Two weeks is a great length for a Greek vacation. You'll have plenty of time to see multiple islands and historic mainland sites, taking part in cultural or outdoor activities along the way. These itineraries explore the possibilities: get active on some of the Cyclades lesser-known islands, dive into ancient mythology, enjoy a laidback beach holiday, and more.

Itinerary #1: Get Outdoors on Tinos, Naxos, and Ios

Hike, surf, horseback ride and more as you hop between lesser-known Greek islands. Catch a wave at Kolymbithra beach, dive into Naxos, and cruise the waves of the Aegean—adventure awaits around this itinerary's every turn. 

Set out across the surf in Mylopotas Bay

Arrive in Athens and take an early ferry to Tinos—an island that has remained under the radar despite its fascinating history, great outdoor activities, and glittering beaches. Here you'll hike along the famed marble route and explore the 80 iconic windmills dotting the island. Next up is guided climbing at Exomvourgo, a granite rockface with more than 90 well-maintained routes from beginner to expert level. At the top, you'll be rewarded with 360-degree views. 

Wrap up your time on Tinos at Kolymbithra beach for a day of surf lessons or paddleboarding among chic seaside surroundings. This protected cove on Tinos's northern coast is one of the island's best spots for water activities. Then, ferry to Naxos for a diving excursion. Learn the scuba basics before heading to dive sites teeming with sea life, including small rocky islands, reefs, and caves.

You'll also have the chance to check out the villages and attractions on the west side of Naxos via bike tour and guided horseback ride. Then, on to Ios, where you'll check out the coastline while cruising in a luxury speedboat. Visit spots of interest all along the coastline, including underwater caves and shipwrecks perfect for snorkeling.  Your next activity is a half-day canoe trip in Mylopotas Bay to a cove perfect for catching some sun and having a picnic lunch.

Finally, return to Athens and get one last look at the city with a mellow bike ride around fun neighborhoods and historic sites. Learn more

Itinerary #2: Historic Mainland Greece, Cyclades, and Crete

Travel through the rich mythology and history of Classical Greece from the mainland to the islands and back. You'll start and end in Athens, continuing into the islands with stops at the sacred site of Delos, prehistoric Akrotiri, and the Palace of Knossos.

Caryatid Porch of the Erechtheion

Welcome to Athens! First off, experience the ruins of mighty Acropolis, the iconic 5th-century BCE complex overlooking the city. Tour the entire settlement with an English-speaking guide who will share the stories of the country's most famous monument. Complement your tour with a trip to the nearby modern Acropolis Museum.

Next is a day trip to Delphi, once home to priestesses of Apollo who Ancient Greeks believed could predict the future. Take a guided tour through this sprawling archaeological site, with stops at the Treasury of the Athenians, the Temple of Apollo, and expansive theater. Then, ferry to glamorous Mykonos. Kick things off with a morning boat ride to the archaeological site at Delos, a small island that was the center of the Cyclades during the Classical era and the mythological birthplace of twin deities Apollo and Artemis. 

From Mykonos, you'll ferry to Santorini. Check out on of the Aegean's most significant prehistoric settlements at  Akrotiri, hidden away at the southern tip of Santorini on the slopes of the caldera. Crete is next on your list, the largest of the Greek isles. Explore the magnificent Palace of Knossos, the evocative Bronze Age site believed to be Europe's oldest city. Follow it up with a visit to Heraklion, strolling the old city's medieval streets and Venetian architecture. 

Return to the mainland for tours of Mycenae, Napflio, and the site of the first Olympic Games at the archaeological site of Olympia. End your trip with a sunset toast on the Athenian Riviera. Learn more

Itinerary #3: Enchanting Northern Greece and Corfu

Go from Greece's second city of Thessaloniki to living like the proverbial pasha in lakeside Ioannina, then up to the clifftop monasteries of Meteora. Continue on through the stone Zagori mountain villages to wrap up your journey on the shores of Corfu.

Clifftop monasteries of Meteora

Your journey begins in Thessaloniki—after landing in Athens, it's just a short flight to this historic northern city. Start with a walking tour, scoping out the UNESCO World Heritage-listed Byzantine churches and Roman ruins. You'll also visit Ano Poli (Upper Town), where many of the ancient city's main defensive structures were built due to its hilltop position. 

Next, hit the road to neighboring Vergina, the first capital of ancient Macedonia. Explore the royal tomb of King Philip II, father of Alexander the Great, and visit the museum to see his burial artifacts. Stop in the town of Naousa for lunch at one of its many tavernas before continuing on to Kalabaka.

On day four, ascend to the six cliffside monasteries at Meteora. They sit perched atop high rock formations, but are still inhabited and used by monks and nuns today. The area is one of the largest pilgrimage sites in Greece. Then head to Ioannina, a lakeside city that was once the center of the Enlightenment in Greece, with well-preserved buildings, examples of Ottoman architecture.

The fairytale Zagori villages are next on your list, a group of 40 well-preserved stone compounds set among the peaks, rivers, and gorges of Pindos. Walk among small farms and bridges unique to the region, and end your time in Zagori with a traditional cooking class. From there, ferry to Corfu. Eat your way around Old Town on a guided food tour, where you'll get to know the local food scene and learn the history of Corfiot cooking. Wrap up your trip with more Corfu exploration on a Jeep safari and Odessey-themed boat tour. Learn more 

Itinerary #4: Laidback Athens, Mykonos, Santorini, and Crete

Start your vacay with street food and native wines in Athens before heading to glamorous Mykonos and Santorini. Then on to Crete, where turquoise lagoons and village strolls ensure you're fully blissed out. 

"Little Venice" on Mykonos

Begin in Athens, home to the iconic Acropolis and so much more. After visiting the historic landmarks, take a food tour: meet your guide in Syntagma Square to sample from the city's street stalls, learn about the Mediterranean diet, and explore neighborhoods off the tourist track. Spend the next day tasting the varietals of Nemea, one of the country's most important wine regions.

On day four you'll ferry to Tinos, an island known for its marble crafting—you'll see why as you follow the famous "marble route" from raw materials to artists' workshops. Mykonos is next, and you can spend your first day here strolling the cosmopolitan streets, shopping in glamorous boutiques, or lounging on the sand. If you'd prefer a more guided experience, opt for a cooking class to learn about Greek ingredients—you'll leave with a mastery of olive oil, local seafood, and more.

Days 8 and 9 will be spent on Santorini, where history buffs can check out the Archaeological Museum in Firos before a semi-private catamaran cruise around the island, stopping at Red Beach and White Beach to swim and sun. From there, head to Crete to enjoy some of the most beautiful beaches in the world. Go by boat to Balos and Gramvousa beaches, home to stellar swimming, and protected animal and plant species. You'll also take a guided tour of Apokoronas—the region's seven villages are home to a number of historic sites.

End your trip on the Athenian Riviera, full of both history and stunning island views of the Saronic Gulf, with one of the best sunset views Greece has to offer. Learn more

For more Greece trip ideas, see all of our 2-week tours and itineraries.