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Ready and Roam / Santorini, Greece

Ready and Roam / Santorini, Greece


Santorini is a small, crescent-shaped Greek island that has easily become one of the most popular travel destinations in the world. White and blue villages, crystal clear water, freshly grilled fish… Those pictures on Instagram don't lie, Santorini is gorgeous, but you really must experience it for yourself. Often visitors will island hop, as R&R contributor Jen Peterson suggests, in which case you should consider the often overlooked island of Naxos or the ultra charming island of Milos — accessible by ferry service, multiple times a week and less than 2 hrs from Santorini. If you are looking to add some culture to your Greek vacation, Jess recommends spending Four Days in Athens before or after your trip.



Best time to GO: Plan your visit in April - June or Late September - early October, this is your best bet for summer weather and slightly less crowds.

If you live outside of Europe, you'll have to fly to Athens first. From Athens (ATH) we flew into Santorini (JTR) on Olympic Air. Olympic Air offers really great flight options from Athens to Santorini and it only takes only an hour to get there. There is a ferry that runs to and from the island, but it takes close to eight hours (each way) and strikes among the workers are common. We really didn't want to risk our ferry being cancelled or give up almost two full days of exploring, so we spent a few extra bucks to fly and I am glad we did. It was straightforward and super quick. The airport is located on the eastern side of the island. If you arrive by ferry you’ll dock at the main port in Santorini about 20 minutes south of the capital city of Fira. Cruises to nearby islands depart from here, so make sure you arrive early and prepare for crowds. When you arrive in Santorini you’ll want to secure a taxi unless your accommodations offers a shuttle. It doesn’t matter where you are based there are buses, taxis, quads and cars to hire everywhere. The buses in Santorini are called KTEL. They run frequently, are super cheap and will take you all around the island, but they don’t always keep a reliable schedule. You will need local currency (Euro) for the bus.



Santorini's official name in Greek is Thira (Thera). You'll see it listed interchangeably. Santorini is a volcanic island - technically, it's an active volcano. Thousands of years ago, the center of the island collapsed into the sea creating an open sea lagoon. The sea lagoon is called the “caldera.” You can see the Caldera from the entire western side of the island, not just Oia.



Oia - is the most famous place to stay in Santorini. It is known for spectacular sunsets. Prices in Oia are higher than most other places on the island but it’s a wonderful place to stay especially if you find a good deal or you’re celebrating and want to splurge.

The Sea Captains House / best rates

The Sea Captains House is located in Oai at the northernmost point of Thira. It comes highly recommended by R&R contributor Christina Sandok. Who stayed at this sweet boutique hotel, with only 6 rooms, for her honeymoon. The Sea Captains House is incredibly affordable for the area with it’s breathtaking views and iconic Greek village setting.

Property Rental / Hector Luxury Cave

In the old part of the Oia village at the top of a cliffside, you’ll find the most magical “cave” studio apartment with a dip pool. This is a stunning clean and modern property offers a patio and unbelievable views.

Fira - is a great starting point for those that want to see and do everything. The one downside to Fira is that’s where the majority of cruise ship passengers spend their time on shore. There's a fancy calendar, linked here, that shows you which ships will be in Santorini, when they'll arrive/depart, and the maximum number of passengers. This won’t be an issue if you plan to spend your day on other parts of the island, but it’s certainly something to consider.

Petini's Place, Fira / check rates on

My philosophy when traveling is to find an affordable option that's central and easy to find. The reality is, I tend to spend very little time in my room because I prefer to be out exploring. Petini's Place is in a great location only a short walk to the bus station and Archaeological Museum. The guest house offers only 6 private rooms with all the comforts you’d expect. It has a simple rooftop for watching the sunset and it was a great price.

“It's located above the owners souvenir shop with easy gifts for all your loved ones!”

Anteliz Suites / check rates on

This is a relaxed boutique hotel with panoramic views offers a variety of accommodations, including a private villa for up to 6 people. While it’s on the higher end for the Fira area it’s still quite affordable luxury.

Imerovigli - is as a little more off the beaten path (between Oia and Fira), which means less tourists and a better value than Oia with the same great views. There are some wonderful restaurants in Imerovigli as well, and it's only about a 20-30 minute walk from Fira.

Above Blue Suites / check rates on

Located at the highest point of the famous Caldera Cliffs, this all suites property offers privacy as well as breathtaking views of Santorini’s endless sunset. A private champagne breakfast is only one of the many luxurious amenities, including a spectacular freshwater swimming pool, cave bar and massage services.

Cavo Tagoo Santorini / check rates at

While this is a splurge for sure, this historic luxury boutique is exactly as you’d imagine a stay in Greece. Additionally, it’s family friendly and offers stunning views in a less commercial area.

