14-Day Athens, Crete, Naxos & Santorini Custom Greece Vacation

Welcome to Athens, a destination where historical glory meets with a modern energy. As one of the world's most lasting cities, Athens provides far more than its famous archaeological sites. It's a vibrant, continuously evolving metropolis. Your first impression will undoubtedly be the magnificent Acropolis, a monument directly to the city's profound history and its foundational role in Western civilization. From the extensive ancient remains integrated throughout the urban landscape to its dynamic local districts, Athens perfectly balances the historical narrative with a contemporary urban experience.

Upon your arrival, you'll complete your check-in and have some time for relaxing before your first city exploration. We recommend starting with Plaka neighborhood, characterized by its narrow streets, traditional white buildings, vibrant cafés and quality artisan boutiques. The environment is notably charming and welcoming, with local people selling handmade jewelry, ceramics and leather products. This is an excellent moment to pause for a classic Greek coffee or to try an authentic traditional pastry like baklava or the popular loukoumades.

Today is a deep dive into Greek civilization through one of the country’s most important collections: the National Archaeological Museum. With your private, state-licensed guide, you’ll explore key highlights from a very big collection.

Your guide will direct the tour to show you the essential artifacts which include outstanding sculptures, beautiful jewelry, artistic pottery and historical items that demonstrate both regular existence and significant cultural accomplishments. The Antikythera Mechanism stands as a major attraction for you because this 2,000-year-old device was discovered in a shipwreck and is considered a groundbreaking example of ancient analog technology.

The museum visit will be followed by a panoramic city drive which will require you to change your point of view. The route provides an excellent way to explore Athens' architectural design and important sites while minimizing your need to walk additional distances. The tour will lead you through the Panathenaic Stadium, Zappeion Hall and Monument of the Unknown Soldier before you might witness the official guard exchange ceremony (if time allows).

Inclusions:

• 4-hour private tour
• Hotel pick-up and drop-off with a private vehicle
• 2-hour guided tour of the National Archaeological Museum
• 1.5-hour panoramic vehicle tour
• Private services of a state-licensed guide
• Entrance fees

Today you leave Athens for the Peloponnese, combining legendary archaeology with a relaxed taste of local winemaking.

A brief stop will be made at the Corinth Canal which separates urban areas from rural territories. The next stop will be Mycenae, a major Bronze Age settlement that is connected to the stories of Homer. Your state-licensed guide will lead you through the Lion Gate to show you the remaining structures of the citadel which include its large walls, its well-known tholos burial sites and then you will visit the museum to gain more information about the site.

In the afternoon, you’ll head to Nemea, one of Greece’s best-known wine regions. At a boutique winery, you’ll meet the team behind the bottles, learn about the production process and enjoy a guided tasting of four wines. The day includes a lunch featuring local Peloponnesian cuisine. This is a relaxed finish that balances the historical side of the excursion.

Inclusions:

• Full-day private excursion (approx. up to 7 hours)
• Hotel pick-up and drop-off (vehicle)
• 1.5-hour Mycenae archaeological site and museum guided tour by a local state-licensed guide
• Entrance fees
• Winery visit & tasting of 4 wines
• Lunch featuring local Peloponnesian cuisine

Today you arrive in Crete and settle into Chania, one of Greece’s most atmospheric towns and an ideal base for exploring western Crete.

Chania’s Old Town is wonderfully walkable, with Venetian buildings, fountains and a lot of small streets that invite slow exploration. The Venetian harbor is the classic focal point, but the charm is often in the details: a tucked-away courtyard, a small bakery or a quiet street where history feels close.

The Corinth Canal creates a brief stop which separates urban areas from rural territories. The next stop will be Mycenae which served as a significant Bronze Age settlement that connected to the stories of Homer. Your state-licensed guide will lead you through the Lion Gate to show you the remaining structures of the citadel which include its massive walls and its well-known tholos burial sites before you visit the museum to learn more about the site.

