Two weeks in Greece is a superb amount of time to immerse yourself in the country's history and luxury. Athens, Mykonos, Naxos, Santorini, and Crete are top destinations and offer 5-star accommodations, world-class dining, and opportunities to explore by bike, on foot, and with a paddle in hand. Or, swap in the Peloponnese peninsula for a deep dive into Greek mythology. Another option is to take to the sea for a thrilling sailing excursion amid the Cyclades.

Itinerary #1: Luxury Highlights of Greece: Athens, Mykonos, Naxos, Santorini & Crete

Experience the renowned highlights of the Athenian Riviera and the captivating Cyclades on this luxury-infused two-week getaway. Each day has been specially crafted to introduce you to must-see wonders in style, making this itinerary perfect for first-time travelers who appreciate the finer things in life. Tour the famous Acropolis, sample oysters straight from a farm on Mykonos, cruise along Naxos' unspoiled coastlines, and dine with sunset views on Santorini.

Stay two nights in a cliffside hotel in Mykonos (photo courtesy of Cavo Tagoo Mykonos)
Stay two nights in a cliffside hotel in Mykonos (photo courtesy of Cavo Tagoo Mykonos)
Day Highlights Overnight
Day 1 Arrive in Athens, Tour the Acropolis & Museum Athens
Day 2 Explore the Athenian Riviera: Temple of Poseidon & Fine Dining Athens
Day 3 Ferry to Mykonos, Oysters & Bubbles Experience Mykonos
Day 4 Luxury Catamaran Cruise, Evening Walking Tour Mykonos
Day 5 Ferry to Naxos, Guided City Highlights Tour  Naxos
Day 6 Full-Day Boat Tour of South Naxos & the Cycladic Islands Naxos
Day 7 Ferry to Santorini, Sea View Dinner at Lycabettus Restaurant Santorini
Day 8 Santorini Island Tour with Beaches, Wine Tastings & Historic Sites  Santorini
Day 9 Ferry to Crete, Explore the Capital City of Heraklion Heraklion
Day 10 Tour Knossos Palace & Heraklion Archaeological Museum Heraklion
Day 11 Transfer to Chania, Walking Tour of Old Town, Food & Wine Tastings Chania
Day 12 Secrets of Eastern Crete: Monasteries, Mountains & Villages  Chania
Day 13 Sailing Cruise to Balos & Gramvousa Island Chania
Day 14 Depart Chania  

Welcome to Greece! Your tour kicks off in Athens, and over a two-day stay, you'll tour the famous Parthenon, embark on a private trip along the Athenian Riviera, and enjoy dinner at the premier Ithaki. Your next destination, the dazzling island of Mykonos, introduces you to the luxuries of the Cyclades through an exclusive oyster farm visit, followed by a private catamaran adventure. More delightful sea excursions await on the island of Naxos, including a boat tour of remote coves. You'll also find ample time to enjoy the amenities of your 5-star accommodation, 18 Grapes, before ferrying to Santorini.

Renowned for its cliffside villages, volcanic beaches, and serene interior, Santorini exudes luxury, and during your stay, you'll indulge yourself through fine dining and a full-day guided tour. Afterward, continue to Crete, your home for the final five days. The bustling town of Heraklion is your kicking-off point, and through visits to intriguing museums and the ancient Knossos Palace, you'll find an abundance of history to uncover. Then, transfer to Chania, where an off-the-beaten-path driving tour and a dreamy cruise to unspoiled beaches round off your sunkissed adventure. Learn more

Itinerary #2: Luxury Greek Gastronomy Tour: Athens, Nafplio, Santorini & Naxos

With enchanting vineyards, family-run farms, and an abundance of fine-dining restaurants, Greece is the ultimate destination for foodies—and this gastronomy-focused tour introduces you to the finest of each. Starting on the mainland, you'll taste your way through Athens' premier eateries and dine alongside a private chef in Nafplio. Then, fly to the Cyclades, where extended stays on Santorini and Naxos introduce you to each island's traditional villages, authentic cafés, and unspoiled coastlines.

