16 Days in Greece - 6 Unique Itinerary Ideas

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

From legendary mythological sites to buzzing beach bars, Greece is filled to the brim with bucket-list-worthy experiences, and this well-rounded highlights tour features the best of them. Ponder the striking Parthenon, laze on Mykonos' famous beaches, explore the coastlines of Santorini by catamaran, and hike the striking Samaria Gorge in Crete. In addition, guided countryside tours, a cooking class, and time for independent exploration ensure you're introduced to each destination's authentic side.

Welcome to Greece! Your adventure begins in Athens, where, over three days, you'll check out the city's ancient highlights and venture to the Archaeological Site of Delphi. Next, fly to the glitzy island of Mykonos and treat yourself to an afternoon of beach hopping, followed by a guided tour of the island's charming villages and rural farms. Nearby is the island of Delos, home to mythological sites, which you'll also visit before ferrying to Santorini. This island is famous for its rugged volcanic terrain and whitewashed buildings, and you'll experience both while exploring on foot and by catamaran. 

From Santorini, another ferry ride brings you to Heraklion, Crete's capital, and through a short but immersive two-night stay, you'll explore its Palace of Knossos and lovely Tsimiski Street. Afterward, transfer down the coast to Chania, which will be your home for the following four days. Stroll through its Old Town, conquer a stunning hike through Samaria Gorge, wander amid olive groves in the region of Apokoronas, and create a Cretan feast alongside locals in Vamos. Then, return by plane to Athens, where an evening of wine bar hopping wraps up your brilliant adventure. Learn more

Itinerary #2: Historic Tour Through Mainland Greece & Crete

Experience the ancient wonders of classical Greece on this immersive history-focused itinerary. Perfect for those eager to delve into the world of Greek mythology, you'll hop between ancient cities, majestic temples, and insightful museums. Highlights include the Archaeological Site of Olympia, Delphi's Temple of Apollo, and the must-see Parthenon. Additionally, a four-day stay in Crete rounds out the adventure with beach days and time to explore dreamy Old Towns independently. 

Your history-infused adventure begins in Athens, and a short but immersive stay ensures you have time to visit the Acropolis, Parthenon, and other city highlights. Next, transfer to the coastal city of Nafplio and explore the Archaeological Site of Mycenae, the Sanctuary of Asklepios, and the Fortress of Palamid. Then, over the following few days, continue checking out the best of mainland Greece's historical highlights, including Sparta, Olympia, Messene, and the Old Town of Nafpaktos. Eventually, you'll reach Delphi and settle in for a two-night stay in this once-regarded center of the world.

The second leg of your journey starts with a transfer north to Meteora, where you'll pause to explore its impossible cliff-perched monasteries, followed by a two-night stay in Thessaloniki. This gives you ample time to take in the city's bustling squares, Ottoman fortress, and Roman ruins before flying to Crete. Your first base here is Heraklion, and besides being the island's buzzing capital, it's also home to the sprawling Knossos Palace and imposing Rocca a Mare Fortress. After checking both out, transfer to Chania and spend your remaining days lazing at the beach, museum hopping, and exploring by Trikke. Learn more

Itinerary #3: Island Hopping From Athens Across the Cyclades

On this ultimate island-hopping getaway, you'll venture off the trodden trail to uncover the historical and natural highlights of six stunning Cyclades islands. Taste your way between dreamy wineries on Mykonos, admire the thought-provoking Temple of Apollo on Naxos, and explore Santorini's rugged volcanic landscapes by Jeep. In addition, spend two nights each on the lesser-visited islands of Paros, Sifnos, and Milos, which are home to ancient ruins and quaint villages waiting to be discovered.

Before heading to the islands, your adventure begins with a two-day stay in Athens—perfect for unwinding and checking out iconic sites. Then, fly to Mykonos, where you'll venture beyond the packed beaches to quaint villages, wineries, and organic farms. Afterward, a short ferry journey brings you to Naxos, and over a three-day stay, you'll have plenty of time to explore independently, embark on a history and food tour, and spend an enchanting day onboard a catamaran. Next, hop over to the lesser-visited island of Paros and dedicate a day each to a cooking class and a tour of nearby Antiparos. 

Continuing your island-hopping journey, you'll next find yourself horseback riding and trekking around Sifnos. In addition, spend an afternoon popping into quaint cafés and boutique shops in the capital city of Apollonia before setting your sights on Milos. Here, over a two-day stay, you'll have time for an immersive food tour as well as a spectacular hike from the ruins of Phylakopi to Sarakiniko Beach. Then, on Day 14, set your sights on Santorini and spend your remaining time exploring by Jeep, beach hopping, and savoring postcard-perfect vistas until the time arrives to board your departing flight. Learn more

Itinerary #4: Active Adventure in Greece: Hiking, Cycling, Swimming & Kayaking

Ideal for those who enjoy keeping active while traveling, this adrenaline-filled adventure gets you out hiking, cycling, and kayaking among the idyllic landscapes of mainland Greece and the Cyclades islands. Starting on the Attica peninsula, hop between Athens, Nafplio, and Sparti—all of which are brimming with impressive reminders of the Roman Empire. Then, spend the second leg of the journey in Crete, Santorini, and Naxos, where you'll conquer treks through a gorge and the summit of Mount Zas and delight in unhurried time to explore coastlines by kayak and catamaran.

