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Cyclades Islands Multi-Activity Adventure

7 days
•
Start and end in Athens
4.7
9 traveler reviews
  • Scenic cliffside village with white houses.
  • Hikers walking along a trail with a view of the Aegean sea.
  • Coastal town with white buildings and a harbor.
    View all

  • Oh those amazing green/blue waters! It was our first sailing adventure and it left me looking for more.

    Cyclades Islands Multi-Activity Adventure reviewer 1
    Samuel, traveled in November
    5.0
  • Two people jumping on a mountain overlooking the sea.
  • Sailing ship at sea with a backdrop of a hillside town.
  • People horseback riding along a scenic beach path.
  • Group of people resting during a hike with a view of the sea.
    View all
From
US $1,992 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

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2026

Jan
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Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

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Plan your adventure:
Operator
Trails Beyond
Explorer
Curated to ignite your sense of adventure
Group Tour
Join a group and forge lifelong friendships
Fully Guided
An experienced guide will be with you for the entire tour
Medium Intensity
Travelers should be comfortable with somewhat-demanding activities
Guided in English
Group Size 4 - 16
Ages 8+
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Piraeus to Naxos

    Start point
    Πύλη Ε7 (Gate E7), Ακτή Μιαούλη, Pireas, Attica, Greece (Piraeus port, exact gate TBA)
    Meals
    Dinner (Welcome dinner)

    Included Activities

    • Ferry to Naxos
    • Hike to Chalki village via Moni with Byzantine churches
    • Walking tour of Naxos town (Chora) - Venetian castle and old town
    • Walk to Portara marble gate at sunset
    • Welcome dinner

    Optional Activities

    • Lunch in Naxos
    • Swimming in the sea
    Landmarks
    Panagia Drosiani
    Chalki village
    Tragea valley
    Moni village
    Venetian castle
    Portara
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  2. Day 2

    Naxos

    Meals
    Breakfast, Lunch (Traditional family-run taverna in Melanes)

    Included Activities

    • Inland hike across Naxos - Kurunochori to Melanes
    • Explore Kouros statues
    • Visit abandoned Jesuits monastery
    • Lunch at traditional family-run taverna in Melanes
    • Visit Temple of Demeter near Sangri
    Landmarks
    Kurunochori village
    Mili village
    Ano Potamia
    Kato Potamia
    Kouros statues
    Jesuits monastery
    Melanes village
    Temple of Demeter
    Sangri village
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  3. Day 3

    Naxos

    Meals
    Breakfast

    Included Activities

    • Hike to Mount Zas summit
    • Walk to Cave of Zeus
    • Visit Aria Spring
    • Walking tour of Naxos Chora with Venetian Castle and Portara, OR visit to Chalki village citrus distillery and Kitron liquor tasting

    Optional Activities

    • Lunch at local taverna in Filoti
    Landmarks
    Mount Zas
    Filoti village
    Agia Marina church
    Cave of Zeus
    Aria Spring
    Venetian Castle
    Portara
    Chalki village
    Itinerary Image 1Itinerary Image 2
  4. Day 4

    Naxos to Santorini

    Meals
    Breakfast

    Included Activities

    • Ferry to Santorini
    • Wine tasting experience with local wines
    • Walking tour of Fira

    Optional Activities

    • Horse-riding tour
    • Cooking class
    • Bike tour
    • Walk around Chora streets
    • Shopping for local products and souvenirs
    • Beach time
    Landmarks
    Fira
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 5

    Santorini

    Meals
    Breakfast, Dinner (BBQ dinner on board yacht)

    Included Activities

    • Hiking trail from Fira to Oia along Caldera cliff edge
    • Sailing cruise within the caldera
    • Swim in Hot Springs
    • BBQ dinner onboard
    • Sunset viewing from yacht deck

    Optional Activities

    • Lunch in Oia
    • Shopping in Oia
    Landmarks
    Fira
    Firostefani
    Imerovigli
    Skaros
    Oia
    Ammoudi Bay
    Hot Springs
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  6. Day 6

