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Greece: Athens & Island Explorer

(2 customer reviews)

The Greek islands offer so much beauty and variety that it’s hard to pick which islands to go to! Our most popular tour is Athens, Naxos and Santorini, and our May 2026 departure has an optional 4 nights on the amazing island of Crete. Whether you’re looking for a relaxing beach-getaway or a deep dive into ancient history or off-the-beaten-track hiking, we’ve got you covered. ** The hikes can be optional if you prefer other activities.
Duration: 7 nights (with optional 4-night Crete extension)
Dates: 2026: May 25. Other dates available upon request, contact us for details.
Trip starts/ends: Athens / Santorini (or Crete if you take the extension)
Activity level: 1 - 2+ – GENTLE with some rocky terrain: You can enjoy the islands with an easy “light active” tour or add some hiking of varying levels of difficulty [more info]
Group size: min 6 - max 14

Highlights

  • guided visit of the Acropolis and Acropolis Museum
  • orientation walk through Athens’ Plaka district
  • hike on Naxos past a Crusader castle and explore the Venetian citadel in town
  • visit and have a tasting at a traditional ‘kitron’ distillery on Naxos
  • take to the sea with an all-day catamaran trip along the coast of Naxos
  • Enjoy comfortable hotels on wide sandy beaches in both Santorini and Naxos
  • enjoy spectacular views on a hike along the crater rim on Santorini
  • visit of the ancient Minoan site of Akrotiri
  • enjoy a short kayak adventure along the coast of Santorini
  • taste local wines on Santorini
    CRETE EXTENSION:
  • hike to one of Crete’s most beautiful beaches for a swim in the azure waters
  • try your hand at local cuisine at a cooking lesson with a local family
  • stay 3 nights in the delightful town of Chania
  • see the Minoan ruins of Knossos and/or the fabulous archaeological museum in Heraklion

    ** this tour includes a few short hikes but there are activities you can do if you don’t want to hike (or kayak)
    We can run our Greek Island tour many ways so contact us if you’d like a different configuration of islands!  

Trip price includes

  • 7 nights in 3 and 4-star hotels
  • 7 breakfasts, 5 dinners, 3 lunches and 1 wine tasting
  • sea kayak on Santorini
  • all-day private catamaran trip on Naxos
  • all visits and transfers as per itinerary
  • at least 1 bilingual guide to accompany you throughout the week

Not included

  • 2 dinners & 3 lunches
  • onward transport from Santorini island (or Crete)
  • airport transfer on arrival in Athens
  • drinks other than water at meals
  • anything not mentioned in the inclusions

ITINERARY

Athens – Naxos – Santorini Itinerary (with Crete extension): 

Days 1 & 2: Athens & the Acropolis
Meet your guide at your hotel this afternoon for an informal walk around the city followed by drinks and dinner. We visit the Acropolis and Acropolis Museum the following morning before taking the ferry to Naxos so you may want to arrive a day or two early if you’d like more time in Athens. 1 night Athens.

Days 3 & 4: Explore Naxos Island
See the Acropolis this morning and then take an afternoon ferry to the island of Naxos, the biggest and greenest of the Cyclades island chain. It has been a center of civilization for millennia and then became capital of the Cyclades Archipelago when the whole area was under Venetian control. We’ll stay near a wide sandy beach just outside of the old town and have a variety of fun activities, from hiking to sailing to exploring the ancient Venetian citadel. 3 nights Naxos. 

Days 5-7: Hike & Kayak on Santorini Island
Take a short ferry hop from Naxos to the spectacular island of Santorini, whose white-washed houses and black-sand beaches have captivated visitors for decades. The island used to be a massive volcano but an eruption in c. 1600 BC left only a dramatic crescent around a watery crater, which led some to link the island to the lost city of Atlantis. We’ll hike the crater rim, spend a morning exploring the coast in sea kayaks, and see some amazing ancient ruins, where you’ll see 3-story houses and indoor plumbing from 4,000 years ago! 3 nights Santorini.

Day 8: Tour Ends in Santorini
Your tour ends this morning in Santorini since there are various options for continuing your journey. You can take a ferry back to Athens or else hop a short flight if you’re going directly to the airport. Or continue your exploration and visit another island!

*** Days 8-11: Crete Extension
You’ll love the beautiful beaches, colorful towns, and fascinating history of this Greek island that holds tightly to its local traditions. It’s one of the biggest islands in the Mediterranean and was home to the powerful Minoan kingdom. We have a few walks plus a hands-on cooking lesson and wine tasting and stay in the charming town of Chania plus one night in Heraklion. 4 nights Crete.

