Stride climate

Trip Type : Group Tour
Cyclades Islands Adventure tour

Cyclades Islands Adventure

Trails Beyond
5.0 . Excellent
100%
Travel Style: You will have solid amounts of both free time and structured time with some activities and meals included. Mixed
Physical Level: Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps. Moderate
Lodging Level: 3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards. Premium - 4 star
7 days
From: $ 1,232 $ 176 / day
Checking price

Overview

Highlights

  • Explore the largest of the Cyclades islands, Naxos
  • Visit Venetian castles and traditional villages in Naxos
  • Visit the traditional citrus distillery in Naxos and sample their famous locally produced liqueurs
  • Sail, swim, dive and go kayaking in the crystal clear waters of Small Cyclades islands on a daily sailing adventure
  • Enjoy the worldwide renown sunset in Oia
  • Discover the archaeological site of Akrotiri, also known as the “Greek Pompeii”
  • Sail inside Santorini’s caldera and swim in the hot springs!
  • Take a wine tour and taste the marvelous Santorini wines

Short Description

When you think about Greece, the first things that come to your mind are white – cub houses, blue crystal clear waters, sandy beaches and sun? Are you looking for an unforgettable summer holiday with an authentic touch of culture and adventure? If yes, then this is the right exploration for you!

Join us and explore the hidden side of two Greek islands, Naxos & Santorini… go trekking in ancient trails, sea kayaking in Santorini’s caldera, sailing or horseback riding among Naxos’ white sand beaches, enjoy a wine tour in Santorini's volcanic vineyards, visit traditional villages and Venetian castles, monasteries and important archaeological sites, taste some delicious Greek food and of course, meet the local people and immerse yourself in their slow pace way of life!

Whether you are a couple, group of friends, solo traveler or family, this exploration is ideal if you want to enjoy a unique experience in the Aegean Sea, beyond the beaten path…

Groups are between 25-60 people, typically ~30-40. Usually there will be many opportunities to split off and enjoy meals and excursions in smaller groups. This is the most economical way to travel, saving up to 40% versus booking the same itinerary yourself.
Trip Type Group Tour
Spend most of the time outdoors. Common trip themes and activities include cycling, hiking, kayaking, whitewater rafting.
Itinerary Focus Active
3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Lodging Level Premium - 4 star
Flights & Transport Only ground transport
Start City Athens
End City Athens

Trip Includes

  • Trails Beyond tour leader for the whole trip, local guides & activity instructors
  • 6 days of accommodation in 3* hotels, based on double occupancy (for 4* accommodation, please contact us)
  • All meals, as indicated on the trip notes (6 breakfasts, 2 dinners)
  • All Ferry tickets (Athens to Naxos, Naxos to Santorini and Santorini to Athens)
  • All necessary ground transfers on the islands
  • Entrance fees to sites listed in the tour itinerary
  • Cost for all activities included in the tour program (2 sailing cruises, 3 hiking & 1 walking tours and 1 wine tour)
  • All taxes

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Itinerary

Day 1: Athens – Naxos 

Meals: Dinner

Accommodation: 3* Hotel in Naxos

Walking duration: 1 – 1.5 hours

Distance: 2 – 2.5 km

Level of difficulty: easy

Early in the morning, we meet at Piraeus port, where you will be welcomed by your tour leader! We board the ferry to Naxos island, the largest of the Cyclades islands (approx. 5 hrs by ferry).  Upon arrival and check in at the hotel, you will have free to relax at your hotel, spend some time at the beach or enjoy a cup of coffee in one of the front side cafes. In the afternoon, we will enjoy a welcome tour in Naxos town (Chora). We will visit the Venetian castle and the old town, while our guide will give us a good insight on the history and culture of the island.  Before dinner, when the sun goes down, we will not miss the chance to walk through the paved footpath towards the islet of Palatia and admire the impressive marble gate of Portara and the stunning sunset views it offers. In the evening, we will enjoy a welcome dinner during our first day all together!

Day 2: Naxos inland hiking 

Meals: Breakfast

Accommodation: 3* Hotel in Naxos

Hike duration: 3.5 – 4 hours

Distance: 6.5 km

Level of difficulty: easy to moderate

Enjoy a good breakfast today, as we will explore hiking the best of Naxos inland, with its fertile valley, olive groves, vineyards and traditional villages.