The harbor to lighthouse walk provides a relaxing opportunity to stretch your legs before you start your day while the market and backstreet area offers the best selection for purchasing local delicacies. The evening provides an ideal setting to experience Crete for the first time through a casual walk along the harbor followed by a basic meal and an early bedtime after a tiresome day.

Today is designed to introduce Crete through its flavors. This private experience combines local tastings with a hands-on cooking workshop.

You’ll begin at a local olive mill to see how olive oil is produced and why it’s central to the island’s identity, followed by a tasting. You’ll then visit a small winery in a quieter setting to taste Cretan wines and learn how the island’s landscape shapes them.

The highlight is a cooking class where you’ll prepare traditional dishes using local ingredients. Afterwards, you will enjoy the meal you helped create. It’s the kind of day that makes you understand Crete in different ways.

Inclusions:

• 8-hour private experience
• Hotel pick-up and drop-off (vehicle)
• Private services of an English-speaking escort
• Wine, olive oil and food tastings
• Traditional Cretan meal
• Commemorative gifts

Today is all about Crete’s western coastline! You will visit two iconic beach settings in one day.

You’ll begin at Falassarna, known for its long stretch of sand and open horizons. It’s a great place for a swim and a truly “wide” coastal view. Afterward, you’ll continue by boat toward Balos Lagoon, famous for turquoise water colors and soft white sand. Once there, feel free to swim, to walk around, to find a quieter corner or simply relax and take in the landscape.

With your private escort and skipper handling the logistics, the day stays easy and unhurried. We recommend bringing sun protection and a light layer for the boat, as conditions can change on the water. It’s a pure nature highlight that balances the cultural depth of the other days in Crete.

Inclusions:

• 8-hour private experience

Hotel pick-up and drop-off (vehicle)

• Private services of an English-speaking local escort & skipper
• Bottled water per person

Notes:

• Exclusions: meal.
• What to bring: comfortable clothing and footwear, swimsuit, beach towel, sunscreen, hat, light jacket.

Your journey today leads you to Heraklion, the biggest city in Crete and its diverse cultural heritage.

The Venetian-era port of Heraklion together with Koules Fortress establish themselves as essential landmarks while the city reveals its different time periods through its building designs and public activities. You can now relax during this evening by taking a walk around the harbor or visiting the market or trying the local cuisine which will show you the city's dining energy.

We can provide you with suggestions for a relaxed walking path through the historic district which matches your speed and some restaurants that serve traditional Cretan cuisine. The city of Heraklion provides an excellent starting point because it offers convenient access to all necessary locations. Additionally,  its active atmosphere makes it perfect for beginning your journey to Knossos and the surrounding mountains on the following day.

The tour starts at Crete's most famous archaeological site before moving to the Dikti Mountains for a private day which combines historical exploration with natural beauty and traditional village experiences.

Your first stop will be the Palace of Knossos which stands as the main archaeological site of the Minoan civilization. Your tour will lead you through the site's design and essential sections while sharing historical accounts about King Minos and the Minotaur. Your guide will explain and try to distinguish to you the difference between mythological and archaeological evidence.

Afterward, you’ll travel through quieter back roads and villages before reaching the Lassithi Plateau. Expect mountain views, a pause for Greek coffee in a local kafeneion if you’d like and an authentic meal at a traditional taverna.

Inclusions:

• Approx. 8 to 10-hour private experience
• Hotel pick-up and drop-off (vehicle)
• Private services of an English-speaking professional guide
• Greek coffee in a local kafeneion
• Entrance fees

Today you arrive in Naxos, the largest and greenest island in the Cyclades. It is known for mountains, fertile valleys and a strong sense of local life.

Naxos blends classic Cycladic architecture with Venetian castles, monasteries and medieval churches, especially as you move inland. Near the port, the iconic Portara, the marble gateway of the unfinished Temple of Apollo, offers a memorable first impression and a beautiful sunset viewpoint.

If you have time later in the day, Naxos Town (Chora) is wonderful for an easy evening walk: narrow lanes, small shops and a slightly more “local” feel than many Cycladic capitals. It’s also an excellent place to try Naxian specialties, often featuring island-grown produce and the famous local cheeses.

