. But you should really take some time to just chill! Take leisurely strolls through the laneways and snap pictures of the beautiful blue-roofed buildings. Grab a Donkey Beer or a bottle of sweet red wine and lay by the pool. Enjoy the romance of the island, and raise a glass to the setting sun.

13. JTR Airport is Tiny and Basic

Santorini’s international airport is honestly pretty awful. After passing through security, you will find yourself in a single waiting area for all flights. Food options are extremely limited, but more importantly, so are seats! We had nowhere to sit, because the space was so crowded. Give yourself time before your flight, but expect an unpleasant wait. Maybe they’re trying to get you to stay, by keeping the airport so crummy!

Final Thoughts

Santorini is an absolutely magical place. We traveled all the way around the world, with Santorini as our final stop, before heading home. Even with all of the beautiful places we saw during our trip, Santorini stands out in our minds as one of the absolute highlights. You simply have to experience the island for yourself to fully understand.  Use a card like the Chase Sapphire Reserve to make this all possible.  The bonus on this card covered our entire hotel stay, which would have been very expensive otherwise!

Learn about this card, as well as other travel rewards credit cards here.