Active Athens, Mainland Greece, Cyclades, and Crete - 23 Days

Day 1: Arrive in Athens, Welcome Dinner

Welcome to Greece! You'll begin your trip in Athens, home to both the iconic Acropolis and so much more. The mythology of this spectacular city precedes it, with towering temples to Classical deities and the ruins of ancient marketplaces rubbing shoulders with lively nightlife, crowded flea markets, and contemporary cuisine. Make the most of your time in the city at some of these spots:

• Check out the views of the can't-miss Parthenon. (Pro tip: The Parthenon is the temple, the Acropolis is the hill.) This temple to Athena has enchanted visitors since its construction was completed in 438 BC. It's probably the first thing that comes to your mind when you think of ancient Greece and is visible from many of the city's high points.
• Stop at the sprawling National Museum for a crash course in ancient iconography. Be sure to seek out the room housing the Antikythera mechanism, essentially an ancient astronomical computer.
• Visit a smaller archaeological site at the Tower of the Winds, then stroll down neighboring pedestrian Aiolou Street to stop at shops and cafes. 
• Find your perfect souvenir or sun hat in the busy stalls of the Monastiraki flea market. 

In the evening, you'll sit down to enjoy either a welcome dinner with views of the Acropolis or wine tasting in a bar in downtown Athens.

Day 2: Athenian Riviera Bike Ride

Take a pedaling loop from the Athens city center on this bike tour. You'll start by seeing some highlights of the city, including the Plaka neighborhood, Petralona, and the Roman Agora. Pass through the Thission neighborhood as well as past the ancient cemetery of Kerameikos. Views of the Acropolis and Parthenon are, of course, provided.

Feel the sea breeze on your face as you leave the city and head toward the coast out to the Athenian Riviera. Scope out the luxurious speedboats and yachts docked in the marinas as you spin past palm trees and views of the Saronic Gulf over the course of 4.5 hours. You'll bike back to the city center on a somewhat uphill route, making this best for people with some degree of cycling experience or athletic ability.

Day 3: Day Trip to Meteora

Travel by train across the Central Greece countryside for a day among the famous monasteries of Meteora. These religious buildings sit atop rock formations that are more than 60 million years old. You'll tread the same paths that monks used for hundreds of years to reach these holy places, perched close to 1,000 feet in the air above the canyons of the Pindos range. Before the paths were constructed, the monastery residents used nets and rope ladders to hoist goods (and sometimes their fellow clergy) to the clifftops. 

The roughly five-hour train ride will take you from Athens through the rural landscape to Kalabaka, the town gateway to Meteora. You'll meet your guide and be transferred up to Meteora itself for three hours among the monasteries. You'll see all six of the monasteries, with visits inside one or two of them for a glimpse of what the ninth-century monastic life may have been like. There will also be stops for photos and other detours along the way before your return to the train station and Athens.

Day 4: Fishing Boat Adventure in the Saronic Gulf

Hop onboard with a professional fisherman to get up close and personal with the Saronic Gulf. You'll start in Athens' port suburb of Piraeus in Pasalimani, the port's hub for small fishing boats. Board a kaiki, a traditional fishing boat, where your fisherman guide will teach you all about their fishing techniques. Take in the scenery as you sail out to your first fishing grounds, where you'll observe traditional paragadi fishing methods. 

Your second stop will be Fleves island, where you can put these lessons into practice with a provided fishing rod or join the fish instead, with a swim in the clear waters. Lunch will be served onboard (fish included, naturally) before you head back to check the paragadi for any fresh catches. The day's spoils will be divided for you to take back with you and enjoy later at your leisure.

Once you've returned to shore, check out Piraeus in the evening light before you return to the city center. Stroll through Pasalimani, then stay for a drink or two in one of the open-air cafes along the Gulf of Zea.

Day 5: Day Trip to Spetses

Catch a morning catamaran out to the island of Spetses. Though it may look like just a small fragment that has broken off from the Peloponnese on a map, this island has been occupied since the Mesolithic Age and was the first of the Greek islands to raise the flag of the revolution against the Ottomans in 1821. It now draws a more boutique crowd to its quiet streets, where private cars are banned from many parts of the town.

