No trip to Greece is complete without enjoying the open sea! With endless coastline, thousands of islands, and warm waters ideal for swimming, you can craft the perfect sailing itinerary to match your interests. Enjoy the quieter islands of the Ionian Sea, or discover the energy and history of the Cyclades in the Aegean Sea. Or, stay close to the mainland and explore the coast of Nafplio, the Peloponnese Peninsula, and the Saronic Gulf. Whatever you choose, a sailing adventure awaits you in Greece!
Best of Syros
Spots like the medieval hilltop village of Ano Syros are well worth the climb, as are ventures out to the chapel of Agios Stefanos, built within a sea cave in southwest Syros, or to the northern coast of the island to catch a sunset off San Michali.
Previous kimkim travelers have gotten a hands-on glimpse of Syros’s ancient tradition of wooden boat construction with a ride aboard a boat fashioned in the traditional style, as well as sampled the island’s specialty loukoumi and chalvadopita sweets. Take a hike through the island’s nature preserve, fragrant with native herbs and sea views, and enjoy a secluded beach before boating back to town.
Chat with a local specialist who can help organize your trip.
Although most are uninhabited, Greece has over 6,000 islands dotting the waters of the Aegean and Ionian Seas. It's no wonder they attract travelers from all over the world with diverse history, unique culture, sandy beaches, and incredible natural surroundings. The two most popular clusters include the Cyclades Islands in the heart of the Aegean and Greece's southernmost and largest island, Crete. Combining the two constructs an ideal vacation filled with some of the most beautiful coastlines and ancient history in Greece.
Many of the colorful sea captain's houses that dot the Syros waterfront have been turned into hotels, allowing travelers to truly experience the island's past during their visit. Stay in one of the neoclassical buildings in the Vaporia neighborhood of the island's main town of Ermoupoli, or head to one of the beaches if you prefer more space.
Discover Greece's distinct culture and gastronomy, starting in Athens with a private tour of the Acropolis and a hands-on cooking class, followed by a transition to some of the most beautiful islands of the Cyclades. Begin in Syros for food tours and explorations of medieval cities, then head to the hidden gem of Tinos for some of Greece's best cuisine, plus a visit to marble villages, an art workshop, and an afternoon swimming in the Aegean Sea. End your trip in Naxos where you'll discover ancient sites, historic streets, medieval monasteries, and, of course, delicious, locally-sourced cuisines, the pride of the Greek Islands.
Athens, Naxos, Tinos, Ios, and Syros are a classic pairing for travelers headed to Greece. To make the most of your trip, maximizing time between travel days at each incredible stop, you'll want to plan your trip for about 10 to 14 days. Arrange your perfect trip to Athens, Naxos, Tinos, Ios, and Syros with the itinerary ideas below.
Take 12 days to explore some of the lesser-known islands of the Cyclades. Start by sampling street food in Athens before venturing out to sea. You'll stop on Syros, Tinos, Naxos, and Ios, with enough stately homes, savory food tours, and sunny beaches to keep you in serenity long after your trip is over.
White domed buildings, blue seas, freshly baked baklava, and more await on this 13-day itinerary. You'll hit up all the hallmarks of the Cyclades but beat the crowds with stops in Syros, Tinos, Naxos, and Ios. Start with a food tour in Athens to fuel up before you ferry out to tour the mansions of Syros, bike past the beaches of Naxos, and more.
While away for two weeks in lesser-known islands, get a taste of Athens with this itinerary that focuses on relaxation. Whether hiking amid the marble-rich hills of Tinos or tasting fresh produce on Naxos, these four Cycladic islands will have you asking, "Santorini, who?" in no time.
As the ultimate sailing adventure through Greece's coveted Cyclades Islands, this tour combines bustling city life with tranquil villages nestled in the Aegean Sea. From some of Europe's best nightlife to humble fishing towns and secluded beaches, travelers will enjoy Greece's rich and varied heritage. Enjoy sunsets and local seafood while discovering important and ancient archeological sites, all from the comfort of a private yacht.
Hideaway from the rest of the world as you discover the Cycladic islands that you may not have heard about—yet. Spend 15 days visiting Athens and the islands of Syros, Tinos, Naxos, and Ios. They may not be as famous as their glittery neighbors but have plenty of culture, history, and straight-from-the-Aegean seafood to keep you satisfied.
See the lesser-known side of the Cyclades on this 16-day island itinerary. After sampling the street foods of Athens, you'll ferry off to the Cycladic islands that deserve just as much of the spotlight as their more-famous siblings. Tour the mansions of the Cycladic capital on Syros, explore the Tinos marble scene, bike the beaches of Naxos, and see the villages and vineyards of Ios before your return to Athens, accompanied by the sweeping of the Aegean Sea.
Cruise like a celebrity through the glittering waters of the Cyclades on this nine-day itinerary. The Cyclades are some of the most quintessential Greek islands, and you'll see seven of them from the decks of your yacht, along with plenty of time to explore onshore. From lesser-known spots like beach-lined Milos and petite Antiparos to favorites like bustling Naxos and cosmopolitan Mykonos, you'll scope out this island chain in style.
Channel the spirit of some of Greece's most famous tales as you sail through the Aegean on this nine-day itinerary. Start off by paying the proper tribute at the Temple of Poseidon before you start on your way to Kea, followed by the villages of Kythnos. Visit the capital of the Cyclades on Syros and the home of the Cyclops on Serifos, then search for the Venus de Milo's cousin on Milos before you end your trip on the double beach of Kolona.
These four Cycladic islands haven't graced as many guidebook covers as their glitzier cousins, but that means there's more here for you to discover without battling hordes of selfie sticks. Take 10 days to tour Syros, Tinos, Naxos, and Ios on this itinerary, with pilgrimage sites, culinary experiences, and more.
What better way to unwind than spending 11 days sampling the culinary selections from across the Cyclades surrounded by the sea? You'll start this trip with a street food tour of Athens, then head to less famous yet beautiful islands, stopping in Syros, Tinos, Naxos, and Ios to sip wine, sample fresh produce, and even learn how to recreate the recipes at home.
Athens · Greek Islands · Cycladic Islands · Santorini · Crete · Naxos · Mykonos · Chania · Peloponnese · Northern & Central Greece · Nafplio · Tinos · Heraklion · Meteora · Ionian Islands · Zagori · Thessaloniki · Corfu · Nafpaktos · Sparta & Mani · Paros · Delphi · Olympia · Mani Peninsula · Monemvasia · Rhodes · Dodecanese & Northern Aegean Islands · Milos · Kalamata · Rethymno · Corinth · Saronic Islands · Sifnos · Gortynia · Messinia · Hydra · Sparta · Sifnos Port