The program for this morning explores the ordinary aspects of Naxos which include its villages, their connection to olive oil production and the basic traditions of Mediterranean dining.

You will head to Kaloxylos in the interior to experience a 100-year-old olive press facility which offers both a presentation and wine tasting experience with farm-to-table starters from the local area. The peaceful path runs through olive groves  and it creates a peaceful natural setting while your local guide will explain how farming practices and annual cycles transformed the island throughout history.

The tour will conclude at Chalki where you will enjoy a traditional meal with homemade dessert before visiting a historic family distillery which has operated for more than 120 years to taste their local liqueur. The genuine relaxed atmosphere of this morning creates a distance from tourist areas that gives you freedom to choose between spending time at the beach or returning to Chora in a peaceful manner.

Inclusions:

• Approx. 4 to 5-hour private experience
• Services of an English-speaking local expert
• Olive oil tasting & farm-to-table starters
• Local family-style lunch with galaktoboureko dessert

Today is your active highlight in Naxos: a guided hike on Mount Zas, the highest peak in the Cyclades and a landscape wrapped in Greek mythology.

The trail begins at the trailhead where you will join an expert mountain guide for a hike that offers breathtaking Aegean views while you discover the native plants which grow in this area. The hiking trail maintains a moderate to challenging difficulty level as it features irregular terrain and extends to the entire three-hour expedition (1.5 hours per direction).

If you’re not used to hiking, don’t worry! The key is steady pacing and good footwear. The reward is a sense of scale and openness that’s hard to find elsewhere in the Cyclades. It definitely adds a completely different dimension to your Naxos stay.

Inclusions:

• 3 to 4-hour private experience
• Hotel pick-up and drop-off (vehicle)
• Private services of an English-speaking mountain guide

Notes:

• What to bring: trainer shoes, hat, water bottle.
• Keep in mind: moderate/demanding hike, approx. 4.6 miles total, uneven terrain in sections.

Your arrival in Santorini brings you to a destination famous for its caldera views, its white painted villages and its distinctive volcanic terrain that creates its iconic appearance.

Santorini’s identity is shaped by volcanic activity: powerful eruptions created the caldera, the sea-filled crater that defines the island’s sweeping cliffside panoramas. This is a destination made for slow moments: a coffee above the water, a sunset walk or dinner with the view doing most of the talking.

We can help you determine when to view the sights by showing you when the light is best and the crowds are minimal and we can also recommend short walking routes that start from your current position. The objective is to experience Santorini's beauty while avoiding the need to actively pursue it because the most precious experiences often stem from basic moments.

Today you experience Santorini from the water on a small-group catamaran cruise. It’s a relaxed, memorable way to see the caldera and the island’s volcanic coastline.

The port transfer will lead you to your catamaran where you will meet an English-speaking captain and crew who will start your journey. The cruise will take you through impressive coastal features while you can swim at Hot Springs, explore Red Beach and White Beach through snorkeling activities with snorkeling gear available on the ship.

A BBQ-style lunch with Greek dishes and drinks is served on board and the limited group size keeps the atmosphere comfortable. After returning to port, your transfer takes you back to your hotel, leaving your afternoon free for more caldera time.

Inclusions:

• 5-hour small-group excursion (max 20 participants)
• Hotel pick-up and drop-off (vehicle)
• Services of an English-speaking captain & crew
• Lunch and drinks on board
• Snorkeling equipment
• Towels & blankets (to be returned to the crew)
• Map with extensive info on landmarks and destinations
• Floating devices
• WC and facilities for rinsing off seawater (ask the crew)

On your final day in Greece, you’ll take a transfer to the airport for your flight back to Athens. After arriving at Athens Airport, check in to your international flight and depart Greece.

As you bid farewell you’ll carry the memories of your Greek adventure to Athens, Mycenae and Nemea’s winery culture, Crete’s flavors and beaches, Naxos’ countryside traditions and mountain views and Santorini’s caldera, back with you. Share your stories with friends and family and remember the unforgettable experiences you had on this incredible journey with Tailored by Locals.