    Santorini

    Meals
    Breakfast

    Included Activities

    • Visit Pyrgos traditional village
    • Explore Kasteli Castle ruins
    • Visit Monastery of Prophet Elias
    • Hiking descent to Ancient Thera archaeological site
    • Hike to Perissa
    • Visit Akrotiri archaeological site

    Optional Activities

    • Lunch in Perissa
    • Swimming in Perissa
    • Water sports
    • Scuba diving
    • Walk along black sandy beaches
    • Sea kayaking alternative from Akrotiri - south coast paddle with Red and White beaches, snorkeling, swimming and light picnic
    Landmarks
    Pyrgos
    Kasteli Castle
    Monastery of Prophet Elias
    Ancient Thera
    Messavouno mountain
    Perissa
    Perivolos beach
    Akrotiri
    Red Beach
    White Beach
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  7. Day 7

    Santorini to Athens

    End point
    Πύλη Ε7 (Gate E7), Ακτή Μιαούλη, Pireas, Attica, Greece (Piraeus port)
    Meals
    Breakfast

    Included Activities

    • Ferry to Athens

    Optional Activities

    • Explore Fira town
    • Shopping for souvenirs
    • Optional activity of choice
    Landmarks
    Fira
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What's Included

Expand All
  • Accommodation
  • Guide
  • Meals
  • Additional Services
  • Transport

What's Not Included

  • Flights
  • Insurance
  • Optional
  • Additional Services

Adventure Type

Choose the type of organized adventure that suits your preferences.
  • Group Adventures
    Join a group and forge lifelong friendships.
    What to expect
    • Group of 16 travelers max.
    • Fast booking confirmation
    • Carefully planned itineraries
    • Travel with like-minded people
    Starting at
    US $1,992 / traveler
    Check availability
  • Personalized Adventures
    Customize an existing itinerary or create your own.
    What to expect
    • Travel with your own group of min. 2 travelers
    • Choose your preferred dates and duration
    • Upgrade your accommodation
    • Customize the itineraries
    After requesting a quote, we will get back to you with a price based on your requirements.
    Request quote

Operated by

Trails Beyond

4.9
(96 reviews)

Number of tours

13

Age Range

5 to 89 years old

Response time

within 1 day

Response rate

100%

Trails Beyond is a boutique tour operator in Greece, offering unique guided...

Read more

Your Peace of Mind Options

Cancellation Policy

A transparent overview of applicable fees.

Travel Insurance

Be covered for any unforseen circumstances.

Traveler Moments

  • Two people jumping with a scenic ocean view.
  • Scenic cliffside village with white houses.
  • Women posing with ocean view and 'Santorini 2018' written.
  • Wine glasses raised against a coastal backdrop.
  • Man standing on a boat near a turquoise sea and distant mountains.
  • Sailing ship at sea with a backdrop of a hillside town.
  • People lounging on a black sand beach with umbrellas and sunbeds.
  • Hikers walking on a trail with a distant view of a town and sea.
  • Whitewashed church with domed roof against a blue sky.
  • Coastal town with white buildings and a harbor.
  • Sailboat cruising through calm waters with islands and mountains in the background.

Traveler Reviews

4.7
Overall rating based on 9 Reviews
  • Itinerary
    4.6
  • Transport
    4.7
  • Guide
    5.0
  • Accommodation
    4.7
  • Food
    4.6
  • Tour Operator
    4.9

