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3-4 Day Travel Itinerary: Santorini and Mykonos Islands

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Blue Dome | Santorini Island, Greece | Santorini and Mykonos Travel Itinerary
Blue Dome | Santorini Island

This 3-4 day travel itinerary explores the exceptionally beautiful Greek islands of Santorini and Mykonos.

Everyone knows photographers are tricksters. They lighten, darken, and add pops of color. Greece’s Santorini Island is one of the few spots in world where the natural beauty of the blue-domed landscape is more incredible in person than any photograph you might have seen. The nearby island of Mykonos, also graced with sun-bleached buildings and brilliant blues, is equally gorgeous – but with a very different personality.

This trip planner includes two days and one night on Santorini; and concludes with one night and a day on Mykonos. The itinerary can easily be extended to 4 days; giving yourself time to explore all the best things to do in Santorini and Mykonos.

Windmills | Kato Myli Ridge | Mykonos Island Greece
Windmills | Kato Myli Ridge

The island of Santorini (official name ‘Thera’) is part of a chain of islands in the Sea of Crete. The archipelago is arranged around the center of a flooded volcano (caldera). Roughly three-quarters of this ring is the crescent-shaped Santorini Island.

Caldera, Santorini Island, Greece | Things to do in Santorini
Caldera, Santorini Island, Greece

Santorini’s western coast is a semi-circle of soaring cliffs. Atop these bluffs, a line of white-washed villages perch between the deepest blue sea and sky imaginable. Santorini is a tantalizing fusion of bold color, breathtaking vistas, and dizzying heights.

If you are only in Santorini for one day, consider taking a comprehensive island tour such as Santorini: Top Sights Day Trip, Wine Tasting, & Oia Sunset Tour.

The Blue Domes of Oia. Santorini Greece, Things to do in Santorini
The Blue Domes of Oia. Santorini

Mykonos Island shares Santorini’s striking white architecture and brilliant blues. Everything on Mykonos is closer to the sea, though. The island is rugged, rocky, and dotted with beaches. Mykonas Town is bursting with Greek crafts and culinary delights. It is a traditional fishing village that turns into an upscale tourist town after dark.

If you can only be in Mykonos one day, consider taking a comprehensive island tour such as: Mykonos Guided Highlights Tour.

Fishing Boats in Mykonos Town, Mykonos Itinerary, Mykonos Island Greece
Fishing Boats in Mykonos Town
Santorini and Mykonos Travel Itinerary At A Glance, Greek Islands

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Day 1: Tour of Santorini Island and Evening in Oia

Randy and I recommend that you book a room in the village of Oia (Ia) for your first night’s stay. The village is charming with panoramic views of the Aegean Sea. Although less of a transportation hub than the capital, Fira, it is calmer. Check into your lodging and set out to explore the village.

OIA has one main road that runs along the outside of the community. A cliff-side walkway traverses the middle of the town. Restaurants, shops and hotels shoot off the walkway into meandering pathways. There are cobblestones, stairs, sharp angles, and magnificent views at every turn.

Agios Georgious Church, Oia, Santorini Island, Santorini Itinerary
Agios Georgious Church, Oia
Ia, Santorini Island Greece | Things to do in Santorini
Ia, Santorini Island, Greece

This afternoon, the itinerary begins with an overview of the island. There are many types of tours to choose from.. Pick a tour that coincides with your interest and pocketbook.

Pyrgos | Santorini Tour, Greek Islands
Pyrgos | Santorini Island


Built along the side of a hill, Pyrgos is a small mid-island village of about 500 inhabitants. It is less developed than the cliff-side towns, making it a scenic, relaxing stop. Its quaint medieval houses and winding pedestrian streets (designed to confuse marauding pirates) will take you back in time. See the Castle of Pyrgos (1580) . The village is the highest settlement in Santorini and there are fantastic views at the summit of the hill.

Top of the Pyrgos Village. Santorini Island | Things to do in Santorini
Top of the Pyrgos Village

Monastery of Profitis Ilias

The Monastery of Profitis Ilias sits at the top point of the island. From this vantage, there are all-encompassing 360’ views. At one time, the monks ran a secret school on these premises. There is a small museum and chapel to visit.

