Excellent
Greece Itinerary 2 Weeks: Across Athens, Meteora & the Aegean Isles
15 Days
6 Stops
Private transfer
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From$6,800
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Trip curated by Roman Karin
ExpertMy team and I crafted this trip! Want to make it even more your style? Let’s chat — you can book a free planning call with me.
My team and I crafted this trip! Want to make it even more your style? Let’s chat — you can book a free planning call with me.
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Athens
Day 1 - 4
Dominating the Attica region of Greece, the country’s capital, Athens, is one of the oldest cities in the world. For over two and a half centuries, the astonishing Greek temples and monuments of Athens have continued to intrigue and amaze visitors from around the world. This icon of western civilization seamlessly combines ancient history with modern architecture and a surprisingly lively atmosphere. This is particularly apparent in areas at the foot of the Acropolis, Anafiotika, Plaka, Monastiraki, and Thissio where visitors will find numerous extraordinary Neoclassical buildings, trendy and traditional cafes, and shops, and narrow winding streets with historical treasures at every turn. Once you have enjoyed a history and art fix, try some mouth-watering Greek cuisine at one of the city’s fine local restaurants before indulging in the insatiable nightlife at the chic cocktail bars and waterfront dance clubs.
Your accommodation
Acropolian Spirit Boutique Hotel
Centrally located in Athens, Greece, the Acropolian Spirit Boutique Hotel is an excellent accommodation option for leisure and business travellers. The hotel offers well-appointed and comfortable rooms and suites equipped with central heating/cooling, TVs, mini-fridges, private bathrooms, hairdryers, safety deposit boxes, and toiletries. Guests can start each day with a delightful breakfast buffet on-site. Facilities and services include a 24-hour reception, a restaurant, a bar, room service, a lobby lounge, wake-up calls, and Wi-Fi.
Your activity
Athens City Tour with Acropolis
Explore some of Greece’s greatest treasures and the best of modern Athens on this zero-carbon, 3.5-hour morning sightseeing tour. With an expert guide, enjoy a coach tour of Athens’ major landmarks, including the Greek Parliament and the Panathenaic Stadium, before exploring the Acropolis on foot to see the majestic Parthenon and other highlights.
The tour begins with a panoramic drive around Syntagma Square, passing the National Garden, Hadrian’s Arch, St. Paul’s Church, the Parliament, Tomb of the Unknown Soldier, the Catholic Cathedral, and Schliemann’s House. Continue past the Athens Trilogy—the University of Athens, the Academy of Athens, and the National Library—while your licensed guide shares insights into Athens’ rich history, both ancient and modern.
Pass by the Panathenaic Stadium, the site of the first modern Olympic Games in 1896 and the only stadium built entirely of white marble. Continue past the Zappeion and the Temple of Olympian Zeus before arriving at the Acropolis, a UNESCO World Heritage site. Here, explore the Propylaea, the monumental entrance blending Doric and Ionic architecture, the small Temple of Athena Nike perched on a rocky outcrop protecting the citadel gate, and, of course, the Parthenon and the Erechtheion with its famous Porch of the Maidens.
This half-day Acropolis tour allows you to experience one of the world’s top UNESCO heritage sites while saving valuable time, making it a perfect introduction to Athens’ history and culture.
Milos
Day 5 - 6
Picturesque white-washed villages cover the dramatically carved landscape of the volcanic Greek island of Milos or Melos, the southwesternmost island of the Cyclades, found just north of the Sea of Crete. For history enthusiasts, be sure to visit the Archaeological Museum, with artefacts from the Neolithic to the Byzantine periods, The Ancient Roman Theater of Milos, The Venetian Castle, The Mining Museum in Adamas and the early-Christian Catacombs, a glorious archaeological spectacle dating from the 1st to the 5th century AD. For a more leisurely exploration, swim in the crystal-clear turquoise waters that lap gleaming white rock formations, rugged cliffs and sea caves on the many secluded beaches. Plaka, a hilltop town and the de facto capital, is where to find several inviting restaurants, quaint cafes, Greek and European pastries, coffee and sweets. End the day by unwinding with a leisurely soak in the mineral springs, which physicians have recommended since the time of Herodotus.