Dine overlooking the South Aegean on Naxos island (photo courtesy of 18 Grapes Hotel Naxos)
Dine overlooking the South Aegean on Naxos (photo courtesy of 18 Grapes Hotel Naxos)
Day Highlights Overnight
Day 1 Arrive in Athens, Welcome Dinner with Acropolis View Athens
Day 2 History & Cuisine of Athens Tour, Wine Tasting  Athens
Day 3 Transfer to Nafplio, Self-Guided City Tour, Dine with a Private Chef  Nafplio
Day 4 Nafplio Sightseeing Excursion, Dinner & Music at Local Restaurant Nafplio
Day 5 Nemea Winery Tour & Tasting  Nafplio
Day 6 Fly to Santorini, Evening of Dinner & Wine Santorini
Day 7 Free Morning to Explore, Sunset Catamaran Cruise & Barbecue  Santorini
Day 8 Oia Organic Farm Picnic, Vineyard Excursion & Wine Tasting Santorini
Day 9 Ferry to Naxos, Flavors of Naxos Old Town Tour Naxos
Day 10 Naxos Island Tour, Farm Visit with Wine & Cheese Tasting  Naxos
Day 11 Sailing Excursion Around Naxos & Small Cyclades Islands Naxos
Day 12 Explore the Beaches & Villages of Naxos, Traditional Naxian Dinner Naxos
Day 13 Return to Athens, Excursion Along the Athenian Riviera & Dinner  Athens
Day 14 Depart Athens  

Let's hope you've arrived in Athens with an appetite. Your journey begins with fine dining under the Acropolis, followed by a local restaurant's food tour and a private wine-tasting experience. Next, transfer to Nafplio, where three days of history and gastronomical experiences await. Dine with a private chef, visit ancient fortresses, and spend a delightful day winery hopping in the Nemea region. Afterward, a quick flight whisks you to Santorini, and upon arrival, you'll discover why this Cyclades island is renowned for its upscale vibe as you laze at the 5-star Vedema Resort and savor a private sunset cruise.

On your final day in Santorini, team up with a knowledgeable guide to visit an organic farm and millenia-old vineyards, then ferry over to Naxos and check into the serene 18 Grapes luxury hotel for a three-day stay. This island is renowned for its rugged coastlines and storied interior, which you'll fully experience through a full-day farm and village tour and a leisurely cruise onboard a sailboat. Additionally, tuck into quaint restaurants and enjoy uninterrupted time at pristine beaches before returning to Athens. A superb driving and dinner tour through the Athenian Riviera rounds off the adventure. Learn more

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Itinerary #3: Luxury Journey Through Ancient Greece: Athens, Crete & Peloponnese

History enthusiasts with a penchant for the finer things in life will find this two-week journey through Crete and mainland Greece the perfect fit. Join private guides for insightful tours of the Acropolis, Knossos Palace, ancient Olympia, and the Temple of Apollo. In between, refresh at exclusive accommodations chosen for their privileged location and take to the sea for a splendid day trip to the islands of Hydra, Dia, and Santorini. 

See the world-famous Temple of Erectheion at the Acropolis
See the world-famous Temple of Erectheion at the Acropolis
Day Highlights Overnight
Day 1 Arrive in Athens, Greek Cooking Class, Cocktails in Plaka Athens
Day 2 Best of Ancient & Modern Athens, Tasting Menu at Aleria Restaurant Athens
Day 3 Boat Trip to Hydra, Explore the Island on Horseback, Beach Leisure Time Athens
Day 4 Fly to Heraklion, Snorkeling & Sunset Dia Island Cruise Heraklion
Day 5 Discover the Secrets of Eastern Crete: Monasteries, Mountains & Villages  Heraklion
Day 6 Day Trip to Santorini, Explore the Island's Villages Heraklion
Day 7 Transfer to Chania, Knossos Palace, Local Villages & Winery Tour Chania
Day 8 Tour Crete's Highlights: Rethymno, Argiroupolis & Kournas Lake Chania
Day 9 Fly to Athens, Tour Mycenae, Highlights of Naplio, Transfer to Olympia Olympia
Day 10 Walk in the Footsteps of Olympiads at Ancient Olympia, Transfer to Galaxidi Galaxidi
Day 11 Tour of Galaxidi, Highlights of Delphi & Amfissa, Transfer to Meteora Meteora
Day 12 Explore the Meteora Area, Vineyard Wine Tasting, Meteora Sunset Drive Meteora
Day 13 Discover Meteora's Monasteries, Transfer to Athens Athens
Day 14 Depart Athens  