The annual Armata festival celebrates one of the major Spetsiot naval victories of the war for independence and attracts swarms of visitors. But you can explore this history at any time of year at Bouboulina's Museum, devoted to Laskarina Bouboulina, a heroine of the Greek revolution. You may have already been greeted by her statue in Dapia Square. 

Head to Zogeria Bay to find a favorite secluded beach, accessible by boat taxi or a roughly 4-mile bike ride from the main town. If you're up for it, it's easy to circumnavigate the island with a rental bike (or e-bike), stopping at lots of beautiful viewpoints and beaches along the way. If you'd prefer a livelier scene, while away your day at Kaiki Beach Club, complete with sun loungers, water sports and games, and an onsite restaurant.

Dine at On the Verandah on the terrace of the Grand Poseidonion hotel. This chalet-inspired boutique hotel has been housing Greek glitterati since 1914, and the creative Greek contemporary fare is good enough to compete with the impressive ocean view.

Late in the day, you'll hop back on the ferry to Athens and be transferred back to your hotel upon arrival.

Day 6: Ferry to Tinos

Take an early ferry to Tinos, one of the most overlooked islands of the Cyclades. Tinos has remained under the radar for many years, overshadowed by its celebrity neighbor of Mykonos and seen mainly as a religious destination. Those who continue to believe that, however, are missing out on an island with fascinating history and culture, winding streets, great outdoor activities, and glittering beaches.

The imposing Panagia Evangelistria should not be overlooked, as Tinos is also known as the island of the Virgin Mary. Its icon is believed to have healing powers, and the annual August pilgrimage is a key part of the island's identity as churchgoers crawl on their knees toward the temple as a sign of piety.

If pilgrimage isn't quite your scene, there are also nearly 80 windmills to be explored, Venetian ruins, hiking at Exomvourgo mountain, and beaches for any moods. Try the island's craft beer from Nissos brewery or sample the cheeses at the shop belonging to the Cheese Cooperative of Tinos. Keep an eye out for the many painted dovecotes around the island as well, small white pigeon homes dotting the countryside of which there are nearly 1,000.

Day 7: Volax to Agape Hike

Take one of the island's top hikes today with your expert guide, experiencing scenery ranging from lunar landscapes to medieval churches. You'll hike for approximately 3.5 to four hours, covering about 4-5 miles (7-8 km) but can extend the experience with an afternoon swim for up to six to seven hours.

You'll start in Volax, where the landscape is covered with large, smooth granite rocks that geologists believe emerged from the sea millions of years ago. In the midst of the rocks, at the foot of Exomvourgo hill, you'll find a petite village. This town has been home to famous basket weavers for centuries, some of whom you may still spot practicing their craft with bamboo, willow, and osier shoots along the town's streets.

Ascend up a path of medium difficulty level past dovecotes and watermills. The trail will lead you to the town of Agape, also the Greek word for love. This Catholic village maintains its medieval influence in its arches, traditional houses, and narrow alleys across the multi-level town. 

End in Kolymbithra for a swim to cool off after your exertions. You'll also enjoy lunch at a taverna Kalloni village, with dishes such as froutalia (an egg dish with sausage and potatoes), roast beef with tomato sauce, local cheese, louza cured ham, and other seasonal touches.

Day 8: Surfing at Kolymbithra Beach

Head out to Kolymbithra beach for some surf lessons and seaside chic surroundings via your own transportation method or a transfer from your hotel. This protected cove on Tinos's northern coast is one of the island's best spots for water activities. You'll receive a 90-minute lesson from an experienced surfer who will have you hanging ten in no time.

If you aren't interested in surfing, stand-up paddleboarding is also available.  Stick around to practice your new skills for as long you like, or relax under the mushroom-shaped umbrellas. The beach is lined with tavernas using ingredients grown or caught on the island. 

Take a historical stop at the sanctuary of Poseidon, once one of the god's most significant ancient sanctuaries and also home to worship of Amphitrite. The archaeological site is located near Kionia beach and includes the main temple along with baths, an altar, and a fountain.

Day 9: Rock Climbing at Exomvourgo

Scale the granite formations of Exomvourgo with today's outing. This central mountain offers craggy faces with more than 90 well-maintained routes for all climbing levels, from complete beginners to experts. You'll work with your guide to select the path that's best for you as you ascend with the help of top-rope equipment.