Your accommodation
Thalassitra Village Hotel
Located in Adamas, Greece, Thalassitra Village Hotel is a short drive from the Ancient Theater of Milos and very close to Milos oneiro. Accommodation consists of spacious rooms, equipped with a private bathroom, coffee/tea maker, a fridge, and a multichannel TV. Guests can look forward to dining at Taverna Barko and Let's Meat, a short walk from the hotel.
Your activity
Romantic Dinner on board
Aboard a 42’ monohull sailing yacht, the experienced crew will take you out to witness a mesmerizing sunset off the coast of Klima. As the sun dips below the horizon, a candle-lit dinner awaits you on board in the middle of Adamas Bay, allowing you to enjoy the lights of the port reflecting on the sea. Dinner and drinks are included, and the discreet presence of the crew ensures a luxurious and unforgettable experience.
Naxos
Day 7 - 8
Situated in the Aegean Sea, the Greek island of Naxos is the largest of the Cyclades Archipelago. Its fertile landscape features ancient ruins, quaint mountain villages with sheep-dotted slopes, and vast stretches of magnificent beaches. With their crystal-clear waters, soft white sands and watersports such as swimming, windsurfing, kitesurfing and surfing on offer, the beaches here provide the ultimate holiday experience, while the island’s lush interior makes it an ideal destination for hiking and mountain biking enthusiasts. Make sure to visit the mysterious Cave of Zas, filled with incredible stalactite formations and dedicated to Zeus in ancient times. The wide variety of historic attractions includes breathtaking Venetian mansions, Byzantine country churches, and the medieval old quarter of Kastro, with its centuries-old stone paving, arches and buildings.
Your accommodation
Nissaki Beach Hotel
Nissaki Beach Hotel is located near the beach of Saint George in Naxos Town. The hotel features spacious suites with modern amenities, including large windows overlooking the surrounding areas, Wi-Fi, TVs, coffee/tea facilities and air conditioning. Guests can enjoy delicious meals at the on-site restaurant and have refreshing drinks at the lobby bar. Other facilities include an outdoor bar, spacious lounges, a swimming pool with a hydro-massage area and pool loungers.
Your activity
Photography Tour Naxos
Beautiful beaches, golden sunsets, the Venetian citadel, the lively old market, Portara - the island's
landmark - along with mountain views and stunning landscapes create the perfect backdrop for your
experience. A professional photographer will not only guide you to the most photogenic spots of Naxos
but will also share practical tips and a short photography lesson, helping you improve your skills while
capturing the island through your own lens.
Immortalize your holiday moments with a photo tour that combines exploration and learning. Stroll
through picturesque alleys and traditional villages, discover hidden corners, and take part in a hands-on
photography experience. With professional guidance, you will capture images that reflect both the beauty
of Naxos and your personal perspective, creating memories that will last long after your journey.
Naousa
Day 9 - 10
Naoussa is a beautiful, authentic-feeling fishing village set on the north side of Paros, Greece, 10 kilometres east of Parikia (the capital city). A 15th-century Venetian Fortress watches over the port, where it once defended the city against pirate invasions. The Piperi town beach provides the perfect place to take a dip in the crystal clear waters, for which the town is famous, along with its true-to-culture atmosphere and brightly coloured sea-facing bars and restaurants. Take a full-day sailing cruise, enjoy the freshest, most traditional seafood dishes, and explore the winding cobbled alleyways up the hill.
Your accommodation
Sandaya Luxury Suites
Nestled within the beautiful area of Naoussa, the capital of Paros, Sandaya Luxury Suites is nearby ample amounts of attractions including the Venetian Harbour and Fort, the Wine Museum, Paros Park and the crystal clear waters of Kolymbithres beach.
The well-appointed hotel boasts nine suites, each featuring luxurious furnishings, contemporary decor and modern amenities including a minibar, coffee machine, flat-screen TV, Wi-Fi, air-conditioning and outdoor furniture overlooking beautiful views.