Kamari - is near the beach. It’s close to the airport as well and you'll definitely get a better hotel price staying in this area. None of the towns on the western side of the island (Fira, Oia, Imerovigli) have access to the beach but it’s very easy to explore Santorini when you are ready to go seeking those famous sunsets.

Aegean Gem / check rates on

This ‘gem’ property is less than a mile from the Kamari black pebble beach. It offers a garden, terrace, swimming pool, lounge and bar. They have four suite options, two with a hot tub and two accommodating up to 3 people.

Rtip: If you are spending any time on the nearby island of Naxos, you must stay at family owned Hotel Grotta. Roam Guide, Jen Peterson says she experienced the best service she’s received anywhere in the world — nightly house-made wine and handwritten notes waiting for us on our balcony when we returned from exploring.

Photo Credit: The Sea Captain’s House

Photo Credit: The Sea Captain’s House


It's pretty easy to get around the island, and you’ll certainly want to explore. We rented a car which allowed us to visit a few less-accessible sites. One morning, we drove out to the Black Beach, around Pyrgos (a preserved village with excellent views of the island) and to the Akrotiri Lighthouse. After grabbing lunch back in Fira at FalafeLAND we spent the afternoon in Kamari, laying on beach chairs at the black pebble beach and eating gelato from Quicky's. It was a dream.

Relax on a Catamaran Cruise

There are a number of catamaran companies to choose from and they all offer amazing views, operating similar routes for a comparable price. They also offer round-trip transfers from your hotel. We booked Caldera Yachting’s daytime catamaran cruise, which departs around 9am and returns at 3. I could not have asked for a better experience. The option we chose (Caldera Gold Cruise) sailed from Vlichada Beach to Ammoudi Bay (Oia). We made two stops for swimming and snorkeling, plus a third stop for lunch (cooked on the boat). The food was great, wine was free, and the staff was so helpful. I am really happy that we did a daytime cruise, which allowed us to spend the afternoon in Ammoudi Bay, cliff jumping and eating fresh seafood while watching the sunset from the port. There are sunset cruises available, but I prefer to take in my sunsets from land.

Swim in the Aegean Sea

Don't leave Santorini without exploring Ammoudi Bay! The Bay of Ammoudi is the most delightful port tucked below the town of Oia, known for its fresh seafood and incredible cliff jumping. Facing the water in Ammoudi Bay, head left, through the restaurants and around Agios Nikolaos rock. There are no signs, so you just have to trust the weathered path to get you there. You'll likely see some other swimmers jumping off the adjacent rocks. Since our catamaran cruise ended in Oia, we let them know that we didn't need a transfer back to the hotel and opted to take the bus home after spending the afternoon in the bay. If you don’t arrive by catamaran you may find parking difficult. In that case you may want to consider taking the KTEL bus and walking down the stairs to the waters edge. Other travelers opt for a donkey ride as part of their visit.


Rtip: If you are looking for another calm place to swim in the Aegean sea, you should consider nearby Armeni Bay. It's a bit abandoned as most tourists opt to visit the aforementioned Ammoudi Bay (with all the good seafood). However, if you are looking for privacy this old port has a different kind of charm. Be warned though, there's only one restaurant, nowhere to change, and it’s quite a dubious walk down.

Get Lost on Foot

One of the best ways to spend time on Santorini is wandering the narrow pathways, searching for the famous blue domes and taking it all in. Each winding turn will offer yet another beautiful view. You're on a small island and will eventually you will find your way back.

Hike to Skaros Rock

Almost everything you read will suggest a hike from Fira to Oia (or vice versa). This is a much longer hike than you might imagine and by the time you get to Oia many are too exhausted to explore the beautiful village. Instead of hiking from Fira to Oia, I recommend hiking Skaros Rock in Imerovigli. You can take a cab or bus to Oia later in the day or that evening to watch the sunset.


“This hike is 100 times better and there's a hidden chapel built into the cliff... Need I say more?”

From Fira - walk north out of town towards Skaros Rock. You'll pass through Firosefani first and continue following signs to Oia. You'll reach a fork in the road when you reach the Blue Note restaurant in Imerovigli, signs will encourage you to go right, but you will want to go left for Skaros Rock. You'll see the Church of Anastasi, then continue right. The path down (left) to Skaros Rock starts just below Mezzo restaurant, as seen here. If you need more direction to the path itself, Santorini Dave does a really good job of explaining it with photos. As you walk towards Skaros Rock, you'll have two choices. To your right, is a path that leads you to the top of Skaros Rock and is a pretty intense hike from what fellow travelers told us. To your left is a path that leads you down the mountain. Keep following the path to the hidden church at the bottom! We were the only people there for at least 20 minutes and it was so peaceful!