Your active adventure kicks off with a day in Athens, where you'll quickly overcome jet lag while exploring intriguing neighborhoods alongside a guide. Then, over the following four days, head out of the city to uncover the Attica peninsula's ruins-dotted landscapes. In the coastal town of Nafplio, hike to fortresses guarding the city and explore by e-bike, and in the city of Sparti, trek to the summit of Mount Taygetus and cycle through the nearby Laconia countryside. Next, catch a flight to Chania on Crete and celebrate your arrival with a thrilling Trikke tour, followed by a full-day hike through the dramatic Samaria Gorge.

While in Chania, you'll also dedicate a day to hopping between wineries and impressive Samaria National Park viewpoints before transferring to Heraklion. This picturesque capital is brimming with storied sites, which you'll discover during an ancient Minoan trail sunset safari and a visit to the Cave of Diktaion Andron. Afterward, spend two days on the island of Santorini, cruising onboard a catamaran and exploring by kayak and horseback. Then, ferry to Naxos and round off your adventure with a thrilling hike to the summit of Mount Zas and a delightful dinner at a waterfront restaurant. Learn more

Itinerary #5: Cyclades & Peloponnese Culinary Heritage

To discover the finest food of Greece, one must venture off the tourist trail to local farms and small villages, which is exactly where this flavorful culinary experience leads you. Through immersive visits to countryside farms, vineyards, and homes, you'll learn the craft of olive oil production, the use of Greek herbs, and the art of winemaking. In between meals, walk off your indulgences through insightful tours of archaeological sites, museums, and storied towns.

Upon landing in Athens, you'll be introduced to Greece's famed cuisine during a welcome dinner overlooking the Acropolis. Then, following a detour to the Archaeological Site of Mycenae, transfer to Nafplio, which will be your home base for four days. While here, you'll delve into the region's fresh cuisine through visits to local farms, three picturesque wineries, and a rural village renowned for its olive oil production. Afterward, board a ferry bound for the island of Tinos, where an extended visit provides ample time to explore independently, join a local to cook up a Greek feast, and museum hop.

Next on your agenda is a three-day stay on the island of Mykonos, the first of which you'll spend lazing on its pristine beaches. Then, thanks to a local farm visit and a village and countryside tour, you'll discover the island's lesser-visited interior. After another ferry journey, you'll find yourself on the island of Naxos, where a scenic hike to the summit of Mount Zas awaits. With your appetite reignited, dig into Naxian cheeses, confections, and wines during a food tour before catching a flight back to Athens and wrapping up your culinary adventure with a delightful cooking class. Learn more

Itinerary #6: Mainland Greece Road Trip

Take the reins and uncover the historical sites and remarkable landscapes of mainland Greece on this epic 16-day road trip. Ideal for travelers who enjoy a fast-paced trip, you'll overnight in eight different destinations and detour to numerous archaeological sites and charming villages. Notable highlights include a boat trip to Nafplio Bay, a visit to the ancient city of Epidaurus, side trips to Sparta and Olympia, and a wander through the Palace of Nestor.

Prior to hitting the open road, your adventure begins with three days of discovery in Athens. Meander through the Acropolis, ponder the Temple of Olympian Zeus, and taste your way through the Varvakeios Market. Then, collect a rental car and drive to Nafplio, where you'll boat to Bourtzi Fortress and hop between the region's famed wineries. You'll also dedicate a day to roaming the Archaeological Site of Mycenae and the ancient city of Epidaurus before continuing to Mystras. As the once capital of Byzantine, this town is brimming with well-preserved ruins, which you'll explore on a self-guided tour.

Next, your road trip shifts into a higher gear, and you'll make your way from Monemvasia, across to the west coast of the Peloponnese peninsula, and up to Nafpaktos. Throughout, there's plenty of opportunity to pause and take in your storied surroundings. Enjoy lazy meanders through quaint villages, explore the Palace of Nestor, and tour the Archaeological Site of Olympia. Then, after taking a break from driving during a free day in Nafpaktos, slowly make your way back to Athens, stopping in Galaxidi, the Archaeological Site of Delphi, and the Holy Monastery of Hosios Loukas en route. Learn more

More Great 16-Day Greece Itineraries

Looking for more inspiration for your trip to Greece? Check out these other 16-day Greece itineraries, with outdoor adventures, cultural trips, and best-of tours to hit the highlights.