*** Day 12: Tour Ends on in Chania, Crete
Your tour ends this morning in Chania since there are various options for continuing your journey. You can take a ferry back to Athens or else hop a short flight if you’re going directly to the airport. Or continue your exploration and visit another island!

CONTACT US FOR A MORE DETAILED ITINERARY


****************

Other Islands:

  • Amorgos: this far-flung Cycladic islands is quiet and off-the-beaten-track, so makes a nice alternative to Santorini
  • Hydra: a quick hop from Athens, this island is traffic free and has no cars!
  • Poros: just an hour from Athens, this pretty island is a nice break from the city
  • Andros: this island lies en route to Naxos from Athens for an added stop
  • Tinos: between Andros and Naxos, it has a historical church that’s famous in Greece as a pilgrimage site as well as numerous hikes and a sweet port town
  • Rhodes: farther southeast, this larger island played a critical role in the history of the Crusades as home to the Knights of Saint John (later The Knights of Rhodes). Use it as a base for exploring the Dodecanese island chain.
  • Other…? We’re happy to add new islands to our repertoire!

 

2026: from €3,850
[info on prices]

2 reviews for Greece: Athens & Island Explorer

  1. Mary –

    Such a wonderful trip! We have been traveling with Claire for years and she never disappoints. Highlights of this tour included the archeological site at Akrotiri and a fabulous kayaking day on Santorini. And Naxos is the perfect Greek Island — uncrowded, scenic, and with beautiful beaches and historic sites!

  2. Andrea E. –

    We just completed this amazing trip with Claire and her local tour expert in Greece and the Islands. We LOVE putting ourselves in Claire’s hands because we know (having enjoyed an amazing tour in Italy with her years ago) that she scouts all the best untouristed hotels and restaurants for amazing beach locations with easy access to towns and the most amazing culinary experiences (indulging us in a dessert specialty and bakery treat every so often). Her hiking, kayaking, and sailing excursions are nothing short of spectacular fun. Claire’s hunt for historical and scenic adventure (not to mention her professionalism and ongoing friendship) is what is going to set the Wild Sage experience above other travel companies. I can’t wait to schedule our next trip–THANK YOU!

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Activity Levels

Some tours have a range of activity levels through the week, where some walks may be more challenging than others, but this will give you a general idea of the type of walking/hiking involved on your tour.

1 – EASY: City walking, all or mostly paved, minimal climbing
2 – GENTLE: Moderate hills & easy terrain
3 – MODERATE: Some sustained hills with occasional steep grades on a mix of terrains
4 – HIKE: Classic hiking with rough/rocky terrain, sustained hills, and longer mileage
5 – CHALLENGING: Challenging hiking with steep climbs and descents over rocky terrain and some longer mileage

See below for more detail:

1 – EASY: City walking, all or mostly paved, with minimal climbing (though some cities may have steeper inclines). Archaeological sites may be unpaved but the grades and difficulty level is easy. TOURS: Sicily Coast-to-Coast and any “light active” version of a tour

2 – GENTLE: Moderate hills & easy terrain
The terrain is easy to navigate with packed earth or gravel roads. There are some climbs but nothing too challenging. TOURS: Tuscany, Puglia, Provence
[2+ The “plus” indicates more challenging terrain though the walks are gentle].

3 – MODERATE: Some sustained hills with occasional steep grades and rocky terrain
Here you find a mix of terrain with some steep stretches.
TOURS: Corsica, Sardinia, some of the Dolomites tours, and some hikes on the Greek Islands
[3+ The plus indicates rockier terrain or lots of stone steps (Amalfi, the Cinque Terre) or greater elevation gain/loss (the Dolomites)].

4 — HIKE: Classical hiking with rough terrain, sustained hills, and more mileage. These hikes are on a mix of rough terrain, sometimes involving steep stretches and difficult footing. TOURS: some of our hikes in Sardinia, some of the days in the Cinque Terre, some of the variants of our Dolomites tours.

5 – CHALLENGING: Longer days, challenging climbs, rocky terrain. We don’t do a lot of seriously challenging tours but we do have a Dolomites trip where we hike from hut to hut, so that’s probably the closest we get to a 5.

Info on prices

Prices indicated are usually for a minimum of 6 people (some tours may be different, see each tour page for specifics) and our basic itinerary based on double occupancy. A “single supplement” covers hotel prices only, we apply no extra fees. Departures with fewer people or with upgraded hotels will have a higher price. We can organize private departures for any number of people but prices vary depending on number of participants. Please contact us for details!