14 days in Cyclades

Begin your yacht journey in Kea (Tzia) by arriving at Vourkari’s charming marina, where colorful boats line the quay and you can enjoy a leisurely coffee at a waterfront café. From there, sail to Otzias Bay for a refreshing morning swim in calm turquoise water, before continuing to Korissia to stroll along the harbor promenade. Climb up to Ioulis, the island’s whitewashed hilltop capital, wandering narrow lanes and pausing to see the ancient Lion of Kea, carved into rock outside the village centuries ago. Enjoy a relaxed lunch at a taverna overlooking the sea, sampling local cheese and honey. In the afternoon, anchor off Gialiskari or Sykamia beach for swimming and snorkeling in clear water framed by pine-covered hills. As the sun sets, drop anchor in the sheltered bay of Vourkari for a quiet dinner aboard beneath the stars.

WHAT TO SEE
Vourkari harbor, Lion of Kea, Ioulis (Chora), Otzias Bay, Korissia

WHAT TO EAT & DRINK
Sample Kea’s excellent local cheeses and prized thyme honey, alongside fresh-caught fish served simply with island olive oil. Pair your meal with a glass of local wine as you watch the sun dip behind the hills.

Begin your yacht journey in Kythnos by arriving at Merichas, the island’s main port, for a coffee at a harborside café before setting sail. Head to Kolona, one of the most striking anchorages in the Cyclades, where a narrow strip of golden sand connects the coast to the islet of Agios Loukas, with turquoise water on both sides ideal for swimming and snorkeling. Continue to Loutra, known for natural thermal springs bubbling into the sea, a truly unique spot for a soak. Later, visit the traditional village of Dryopida, with its whitewashed houses, tiled roofs, and winding alleys, for a relaxed lunch of local cheese pies and grilled meats. As afternoon turns to evening, cruise to Apokrousi or Fikiada beach for a peaceful swim. Spend the night anchored off Kolona, watching the sky turn pink before a starlit dinner on deck.

WHAT TO SEE
Kolona beach, Loutra thermal springs, Dryopida village, Merichas harbor

WHAT TO EAT & DRINK
Taste Kythnos’s soft “sour” cheese of Thermia and kopanisti, along with pasteli sesame-honey sweets and thyme honey rated among the finest in Greece. Enjoy them with local sausages or a glass of traditional Thermia wine.

Begin your journey in Serifos by arriving at Livadi, the island’s main harbor, for a fresh coffee before setting off along the rugged coastline. Sail to Psili Ammos, one of the finest sandy beaches in the Cyclades, ideal for swimming in shallow, crystal-clear water. Continue to Agios Sostis or Sykamia Beach for quiet snorkeling among rocky coves. In the afternoon, head into Chora, Serifos’s dramatic hilltop capital crowned by a Venetian castle, and wander its whitewashed lanes for a relaxed lunch overlooking the sea. Back on board, cruise along the coast to discover secluded bays perfect for an afternoon swim. As evening approaches, anchor in the sheltered waters of Livadi Bay, watching the lights of Chora glow above the harbor while enjoying dinner under a starlit sky.

WHAT TO SEE
Chora (Serifos Town), Psili Ammos beach, Livadi harbor, Agios Sostis

WHAT TO EAT & DRINK
Sample Serifos’s cured pork louza and its distinctive “cheese of the pit,” a peppery gruyere-style cheese aged underground, alongside chickpea soup slow-cooked in a clay pot. Pair them with a glass of the island’s revived Serifiotiko white wine or a taste of souma, the traditional local grape distillate.

Begin your journey in Sifnos by arriving at Kamares, the island’s picturesque port, for a morning coffee beside the harbor before heading ashore. Climb up to Apollonia, the whitewashed capital strung along a ridge of windmills and chapels, or visit Kastro, the medieval hilltop village with sweeping views over the Aegean. Sail on to Vathi, a calm, horseshoe-shaped bay perfect for swimming and paddleboarding, or continue to Platis Gialos for a relaxed lunch of local specialties at a seafront taverna. In the afternoon, visit the iconic Chrysopigi Monastery, perched dramatically on a rocky outcrop above the sea, before anchoring nearby for a swim in clear turquoise water. As the sun sets, drop anchor in the shelter of Vathi Bay for a peaceful evening on deck.

WHAT TO SEE
Kastro village, Apollonia, Chrysopigi Monastery, Vathi Bay, Platis Gialos

WHAT TO EAT & DRINK
Savor Sifnos’s famous revithada, a slow-cooked chickpea stew baked in a clay pot, and mastelo, tender lamb or goat cooked in wine with dill. Round off your meal with manoura, the island’s cheese aged in wine must, and a glass of local wine.

