Island Hopping From Athens Across the Cyclades - 16 Days

Day 1: Arrive in Athens, Self-Guided Tour of the Capital City

Welcome to the vibrant capital of Greece, Athens! Meet your driver at the airport to transfer to your hotel, then go ahead and explore the city on your own. An excellent place to start is the central Syntagma Square, where, if you time it right, you'll witness the Changing of the Guard ceremony in front of the Tomb of the Unknown Soldier and the Hellenic Parliament. Then, trek up the hill along Dionysiou Areopagitou, a pedestrian-friendly street lined with shops and cafés, toward the UNESCO-listed Acropolis of Athens, an ancient citadel perched atop a rocky outcrop overlooking the city.

At the top, marvel at the Parthenon, a temple dedicated to the goddess Athena. Admire the sheer magnitude of the temple's Doric columns, then continue to the Erechtheion, an Ionic temple with six caryatids—graceful female statues serving as support columns. Wander through the archaeological site, soaking in the far-reaching views of the cityscape below before heading back down to the Acropolis Museum. Browse the collection of artifacts, statues, and friezes detailing the development of Athenian culture, and walk over the glass floor to see the ancient ruins below.

Day 2: Half-Day Trip to Sounio, Watch the Sunset at the Temple of Poseidon

Enjoy a free morning to visit the National Archaeological Museum. Browse the collection of artifacts spanning thousands of years, from intricate sculptures of the Archaic period to the beautiful pottery of the Classical era. Be sure to visit the Mycenaean and Minoan galleries, featuring treasures of ancient civilizations that preceded classical Greece. Then, end your morning in Monastiraki, a neighborhood known for its flea market and vibrant atmosphere. Stroll along the cobblestone streets past street-food stalls and tavernas serving authentic Greek cuisine to find somewhere for an early lunch.

Leave the city behind this afternoon as you join a guided tour one hour south to Cape Sounio (Sounion) on the southern tip of the Attica Peninsula. Once there, unwind on Legrena Beach's soft golden sand and swim in the turquoise water before visiting the Temple of Poseidon, perched atop a rugged cliff overlooking the Aegean Sea. Explore the Doric temple dedicated to the god of the sea to discover its well-preserved columns and inner chamber, then watch as the sun begins its descent over the sea, transforming the temple into shades of orange and pink before returning to Athens.

Day 3: Fly to Mykonos, Traditional Island Villages & Farm Tour

Say goodbye to Athens this morning as you start the island-hopping portion of your trip with a one-hour flight to Mykonos in the Cyclades island group. Meet your driver outside the airport and transfer to your hotel, where you'll leave your bags before venturing out on a four-hour tour of the area. Follow your guide to a scenic viewpoint overlooking the island's charming Old Town, known simply as Chora to the locals. Admire the maze of streets lined with whitewashed buildings and bougainvillea-covered alleys before continuing to the fishing village of Agios Ioannis.

Day 4: Hiking Excursion in Mykonos, Winery Tour & Wine Tasting

Lace up your hiking shoes and prepare for a moderate 4-mile (6 km) trek through the countryside, starting at Mykonos Vioma Organic Winery and Farm. Follow your knowledgeable guide down an ancient donkey path, once used for transporting goods, enjoying views of the vast Aegean Sea. Stop at a traditional Mykonian church to learn about the island's religious traditions before continuing to the crescent-shaped Merchia Beach. Take a well-deserved break on the rocky shore and enjoy a refreshing glass of organic lemonade paired with a traditional dessert.

After refueling, jump in the water to cool off and partake in an underwater photo shoot with your guide. When you're ready, follow the path back up the hill to the fertile valley around Ano Mera until you see the vineyard in the distance. Treat yourself to a delicious Mykonos lunch and wine tasting overlooking the surrounding sea and arid landscape ideally suited to grape growing. Then, tour the vineyard and learn about the meticulous winemaking process, from cultivating organic grapes using traditional methods to storing the finished produce in the on-site cellars. 

Day 5: Ferry to Naxos, Discover the Largest of the Cyclades Islands on Your Own

The next island on your itinerary is Naxos, the largest of the Cyclades islands. Transfer to the port to catch a 1.5-hour ferry to Naxos, where another driver will be waiting to take you to your hotel. After refreshing, venture out to explore the city built upon the ruins of an ancient settlement from around 4000 BCE. Wander to Agios Georgios Beach in the city center for views of the crystal-clear waters, ancient ruins, and the surrounding Naxian landscape. To discover more of the area, head half an hour inland by bus or taxi to Apiranthos, a picturesque village on the slopes of Mount Fanari.

Meander through the marble-paved alleys past houses, towers, and churches crafted from stone, and stop at a traditional artisan shop to buy beautifully stitched embroideries by local women. Enjoy lunch with views of the Naxian mountain ranges, then explore one of the village's five museums. On the way back, stop at Sangri to visit the Temple of Demeter, dedicated to the goddess of fertility, harvest, and agriculture. Explore the well-preserved remnants of this sixth-century BCE Doric-style temple to admire the towering columns before returning to your hotel.

