Oia is one of the most famous destinations in the world especially for couples and honeymooners. With its beautiful and intricate cliff and cave house architecture, full of infinity pools and jacuzzi for relaxing while enjoying panoramic views of the Caldera Bay Sea and its romantic sunset, no wonder it is one of the world’s top destinations.

The average stay in Oia is 3 nights, for the sake of this article we will assume that you will have 3 full days on the island staying in Oia and we would not recommend any less to make your stay worthwhile. You can pick a few of the options that we will recommend below and choose to relax more at your hotel, or follow entirely through if you want to fill your stay with experiences.

1st Day

Welcome to Oia

Use your 1st day to explore the village, browse shops, have a coffee or lunch with a view and enjoy the sunset. Oia from one end to another takes about 20 minutes by foot. It is not hard to navigate, there is one main marble pedestrian road that connects the whole village. If you want to avoid the masses, either take a walk at 8 am in the morning or after 11 pm.

The south end would be Saint George Church and the other end is the old castle ruins that people visit from all over the island to watch the famous Oia sunset. Along the main pedestrian road, you will see all kinds of shops you can think of, souvenir shops, jewellery shops, clothing boutiques, restaurants and cafes.

You will have your breakfast most likely at your hotel or villa, but there are restaurants too, that offer breakfast with the enticing Caldera view. Pelekanos Restaurant is one of them. Top rated on Tripadvisor, it offers magical views, attentive service and quality food. This venue is suitable for breakfast, lunch, or to enjoy a romantic sunset dinner.

In mid-summer it can get really hot in Santorini, around 36 degrees Celsius (96 Fahrenheit) . While you are out on the streets browsing the shops, grab some freshly made gelato from Lolita΄s. It is top rated, with a variety of flavours that will cater to everybody and is the best place to get ice cream on the island. While you are there you may also choose to cool down with a chilled take away cocktail from Boozery right next to Lolita’s.

Another place that is highly recommended is Melitini. It offers authentic Greek Tapas (Mezze) and stays true to the traditional Greek tavern-like experience. You can have lunch here or dinner. Reserving a table is a good idea as it is difficult to find open tables without one.

Enchant your 1st day in Oia with romance and have a sunset dinner. Reserve a table as soon as possible in one of the following sunset view restaurants: Pelekanos, Oia Gefsis, Pacman, Ellinikon, Meze Meze in Finikia Traditional Settlement near Oia (about 10 minutes by car from Oia).

Other notable restaurants in Oia : Lycabetus (fine dining) , Candouni (live Greek bouzouki music 3 times a week).

2nd Day

It’s time to go on an adventure!

Embark upon a Catamaran and cruise along Santorini’s south coast and the Caldera Bay. The itinerary includes the Red Beach, the White Beach and the Volcanic Hot Springs. The crew will serve you a full Greek Lunch or Dinner depending which tour you will pick.

Our company Explorer1 Yachting offers premium quality private tours and impeccable service from start to finish. We will arrange your hotel pickup and drop off so that you are completely worry free. Pick either the Day Cruise that starts at 10:30 am or the Sunset Cruise that starts at 15:30. Both tours last about 5 hours.

If you choose the Day Cruise, you will be back in Oia at your hotel at about 16:00. You will need some rest after the day on the sea and recharge batteries for an evening outing. Book a table in Amoudi Bay, a small harbor in Oia with fish taverns, located right underneath the north side Caldera Cliffs. You will get to enjoy your lunch or dinner here right on the docks next to the sea.

Amoudi is hard to access, you will either have to use the steps, (about 300) or get  a car to take you there. It is notoriously congested and very hard to find parking, especially for cars. Its peak hours are 15:00 and 21:30 when Catamarans load and unload people on the dock.

If you choose the Sunset Cruise, you will have free time until around 13:30 when you should be getting ready for your cruise pick up location. Use the time to relax in your hotel or take a stroll in the village. You will be back in Oia at about 22:00 after your Sunset Cruise.

3rd Day

Let’s explore Santorini

Your 3rd and final full day on the island has come. Explore other towns, visit a black sand beach and a winery. You can either rent a car (quads-ATVs are dangerous) or hire a private tour company if you want to be completely stress free and have a tour tailored to your preferences.

Santorin is well known for its wine industry for centuries. The assyrtiko grape which is indigenous to Santorini gives the wine its unique character. Visit 1 of the 15+ local wineries and go on a wine tasting tour. Check our Santorini Top 10 +1 Things To Do for winery recommendations.

Visit Perissa-Perivolos, Santorini’s longest black sand beach. You will find a variety of water sports there, beach bars, and restaurants to have lunch. Some noteworthy restaurants are : Savvas Popeye, 41 Restaurant and Sea Side

Explore the rustic traditional towns the island has to offer. The towns of Pyrgos, Akrotiri, Megalochori and Emporio are in an almost pristine condition in contrast to the rest of the island that has been modernized due to tourism. Walk through their small alleys, admire the architecture of the Captain Houses, capture your memories and fill your social media with postcard-like pictures.