Starting from the village of Moni, crossing old marble paths and the Tragea plateau, we will end up in the picturesque village of Chalki after approx. 3.5 hours and we’ll visit the traditional citrus distillery, where will be able to sample their famous locally produced liqueurs.

After lunch, we will visit the picturesque villages of Filoti and Apeiranthos, the most well – known and traditional villages of mountainous Naxos.

Day 3: Daily sailing to Small Cyclades

Meals: Breakfast

Accommodation: 3* Hotel in Naxos

Today we will set off on a daily sailing tour with destination Iraklia and Schinousa islands, two secluded earthly paradises in the Aegean Sea that will captivate you for their crystal clear, turquoise waters and their calmness! A day full of surprises, fun and adventure! Snorkeling, diving with a sea scooter, kayaking and much more will definitely give you an unforgettable experience!

Day 4: Naxos – Santorini

Meals: Breakfast

Accommodation:  3* Hotel in Santorini

Nobody can resist the charm of the never-ending, golden Naxos beaches and its clean, greenish blue waters. So today get ready to explore some of them on a horse ride*!  Depending on the season and the weather, we will also have plenty of time to enjoy swimming and snorkeling in the crystal clear waters of the Aegean Sea. Alternatively, you can enjoy your last morning in Naxos leisurely, go to Chora for shopping or simply walk around the narrow alleys and enjoy your coffee in one of the charming cafes across the side front.

 In the afternoon, we will take the ferry to Santorini. Prepare yourself for this striking, magical, volcanic island and feel its unique and inspiring aura! The views from the boat once we enter the caldera are simply stunning and captivating…

Our first day in Santorini includes a wine tasting experience of signature local wines and a walk around the capital city of the island, Fira.

*Horseback riding/ mountain biking are optional activities. You may consult your tour leader for options, prices and availability.

Day 5: Hike Fira to Oia & Sunset Sailing cruise

Meals: Breakfast and Dinner (BBQ on board)

Accommodation:  3* Hotel in Santorini

Hike duration: 3 – 4 hours

Distance: 9 km

Level of difficulty: easy to moderate

Today we will take the hiking trail that leads from Fira to Oia, all the way along the Caldera cliff edge. It is a scenic route with no particular difficulties, offering spectacular views over the caldera. Passing by Firostefani, Imerovigli and Skaros, we will finally reach the picturesque settlement of Oia in approx. 3 hours. Once in the picturesque village of Oia, you will have free time to walk around its picturesque streets, visit the tiny beautiful shops or relax in one of the numerous cafes/restaurants with roof top terraces offering fantastic caldera views and enjoy your lunch.

Later on we’ll follow the steps down to Ammoudi bay, where we’ll board a beautiful catamaran yacht and enjoy a memorable sailing cruise inside the caldera. You will have the chance to swim in the Hot Springs, discover more of Santorini’s beauties and enjoy BBQ dinner on board, prepared by the crew.  On top of that, you will enjoy Oia’s famous sunset right from the deck!

Day 6: Santorini South Discovery

Meals: Breakfast

Accommodation:  3* Hotel in Santorini

Today we will enjoy a fantastic day in Santorini, discovering the natural and historical beauty of the south! In the morning, we will first visit the traditional village of Pyrgos, which was declared as a “protected settlement” in 1955. Pyrgos is a typical Fortress Settlement of the Cyclades islands and on its hilltop you can find ruins of Kasteli Castle, one of the five 'kasteli castles' on the island. We will afterwards head towards the monastery of Prophet Elias, located on the highest hill of Santorini, offering 360 panoramic views of the island! From there a breathtaking, yet slightly rough, descending trail begins that will take us to the archaeological site of Ancient Thera. Located at 360m height, on Messavouno mountain, it was named after the mythical king of the island, Theras, and was inhabited since the 9th BC century.

From there, we will follow the descending hiking path towards Perissa. Once there, you will have free time to relax, enjoy swimming, water sports, scuba diving or a walk along the long black sandy beaches of Perissa and Perivolos and lunch in one of the seaside restaurants.