Monastery of Profitis Ilias | Santorini Island on a Santorini Itinerary
Monastery of Profitis Ilias

Venetsanos Winery

The Venetsanos Winery sits on hill above the Port of Athinios. The Venetsanos family has produced wine on the island for generations. The highlight of any visit is sure to be the wine tasting and enjoying some traditional Greek meze platters on the magnificent Sunset Terrace. To see more wineries check out the winery tour.

Venetsanos Winery | Santorini Island | Things to do in Santorini
Venetsanos Winery | Santorini Island

Red Beach

If you love beaches, Red Beach is a great choice. The rocks and sand are an other-worldly red hue. There is a tavern for drinks and snacks. With the soaring cliffs and the infinite Aegean Sea, it is easy to feel alone (even on a crowded beach).

Oia Town

Be back in Oia in time for the sunset. As the sun dips, stroll along the narrow crooked lanes. Marvel at the shops full of blue glass, jewelry, and wooden fish. Investigate the stairways that seem to drop off into the air. You are apt to pass flowers blooming, stray dogs sleeping, and if you are lucky, a donkey or two. If you want to splurge do a private Oia Village photoshoot of your group.

Stairway to Nowhere | Oia | Santorini Island, Santorini Greece
Stairway to Nowhere | Oia |

As the sun drops, make your way to the southern end of town and locate the Oia Castle to watch the sun set. As dusk falls, the colors of the sky dance against a backdrop of windmills, cubes and domes.

Ready for Sunset, Oia Castle | Things to do in Santorini, Greek Islands
Ready for Sunset, Oia Castle
Caldera at Sunset, Santorini Island, Trail between Oia and Fira, Greek Islands
Caldera at Sunset, Santorini

Later, enjoy dinner at one of cliff-side restaurants on the edge of the caldera. Or, do a sunset cruise with dinner on the Mediterranean Sea (and unlimited drinks).

Sunset in Fira, Santorini Greece on a Santorini Itinerary
Sunset in Fira, Santorini Island, Greece

Day 2: Hiking from Fira to Oia. Ferry to Mykonos

Have a hearty breakfast and pack for a hike (at a minimum hat, sunscreen, water, and camera). The itinerary calls for a roughly 6.5 mile (10km) hike from Fira to Oia. With sturdy shoes and an average level of fitness, you should be able to navigate the trail. There are uphill and downhill climbs, but the main challenges are the sun and the heat.

If you would feel more comfortable attacking this hike as part of a tour, check out this Caldera Hiking Tour from Fira to Oia.

Oia, Santorini Island on a Santorini Tour, Greek Islands
Oia, Santorini Island, Greece

The trail starts in the village of Fira. It passes though the villages Firostefani and Imerovigli, and ends back in Oia. Hiking along the caldera’s rim, you will enjoy breathtaking skylines as the trail, the cliff-side villages, and the sparkling, blue sea spread out in front of you. It is glorious.

Oia and Fira Trail | Santorini Greece | Things to do in Santorini
Oia and Fira Trail | Santorini, Greece

Plan for a 3-4 hours hike, plus travel time. The trail has paved portions, cobblestones, stairways, and dirt path. To get started, take the bus from Oia to Fira. It runs often, it’s cheap, and takes about 30-40 minutes.


You can do this hike beginning at either end. The hike is equally (or more) spectacular in the late afternoon/sunset hours. The hike can be split up into smaller segments if you do not want to tackle the entire length. Each village provides a natural starting and stopping point, and you can catch the bus back to Oia.

Village of Oia | Santorini Island | Greek Islands
Village of Oia | Santorini Island

Hike from Fira to Oia

When you get off the bus in Fira, find the main pedestrian walkway. Head north to the unofficial trailhead, the Atlantis Hotel. You will follow this trail for the next 6.5 miles. There are occasional markers, but there are also lots of “Ys” in the path. Always keep the ocean to your right and you will meet back up with the trail. About mid-way there is a short section of the trail that joins with the highway. Walk north with the ocean on your right.