Begin your yacht journey in Milos by arriving at Adamas, the bustling main port, for a morning coffee before setting sail along the island’s dramatic volcanic coastline. Head to Sarakiniko, a striking lunar landscape of smooth white rock meeting deep blue water, perfect for swimming and cliff-jumping. Continue to Kleftiko, the legendary sea caves and rock arches once used as a pirate hideout, where you can snorkel through hidden grottoes and turquoise coves. Stop in Klima, a colorful fishing village with brightly painted boathouses built into the rock, or visit Plaka, the island’s hilltop capital, for a relaxed lunch with sweeping caldera views. In the afternoon, anchor off Firiplaka Beach for sunbathing on golden-red sand. As evening falls, settle into the sheltered waters near Kleftiko for a magical sunset and a tranquil night at anchor.

WHAT TO SEE
Kleftiko sea caves, Sarakiniko, Klima village, Plaka, Firiplaka Beach

WHAT TO EAT & DRINK
Try Milos’s signature ladenia, a tomato-and-onion flatbread often called Greek pizza, alongside sweet watermelon paired with local manoura or ladotyri cheese. Round off your meal with capers picked from the island’s cliffs and a glass of crisp local wine.

Begin your journey in Kimolos by arriving at Psathi, the island’s small port, where a quiet coffee sets the tone for an unhurried day. Walk up to Chorio, the fortified hilltop town with its medieval castle and whitewashed lanes, for a glimpse of authentic island life untouched by crowds. Sail around the coast to Prassa Beach, framed by colorful volcanic cliffs, for swimming and snorkeling in clean, clear water, or explore the sea caves near Klima for a more secluded dip. Stop for a relaxed lunch of local cheese pies and fresh fish at a taverna near the port. In the afternoon, cruise to Aliki, a calm bay with shallow turquoise water ideal for a leisurely swim. As evening approaches, anchor in the sheltered waters off Psathi or Aliki as the sky fills with stars.

WHAT TO SEE
Chorio (Kimolos Town), Prassa Beach, Aliki Bay, Klima sea caves

WHAT TO EAT & DRINK
Taste Kimolos’s tangy xyno goat cheese and manoura, a hard cheese aged in wine lees, along with ladenia flatbread and tirenia cheese pies. Pair them with local capers packed simply in salt and a glass of tsikoudia, the island’s traditional spirit.

Begin your journey in Folegandros by arriving at Karavostasi, the island’s small port, for a morning coffee before climbing toward Chora, the dramatic hilltop capital perched on a sheer cliff edge above the sea. Wander its car-free squares and whitewashed churches, then sail around the coast to Agkali Beach, a sheltered bay backed by hills, perfect for swimming and relaxing on the sand. Continue by boat to Katergo Beach, accessible only from the sea, where clear turquoise water and dramatic rock formations make for exceptional snorkeling. Stop for a relaxed lunch at a taverna overlooking Agkali Bay, savoring handmade pasta and local cheese. In the afternoon, anchor off Katergo or a quiet nearby cove for sunbathing and a peaceful swim, then settle into a sheltered anchorage near Agkali for a quiet dinner beneath a star-filled sky.

WHAT TO SEE
Chora (Folegandros Town), Agkali Beach, Katergo Beach, Karavostasi

WHAT TO EAT & DRINK
Sample Folegandros’s matsata, handmade pasta traditionally topped with local skliro cheese, and sourotenia, a savory pie of soft cheese and onion. Pair them with the island’s manouri and melichloro cheeses, made from fresh sheep and goat’s milk, or a glass of local wine.

Begin your journey in Santorini by mooring near Ammoudi Bay beneath Oia, where you can enjoy a fresh coffee as fishing boats bob in the tiny harbor below the cliffs. Sail along beneath Oia’s whitewashed houses and blue domes clinging to the caldera rim, ideal for jaw-dropping photos. Continue along the dramatic caldera to Fira, wandering its cliffside lanes, browsing local galleries, and savoring a leisurely lunch with volcano views. Head south to Red Beach near Akrotiri, where rust-colored cliffs meet clear water perfect for swimming and snorkeling, then continue to the black sands of Kamari for an afternoon dip. As the sun begins to dip, anchor off Thirassia or beneath the caldera itself to watch the legendary Santorini sunset paint the cliffs gold, before a tranquil night at anchor.

WHAT TO SEE
Oia, Fira and the Caldera, Red Beach, Akrotiri archaeological site, Thirassia islet

WHAT TO EAT & DRINK
Try Santorini’s famous fava (a silky yellow split-pea puree), tomatokeftedes (tomato fritters), and crisp white eggplant salad, all grown in the island’s volcanic soil. Pair them with a glass of Assyrtiko, the island’s signature dry white wine, or the sweet, sun-dried Vinsanto.

Begin your journey in Ios by arriving at Gialos harbour, where a fresh coffee by the waterfront sets the tone for the day. Sail to Manganari Bay on the island’s south coast, a string of sheltered turquoise coves perfect for swimming and snorkeling away from the crowds. Continue to Mylopotas Beach, one of the Cyclades’ finest stretches of golden sand, ideal for a relaxed swim. In the late morning, head up to Ios Chora, wandering its whitewashed lanes, chapels, and windmills, and pausing for a traditional lunch overlooking the Aegean. In the afternoon, visit the reputed Tomb of Homer near Plakoto for sweeping views, before anchoring off a quiet cove near Manganari for an evening swim, sundowners, and a peaceful night at anchor.

