The Best Santorini Itinerary

There’s something really magical about Santorini. Just mentioning the words “Greek island” evokes images of dramatic cliffs jutting out into the shimmering blue Aegean Sea, and precarious houses built in white with blue vaulted ceilings. We worked out the best three to five day itinerary for Santorini.

The Best Santorini Itinerary

Every year, two million visitors come to Santorini (usually by boat) in search of wineries, ancient ruins, boutiques, black and red lava pebble beaches, boiler house walks, Greek taverns and sunsets.

There is much to see and do, but thanks to the relatively small size of Cyclades Island (approximately 30 square miles), you can experience most of the magic in three full days and then return to the island via Paros, Mykonos and Naxos.

Recommended Hotels

Andronis Luxury Suites
San Marino Suites

Best Time To Go

The days of the week do not matter in Santorini, an island that is very dedicated to tourism, as everything is open seven days a week. What matters is the season: many of the hotels, tour operators, ferries, restaurants, shops and almost the whole town of Oia are close from before November until the end of March.

It is hard to believe, but Santorini has cold winters and strong winds. Most hotels use this time to renovate. That said, if you are here in high season (late May to August), you will have warm weather and sunny days, and lots of people.

Day 1: Walk (or ride a donkey) to Cliff Jumping

We recommend starting at Fira, as the picturesque, central town is where the ferries drop off passengers. Get up early and have breakfast at your hotel. Some of our favorite foods in Santorini were the free hotel breakfasts, which generally consist of at least Greek cakes, eggs, fresh fruit and coffee.

Put on comfortable walking shoes and follow the impressive pedestrian path that winds along the Aegean Sea from Fira to Imerovigli and eventually to Oia. The walk takes three to four hours at a leisurely pace and is an ideal way to get your bearings on the island, while appreciating the natural beauty and architecture.

The pit stops to take pictures in blue-domed churches with irregular backgrounds on the cliffs will definitely slow you down. Bonus points for going to Skaros Rock (follow the steps next to the Blue Note restaurant in Imerovigli), where scenes from “Mamma Mia! were filmed. The road is paved and well signposted through the villages, although it gets quite rocky and steep in the last and most remote part north of Imerovigli, which is where you can rent a donkey if you want a break.

Please note that there are no public toilets along the way. If you leave Fia around 8 a.m., you should arrive at Oia at noon, just before the hottest part of the day.

Oia is the crown jewel of the perfect postcard villages (you just passed the rest of them) that stick to the side of the Santorini cauldron. It is also the busiest and most expensive village on the island.

Have lunch at one of the many restaurants overlooking the cliff if you are still in love with the views of the caldera. Melitini offers Greek-inspired tapas that can be shared and has a rooftop patio. After lunch, it’s time for shopping or cliff diving. Santorini does an excellent job of providing authentic Greek items.

Souvenirs that can be covered include leather sandals, jewelry made from lava stones, local wines and “evil eye” knick-knacks. In Oia, the pedestrian path is crowded with boutiques and eventually leads to the tip of the island. It’s easy to spend a whole afternoon shopping, but if you want to get in the water, you’re still in the right place.

Adventure lovers should skip the shopping and walk to the end of Oia along the road that leads to Amoudi Bay. Hundreds of steps lead to the water, where the sailing excursions start, and there are several seafood taverns.

Hug the edge of the cliffs until you see a small island (with a church) and probably people jumping off small cliffs into the Aegean Sea. In the taverns you can enjoy dinners and sunsets, or rent a donkey to come back for dinner and watch the sunset on the cliff.

The old church (which is perched on a high rock) is usually packed with tourists looking for epic sunset views. After dark, it’s easy to catch a local bus back to Fira, where you’re likely to be more than ready to sleep.

Day 2: Board a boat and check out a bodega

After spending the first day walking through the villages and looking at the Aegean Sea, it’s time to get out on the water. Santorini Sailing offers a great selection of half-day trips that can include snorkeling, swimming, a visit to the hot springs (which are actually cold), meals, alcoholic beverages and sunset views.

If you have time, definitely consider taking a full day of sailing. For those with limited time, we suggest a five hour sail in the morning with some stops for diving and a delicious Greek style lunch served on the boat. It is amazing to see the cliffs and beaches of Santorini from the water. The price of the tour includes transportation from the hotel.

Back in Fira, you will have some time to browse the shops on the way to the pedestrian boiler (very similar to what you will find in Oia, but with more bohemian atmosphere and cheaper prices). Then it’s time to go to Santos Winery for a short visit, dinner, sunset views and, of course, wine.

This is not an intimate experience, the parking lot is usually crowded with tour buses, and the facilities are huge. That said, it’s a lot of fun and a great way to learn about wine production on the island. The wine (and the foodie gift shop) is much better than the food, but you should still take a bite to accompany the wine flights.

There are also incredible views of the caldera and sunset from the outdoor terrace. Some restaurants in Fira offer live music, but there is little in the way of nightlife. Most visitors go to bed early and get up early.