Shopping in Santorini | Things to do in Santorini | Greek Islands
Shopping in Santorini

As you leave Fira and the adjoining Firostefani, the number of hikers will begin to thin. Likely, there will be long stretches of path when there is only you, the sea and sky, volcanic rock, and a village in the distance. Eventually, you will come to the lovely village of Imerovigli. Here you will pass the famous Skaros rock. If you are going to stop, this is a good place for a drink and a snack.

Skaros Rock, Santorini, Island | Santorini Tours
Skaros Rock, Santorini, Island

Back out on the last leg of the trail, when you are once again enveloped by the open air and endless shades of blue. Too soon, you will be descending the trail into Oia. Head to your hotel, shower, grab your bags, and take a taxi to the Port of Athinios for a ferry ride from Santorini to Mykonos. Or, if you have the time, spend one more night in Santorini before taking the ferry to Mykonos Town in the morning.


To make the 3 day itinerary work you need to purchase your ferry tickets ahead of time and get an early start on the trailhead. The Port of Athinios tends to get very crowded. Make sure you allow yourself enough time to make your connections. There are several ferry companies to choose from, the last ferry to Mykonos generally leaves mid-afternoon.

Little Venice, Mykonos, Greece | Mykonos Itinerary
Little Venice, Mykonos, Greece

Drop your bags at your hotel in Mykonos Town, and rest for a while. Have a drink, and take a siesta. Early evening, head out to explore. Mykonos Town (Hora to the locals). Walk to the Kastro medieval quarter with its white washed Cycladic buildings, narrow alleys, and churches.

Beach on Mykonos Island Greece | Things to do in Mykonos
Mykonos Island, Greece

Next, wander to the fishing port where wooden boats bob in the sea. Then, find Little Venice, a waterfront quarter full of restaurants and hotels. Finally, see the Kato Myli ridge with a line of windmills in one direction, and Little Venice across the harbor. If you prefer not to self-navigate, try a Mykonos walking tour.

After you have seen the sights have drinks, dinner, and shop. The later it gets, the livelier the atmosphere becomes. Another idea is to get out on the water with a sunset boat party with open bar and DJ.

Coast of Mykonos Island,Greece | Mykonos Itinerary on the Greek Islands
Coast of Mykonos Island, Greece

Day 3: Mykonos Beaches

Sleep in, then jump in your bathing suit. Mykonos has a fantastic coastline and crystal-clear water. A footpath connects a number of island beaches (Psarou, Platys Gialos, Agia Anna, Paraga, and Paradise). This means if you visit one, you can easily wander to another.

Boating Mykonos Island Greece | Things to do in Mykonos
Boating Mykonos Island, Greece

Water sports and boating around the island of Mykonos are exciting (the sea is often choppy), and incredibly stunning. If you have to pick one beach to go to, we vote for Paradise Beach. The shore is clean and the sand is fine. There are bathrooms, changing rooms, chairs for rent, food, and drinks on site. This tour goes to Paradise Beach.

Paradise Beach, Mykonos Island Greece | Mykonos Itinerary
Paradise Beach, Mykonos

Water sports and boating around the island of Mykonos are exciting (the sea is often choppy), and incredibly stunning. If you have to pick one beach to go to, we vote for Paradise Beach. The shore is clean and the sand is fine. There are bathrooms, changing rooms, chairs for rent, food, and drinks on site. It is a perfect spot to say ‘adio’ (goodbye) to the island. This tour goes to Paradise Beach.

Lounging Paradise Beach, Mykonos Island Greece | Things to do in Mykonos
Lounging Paradise Beach, Mykonos

Another very popular activity that gets you out on the water in Mykonos is to visit the Delos archeological site. Delos Island is the mythological birthplace of Apollo. The island was an important religious gathering place; on it are the remains of several temples to explore. This catamarran tour combines a visit to Delos and Rhenia with lunch.

Kalimera! (Good day!) Laura and Randy

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