Your activity
Cruise Around Antiparos & Despotiko
Embark on unforgettable new adventures aboard our traditional Kaiki, a wooden motorboat typically used by fishermen, as we explore the stunning islands of Antiparos and Despotiko. We'll arrange a convenient transfer from your hotel (or a nearby stop) to the port of Pounta.
Get ready to uncover the hidden gems of the Aegean Sea that are only accessible by boat. With crystal-clear waters, you'll truly feel like you've stepped into paradise! Our journey begins at 10:00 am from the Pounta port, where we will guide you to breathtaking beaches, sea caves, and small islands, leaving you in awe of the exotic destinations around you. This cruise offers a unique opportunity to reconnect with the untamed beauty and natural wonders of the area.
While the following itinerary is indicative, our captain will select the best locations for each cruise based on the weather conditions, ensuring you have an extraordinary experience around Antiparos and Despotiko islands. Discover the enchanting Panteronissi, where the turquoise waters will make you feel as if you're swimming in a vast pool crafted by nature herself. The wild landscapes of the southeast coast feature cliffs that dive into the sea, creating a chain of caves, including the captivating cave of Mastichari. Enjoy several stops for swimming in these crystal blue waters!
During the trip, we'll provide morning coffee, a snack, and a BBQ lunch featuring either chicken or pork skewers, paired with two types of salads, tzatziki, pita bread, and of course, local beverages such as white house wine, soft drinks, and mineral water. For dessert, indulge in delicious fresh fruits. We'll return to the port of Pounta at 4:30 pm, followed by a transfer back to your hotel or a nearby stop.
Oia
Day 11 - 13
Known as one of the most picturesque villages on the spectacular Greek island of Santorini, Oia, also known as Megalohori, is a quiet village scattered over a hillside on the island’s westernmost point. It features traditional white-washed Greek buildings and a labyrinth of steep alleys and narrow streets and is encircled by countless vineyards, providing it with its fame for top-quality wines. Visitors can sample an array of delicious varietals from the famous Boutari Winery, enjoy a mouth-watering traditional meal at one of the many village square tavernas, and immerse themselves in the local culture in a variety of ways. The town provides the opportunity to take cooking classes, learn the language, and participate in a Greek singing lesson. Don’t miss the local Greek music evenings at the Geromanolis tavern every Saturday night.
Your accommodation
White Pearl Villas
White Pearl Villas is seductively nestled on the cliffs of Oia Santorini, where the awe-inspiring sunset dazzles the eye of the beholder with its unreal fiery mix of red, blue, yellow, and orange hues and the infinity of the azure water stretching to the horizon. Guests can choose from a variety of villas, all beautifully decorated and well equipped. General facilities and services available for guests' convenience include a range of breakfast options, airport transfers, daily housekeeping, luggage storage, car and motorbike reservations, day excursions, tours recommendations and more.
Your activity
Volcan View Candlelight Dinner
For a majestic dining experience full of romance, enjoy a private candlelight dinner with outstanding views to the sunset and the imposing caldera. The candlelight dinner is offered at an isolated spot of the property, with exquisite sunset views that ensure absolute dining pleasure. Delicious dishes, made of the best local products, compose the perfect ambience for romantic moments in Santorini. Enchant your senses and feel the emotions overflowing!
Homemade bread
- TUNA Marinated with citrus, fava, Grape and pistachio
- MUSHROOMS Variety mushrooms with topinambur cream, soya glaze and sesame
- BEEF Slices with celeriac root, wild greens and lemon sauce
- SEAFOOD TARTAR With grilled lettuce, aioli sauce
Main Course
- FISH OF THE DAY Fillet with artichoke, asparagus and lemon egg sauce
Or
- LAMB With vegetables and lemon sauce with fresh oregano
Dessert
WALLNUTS CAKE With Tiramisu cream and caramel sauce
Athens
Day 14 - 15
Dominating the Attica region of Greece, the country’s capital, Athens, is one of the oldest cities in the world. For over two and a half centuries, the astonishing Greek temples and monuments of Athens have continued to intrigue and amaze visitors from around the world. This icon of western civilization seamlessly combines ancient history with modern architecture and a surprisingly lively atmosphere. This is particularly apparent in areas at the foot of the Acropolis, Anafiotika, Plaka, Monastiraki, and Thissio where visitors will find numerous extraordinary Neoclassical buildings, trendy and traditional cafes, and shops, and narrow winding streets with historical treasures at every turn. Once you have enjoyed a history and art fix, try some mouth-watering Greek cuisine at one of the city’s fine local restaurants before indulging in the insatiable nightlife at the chic cocktail bars and waterfront dance clubs.
