Greek Island Hopping Via Sailboat Charter

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Advisor - Jen Barnes
Curated By

Jen Barnes

  • Active Travel

  • Adventure Travel

  • Beaches

  • Family Travel

  • Greece

  • Outdoors

  • Local Food

  • Multi-City

  • Beach Town

  • Sightseeing

The views of a whitewashed Greek city from water.
Curator’s statement

Greece is a fabulous destination in itself, but island hopping via sailboat charter takes Greece to epic levels. This type of vacation gives you and your family an opportunity to see some of the smaller islands with less crowds. A typical summer sailing charter from Paros will entail 6-7 nights on the sailboat where you will sleep under the stars in a cozy berth. Charters are also available for up to 14 nights. Days will be spent on different islands exploring and enjoying. You will also have ample time on the water with some adventurous sailing. You can flex your skills, or sit back and let your captain take care of it all. Either way, you'll enjoy the beauty of the Aegean Sea along the way. Routes will vary depending upon your preferences, but also the winds. No two sailing charters are exactly alike, which adds to the adventure!

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Where to stay in Paros, Greece

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Things to do in Paros, Greece

A woman walking to a white and blue city in Greece.

Each island offers different experiences and has its own flavor. Many of the Cyclades Islands have a choice of secluded beaches perfect for relaxing in the sunshine and taking a dip in the refreshing Aegean Sea during the day. Some islands have bicycles or ATV's to rent to explore and adventure. Or perhaps you may seek out a hike or walk along the cliffs to enjoy the sea views and the island breezes. Head back to your charter boat to clean up before your dinner reservations. Dinner will typically be al fresco where you can indulge in an Aperol Spritz and the best Greek salads you will ever experience. The town centers of even the smallest islands will have local shopping and eateries, which are open late into the evenings after dinner. The locals and tourists alike will keep the town bustling as everyone is out being social, even families with small children. Make your way back to your charter boat and fall asleep with your berth windows open and the rocking of the sea waves. When you wake in the morning, set sail for the next island or plan some time to snorkel, stand up paddleboard or swim in a gorgeous cove.

Day trips

Islands to consider for your day visits:

  • Folegandros

  • Ios

  • Milos

  • Sifnos

  • Naxos

  • Paros

  • Antiparos

  • Schoinoussa

I'm going to be super honest here and tell you that we skipped Mykonos because we wanted to avoid crowds and the party scene. We also skipped Santorini and we do not regret it at all. You CAN do the Greek Isles without seeing the two that everyone talks about. I promise you will still get great photos and create amazing memories.

Places to eat & drink in Paros, Greece

Waterfront restaurant in Greece.

Restaurant choices will depend entirely on which islands you visit, of course. But I will impress on you that if you are sailing during high season (June-September,) you will want to have your captain make sure to get you reservations. Your captain has developed relationships with the locals over the years and is familiar with the restaurant types and their offerings. Try to catch the sunset before dinner, and then walk the town shops after dinner to digest.

A few favorites include:

  • Lord Byron on the island of Kos, which is kitchy and strange, but the portions are huge and the food incredible.

  • Deli on the island of Schoinoussa has the best fava I have ever had and will ever have I'm sure of it. We never even got a menu here. The kitchen just sent dishes out, but we did have a table near us with allergies and they were accommodated beautifully.

  • On the island of Naxos, if you have a car drive up to the interior of the island to Rotunda to have unbelievable views and delicious food.

Need to Know

A pro tip: The winds in the Cyclades during high season can be insane and make for epic sailing. Catamarans are more likely to have to stay in port on a very windy day in the Cyclades, but a monohall can handle the winds just fine. You know your people and your preferences so choose wisely. Sailing means different things to different people. If you are more comfortable with a performance yacht, those charters are also available and offer a full crew at the ready for you. You can make this as rustic or as glamorous as you wish.

Looking for more travel tips? Check out this guide: A Family-Friendly Adventure to Costa Rica.

Advisor - Jen Barnes

Travel Advisor

Jen Barnes

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This guide is part of our ongoing series on travel to Greece.