Recognized as one of the favorite and most famous islands of Greece (and rightly so!), Santorini sits atop the rim of an extinct volcano with most of the iconic views facing the inner caldera. The sapphire domes atop bright white buildings along the cliffs is postcard perfect. The picturesque views are courtesy of most of the city's higher location above the steep cliffs, accessed by either a cable car ride or, for the more adventurous, a mule ride traveling up cross back trails along the hillside.

Although the island of Santorini boasts wineries, vast olive tree orchards, and beautiful sea views, the common provinces are divided between the two towns of Oia and Fira. Oia is located in the northern part of the island, while two miles south lies Fira, located directly west of the airport and situated closer to the sea ports for passing cruise ships. Imerovigli is another popular but quieter village adjacent to Fira located in between Oia and Fira. Oia and Imerovigli are more romantic and secluded with the best views and sunsets, but Fira has more restaurant options, clubs, shopping, and nightlife but also has nice views.

I stayed at the Cosmopolitan suites in Fira and had an awesome stay with an ocean view room with a terrace adjacent to the swimming pool. The location was perfect with easy accessibility to restaurants and shopping. Breakfast was served in our terrace and views from the infinity pool were gorgeous.

when to go

The temperature is maintained warm throughout the year, however, it may spike to higher temps during the summer and early fall months. As with most European/Mediterranean areas, tourism spikes during July through late August, so reserve your favorite hotel early, and pack light as the humidity will limit how comfortable you may feel wearing more than one thin layer of clothing. Shoulder season may afford better rates.

things to do

Fira to Oia hiking trail - Three-four hour 7 mile walk/hike from Fira to Oia with picturesque views of the coastline and local architecture. Make sure to bring water, sturdy shoes, and sun protection. Can get very hot in the summer. You could always take the bus back or stop at shops or restaurants along the way for a drink or a meal to re-fuel. Another option is to arrive at Oia for dinner, watch the sunset, and then take a bus back to Fira.
Sailing/boating - Book a catamaran excursion on the Aegean sea to view the dramatic cliffs of Santorini from the ocean, stop for swims at private beaches and coves.
Amoudi Bay - Turquoise waters with red cliffs, this charming bay is accessible from 200+ steps down from Oia, seafood restaurants and cafes.
Watch the sunset in Oia, a beautiful golden orange against the white-washed buildings.
Skaros Rock (Imerovigli) - Panoramic views of the caldera and the sea. Entrance to the right of Grace Hotel. Nice sunset views. Wear sturdy shoes. 15 minutes to the steps and can climb up the rock to the very top if you are feeling adventurous.
If you have a couple extra days, consider adding on Crete or Mykonos to your trip.

transportation

You can get around conveniently via bus or taxi. To get from the port to the cliffs of Fira or Oia, you could also take a mule ride or cable car ride up. Some hotels offer shuttles to the beach and shopping centers.

where to stay

Most people choose to stay in a caldera town as opposed to the beach as rooms up on the cliffs boasts the most incredible views.

Cosmopolitan Suites (Fira) - Beautiful boutique hotel with stunning views of the caldera and volcano, rooms with balconies with sea views from where you can enjoy breakfast, an infinity pool, convenient location to shops and restaurants (request the room to the right of the pool with a private balcony).
Grace Santorini (Imerovigli) - Luxury boutique hotel located on the highest post of the caldera, the hotel offers spacious villas with plunge pools, views of Skaros Rock, champagne breakfasts, an infinity pool, and beautiful sunsets.
Katikies Hotel (Oia) - Luxurious and romantic 5-star boutique hotel with cycladic white-washed rooms with a private terrace to incredible views of the caldera, champagne breakfasts from your terrace, three infinity pools, delicious restaurants, great service, free beach transfers from the hotel, in a convenient location to explore charming Oia.