Your accommodation
The Athenian Callirhoe Exclusive Hotel
The Athenian Callirhoe Exclusive Hotel is perfectly situated in the heart of Athens City, Greece, near the Kallimarmaro Stadium, the Acropolis, the Brand New Acropolis Museum, and Plaka. The hotel’s cosy and elegantly decorated rooms and suites feature tea/coffee-making facilities, central heating/cooling, workspaces, private bathrooms, minibars, hairdryers, flat-screen TVs, and laptop-sized safes. Accommodations with balconies are available. Facilities and services include restaurants, a bar, daily housekeeping, a sauna, a gym, and Wi-Fi.
From$6,800
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Plan with professionals who are explorers themselves.
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Everything is bundled in one place and perfectly planned.
9+ Transfers coordinated
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Excellent
Why plan with an expert?
170+
Plan with professionals who are explorers themselves.
48+ hours of time saved
Our experts plan and book for you.
21+ Bookings managed
Everything is bundled in one place and perfectly planned.
9+ Transfers coordinated
For optimal transport and comfort.
Excellent
Itinerary inspiration
Experience the essence of Greece on this two-week itinerary—a little over 14 days of ancient landmarks, breathtaking landscapes, and idyllic island life. Begin in Athens, where the Acropolis, Parthenon, and charming Plaka district reveal the cradle of Western civilization. Venture north to the dramatic monasteries of Meteora, perched atop towering rock formations, before returning south to follow the call of the Aegean.
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Your island-hopping journey begins in Milos, famous for its otherworldly beaches and sea caves. Continue to Naxos for mountain villages, local food tours, and kayaking around the Portara. On Paros, soak in coastal beauty and cruise to Antiparos for hidden coves and turquoise waters. Conclude your adventure on Santorini, where volcanic cliffs, vineyard tastings, and the iconic Oia sunset make for an unforgettable finale. Private transfers, scenic boat rides, and boutique hotels throughout ensure a seamless experience. This Greece itinerary combines history, mythology, and island serenity—crafted for travelers who want to see it all in just over two inspiring weeks.
Highlights:
Day 1 - 4: Athens
Day 5 - 6: Milos
Day 7 - 8: Naxos
Day 9 - 10: Paros
Day 11 - 13: Fira
Day 14 - 15: Athens
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Tips for your Greece adventure
For this extensive itinerary that covers both the mainland and the islands, the shoulder seasons of late spring (April to June) and early autumn (September to October) are ideal. You will enjoy excellent weather for exploring the ancient sites in Athens and the monasteries of Meteora, while the Cyclades islands will be warm with fewer crowds than in high summer.
The overall cost of this trip is highly dependent on your travel style, as it covers both the Greek mainland and more exclusive islands like Santorini. Generally, a comfortable, mid-range week-long trip to Greece starts at approximately $1,100, excluding international flights. Budgeting for higher costs in popular destinations like Santorini is recommended.
The key highlights of this journey include exploring the historical heart of Athens, culminating at the Acropolis, and witnessing the dramatic, cliff-top monasteries of Meteora. For the islands, don't miss a boat tour of Milos's sea caves and beaches, a wine tasting in Santorini, or trying watersports like kayaking on Naxos and Paros.
When visiting the monasteries of Meteora, be sure to wear clothing that respects the local customs, often requiring shoulders and knees to be covered. For island hopping, factor in potential ferry delays caused by high winds, especially during the Meltemi season, and always book your ferry tickets in advance, particularly for the longer journeys between Milos and the other Cyclades.
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