Rtip: If you are looking to island hop from Santorini for a couple days, the nearby volcanic island of Milos is a wonderful choice. You can a rent a moped to explore the island and discover it’s many breathtakingly “beaches” — the rust toned rock formations of Paliorema Beach, the hidden ladder accessed Tsigrado Beach or the amazing “moon beach” of Sarakiniko Beach, known for its lunar like chalky terrain. Sarakiniko Beach is not far from the village of Mandrakia, home to one of the best seaside tavernas in Greece – Medusa Cafe. If you are overnight on the island we recommend Breeze Milos Boutique Hotel.


I don't do much shopping - but I definitely recommend picking up a bottle or two of olive oil and some Greek pistachios. One thing I always buy is a unique piece of art for my travel wall at home. In this case, I found a ceramic piece that was shaped and painted like one of the doors in Oia. There are a lot of volcanic stone jewelry shops in Fira. I picked up two necklaces with a unique lava stone from a bead store on Mitropoleos Street, on the south side of the Museum of Prehistoric Thera.

Rtip: If you want to seek out some lightweight linen travel wear look for B.Loose in Oia. Their “vacation pants” are perfect for a catamaran cruise in the Mediterranean or a jetsetting day through the Greek isles.

Photo Credit:   B.Loose

Photo Credit: B.Loose


Greeks eat dinner late, really late — usually after 9pm. We enjoyed a few dinners at sunset and a few after sunset. I suggest at some point you order Tomatokeftedes (Santorini Tomato Balls) & Soutzoukakia (Greek Meatballs) but don’t forget to try, Moussaka, the National Dish of Greece. It has three layers that are cooked individually before baking: sliced eggplant, ground lamb with tomatoes, onion and garlic and a Béchamel sauce or savory custard.

Rtip: Contributors say Metaxi Mas is an real treasure for those who want authentic greek cuisine. Views of Kamari Beach, amazing food, central location and comfortable vibe, but make sure you make a reservation.

Near Fira -

Naoussa was my favorite restaurant in all of Santorini. Excellent seafood dishes, live music and one incredible view. We had dinner on the last night at Fanari. It's a great spot to watch the sunset and with a glass of wine. Alali Restaurant at Astarte Suites, near Akrotiri, is a bit upscale and not within walking distance of Fira, but they offer great service and a varied view of the sunset.

In Ammoudi Bay -

You should absolutely order seafood in Ammoudi Bay. While it’s usually packed, it offers the freshest seafood and is worth the wait. There aren’t many restaurants, but Katina Taverna and Sunset Taverna are both excellent choices. At Katina Taverna, we actually picked our fish out of the cooler and they cooked it for us straight away. The tzatziki was also amazing there!

In Oia - The restaurants tend to be a bit touristy in Oia, but that’s certainly more noticeable in the daytime. When you are there for dinner and have a reservation, it can feel much more intimate. You should consider “Lauda Restarunat” at Andronis Boutique Hotel for impressive Greek fine dining in an amazing setting. Whatever brings you to Oia, be sure to get gelato from Lolita's, it’s worth the press.

Rtip R&R contributor Christina Sandok, says Ambrosia Restaurant in Oia is a must hit. It was by far her favorite restaurant while Honeymooning on Santorini.



I highly recommend a visit to Santo Wines in Pyrgos, first for their wine and second for the amazing view. Wine in Santorini is dry, like the climate, and has a really unique flavor because of the rich volcanic soil. Santo offers tours and tastings and has a large shop with local specialties. They're located a little out of town, so you'll need to take a cab, but only once because a second winery, The Venetsanos Winery is only a 15 minutes walk from Santos. Venetsanos was the first industrial winery of Santorini, founded in 1947. Structurally the winery is quite unique and they too offer an amazing view from a terrace where you can sit and taste Assyrtiko (white) and Mavrotragano (red) while enjoying some small bites from the area.

Rtip: If you are looking for a coffee cafe, contributors suggest Passaggio in Oia. Whether it be coffee, fresh juice or smoothie a great place to start your day is on the Passaggio terrace, gazing the sea of the Caldera. As day turns to night they serve cocktails as well.



In hindsight probably should have booked a hotel with a pool - there's not a ton of beach options in Santorini and a pool is really your best bet for cooling down and relaxing.

Photo Credit:  Mark Adriane

Photo Credit: Mark Adriane


Good sunscreen- Supergoop is a must, a swimsuit or two, comfortable sandals and a small packable daypack. It can be a little chilly at night after the sun sets, so make sure you bring a light layering piece to keep you warm.


Click here to see everywhere Jess recommends in Santorini.

What are we missing? Tell us your favorite Santorini secrets in the comments below.

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