2 Weeks in Greece - 5 Luxury Itinerary Ideas

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.

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.

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

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. 

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.

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.

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.