2 Weeks in the Greek Islands - 5 Unique Itinerary Ideas

Itinerary #1: Discover Athens, Mykonos, Santorini & Crete

This 14-day itinerary hits the two most popular Cyclades islands for stunning seascapes, gorgeous beaches, and unbelievable sunsets. Add Crete, the largest of the Greek Islands, teeming with archaeological sites, traditional villages, and rugged nature. Top it off with three sensational days in Athens.

You'll begin in Athens, making the most of your first day at such top attractions as the Monastiraki flea market and the sprawling National Museum. Next day, an immersion in Classical Greek mythology includes the Temple of Olympian Zeus, the Acropolis and, at night, the Athens Observatory. Day three you’ll head to Delphi for a guided tour of this hugely important archaeological site.

Then hop a ferry to Mykonos, known for its iconic windmills, vibrant art scene, and vivacious nightlife. Upon arrival, your afternoon is at leisure for exploring, sunning, or perhaps windsurfing at Ftelia Beach. Your next two days, you’ll explore the island’s authentic heart, away from the tourist bustle; plus take a short ferry ride to the archaeological site at Delos—the mythological birthplace of Apollo and Artemis.

Day seven, head to Santorini, with its classic white-topped cliffs and caldera views. There’ll be time today to follow one of its many walking trails, or simply explore the clifftop village of Fira. Next morning continue to explore the isle at leisure, then enjoy a stroll through Oia, followed by a trip up to the highest peak on the island, then to the medieval villages at Megalochori and Pyrgos, ending with sunset wine tasting at the caldera's edge.

Three full days on Crete are filled with an exploration of the magnificent Palace of Knossos, followed by a guided stroll through Heraklion; a trek through the legendary Samaria Gorge; plus a journey into the fascinating Apokoronas region, with its Ottoman fort, historic churches, folklore museum, and more. Day 13, return to Athens to indulge in a foodies tour before saying goodbye to Greece the following day. Learn more.

Itinerary #2: Relaxing Secret Cyclades

Four lesser-known Cyclades isles—Syros, Tinos, Naxos, and Ios—highlight this sensational 14-day itinerary, chock-full of ancient ruins, pilgrimage sites, fabulous culinary experiences, and more.

Start in Athens, where you'll roam the city’s food stalls and open-air markets as you savor a guided food tour. Day three catch the ferry to Syros for two days. You’ll explore the lovely Cycladic capital, including the medieval hilltop settlement of Ano Syros, and tour the island villages, studded with elegant mansions.

Day five, journey to Tinos, one of the Cyclades’ most under-the-radar and religiously devout isles, known for its marble crafting and scores of windmills and dovecotes. Your three days here include an exploration along the “Marble Route,” with its statues, museums, and workshops; plus, you’ll pick fresh ingredients and learn to cook traditional Greek recipes, consumed alfresco with local wines.

Next, take the ferry to Naxos and unwind as you choose: Maybe hike to the summit of Mount Zas, explore the market of Chalki, or visit the temples of Demeter and Apollo. Next day is another foodies’ delight as you explore time-worn villages, sampling and recreating such trademark treats as loukoumades fried donuts, keftedes meatballs, and local kitron liqueur. Your third day, you’ll cycle around Naxos on a beginner-friendly route from village to village.

Now continue to the delightful island of Ios for a lazy afternoon at the beach and a night for dancing and fun at Far Out Village beach club. You’ll also journey to nearby tiny isle of Sikinos—the "Isle of Wine"—and hike to the Monastery of Episkopi, visit the Folklore Museum, and top it off with a toast from a local winery. Learn more.

Itinerary #3: Discover Rhodes, Crete, & Corfu

Odysseus's journey lasted 10 years as he tried to get home after the Trojan War. Your two-week journey will take less time but be no less memorable, combing a mythology tour in Athens, the medieval sites of Rhodes, Crete’s Palace of Knossos, and some of the places Odysseus set foot on Corfu.

After a brief visit to Athens, head to Rhodes, where you'll explore the UNESCO World Heritage-designated medieval Old Town of Rhodes, including the Palace of the Grand Master of the Knights. Day four is for beach time as you explore the eastern half of the island. Next day you’ll hike a rocky gorge that gives a sublime taste for Rhodes' at its natural best. You’ll wind past olive groves to reach the hilltop Kammiri Monastery before descending through pine forest to the fishing village of Lindos, with its hilltop acropolis.