Considering Athens played a central role in ancient Greek civilization, it's the perfect place to begin your journey through history. Uncover old alleyways in Plaka, stroll through the Acropolis, and experience the island of Hydra's artist splendor by horseback. Next, transfer to Crete's capital, Heraklion, which will serve as your base to cruise to the uninhabited island of Dia and the moon-shaped picturesque Santorini. In addition, visit ancient Byzantine monasteries and tour the Palace of Knossos before transferring across Crete to Chania on Day 7 and checking into the delightful Domus Renier Boutique Hotel

After a leisurely first evening in Chania, join up with a private guide for an insightful tour of surrounding villages and the stunning Lake Kourna. Then, return to the mainland and wrap up your adventure with a five-day journey through the Peloponnese peninsula and central Greece. First up is Olympia, where you'll walk in the footsteps of the first Olympians, followed by an overnight in Galaxadi and a visit to the Temple of Apollo. Next, pause in Meteora for a peaceful afternoon at a family-run winery and explore its famous clifftop monasteries before returning to Athens to catch your departing flight. Learn more

Itinerary #4: Luxury & Adventure in Greece: Athens, Crete & Santorini

Delight in a perfect blend of adventure and luxury on this action-packed two-week trip through Greece. Crafted especially for travelers who prefer limiting travel time in exchange for immersive activities, you'll bike, hike, kayak, cruise, and taste your way through ancient cities and postcard-perfect islands. Spend four days in Athens exploring sites dating back to ancient Greece, then continue to the Cyclades islands of Crete and Santorini, where private cruises, farm-to-table dinners, and visits to traditional villages round off your journey.

Explore the tranquil waters of Crete's Balos Beach with a private speedboat tour
Explore the tranquil waters of Crete's Balos Beach with a private speedboat tour
Day Highlights Overnight
Day 1 Arrive in Athens, Welcome Dinner with Acropolis View Athens
Day 2 Guided Bike Tour Around the City, Acropolis at Sunset Athens
Day 3 Day Trip to Delphi: Hiking, Ancient Olive Groves & the Oracle Athens
Day 4 Sea Kayaking Tour of Sounio & Poseidon Temple, Athenian Riviera Dinner Athens
Day 5 Fly to Chania, Cultural Walking Tour, Food & Wine Tastings Chania
Day 6 Motorboat Cruise to Balos Beach & Gramvousa Islands Chania
Day 7 Hiking Fun in Samaria River Gorge, Authentic Cretan Dinner Chania
Day 8 Transfer to Heraklion, Explore the City, Farm-to-Table Dining Experience Heraklion
Day 9 Guided Excursion to Lassithi Plateau: Cave of Zeus & Knossos Palace  Heraklion
Day 10 Ferry to Santorini, Evening of Dinner & Wine Santorini
Day 11 Free Morning to Explore, Sunset Catamaran Cruise & Barbecue  Santorini
Day 12 Driving Tour Around Santorini, Megalochori Village & Wine Tasting Santorini
Day 13 Guided Hike of Santorini's Caldera, Farm Picnic in Oia Santorini
Day 14 Depart Santorini  

Your active adventure gets off to a thrilling start in Athens, where, over a four-day stay, you'll experience its renowned highlights from unique vantage points. Cycle through the historic center, tour the Acropolis at sunset, hike to the Oracle of Delphi, and sea kayak to the Temple of Poseidon. Afterward, fly to Chania on Crete and refresh at the lavish Domes Zeen Resort before tucking into Old Town's artisanal shops and local restaurants. Then, with two more days in this picturesque port town, you'll have time for a private motorboat excursion and a guided hike through the dramatic Samaria River Gorge.