Reach the summit for 360-degree views and a Venetian castle that was once the capital of the island's defenses. Artifacts have been found on the mountain dating back to the Copper Age, so you never know what you may spot.

Relax afterward at Nissos microbrewery, whose wares you may have already sampled on the beach.

Day 10: Ferry to Naxos

Time to ferry over to bustling Naxos after breakfast. With an active main town where you can shop and admire the Venetian architecture, a historic Kastro (castle) area, and expansive beaches, the island offers opportunities for both laidback relaxation, as well as water or land activities. The rest of the day is yours to unwind as you choose. Try out some of these options:

• Hike up to the summit of Mount Zas, the mythological childhood home of Zeus, the ruler of the gods, and the highest point in the Cyclades.
• Head inland to the town of Chalki, home to the island's oldest market and a petite, shady square perfect for whiling away the afternoon. Stop at the kitron distillery to sample the local liqueur and learn about its distillation process over the years.
• Visit the Temple of Demeter at Sangri on your way. Multiple deities of fertility were worshipped here, particularly the goddess Demeter. The temple was constructed in 530 BC, during the tyranny of Lygdamis, and represents a precursor of classical Athenian architecture. 
• Stroll to the Portara, the entrance to the Temple of Apollo. Construction on the temple began in the sixth century BCE but was never finished, but the still-standing entranceway has become one of the hallmarks of the island. You can find it on the islet of Palatia, just over a causeway from the heart of Naxos Town (Chora).

For dinner, wander up the hill through the streets of the Kastro neighborhood to pick out your favorite of the area's tavernas, where you can sample the island's fresh produce in its best forms.

Day 11: Scuba Diving in Naxos

Have you ever wondered what it’s like to breathe underwater? If you want to find out but aren’t quite ready to take the plunge into a certification course, try it out in Naxos. You'll learn the basics of diving under the direct supervision of a PADI-certified professional, including what the equipment feels like in the water and underwater breathing.

After your lesson, you'll get to try out the real thing! There are several dive sites around Naxos available for your exploration depending on your preferences and the weather on the day. Most of them are roughly 30-60 minutes from the base, and include small rocky islands, reefs, and caves.

Or, if you're already a certified diver, join your guide and spend the day taking the plunge at some of the best dive sites around Naxos.

In the afternoon, enjoy the sea from the surface at St. George beach, a Blue Flag beach and one of the most popular on Naxos. Its location is protected from the winds, making its warm, shallow water perfect for families or anyone in search of a laidback sun bath.

Day 12: Naxos Beaches and Villages Bike Tour

Discover Naxos's hidden spots on today's two-wheeled tour. You'll bike with an expert guide through the villages and attractions on the west side of the island. The western coast is also home to some of the island's best-known beaches, including Agios Prokopios, Agia Anna, Plaka, Orkos, and Mikri Vigla. 

On your way back, you'll see the villages of Vivlos, Agios Arsenios, and Glinado. The beginner-friendly route covers roughly 12 miles (20 km) and will take you about 2.5 hours. 

Spend the rest of your day exploring the main Naxos Chora, especially the Kastro district. Wind up the narrow streets to the Venetian Castle in the center of town, stopping at the neighboring Catholic church, Ursuline school, and Archaeological Museum along the way. Even the houses are part of the experience, once home to the descendants of Duke Venetians.

Day 13: Horseback Riding in Naxos

Get a different perspective on the island from atop one of its resident horses. The stable will work with you to create a ride that suits your age and skill level to maximize your experience and trail route. 

A trip to the village of Apiranthos is a potential ride highlight. Also known as the "marble village" due to its white architecture and marble stone streets, this mountainside spot offers inland views and a slew of museums and crafts to peruse. Listen for the local dialect among the residents, which has remained distinct from the rest of the islands.

Day 14: Travel to Chania

Today, you'll continue onward to Chania, a city (and region) on the northwest coast of Crete. Chania itself is the second largest city in Crete and one of the most scenic spots on an island with stiff competition for that title. Life in this former Venetian city revolves around its charming 14th-century harbor, narrow streets with winding alleys, and colorful architecture influenced by past Ottoman and Egyptian eras.