Then travel to Crete, where you’ll explore the magnificent Palace of Knossos—once home to the fabled labyrinth of the Minotaur—followed by a guided stroll through Heraklion. Your next two days are dedicated to savoring the many facets of Cretan cuisine as you visit a family-run olive farm, learn about the traditional Cretan grape-based spirit called raki, and sample wines on a tour through the Cretan countryside.

Three days on the aristocratic Ionian island of Corfu follow. You’ll indulge in a guided culinary tour, including visits to open-air markets to sample such treats as loukomades (fried dough with honey). Then, tour the Pompeiian-inspired Achillion Palace and other elegant palaces for which Corfu is known… then follow in the footsteps of Odysseus’ mythological journey with a guide. Finally, return to Athens, where you’ll visit the Athenian Riviera and the Temple of Poseidon, including a stellar sunset vista overlooking the Saronic Gulf before departing next day. Learn more.

Itinerary #4: Culture Adventure in Athens, Naxos & Santorini

This two-week itinerary combines a smorgasbord of fun active adventures, from bicycling to sailing, as you savor the best of Athens and two very distinct Cyclades isles, including their ancient and contemporary culture.

Spend three days getting to know Athens before ferrying to Naxos and unwind as you choose: Maybe hike to the summit of Mount Zas, explore the market of Chalki, or visit the temples of Demeter and Apollo. Next day is dedicated to enjoying Naxos’ splendid beaches, while day six you’ll thrill to a full-day catamaran adventure to the "Small Cyclades"—a group of six tiny isles and associated islets.

Day seven is a foodies’ delight as you explore time-worn villages, sampling and recreating such trademark treats as loukoumades fried donuts, keftedes meatballs, and local kitron liqueur. Plus, you’ll also explore inland, traveling to the mountain village of Apiranthos, with its marble streets.

Day nine, head to Santorini, with its classic white-topped cliffs and caldera views. There’ll be time today to follow one of its many walking trails, or simply explore the clifftop village of Fira. Follow this with a day relaxing at Kamari Coastal Village, laid out on a crescent-shaped swath of black sand. Plus, you’ll hike the caldera rim trail between Fira and Oia. Then, on day 12, raise your glasses to your last full day in the islands with a vineyard tour to sample Santorini’s award-winning volcanic wines. Learn more.

Itinerary #5: Family Adventure in Athens and the Cyclades

Have fun with all the family in Athens and the beautiful islands of Mykonos, Naxos, and Santorini on this 14-day family adventure as you experience the best of Classical Greece, enjoying bicycle and horseback rides, plus plenty of time to laze and play on idyllic beaches.

Enjoy Athens with an interactive immersion in Classical Greek mythology begins at the Acropolis with guides specializing kid’s education, while at the National Garden performers recreate the adventures of gods and goddesses. After the curtain goes dine, dine mezze-style on Greek favorites in the atmospheric Plaka district.

Kids will love the ferry ride to Mykonos on day three. Upon arrival, unwind as you choose. Your next three days, you’ll take a short ferry ride to the archaeological site at Delos—the mythological birthplace of Apollo and Artemis; spend a day relaxing and playing on the beach; and visit a traditional farm.

Then ferry to Naxos for four days. After a free day to choose your own activity, you’ll spend a day bicycling to traditional villages and exploring the Venetian castle at Chora. Then mount up for a fun horseback ride to the mountain village of Apiranthos, with its marble streets. Finally, choose your own slice of beach paradise, such as Agios Georgios, popular with families enjoying the shallow waters.

On day 11, take the ferry to Santorini, with its classic white-topped cliffs and caldera views. There’ll be time today to follow one of its many walking trails, or simply explore the clifftop village of Fira. Your three days here includes a donkey ride along the clifftop, plus a full-day sailing adventure to the active volcano in the center of the caldera. Learn more.

More Great 14-Day Greece Itineraries

Looking for more inspiration for your Greece trip? Check out these other 14-day Greece itineraries, ranging from active, to cultural, to luxury, or family-friendly trips.

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