Day 6: History & Food Tour of the Temple of Apollo & Naxos Old Town

Spend today immersing yourself in Naxos' rich culture and culinary delights on a half-day tour, starting with a visit to the Temple of Apollo—a sixth-century sanctuary dedicated to the god of sun and light. Roam the archaeological site to see the only structure still standing, the colossal Portara, a marble doorway overlooking the sea. Continue to the Venetian Castle of Naxos in the Old Town and walk through the towering stone gates following the cobblestone path to explore the castle's imposing walls, amble through its alleyways, and climb its towers for far-reaching views of the town.

Afterward, stroll down the narrow streets lined with whitewashed buildings, colorful bougainvillea, and market stalls full of fresh produce and aromatic herbs. Stop at a local cheese store to try kalathaki (a phyllo pastry filled with local cheeses) paired with a glass of wine. Then, follow your guide to a taverna to sample a variety of mezes (small plates) and Greek delights like moussaka (an eggplant casserole layered with minced meat and béchamel sauce). Savor your meal with two glasses of wine and samples of Cretan raki, a grape-based brandy, and kitron, a citron liqueur.

Day 7: Full-Day Catamaran Cruise Around Naxos

One of the best ways to see Naxos is from the water, so today, you'll board a catamaran for a full-day cruise around the island. Pack your sunscreen, hat, and sunglasses, then head to the Naxos Marina and hop on board. As your captain sets sail from the port, feel the gentle breeze and hear the soothing sound of the waves against the hull. Soak up the sun on the deck or lounge in the shade of the catamaran's canopy while you sail along the coastline, stopping to explore secluded coves, dramatic cliffsides, and hidden beaches only accessible by boat.

Drop anchor for a refreshing swim in the sea while the crew prepares a delicious lunch on board with fresh local ingredients. After your meal has settled, don the snorkel gear provided to discover the pristine underwater world. Look out for damselfish, sea bream, moray eels, octopus, and sea turtles gliding gracefully through the translucent water of this rich marine environment before returning to shore in the afternoon. For dinner, try stuffed zucchini blossoms and octopus cooked with wine at a local taverna.

Day 8: Ferry to Paros, Greek Cooking Class & Local Farm Visit

Bid farewell to Naxos this morning as you transfer to the port for a 45-minute ferry ride to Paros, renowned for its traditional Greek villages and pristine beaches. When you arrive, meet your driver and transfer to your hotel, where you can refresh before venturing out to a local farm just outside Parikia for a three-hour cooking class. Meet the farmers and set off on a tour of the property to learn about the fresh produce growing in the fields. Immerse yourself in the experience by picking the ingredients you need for your meal, then head inside to prepare a three-course Greek meal.

You may cook appetizers and dishes like tzatziki, Greek salad, stuffed lamb, or kakavia, a traditional fisherman's soup. The experienced chef leading your class will choose a menu based on your tastes. When your meal is ready, sit down with your hosts to enjoy everything paired with a homemade lemonade and fresh melon from the garden. Before you leave and return to your hotel, grab copies of the recipes to recreate them for your friends and family back home.

Day 9: Day Trip to Antiparos, Tour the Island's Famed Castle & Cave

Return to the port this morning to catch a short, 10-minute ferry to the laid-back island of Antiparos for a 4.5-hour tour. As soon as you disembark, you'll be greeted by the picturesque harbor and a quaint village of whitewashed houses adorned with bright blue accents. Follow your guide along the cobblestone streets to the 15th-century Castle of Antiparos, built on a hill overlooking the island by Venetians to protect against pirate raids. Ascend the ancient stone steps to reach the castle grounds, where you'll be rewarded with panoramic views of the sparkling sea.

Explore the well-preserved walls and towers while your guide highlights the castle's rich history. Afterward, continue to the Cave of Antiparos and descend 400 steps to the entrance. The effort offers rich rewards as you enter the refreshing depths of the cave, where impressive 45-million-year-old stalactites and stalagmites await. Look for the ancient paintings lining the walls, adding to the cave's mystical allure. In the afternoon, take a ferry back to Paros and transfer to your hotel, or you can continue the tour if you're not too tired.

You can either head to a nearby beach for a refreshing swim and a delicious lunch overlooking the water or walk to the village of Agios Giorgos, known for its traditional taverns serving mouthwatering local dishes, such as ladenia, a savory flatbread topped with tomatoes, onions, and herbs, or a classic souvlaki, marinated meat grilled on a skewer and served with pita, rice, or salad. Once ready, spend the rest of the day relaxing on the beach or discovering the quaint village streets before returning to your hotel.

Day 10: Ferry to Sifnos, Tour the Island on Horseback

Your journey continues with a two-hour ferry ride to the beautiful island of Sifnos, where a driver will be waiting to take you to your hotel. After refreshing, head to a stable in the charming village of Fryogia for a 1.5-hour tour of the island in the saddle of a trusty horse. Complete a short safety briefing, then greet your steed. You'll be paired with a horse based on your riding experience, so don't worry if you're a beginner. Take the reins and set off down the trail, listening as your guide highlights the rich history and culture of the island.

