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Heading to Greece and want to see as many islands as possible? We’ve got you covered with a two-week island hop itinerary that will take you to Santorini, Ios, Paros and Mykonos. Each island has its own distinct flavor, so get ready for a jam-packed holiday. In the summer season there are daily boat connections running between the islands. So get on a plane, jump on a boat and get island hopping.

Days 1-3: Santorini

By Patryk Kosmider

Start your Greek island hop holiday in Santorini, one of the most picturesque towns in all of Europe. Spend three days exploring the island’s black beaches, famous volcano, cliffside houses and blue-domed churches.

Things to do: Stroll through the area of Oia, pronounced ‘la’, soaking in the views and its narrow, winding streets. If you like walking, you can take the hiking trail between Fira and Oia, which gives you amazing views of the Santorini volcano (which devastated the island in the 16th century). Spend the evenings watching Santorini’s famous sunsets from bars or restaurants in Oia, which looks to the East.

Where to eat: Top places to eat include Ambrosia Restaurant, which has stunning, cliffside views, or harborside restaurant To Psaraki, which is known for its delicious fish dishes, such as fried calamari. Be sure to sample the restaurant’s house wine: it’s cheap, delicious and made locally.

Where to stay: Some great places to stay include the incredible Casa Sofia, with a view of the famous volcano from $271, or a more budget-friendly room in Karterados village from $52 a night. 

Day 4-6: Ios

Believe it or not, the sleepy island of Ios is known as one of the best places in Greece to bar hop. Spend two days relaxing on the island’s beautiful beaches, such as Kolitsani beach and Tzamaria beach before checking out the wild party scene in the evenings.

Things to do: Alongside relaxing on beaches, other top daytime activities include a visit to the tomb of famous ancient Greek poet Homer and a trip to the island’s Ancient Greek amphitheater. In the evenings, hit the island’s eclectic bar scene, known for its alternative music and quirky bars. Walk to the top point of Chora, which is the main village on the island, for an incredible view over the island and the sea.

Where to eat: Grab a tasty pizza at La Randa or head to The Octopus Tree, which is a traditional Greek restaurant serving delicious gyros (succulent kebab meat wrapped in a pita and topped with tzatziki).

Two Week Greek Island Hop Itinerary
Photo by La Randa

Where to stay: If you need a place to crash after partying, some great options include this stunning beachside apartment from $113 a night or this apartment with an awesome, large terrace from $156 a night. If you want to find something more budget-friendly you can explore all accommodation options in Ios.

Day 7-10: Paros

Two Week Greek Island Hop Itinerary
Photo by Pexels

After sampling the party scene in Ios, you’ll need some downtime on the beautiful island of Paros. The island is known for its winding alleys, ancient buildings, and beaches with emerald and sapphire waters. Spend three days here, relaxing ahead of your next stop, which is the crazy party island of Mykonos.

Things to do: Rent a moped and spend a few days exploring the island’s beaches. Paros is known for its stunning beaches, many of which are peaceful and non-touristy. The island has a picturesque Venetian port, where you can eat fresh calamari and grilled fish. There’s a 19th-century lighthouse trail that you can walk if you enjoy hiking. Paros is also a great place to try windsurfing, due to its strong winds.

Where to eat: Sample traditional Greek cuisine at the charming Levantis restaurant or head to the popular Koralii restaurant, which is known for its incredible seafood pasta dishes.

Where to stay: Why not relax in this stunning guest house, from $68 a night? Or you can rent this whole private villa with a sea view from $216. If you would prefer a hotel or hostel, you can check out all options in Paros.

Day 11-14: Mykonos

Two Week Greek Island Hop Itinerary
Photo by Jenny

Finish your vacation with a bang on the party island of Mykonos, which is known for its incredible nightlife. Mykonos is the most popular Greek island, and with incredible beaches, stunning villages and a great party scene, it’s easy to see why.

Things to do: Mykonos is a great place for water sports, like jet skiing, pedalo boating or windsurfing. If you prefer to be on land, you can rent a moped and head to the island’s northern beaches, which are known to be less crowded than those in the south. Some of the top northern beaches include Agios Sostis and Fokos beach. After a day of relaxing, spend the night partying at Cavo Paradiso or Scandinavian Bar.

Where to eat: Try the thick, creamy moussaka at Bakalo Greek Eatery Mykonos, eat dinner while watching the incredible sunset at Joanna’s Nikos Place Taverna, or share a mezze with friends at beachside restaurant Yialo Yialo.

Two Week Greek Island Hop Itinerary
Photo by Merle ja Joonas

Where to stay:  The modern Sahas studio apartment from $162 a night is an awesome option, or if you’re trying to stick to a budget this beach-side room for two from $54 could be a great alternative. If you want to check out hotel options, or other budget-friendly alternatives, you can check out all places to stay in Mykonos.

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