3-4 Day Travel Itinerary: Santorini and Mykonos Islands
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 (or more); giving yourself time to shop and have a beach day on each island. We recommend you spend as much time as you can at this heavenly vacation destination!
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.
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.
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.
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Day 1: Tour of Santorini Island and Evening in Oia
Joe 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. If you have any time left in the morning, set out to explore the village.
The village 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.
This afternoon, the itinerary begins with an overview of the island. There are many types of tours to choose from: sightseeing, winery, photography, beach. Cost is usually tied to group size: coach, van, or private car. There are also taxi’s (expensive), scooters (dangerous), and buses (subject to time-tables) to consider. Pick a tour that coincides with your interest and pocketbook. The trip planner outlined below includes the sights on the island that Joe and I enjoyed visiting.
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. There are churches and the Castle of Pyrgos (1580) to explore. The village is the highest settlement in Santorini and there are fantastic views of both sides of the island at the summit of the hill.
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. You can also purchase items produced by the monks.
The Venetsanos Winery sits on hill above the Port of Athinios. The Venetsanos family has produced wine on the island for generations. A visit to the winery includes learning about wine making, wine tasting, and shopping in the vineyard’s store. The highlight of any visit is sure to be enjoying some traditional Greek meze platters on the magnificent Sunset Terrace.
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).
Back in Oia, rest for a bit. An hour or so before sunset, head back outside. Stroll along the narrow lanes that veer off, and wrap back around. Marvel at the shops full of blue glass, jewelry, and wooden fish. Investigate the stairways that seem to drop off into the air, and the spectacular terraces stacked on top of each other. You are apt to pass flowers blooming, stray dogs sleeping, and if you are lucky, a donkey or two.
As the sun drops, make your way to the southern end of town and locate the Oia Castle. Find a spot and settle in as a crowd gathers to watch the sun set. As dusk falls, the colors of the sky dance against a backdrop of windmills, cubes and domes.
Later, enjoy dinner at one of cliff-side restaurants on the edge of the caldera.
Day 2: Hiking from Fira to Oia and Ferry to Mykonos
This morning will be magnificent. 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 challenge is the heat.
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.
Plan for a 3-4 hours hike, plus travel time. The trail has paved portions, cobblestones, stairways, and dirt path. There is little shade and few stores along the way (so pack sunscreen, drinks, and snacks). To get started, take the bus from Oia to Fira. It runs often, it’s cheap, and takes about 30-40 minutes.
TRAVEL TIP 1: You can do this hike beginning at either end. There are inclines/declines in both directions.
TRAVEL TIP 2: The hike is equally (or more) spectacular in the late afternoon/sunset hours. If you are hiking in a cooler season, consider switching the hike with your general island tour from the Day 1 Itinerary.
TRAVEL TIP 3: 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.
The Hike: 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 some form of 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. You will be fine if you remember: Walk north. Ocean on right.
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.
Back out on the last leg of the trail, when you are once again enveloped by the open air and endless shades of blue, you will forget to be tired. Instead, you will only be able to contemplate how wonderful it is to be alive. 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.
TRAVL TIP: 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.
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). The village is small, but has distinct neighborhoods to discover.
There is the Kastro medieval quarter with its white washed Cycladic buildings, narrow alleys, and churches. There is the fishing port where wooden boats bob in the sea. There is Little Venice, a waterfront quarter full of restaurants and hotels. Finally, there is the Kato Myli ridge with a line of windmills in one direction, and Little Venice across the harbor.
After you have seen the sights have drinks, dinner, shop, and then drink some more. The later it gets, the livelier the atmosphere becomes.
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.
There are many ways to travel the roughly 7km from Mykonos Town to this string of beaches. There are private buses, cars, water taxis, rental scooters, and town buses. Joe and I recommend you book a small group boat tour that stops at a beach or two.
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. It is known as a ‘party’ beach, but this is primarily later in the afternoon/evening. 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.
As stated above, if you are able to stay a day or two longer there is plenty more to do. Kalimera! (Good day!) Laura and Randy
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