We will afterwards head south and visit the archaeological site of Akrotiri, also known as the “Greek Pompeii”, one of the most important prehistoric settlements of the Aegean*. Unique findings, two-storey prehistoric buildings and houses, dated back to the Bronze Age, will definitely amaze you! 

*For those of you who love sea kayak, we can arrange an unforgettable sea kayak experience, instead of visiting Perivolos beach. Starting from Akrotiri, you will paddle by the Red and White beaches, discovering the south coast of the island beyond the ordinary way! Views of the spectacular rock formations, swimming and snorkeling in crystal waters, beautiful beaches and a light picnic are all part of this amazing adventure!

Day 7: Santorini – Athens

Meals: Breakfast

This is the last day of our weekly adventure in the Cyclades islands. You have the morning free to explore the town of Fira, purchase any souvenirs you may want, before we take the ferry back to Athens. Depends on your schedule

Availability

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Price From $ 1,232
Price Per Day: $ 176 per day
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Checking price
  • Deposit Price: $ 414
  • Estimated Daily Out of Pocket Costs: $ 20
  • Single Supplement (Single Occupancy): $ 171

Check Current Availability, prices, specials with Trails Beyond.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

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Clark Norton
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Stride Featured in

Stride Feature In

12 Trails Beyond Travel Reviews & Ratings

100%
5.0 out of 5 (100+ reviews)
Excellent 12
Great 0
Average 0
Disappointing 0
Terrible 0
Value
5.0
Guide
5.0
Activities
5.0
Lodging
5.0
Transportation
5.0
Meals
5.0

Cyclades Islands Adventure

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Company Reviews

llevo muy buen recuerdo de este viaje.

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
Ha sido un trekking espectacular. Me han gustado mucho la montaña y sus paisajes, los puentes de piedra y los monasterios tanto en Zagoria como en Meteora. Hemos tenido muy buenos guias que han sabido adecuar los itinerarios en función de la climatología, ya que dos días nos llovió mucho. La comida también me ha gustado. En general me llevo muy buen recuerdo de este viaje.
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Enjoy a trip under Trails beyond guidance.

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
It was an excellent choice of ours to enjoy a trip under Trails beyond guidance. The places were amazing and it seemed like we wouldn’t find our way around if it wasn’t for Dane, our guide, who revealed to us the most special corners of the area we visited. Rafting in Voidomati was so much fun and the hike through vikos gorge was an unforgettable experience. It’s nice to combine the feeling of safety and adventure without losing the leisure feeling of one’s own holiday! We would repeat it any time and recommend it to everybody!
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We enjoyed a lot.

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
It was great: the country, the people,the food …everything!!! The guides were marvelous; they did our trip especial and we enjoyed a lot.

Fantastic guide

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
Enjoyed the trip very, very much and highly recommend Trails Beyond to anyone who wants to travel to Greece beneath the beaten tourist tracks. Danae was such a fantastic guide who really lives her passion to show the unknown parts of her beautiful country to the travellers. Ευχαριστώ πολύ Danae!!!
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Great value !! Don’t miss it !!!

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
This is a really very nice trek, and we have been very lucky with the professional and kindly guides. Greek people is very friendly, and we have been fortunate to share with them home, food, landscape and such nice things. The trip is very rich because is very variate, the impressive Vikos gorg, the nice small towns of Vradeto or Beloki, the refugee in Astraka and the blue Dragonlimmi and at the end the astonishing landscape sharped by mounts and monasteries in Meteora. Great value !! Don’t miss it !!!
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Details

Flights & Transport

Only ground transport

Private Ground transportation and ferry tickets are included in the price

Group Size:

Standard Group

Solo Notes

Single supplement: 140-220€

Accomodations

We stay at 3* superior hotels.

Guides

A Trails Beyond tour guide accompanies the group during the whole trip.

Trip ID#:

CycIslTraBey

Trip Excludes

  • International airfares
  • Travel insurance
  • Transfers to/from Athens airports and to/from Piraeus port
  • Any meals not specified in the itinerary
  • Any beverages or alcoholic drinks during meals
  • Optional activities that are not included in the day-to-day itinerary
  • Other expenses of personal nature and tips

Meals Included:

6 Breakfasts and 2 Dinners

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