Your adventure continues across Crete to Heraklion, and in addition to visiting its Venetian fortresses, you'll head out of town to explore the Cave of Zeus and Knossos Palace. Next, ferry to Santorini and check into the premier Andronis Concept-Wellness Resort, which provides the perfect base to unwind between your upcoming adventures. Start with an indulgent evening at a top restaurant, then delight in a private sunset cruise and hop between the island's archaeological sites and tucked-away villages. You'll also conquer a picturesque hike to Oia before prepping for your onward flight. Learn more

Itinerary #5: Luxury Sailing in the Cyclades: Santorini, Paros & Mykonos

Spend your days exploring beaches, bays, and caves only accessible by boat and your evenings relaxing at 5-star accommodations on this two-week luxury sailing getaway. Ideal for those with an affinity for the sea, each day introduces you to the secrets of Santorini, Paros, and Mykonos and their undeveloped surroundings. By combining daily sailing excursions with land-based accommodations and activities, you'll leave feeling sunkissed and well-introduced to each island's culture.

Sail your cares away on this luxury sailing vacation in the Cyclades
Sail your cares away on this luxury sailing vacation in the Cyclades
Day Highlights Overnight
Day 1 Arrive in Athens, Neighborhood Gems Tour, Sunset Dinner Athens
Day 2 Tour of Ancient Athens, Anafiotika & Plaka, Dinner in the Sky Athens
Day 3 Fly to Santorini, Kallos Spa Experience, Sunset Wine Tour Santorini
Day 4 Day Cruise Around the Caldera with Swimming & Snorkeling  Santorini
Day 5 Day Cruise to Ios, Relax on Maganari Beach & Explore the Island  Santorini
Day 6 Day Cruise to Anafi, Explore the Island, Sunset Wine Tasting  Santorini
Day 7 Day Cruise to Folegandros, Megalochori Sunset Wine Tasting  Santorini
Day 8 Sail to Paros, Explore Naousa, Local Dinner in Paros Paros
Day 9 Day Cruise to Antiparos via Panteronisia & Despotiko Paros
Day 10 Day Cruise to Naxos, Visit the Small Cyclades Paros
Day 11 Sail to Mykonos via Rhenia & Delos Mykonos
Day 12 Cruise Mykonos' Best Beaches, Lunch at Kalafatis Bay, Island Village Tour Mykonos
Day 13 Traditional Greek Cooking Experience, Mykonos Walking Tour Mykonos
Day 14 Depart Mykonos  

Before setting sail, your trip gets rolling in Athens, and with fine dining and a private ancient highlights tour on the agenda, you'll quickly uncover the city's more elevated side. Next, fly to the Cyclades island of Santorini, where the 5-star Canaves Oia Epitome welcomes you to enjoy its many amenities between your upcoming sailing adventures. The first is around Santorini's rugged coastlines to volcanic beaches, followed by day cruises to the islands of los, Anafi, and Folegrandos. Then, round off your stay in Santorini with a serene wine-tasting and sunset tour.

Your next destination is the island of Paros, and again, you'll have a lavish hotel to call home when you're not out sailing. Stretch your sea legs with a meander around Naousa, then embark on two full-day excursions, the first to the neighboring island of Antiparos and the second to Naxos and Schinoussa. Afterward, continue to Mykonos, where a stay at the 5-star Myconian Villa Collection awaits. There's plenty to do on this cosmopolitan island, and a cruise tour of top beaches, an indulgent cooking class, and a private walking excursion provide the perfect conclusion to your adventure. Learn more

More Great 2-Week Greece Itineraries

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


Map of 2 Weeks in Greece - 5 Luxury Itinerary Ideas
Map of 2 Weeks in Greece - 5 Luxury Itinerary Ideas