Greek Island Paradise: Santorini and Mykonos Trip Planning

There’s a reason Greece’s islands are the stuff of legends – their enchanting beauty and rich history captivate travelers from around the world. Among the plethora of Greek islands, Santorini and Mykonos stand out as two of the most alluring and popular destinations. Whether you seek romance and tranquility or vibrant nightlife and culture, these islands have it all. Here are our tips for planning an unforgettable trip to Santorini and Mykonos.

Island Transportation

Given the popularity of Santorini and Mykonos, transportation planning for your island trip is easy to navigate.

• Both islands offer small regional airports that primarily make connections in Athens (if you’re not already staying in Athens). The most popular airline for flying to the islands is Aegean Airlines. Pay attention to baggage limitations as these smaller planes will vary compared to your typical commercial flight. These airports are small! When we flew out of Mykonos there was a small waiting room area with stray cats entertaining the guests.
• You have two options for traveling between the islands:
  • Our recommendation for traveling between islands is to take a ferry. Not only is this option cheap and efficient, but its also a great way to take in some amazing sights along the way. The trip will be approximately 2.5-3 hours between Santorini and Mykonos. Your ferry will stop by other local islands and will cruise through some pristine waters. The easiest way to book your ferry is through the Ferryhopper website.
  • There are limited flight options available between the islands. These flights will be more expensive than ferries, and after you factor in additional airport time, will take approximately the same amount of time as a ferry. Unless boats aren’t your thing, we wouldn’t recommend a flight between Santorini and Mykonos.
• Once on the islands, local buses are the main mode of transportation. These buses are cheap and easy to navigate with stops along the main towns, beaches, and tourist destinations on the island. ATV rentals are another popular option which we’ll go into more below along with foot traffic.
• Note that these islands are frequented by cruise ships so that is an option as well. Visiting on a cruise offers you limited times on the islands and doesn’t give you the ability to take in the popular sunsets or peaceful mornings.

Santorini

Santorini’s breathtaking landscapes are the result of a volcanic eruption, which created a caldera surrounded by high cliffs. The island is dotted with whitewashed buildings cascading towards the sparkling Aegean Sea and famous blue-dome churches. Here are some of our top tips from our stop in Santorini:

Where to Stay

The two most popular spots to stay in Santorini are Fira (the largest town on the island) and Oia. If you’re looking for an upscale boutique hotel and more shopping and nightlife options, Fira is for you. We opted for a more traditional experience in Oia and booked a whitewashed Airbnb location right on the cliffside. There are many of options available in both towns to meet your budget and accommodation needs.

Things to Do

• Watching the sun dip below the horizon from Oia’s famous blue-domed churches is an unforgettable experience that should top your itinerary. Make sure to get there early to secure a good spot along the walkways to take in the view!
• Santorini offers both red and black sand volcanic beaches to explore. These beaches offer many nearby restaurants, shops, and beach lounging furniture. Our favorite stop was at the Kamari black sand beach which we reached by taking a quick bus ride from Fira.
• Much of the island can be explored by foot. We opted to take one of the most famous routes which allows you to walk along the caldera from Oia to Fira. This route takes you past whitewashed buildings and along cliffs with traditional Cycladic architecture and panoramic views of the caldera. If you opt to walk the full route it is approximately 6 miles.
• Exploring the many shops lining the streets and relaxing on the deck of a restaurant after a long day on the island are a must. Keep an eye on cruise ship traffic coming in for the day as the street and restaurants can fill up fast when there are multiple ships coming in. Make sure to partake in some beers from the local brewery: Santorini Brewing Company – we especially enjoyed the Crazy Donkey!
• There are many excursions that you can book while in Santorini including various watersport options. The most popular option is to take a sunset dinner cruise in the caldera.

Mykonos

Known for its vibrant nightlife and cosmopolitan atmosphere, Mykonos offers a lively contrast to Santorini’s romantic charm. Here are some of our top tips from our stop in Mykonos:

Where to Stay

Mykonos has one main town called Chora or more commonly referred to as “Mykonos Town”. Though there are small hotels and resorts scattered around the island, if you are searching for an Airbnb or want to have a hotel within walking distance of attractions, you’ll want to look to stay within Chora. The town is so much fun to simply walk around and explore. We’d recommend finding an Arbnb/rental property and staying right in the heart of all the action.

Things to Do

• Mykonos boasts an array of stunning beaches, from party-centric Paradise Beach to the more tranquil Agios Sostis. Whatever beach you choose you’ll be sure to find plenty of options for food, drinks, and lounging.
• ATV rentals are very popular on Mykonos and a great way to get around the island efficiently. We chose to rent ATVs as a fun way to explore some of the popular beaches during our stay. There are rentals all over the place in Chora and the process was pretty straight forward for us. We simply had to provide our drivers license and fill out a waiver, and we were off. Check out this blog post for a deeper look at renting ATVs in Mykonos.
• Wind through the maze-like streets of Mykonos Town, where you’ll find a treasure trove of shops, cafes, and picturesque corners. Fun fact – the streets were designed this way to confuse invading pirates!
• An iconic feature of this island are the windmills that overlook Chora/Mykonos Town. You can walk up and explore these windmills for some great photo ops. They are especially picturesque lit up at night.

When to Go

Plan your trip between late April to early November for warm weather and an abundance of activities. The closer you could get to the beginning or end of this time frame, the less crowded it will be.

Pack your bags, set your compass for Greece, and get ready to create unforgettable memories amidst stunning landscapes and welcoming locals. We hope this blog gets you set for your trip planning to Santorini and Mykonos! For more travel inspiration, check out our additional blog posts on international travel.