While you're exploring the area, don't miss some of these spots:

• The elevated neighborhoods of Topanas, Splantzia, Kolombo, and Kasteli for panoramic harbor views, Cretan taverns, and architectural history. You can see the ruins of the Minoan city of Kydonia and high walls of former Venetian moats integrated into the city.
• The Municipal Market of Chania and neighboring Municipal Garden to enjoy a coffee amid the shade of the trees or garden clocktower. 
• The Botanical Parks and Gardens of Crete to enjoy Cretan nature at its finest. The special micro-climate formed at this specific area allows plants from three different climate zones to grow in the park.
• The olive-oil-producing region of Vouves, to the west of the city, complete with a museum and one of the oldest olive trees in existence.
• Falassarna and Elafonissi beaches, also to the west, where you can find solitude on the sands.

Top it all off with a sunset drink on the rooftop at trendy Pallas or visit Cafe Koukouvaya for a pastry and a view of Chania town and harbor.

Day 15: Trek Samaria Gorge

After breakfast, you'll be picked up at your hotel nice and early to explore one of Crete's natural wonders. Set amidst the scenery of the White Mountains is the popular hike through Samaria Gorge. The trek takes approximately five hours to cover the gorge's approximately 11 miles (18 km), most of which are downhill and during which you'll spot flora and fauna of all kinds. As your trail nears its end, you'll descend a gentle slope down to the peaceful beach at Agia Roumeli on the turquoise Libyan Sea where you can take a dip and wash off the trail dust. 

There will be time to linger on the sand and relax before you wrap up the outing with a boat trip to Chora Sfakion, where your coach will be waiting to return you to your hotel in Chania.

Day 16: Botanical Gardens Visit and Cooking Class

Experience Cretan cuisine hands-on with today's excursion. You'll surround yourself with the bright tropical gardens and the shade of avocado trees at the Botanical Park and Gardens of Crete. Your trail will lead you under citrus trees and other Mediterranean flora. Learn about the different climates around the island and the produce that grows there before you pick the ingredients straight from the orchards and fields. Put that fresh produce to use in a cooking class led by a local, where you'll learn all about Cretan products and nutrition, and enjoy the flavorful fruits of your labors at its conclusion.

Spend the afternoon wandering Chania's main town, stopping at any spots you've had your eye on over your previous days. Its colorful streets encompass centuries of history, so there should be plenty for you to keep discovering. Head to Kikbar when it's time for a break, located in the former 16th century Monastery of Karolos. This converted building is now home to an art gallery, theater space, and swoon-worthy open air bar.

Day 17: Douliana & Almyrida Nature Walk and Beach Visit, Travel to Vamos

Today, you'll get back to nature with a guided walking tour through the Cretan landscape. You'll walk through abandoned historic villages in Douliana and then travel toward the northern coast to the resort town of Almyrida. Here you'll have time for a well-earned swim and sunbathing session at the shallow beach, with plenty of facilities available for any post-hike needs.

You'll also have earned some room for dessert. Head to the Venizelos Graves next to the Venetian church of Prophet Elias. In addition to the panoramic views of Chania, behind the graves is a local favorite café called Koukouvagia, which boasts a variety of house-made sweets and pastries with outdoor seating.

You'll transfer to the village of Vamos in the afternoon and get settled into your traditional guesthouse. Soak in the slower pace of life in this peaceful corner of Crete.

Day 18: Cretan Delicacies Vamos Tour

Meet the farmers and food specialists of Crete on today's guided tour, exploring the traditional village of Vamos and the surrounding area to meet these creators and sample their products.

You'll start at the local olive oil factory, where you'll learn about its production process and sample some of the fresh oil, along with an explanation of what distinguishes Cretan virgin olive oil from other oils.

Next up, the local cheesemaker. Crete is known for its graviera cheese, a slightly sweet, hard sheep cheese. You may watch the expert on duty as he makes graviera and teaches you about the cheese-making process, with samples of different varieties including graviera, anthotyros, and myzithra. For the older participants, it's also time for your first raki of the day, a grape-based spirit that's also Crete's national drink.

Head to the 14th century Byzantine church of Saint Nicolas on your way to the next stop to take in its frescoes and architectural features. Afterward, you'll arrive in the village of Hiliomoudou, where one of the few hand producers of sheep and goat bells practices his craft. You can watch him work and learn how to distinguish between the sounds of sheep and goat bells while sipping your second raki.

