Welcome to Greece! You’ll begin your trip in Athens, home to the iconic Acropolis. 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. 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.
Depending on how much you want to see and do on the mainland will determine how long you stay.
Day 2: Athens to Syros
Start your morning by heading to Syros by ferry, home to the capital of the Cyclades.
Follow the cobblestone streets through the squares and past architectural features like the Ermoupoli City Hall designed by Ernst Ziller, also responsible for many of the mansions and national buildings in Athens. Visit the Vaporia neighborhood, home to the mansions of 1800s sea captains, or the medieval hilltop settlement of Ano Syros for expansive sea views. The yearly music festival attracts visitors from around the country to the Apollon theater, built in 1864 as a replica of La Scala in Milan.
Day 3 or 4: Syros 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 relaxation, as well as water or land activities. The rest of the day is yours to unwind as you choose. Here are some of the ways to fill your days on Naxo.
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 people watching. Stop at the distillery to sample the local liqueur and learn about its distillation process over the years.
Stroll to the Portara, the entrance to the Temple of Apollo. Construction on the temple began in the sixth century BC and 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.
Spend a couple of days here.
Day 6 or 7: Naxos to Santorini
Ferry to Santorini this morning.
The island’s volcanic history has led to the formation of some of the more unique beaches in the Greek islands, along with the dramatic cliff views on the island’s caldera side. Spend your day relaxing at the beach or catching some exercise—and even more views—from one of Santorini’s more than 12 scenic walking routes, ranging from between two to eight miles each. At dinner, sample the island’s signature cherry tomatoes and white eggplants as guest stars in seafood dishes or the main event.
Day 7 or 8: Santorini
The morning is yours to spend as you will, whether that’s browsing the boutiques of Fira or going to the beach. In the afternoon take a guided tour that will show you a side of Santorini that most travelers don’t see. You’ll check out hidden gems in Oia, the furthest town along the rim of the caldera. Oia’s arty streets are the quintessential Santorini scene. Later, you’ll take a trip up to the highest peak on the island. Bring your camera for the 360-degree views at the top, as well as the many stops on your way down. You’ll also see medieval villages at Megalochori and Pyrgos and the Blue Dome in Firostefani.
In the evening, return to Oia to wander the alleys and linger in the town’s tavernas into the evening and experience a calmer vibe after the sunset crowds subside.
Day 10: Santorini to Crete
Spend one more morning in Santorini to explore however you like, whether that’s a morning on the beach or getting in some last-minute souvenir shopping.
In the late afternoon, 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.
Highlights of this area of Crete
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 the 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, is 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
Spend your day on the pink sands of some of the most beautiful beaches in the world. You’ll be transported by boat to Balos and Gramvousa beaches, where crystal-clear turquoise waters are home to stellar swimming, sunshine, and protected animal and plant species. If you’re lucky, you may even spot a Mediterranean seal. In Gramvousa, you can also choose to hike up to a former Venetian castle or a shipwreck along the beach. Nearby Balos is a shallow, more protected lagoon.
Day 12 or 13
Set off for a guided exploration of the magnificent Palace of Knossos. This 3,500-year-old Minoan palace is a sprawling maze of royal chambers, grand staircases, storerooms, and workshops. The evocative Bronze Age site is believed to be Europe’s oldest city; it flourished for nearly 2,000 years as an economic center, trading with cities across the Mediterranean.
Follow it up with a guided stroll through the streets of Heraklion, exploring the old city’s medieval streets with architecture representing the island’s Venetian past. Highlights include the elegant arches of the Loggia, now in use as the town hall, and the Koules Venetian fortress along the harbor walls. In the afternoon, don’t miss the Archaeological Museum, home to one of the largest collections of Minoan artifacts in the world.
Spend the evening strolling with the locals through the old town of Heraklion. A pleasant pedestrian street connects the port area with the Lions’ Square and its Venetian fountain. Don’t miss “mama’s food” at Anchorage Traditional Mezedopolio nearby.
From here you can fly back to Athens.