A Guide to Greek Island Hopping

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Advisor - Schuyler Bailey
Curated By

Schuyler Bailey

  • Greece

  • Santorini

  • Mykonos

  • Adventure Travel

  • Off-the-Beaten-Path Travel

  • Outdoors

  • Relaxation

  • Mountains

Santorini, Greece sight
Curator’s statement

The Greek islands have captured our fascination for centuries and it's no wonder, they're as diverse as they are beautiful and open a new world at every port. For a once-in-a-lifetime itinerary, the Cyclades offer both famed destinations (Mykonos, and Santorini) and lesser-known gems. And while you could spend days (or weeks) at each of these isles, you can get a good taste with a well-planned 7- to 10-day itinerary.

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Insider knowledge

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Where to stay in Greece

Avax Villa by K&K

Experience luxury and seclusion at Avax Villa by K&K, where stunning architecture, panoramic views, and upscale amenities combine to create an exclusive and unforgettable retreat on the beautiful island of Santorini.

Unlock perks by contacting Schuyler to book your trip.

Things to do in Greece

City on the other side of sea

See the Sites

You know you need a selfie in front of the Blue Dome on Santorini, but have you planned to stand in the gate of Naxos, climb the medieval steps of the fort at Naussa on Paros or visit Homer’s tomb on Ios? Each island holds the stuff of legends. Weave up the cobblestone alleys and seemingly endless stairs to the top of Ano Syros, a medieval hilltop village that looks down upon the modern port city of Ermoupoli. Reward yourself with the view and a drink at Theosis Bar, which is tucked into the ancient stairway.

Get Moving

From kite surfing Antiparos to scuba diving a shipwreck on Naxos, adrenaline junkies can pick their flavor of excitement. If you're ready to get behind the wheel, ATVs are a great way to get around most islands with more flexibility.

For those that prefer the sport of extreme shopping, the port town of in Paros will keep you busy with its meandering alleys chockablock with everything from clothing and jewelry to rarified accoutrements for the home.

Charter a Boat

The best way to island hop across the Greek Isles by far is by boat. Charter Erato, a traditional wooden hulled sailboat, for classic luxury; with room for friends and family (9 cabins to be exact), and an incredible crew (a charming set of captain, chef, and deckhands, no less) who will ensure this is a vacation and not just a trip. Reach out to Schuyler to book!

Places to eat & drink in Greece

An open Area cafe

If you haven't tried Greek food, you will soon be won over by the freshest seafood prepared beautifully on the islands.

On Paros, you can't miss the fishing boats lined up along the seawall—they flank many bars and restaurants in the hip port of Naousa. Meet your meal before it's cooked at the fish case at Siparos, where salt-crusted snapper gets torched table-side for an inferno of flavor.

On Santorini, grab lunch of fresh octopus or squid seaside at Sunset Ammoudi Bay, where the water literally laps at your feet as you dine. Then head to the other side of the island to see where your Assyrtiko was grown with a wine tasting at Domaine Sigalas. If you've tired of seafood, the rooster ravioli at Roka, along with a sunset view on their back porch, will bring you back to earth in the best way.

Photos by Calder Sokolow

Advisor - Schuyler Bailey

Travel Advisor

Schuyler Bailey

Get in touch with Schuyler

Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.

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Looking for more travel inspo? Check out Fora Travel Advisor Maria Chapman's guide, Food and Drinks in Mykonos: A Quick Guide about Restaurants, Bars & Beach Clubs in Mykonos, Greece.

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