- Stroll the seaside town promenades of Aegina and Poros
- Seek solitude on the islands of Leonidio and Kyparissi
- Ride the donkeys through the cobblestone streets of Hydra
- Feed the peacocks on uninhabited, verdant Moni island
|Day 1||Arrive in Athens||Athens|
|Day 2||Sail from Athens to Aegina||Aegina|
|Day 3||Sail to Poros||Poros|
|Day 4||Sail to Spetses||Spetses|
|Day 5||Sail to Leonidio||Leonidio|
|Day 6||Sail to Kyparissi||Kyparissi|
|Day 7||Sail to Hydra||Hydra|
|Day 8||Sail to Moni||Moni|
|Day 9||Return to Athens, Depart|
Day 1: Arrive in Athens
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.
Spend your evening exploring the up-and-coming Pangrati neighborhood or amid the nightlife and mezze of the Psyrri district.
Day 2: Sail from Athens to Aegina
Catch a post-breakfast transfer from your hotel to a marina near Athens to begin your sailing experience. Board your boat and set sail! Today's voyage will take approximately three hours, depending on the winds and your boat's speed.
Your first destination is Aegina, named for the daughter of the river god Asopos who Zeus fell in love with and brought to the island. The city used to rival Athens as the greatest sea power of the region, and operated as the first capital of the newly formed Greek state after the country won independence from Ottoman rule in 1821. Today, Aegina is more famous for its pistachios and the horse-drawn carts that amble along the port next to the traditional fishing boats.
Walk down the port promenade in the evening past the main town's neoclassical buildings, shops, and tavernas to find your ideal sundowner spot.
Day 3: Sail to Poros
Head south across the the sea to Poros, where you can visit the neoclassical architecture and clock tower of Poros town or explore its interior. You can circumnavigate the dual islands, connected by a narrow bridge, in approximately an hour by car.
Much like its neighbor Aegina, Poros also boasts sites from across Greece's historic and religious spectrum. Swap your focus from the previous day to see the full picture of the islands.
Classicists can pay tribute to the sea god at the site of the Temple of Poseidon, both a fascinating ruin in its own right and the site of ancient orator Demosthenes' death. Many of its artifacts have been removed, but remain on the island in the Archaeological Museum.
Jump forward in time and visit the monastery of Zoodochos Pigi, founded in the 1700s at what was believed to be the site of a holy spring. Its quiet whitewashed domes sit on a hillside overlooking the sea—the perfect spot to experience a working monastery.
There's also always the classic Mediterranean activity of resting in the shadow of the pine trees and taking in the waves. Askeli is one of the more popular island beaches to set yourself up for a day of swimming and sunning, followed by an evening enjoying the day's catch at a seaside taverna.
Day 4: Sail to Spetses
Head south 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 or a roughly 4-mile bike ride from the main town. 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.
End your day in style with dinner at On the Verandah on the terrace of the Grand Poseidonion hotel. This chalet-inspired boutique hotel has been housing Greek glitterati since 1914. The creative Greek contemporary fare is good enough to compete with the impressive ocean view.
Chat with a local specialist who can help organize your trip.
Day 5: Sail to Leonidio
The Arcadian seaside town of Leonidio sits at the end of the Dafnon river gorge, just between the ocean and the foot of Mount Parnon. It was once the capital of the Tsakonia region, and signs around town still boast writing in the local Tsakonian dialect—one of the only living languages descended from ancient Doric Greek.
It's also known for its unique eggplants, citrus, and tomatoes, so keep your eye out when browsing the restaurant menus or time your visit to coincide with the annual eggplant festival. Hikers and climbers can make their way up Mount Parnon or the surrounding crags.
Day 6: Sail to Kyparissi
Escape the crowds in quiet Kyparissi, once home to an ancient sanctuary of Asklepios and nigh-unreachable except by boat until the current century. Once the site of pirate raids, it's now an out-of-the-way stop for those in search of somewhere to spend their days lounging on the beach.
Kyparissi also boasts excellent climbing if you're looking for more onshore activity. Though don't expect to resupply in town, as your mooring spot may be a bit of a walk from the center.
Day 7: Sail to Hydra
Round the coast with breakfast in Hydra, the “Grand Lady” of the Argosaronic Gulf. This car-free island maintains a historic charm in the houses that rise like an amphitheater up around the port and donkeys clopping their way through the streets with your luggage. Locals still brag about Sophia Loren's visit to their shores to film "Boy on a Dolphin," along with other storied visitors from Picasso to Leonard Cohen.
Stroll through its winding alleys for a glimpse into the island's naval history, with multiple house museums in the homes of former sea captains. Make your eventual way to the Kaminimarina outside of town. You'll find regular art exhibitions at the Red House, traditional cuisine at Kodylenia's taverna, and a spot to cool off with a leap off the rocks into the inviting waters below.
If you'd rather wade in than jump, sail from the port out to hidden beaches at Vlichos and Limnioniza, where sunbeds await to keep you comfortable on the pebbly shore. As the day winds down, take your pick of the bars on the cliff leading out of the main town for a sundowner cocktail.
Day 8: Sail to Moni
Located off of Aegina, Moni island is so small that it's uninhabited by humans other than the occasional boat-bound visitor seeking tranquility on its shores. Instead, its pine forests are home to Cretan kri-kri goats, peacocks, and inquisitive deer.
Hike up the island's interior mountain to find a former World War II lookout post or simply spend your day in its turquoise waters, challenging yourself with nothing more strenuous than a detour to the seasonal beach bar.
Day 9: 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.