14 Days Greece Travel Itinerary

Two weeks in Greece is an ideal amount of time to see and do everything you want and more, so if you have a trip on the cards and you are looking for inspiration on where to start, what to do, and what activities to include, then this is just the ticket. Let's guide you with this 14 Days Greece Travel Itinerary.
Greek Architecture

Greece is a one-stop shop for all things adventure, culture, and history, but if you don’t have enough time, you may miss out on a thing or two. Luckily, this 14 Days Greece Travel Itinerary fits just about everything you can think of when planning a trip to Greece. 

However, if it is missing anything, do not fret because your In-Destination Expert can help you tailor it to suit you. 

To give you some inspiration, here is what you can expect to get out of two weeks in Greece, with the perfect combination of action, nature, food, and history.

Rough Itinerary

Let us give you a quick rundown of what this 14 Days Greece Travel Itinerary offers. 

  • Day 1. Arrive in Athens
  • Day 2. Athens Highlights
  • Day 3. Arrive in Mykonos
  • Day 4. Sunset Cruise to Delos
  • Day 5. Exploring Mykonos
  • Day 6. Arrive in Naxos
  • Day 7. Discover the food of Naxos
  • Day 8. Naxos catamaran cruise
  • Day 9. Arrive in Santorini
  • Day 10. Wine tasting in Santorini 
  • Day 11. Hiking the Santorini Caldera
  • Day 12. Santorini sea kayaking
  • Day 13. Arrive back in Athens 
  • Day 14. Departure Day

Detailed Itinerary

This 14 Days Greece Travel Itinerary has a great mix of adventure, culture, and so much more, and here is what you can expect from your journey.

Day 1. Arrive In Athens


Today is your arrival day, and you will have some time to enjoy the streets of Athens and a local dinner in the evening before the adventure begins tomorrow.

Day 2. Athens Highlights


Today will be exciting, as you will feast your eyes on some of Greece’s best ancient sites. Your archaeologist guide will take you to some of the main attractions, such as the Parthenon, Nike Temple, and the Erechtheion, and many of the city’s highlights during the day, which are guaranteed to blow you away, so make sure to have that camera at the ready.

Day 3. Arrive in Mykonos

Mykonos at night
Photo by Jack Krier on Unsplash

You will be transported to Mykonos’s bustling island, famed for its nightlife, pristine beaches, and adventurous activities. You will have opportunities to do as you please, whether relaxing on the beach or taking on the challenge of jet skiing, water skiing, wakeboarding, and so much more. If you are an adventure seeker, you will love Mykonos.

Day 4. Sunset Cruise to Delos

Sailing To Delos & Rhenia

After yesterday’s adventures on the water, you have today at your leisure to relax on one of the many remarkable beaches, but if you still have plenty of adrenaline left, why not give some more activities a go. This evening you will take a sunset cruise to Delos UNESCO World Heritage Site, which is said to have been the birthplace of Apollo and Artemis. 

Your guide will take you around this ancient site and give you an insight into the history and legacy of this incredible place. You will also have some time to roam around by yourself to take photos and take it all in. Greece is an enormous open-air museum, no matter where you go, making it a fascinating destination.

Day 5. Exploring Mykonos

Photo by Johnny Africa on Unsplash

Today you will get the chance to discover one of the island’s best-kept secrets, Agios Sostis Beach, which has a quaint taverna ideal for a lunch stop and a vibrant open-air market in the nearby village. It is a day of culture and exploration, so enjoy!

Day 6. Arrive in Naxos

Photo by Lisa Boonaerts on Unsplash

You will be transported to the diverse island of Naxos, known for its food, wine, archaeological sites, and watersports. In addition, you will have the chance to try out some windsurfing or other watersports of your choice in-between getting to know this wonderful island. If watersports are not your thing, you can enjoy wandering around this incredibly picturesque region, with stunning beaches to see and dreamy landscapes to marvel at. The vibes here are magical!

Day 7. Discover the food of Naxos


Naxos is famous for its food, so food lovers can rejoice because today you will take a food tour of Naxos – an island that produces some genuinely delectable products, which will teach you all you need to know about the island’s climate, livestock, and local ingredients. In addition, of course, you will enjoy a day of indulgence, so take it all in.

Day 8. Naxos catamaran cruise

Naxos Catamaran Cruise
Photo by Evangelos Mpikakis on Unsplash

One of the best days of this adventure tour of Greece is the catamaran sailing adventure from Naxos, which will take you to a small chain of islands known as the ‘Small Cyclades’ and allow you to discover some local hidden gems, beautiful scenery, and stunning beaches.

Day 9. Arrive in Santorini

A view of a city in Greece

What can we say? Santorini island is known for its wine and stunning hillside villages, making iconic photo backdrops. Today is a day of leisure; you can spend the day relaxing on the beach, taking a small hike, or visiting a nearby village before watching the sunset over this incredible volcanic island.

Day 10. Wine tasting in Santorini

Wine Tasting In Santorini
Photo by Kamala Bright on Unsplash

Wine lovers will consider this a real trip highlight; we cannot disagree. Santorini is world famous for its wine, and today you will get to try a variety of wines while learning about the long history of wine production, which makes this island stand out from the crowd. So, if you know your wines, be sure to ask questions and learn as much as possible, all of which will prove to be a fantastic experience.

Day 11. Hiking the Santorini Caldera

The Santorini Caldera
Photo by Josh Miller on Unsplash

Santorini is a volcanic island and the perfect place to go on an adventurous hiking excursion. Today you will take on the Fira–Oia hike, a must-do activity on the island. After that, you will hike the Santorini caldera, passing through many quaint cliffside villages. Your guide is on hand to help you learn about the area’s volcanic history, which is fascinating. The hike will take approx. 2-5 hours depending on your speed and fitness level, but it is a hike that is accessible to most.

Day 12. Santorini sea kayaking

A beautiful Greek landscape

Thrillseekers will be excited about the sea kayaking experience, an essential part of this 14 Days Greece Travel Itinerary. You will get the opportunity to take on the island’s south coast by kayak, where you can hop off at any given time for a swim or a snorkel (or both). Your guide will be there to keep you safe at all times and teach you how to become a sea kayaking master.

Day 13. Arrive back in Athens

A guard marching in Athens

Today you will leave the island of Santorini and be transported back to Athens, which is an ideal opportunity to visit some sights you missed at the beginning. There are plenty of museums to see as well as visiting the Plaka neighborhood, and of course, there is always time to try some more local food and wine, to celebrate your adventure tour of Greece – and perhaps plan the next one?

Day 14. Departure

A woman in an airport

Today is your last day, and after one last Greek breakfast, you will have an airport transfer to Athen’s airport to take your flight home.

Best Suited to


This tailor-made private tour is ideal for lovers of food, wine, culture, and adventure. It is worth noting that there are some adventurous activities such as hiking and watersports, so it is recommended that you have a good fitness level, but it is suited to all age groups. Couples, solo travelers, families, and groups will love this tour, and there is something to tick everyone’s boxes, making it an excellent trip for people with varied tastes.

Eco Friendly & Sustainable tours

A wonderful sunset in Greece

Baboo Travel ensures that your money goes towards helping local communities and regenerating mother earth, so you can rest assured that you are doing good for your destination as you travel around. There are many benefits involved, but one of the best is that 85% of your money stays in the destination country, making you feel good about your trip.

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