End as you began at a second olive oil press, this time home to both the rarer organic olive oil and the elusive Cretan kri kri goats, a species only found on this island. See if you can spot them as you sit at the taverna and enjoy a traditional lunch with all the ingredients you've just observed.

Walk off all those samples with an afternoon stroll around Vamos, surrounded by local history and hospitality, before spending the night in your traditional guesthouse.

Day 19: Return to Athens, Sunset at Cape Sounion

Return to Athens in the morning. After you've settled back into the city, you'll be transferred down to the Athenian Riviera, full of both history and stunning island views. Your adventure will take you along the coast to visit the Temple of Poseidon, while being provided with historical background on the way. The views overlook the Saronic Gulf, with one of the best sunset views Greece has to offer. Sip a complimentary beverage and take in the sunset while you listen to music and immortalize the moment with a Polaroid-style photo.

You'll be transferred back to your lodging in the evening just in time for a late (Greek-style) dinner. Or, if you're not ready to call it a night, you can request a drop-off at some of the most popular beach bars to dance until the sun comes up.

Day 20: Visit Mycenae and Nafplio

Start the day early with a guided trip back to a true classic. You may recognize Mycenae from its role in Homer's Iliad: It was home to the famous Helen, whose Mycenean husband King Agamemnon led his people to war when she left him for Paris of Troy. See its Cyclopean walls, whose construction method is still a mystery. They got their name due in part to the belief that only the mythical Cyclops would have been strong enough to lift their boulders.

You'll pass through the Lion Gate with your guide to enter the ruins of the city, wandering past the tombs of Aegisthus and Clytaemnestra and the Treasury of Atreus.

You'll go on to Nafplio, one of the prettiest seaport towns in the Peloponnese peninsula and once believed to have been founded by the son of Poseidon. The town was the first capital of the new Greek state after the war of independence in the 1800s. You'll take a guided stroll through the old town, where you'll pass statues honoring significant figures from Nafplio's history, Ottoman fountains, and Venetian architecture along the winding streets, topped off by the Bourtzi Castle in the middle of the harbor.

Later, don't miss the climb up 1,000 steps to see the view from the Palamidi Castle. Spend a relaxing evening wandering the quiet streets or walking along the waterfront.

Day 21: Coast and Palamidi Castle Foothills Hike

Wear good walking shoes for today's adventure. You'll start with a stroll through the old town, where you'll pass statues honoring significant figures from Nafplio's history alongside Ottoman fountains, and Venetian architecture along its winding streets topped off by the Bourtzi Castle in the middle of the harbor. Accessible only by boat, the castle was built in the 1470s to defend the city, and it still keeps watch at the entrance to Nafplio Bay.  Then, warm up your leg muscles with a climb up 1,000 steps to see the view from the Palamidi Castle.

You'll meet your guide in the afternoon at the harbor lighthouse to hike underneath the castle's towers. The scenic trek will take you along the Arvanitia path along Acronafplia, which lives up to its translation of "the edge of Nafplio." Go all the way to Karathona beach as you learn about the history of the city and its invasions. Feel free to stop at the hidden beaches along the way or take a break at one of the bars. Then, continue to the foothills surrounding the castle, with views of the Artemision mountain as your reward for all that walking.

Day 22: Karathona Beach Kayaking

Swap your pedals for paddles with a four-hour kayak tour in the waters of the gulf. Get in the water at Karathona beach to circle some of the bay's best spots. You'll get a perfect distance view of the Palamidi Castle before you come in for a visit to Bourtzi Castle, complete with panoramic perspective on the city. Take a break for fruit and photos in a small church along the way.

Once you've dried off, head back into town for an evening wander. See if you can find P.D.O. olive oil from Lygourio, near Epidaurus, to bring home the best of a Greek favorite. When hunger strikes, seek out fresh local seafood on coastal Bouboulinas and Miaouli streets or try the local specialty dish of bogana, which features a hearty mix of lamb and potatoes.

Day 23: Return to Athens, Depart

Time to say farewell to Greece. You'll head back to Athens after breakfast to catch your flight, either home or onward to your next adventure.