WHAT TO SEE
Ios Chora, Mylopotas Beach, Manganari Bay, Homer’s Tomb, Gialos harbour

WHAT TO EAT & DRINK
Sample skotyri, Ios’s fiery whipped cheese dip made from soft local cheese, chili, and olive oil, alongside louza, the island’s cured pork fillet. Wash it down with a glass of local Cycladic white wine or a shot of homemade raki.

Begin your journey in Koufonisia by arriving at the small harbour of Ano Koufonisi, where a fresh coffee by the water reveals the laid-back charm of this tiny island. Sail along the coast to Pori Beach, a stunning stretch of golden sand backed by dunes and turquoise shallows, perfect for swimming and snorkeling. Continue to the nearby islet of Kato Koufonisi, exploring its quiet coves and clear waters by dinghy, before returning for a relaxed lunch of fresh seafood at the harbourside. In the afternoon, wander the whitewashed lanes of Chora, browsing small shops and enjoying the island’s unhurried rhythm. As evening approaches, anchor off a sheltered cove near Pori for a peaceful swim and sunset, before a tranquil night at anchor surrounded by the calm waters of the Small Cyclades.

WHAT TO SEE
Pori Beach, Kato Koufonisi islet, Chora (Ano Koufonisi), Fanos Beach

WHAT TO EAT & DRINK
Feast on fresh-caught seafood pasta and patatato, a hearty goat and potato stew shared with neighboring Amorgos, alongside xinomyzithra, a tangy local goat cheese. Round off the meal with xerotigana, honey-drizzled fried pastry, and a glass of local rakomelo.

Begin your yacht journey in Naxos by arriving at Naxos Town, where a fresh coffee by the harbour sets the scene beneath the iconic Portara, the marble gateway of an unfinished Temple of Apollo. Sail down the coast to Agios Prokopios and Agia Anna, two of the Cyclades’ finest sandy beaches, ideal for swimming and relaxing in crystal-clear water. Continue to the long dunes of Plaka Beach for a quieter swim and a leisurely seaside lunch. In the afternoon, venture inland to the mountain village of Halki in the fertile Tragaea valley, wandering its neoclassical mansions, olive groves, and citrus orchards. As evening falls, anchor off a sheltered bay near Agios Prokopios to enjoy a relaxed dinner and sunset over the sea, before a peaceful night at anchor.

WHAT TO SEE
The Portara, Naxos Town (Chora), Agios Prokopios Beach, Halki village, Plaka Beach

WHAT TO EAT & DRINK
Sample Naxos’s famous graviera cheese, made from local cow’s milk, alongside Naxian potatoes grown in the island’s fertile plain. Finish with a glass of kitron, the island’s unique citrus liqueur distilled from local citron leaves, found nowhere else in Greece.

Begin your journey in Paros by arriving at Naoussa, a picturesque fishing harbour with a Venetian castle ruin, where a fresh coffee by the waterfront sets a relaxed tone. Sail around the coast to Kolymbithres Beach, known for its striking granite rock formations and sheltered coves, perfect for swimming and snorkeling. Continue to Parikia, the island’s capital, to explore the Byzantine church of Panagia Ekatontapiliani and wander its labyrinth of whitewashed lanes and shops. Head south for a swim at Golden Beach, a long stretch of fine sand popular for its clear, calm waters. As the afternoon winds down, return to anchor in the sheltered bay off Naoussa to enjoy a traditional seafood dinner by the harbour and watch the sunset, before a tranquil night at anchor.

WHAT TO SEE
Naoussa harbour, Kolymbithres Beach, Parikia and Panagia Ekatontapiliani, Golden Beach

WHAT TO EAT & DRINK
Try gouna, Paros’s traditional sun-dried mackerel from Naoussa, often grilled and drizzled with olive oil, alongside local touloumotyri cheese. Pair your meal with a glass of Paros PDO wine, made from the indigenous Monemvasia and Mandilaria grapes grown across the island.

Begin your journey in Syros by arriving in Ermoupoli, the elegant capital of the Cyclades, where neoclassical mansions rise above the harbor and Miaouli Square buzzes with morning life over a fresh coffee. Wander up to Ano Syra, the medieval hilltop quarter, for sweeping views across the Aegean, or admire the pastel townhouses of the Vaporia district along the waterfront. Sail on to Kini Bay, where sheltered turquoise water is perfect for swimming, then paddle ashore for lunch at a seafront taverna. Continue to Delfini Beach for an afternoon of snorkeling amid quiet coves. As the light softens, cruise toward Finikas, a calm bay favored by sailors for its shelter and clear water, and watch the sunset paint the harbor gold before a peaceful night at anchor.

WHAT TO SEE
Ermoupoli, Ano Syra, Vaporia district, Kini Bay, Finikas

WHAT TO EAT & DRINK
Don’t miss San Michali, Syros’s celebrated hard cheese with protected designation of origin, alongside creamy kopanisti and local loukoumia sweets in flavors like rose and mastic. Pair them with halvadopita, a traditional honey-almond nougat, or a glass of local wine.