Day 3: Hit Red Beach and Katerina’s traditional restaurant

The third day is about the beach. Santorini isn’t immediately known for its beaches (unlike Mykonos), but the southern tip of the island is home to epic black and red lava pebble beaches leading to the calm and clear Aegean Sea. Red Beach is the most difficult to reach in terms of access.

Visitors have to walk from the parking lot, but the incredible formations of red cliffs and underwater coral are worth the stress. There are sun loungers and umbrellas available for rent, and there are a handful of restaurants with beach and snack vendors. For families, or anyone who doesn’t want to walk down a gravel road with a rope handrail to get to the beach, Kamari Beach is the second best option.

The exclusive beach town is relatively flat and there is public parking near the black pebble shore. Charming restaurants and shops line the pedestrian walkway that runs parallel to the Aegean Sea. The water clarity is excellent and water sports equipment such as paddleboards and jet skis are available.

You will not get sunset views from this part of Santorini, but since you are missing the natural spectacle anyway, this is an excellent time to dine at the traditional Katerina restaurant, an incredible family tavern with homemade Greek dishes. It’s hidden away in an anodyne street in the village of Fira.

What to do if you have two more days

If you have a few more days in Santorini, it’s time to go deeper and leave the well-kept tourist route. For more time on the beach (and the closest thing to a party atmosphere), Perissa Beach has karaoke bars, fish and chip shops, and budget hotels that cater to the British. Culture lovers should visit the Museum of Prehistory in Thera and the Museum of Folklore in Lignos to learn more about the history of the island.

If you loved Santos Winery, Venetsanos Winery is a more intimate event and has an incredible restaurant for dinner, as well as views of the caldera. If you loved the architecture of the caldera villages but hated the crowds, the village of Megalochori in the interior has the same romanticism and a more local feel.

Many Greeks still live in the cave houses (instead of turning them into boutique hotels), and there are a handful of Greek taverns with live music every night in the charming village square.

Know before you go

Some visitors arrive in Santorini through the small airport, but the vast majority arrive by boat. Both cruise ships and Greek ferry services (Blue Star Ferries is the only line operating all year round) drop off passengers at the port of Fira.

This is where things get interesting, as the most popular way to get from the quay to the road is to take a cable car or climb 600 steep steps. There are also taxis, donkeys and private buses.

If you are staying in a hotel in the northern villages (Fira, Oia, Imerovigli), we strongly recommend that you arrange transport with the hotel. Some of them are almost impossible to find without a guide, and parking is in lots at the bottom of the cliffs.

Although we refer to the cliffs, the elderly and people with mobility problems should be warned that the old island (produced by a volcanic explosion) can be difficult to cross. Some hotels extend over the cliff (climbing up and down the steps is the only way to reach them), and the northern villages do not allow access to cars.

Buses are reliable, safe and clean, although you may find yourself standing in the aisle. The fare for a one-way trip is about two euros, and you pay your ticket on board a money collector.

Taxis are expensive, so if you plan to really explore the island, the best way to get around is to rent an ATV (available everywhere, and companies will even take an ATV to your hotel room) or a car. Most sailing excursions include hotel pick-up and drop-off services in their rates.

Driving is generally safe, but keep in mind that there is not a single traffic light on the island and it can be distressing to share winding roads with buses, donkeys and quads. Uber is not available in Santorini.

The high season runs from May to September, and many of the hotels, restaurants and shops begin to close their doors in mid-October until around Easter.

Crowds are less in April and October, but the weather is colder (you probably don’t use swimming pools or swim in the Aegean Sea) and days are shorter in October. June, July and August are the busiest months and the island can feel invaded by tourists.

Hotel Picks

The island is world famous for its white Cycladic architecture with details in blue, and that’s what you’re likely to find (with a few exceptions, of course). Space and privacy are issues at Fira, Oia and Imerovigli, where many boutique hotels are built directly on the cliffs above each other, facing the Aegean Sea.

These are also the most expensive hotel options on the island. Move inland and to the south and you’ll find more space, more privacy, bigger pools and lower prices, but you’ll end up having to drive to visit the villages and you won’t get famous sunset views from your room.

For the newlyweds who want the best of the best at Oia, Adronis Luxury Suites has beautiful suites with private Jacuzzis and a spectacular infinity edge pool overlooking the boiler.

For something more modern and youthful, San Marino Suites is surprisingly modern and can be walked to Fira, although it will be uphill. Further on, the Dahlia & Jasmine Collection is a hotel love with low rates, a nice pool and a great breakfast. A bus ride will be required to get to Fira.

Beach lovers would have a hard time finding anything cleaner and more convenient for Kamari Beach than Sea Side Beach Hotel , which also has one of the best seafood and beach restaurants in Santorini. Apanemo is a good selection of family property for charming rooms, ocean views, low rates and very close to Red Beach.

Read more:
When to visit Santorini
Where to eat in Santorini
How to get from Athens to Santorini
Santorini’s Infinity Pools
Exploring Santorini’s beaches
How to get from Crete to Santorini
How to get from Mykonos to Santorini