Enjoy views of rolling hills, vast olive groves, and rugged mountains while trotting along. Stop at the fishing village of Vathy to admire the crystal-clear waters and colorful boats bobbing gently in the harbor. Continue to Agios Stathis Chapel, nestled in a forest of coniferous trees. Dismount and take a break from riding while you explore the whitewashed structure adorned with a traditional blue dome. When you're ready, return to Fryogia and bid your horse farewell, then visit a nearby taverna for a delicious meal.

Day 11: Hiking Excursion Along an Ancient Sifnos Trail to Apollonia

Day 12: Ferry to Milos, Sample Local Delights on a Food & Wine Tour

After exploring Sifnos on horseback and foot, it's time to take a ferry to Milos, the southwesternmost island in the Cyclades group. Meet your driver at the port to transfer to your hotel, where you can refresh after the two-hour ferry ride. When you're ready, join your guide in the lobby and set off on a five-hour food tour, starting in the characterful fishing village of Pollinia, known as the gastronomic capital of the island. Enjoy a wine tasting at a local vineyard paired with a selection of mezes, like pitarakia (cheese pastries) or fresh tomato fritters. 

Continue toward the southern coast to Paliochori, known for its distinct volcanic landscape and mineral-rich hot springs. Indulge in a one-of-a-kind culinary experience, sampling dishes slow-cooked overnight under hot volcanic sand or in natural steam. Ascend to the hilltop village of Plaka next, where you'll visit a local shop to try koufeto, a traditional Milos dessert made with honey, almonds, and sesame seeds. End your culinary tour at an authentic bakery in Katifora to enjoy a refreshing slice of watermelon pie overlooking the island's picturesque port.

Day 13: Hiking Excursion from the Ruins of Phylakopi to Sarakiniko Beach

Have a nourishing breakfast at the hotel to prepare for today's 5-mile (8 km) hike to Sarakiniko Beach, starting at the ancient ruins of Phylakopi, which date back to the Bronze Age. Weave through the ruins, exploring remnants of homes, streets, and public spaces that once thrived here. Follow your experienced hiking guide along the path down the coastline until you reach Papafragas Cave, a deep sea cave carved into the volcanic cliffs by the Aegean Sea's relentless waves. Walk down to the cove and marvel at the crystalline water and towering rock walls.

Then, continue your trek to Sarakiniko Beach. When you arrive, take in the captivating white volcanic rock formations sculpted into unique shapes and textures by centuries of wind and water, creating a lunar-like landscape. Go for a refreshing swim in one of the hidden coves or natural pools, then lie down on the smooth rocks to soak up the sun. When ready, hike back to Phylakopi along the same path and return to your hotel to rest. 

Day 14: Ferry to Santorini, Explore the Island on a Self-Drive Jeep Tour

Today, you'll head to the final island on your itinerary, Santorini, renowned for its whitewashed buildings perched on dramatic cliffs. Catch a 2.5-hour ferry to the island, where a driver will be waiting to take you to your hotel. After refreshing, head out to explore the winding streets, local shops, and traditional architecture, then grab a quick bite to eat at a nearby café or taverna, sampling some local Santorini cuisine like sfougato, an omelet with fried potatoes, onion, and pumpkin, before this afternoon's adventure.

After lunch, go off-road to explore the island in style on a 4WD convoy tour. Meet your transfer driver at your hotel and head to the starting point, where you'll hop in your Jeep and begin self-driving behind the experienced convoy leader. Discover canyons, cliffs, calderas, vineyards, and ancient ruins as you navigate the rugged sand and dirt tracks. Stop to swim at a secret beach and explore other hidden gems that only locals know about. End the tour with a traditional Greek barbecue while you watch the sunset over the sea.

Day 15: Enjoy a Free Morning, Wineries & Sunset Tour

Your penultimate day in Greece begins with a free morning, so you can relax on one of the island's many beaches or explore a nearby village at your own pace. A good option is Fira, the capital of Santorini, where you can discover the narrow alleyways, whitewashed buildings, local markets, and vast Caldera. Start in Fira Square to pop in and out of the artisan boutiques and inviting cafés before you meander to Fira Market to shop for local handicrafts or sample regional wines, olive oil, and honey.

Day 16: Fly to Athens, Depart 

Your journey ends today after spending 16 days discovering Athens and six of the most beautiful islands in the Cyclades. If you have some time before your flight, you can explore more of Santorini on your own. Visit the postcard-perfect village of Oia on the northern tip of the island to stroll along the narrow streets and discover the delightful boutiques housed in whitewashed buildings. Keep an eye on the clock so you can return to the hotel to meet your driver and transfer to the airport in time for your flight to Athens and connecting flight home. Safe travels!

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