Sort by

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  • J
    May 29th, 2024
    5.0
    I very much enjoyed this tour and our Guide, Robert, was excellent. Even though I could not do some of the hikes, due...
    Show more
    Traveled in May 2024
  • S
    November 8th, 2019
    5.0
    We had a most excellent adventure sailing with Danae and Costa in Greece. We did not get to do the original itinerary...
    Show more
    Traveled in August 2019
  • D
    October 23rd, 2019
    4.0
    It was a fantastic experience and Danae was very good. There was a one day general transport strike during our stay...
    Show more
    • Sailboat cruising through calm waters with islands and mountains in the background.
    Traveled in September 2019
    Reply from: Trails Beyond
    Hi Debbie, thank you for your wonderful words! I am glad you enjoyed your holiday with Trails Beyond and I truly hope we get to see each other some time soon, it was a great pleasure to meet you and travel with you guys!! Regards, Danae
    Show more
  • T
    June 11th, 2019
    3.5
    Breakfast at the hotels could be improved, for instance fresh bread at the hotel in Santorini; some Greek...
    Show more
    • Whitewashed church with domed roof against a blue sky.
    • People lounging on a black sand beach with umbrellas and sunbeds.
    • Hikers walking on a trail with a distant view of a town and sea.
    • Sailing ship at sea with a backdrop of a hillside town.
    • Coastal town with white buildings and a harbor.
    • Man standing on a boat near a turquoise sea and distant mountains.
    Traveled in June 2019
  • B
    July 29th, 2018
    5.0
    Such a great experience. Danae was the best. Her knowledge of the areas we visited and enthusiasm to ensure that we...
    Show more
    Traveled in June 2018
  • A
    July 18th, 2018
    5.0
    We used Danae and Trails Beyond to plan and execute a 10 day "trip of a lifetime" to Greece in June of 2018. Now, I...
    Show more
    • Two people jumping with a scenic ocean view.
    • Cyclades Islands Multi-Activity Adventure customer review photo
    • Scenic cliffside village with white houses.
    • Women posing with ocean view and 'Santorini 2018' written.
    • Wine glasses raised against a coastal backdrop.
    Traveled in June 2018
  • E
    July 16th, 2018
    5.0
    Absolutely perfect is the best way to describe our vacation with Trails Beyond! We were beyond thrilled with our...
    Show more
    Traveled in June 2018
  • Cyclades Islands Multi-Activity Adventure reviewer 8
    May 18th, 2015
    5.0
    We had a great time. Naxos and Santorini are wonderful islands to visit. Everything was organized very well, from...
    Show more
    Traveled in July 2014
  • Cyclades Islands Multi-Activity Adventure reviewer 9
    May 16th, 2015
    5.0
    We wanted to spend our holidays in the Cyclades islands but we were looking for someone to show us the secret paths,...
    Show more
    Traveled in April 2015

Dates & Availability

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Select Date

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2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Upcoming departures
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Ends in1d1h8m36s
  • Instant Confirmation
    From Sunday
    10 May, 2026
    To Saturday
    16 May, 2026
    English
    From:
    US $1,992 per person
    Multiple Room Types
  • Instant Confirmation
    From Sunday
    20 Sep, 2026
    To Saturday
    26 Sep, 2026
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    From:
    US $2,121 per person
    Multiple Room Types
  • Instant Confirmation
    From Sunday
    11 Oct, 2026
    To Saturday
    17 Oct, 2026
    English
    From:
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    Multiple Room Types
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What our customers ask about this tour

The content in our FAQ section is subject to change.
All questions
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Try a different search term or ask a question to this adventure's experts
  • O

    Olivia

    Asked on March 24th, 2024

    Are there any dates in June?

    Price / Availability
    Tour Details
    • Trails BeyondOperator•Written March 2024

      Unfortunately we don't have any scheduled trip end of May - beginning of June, but we could send you the price for a private tour and if this is within your budget, you could still enjoy it the two of you. Would you be interested in a quote for a private tour?

  • W

    Wayne

    Asked on February 1st, 2017

    I cannot eat gluten. Can this dietary restriction be accommodated?

    Meals
    • Trails BeyondOperator•Written February 2017

      Yes, gluten free meals are offered, this wouldn't be a problem.

  • P

    Pamela

    Asked on July 1st, 2016

    What islands do you see on the way?

    Other
    • Trails BeyondOperator•Written July 2016

      During this exploration, we visit 2 of the most beautiful Cyclades islands, Naxos and Santorini.

  • S

    Sandy

    Asked on July 1st, 2016

    What are the available activities?

    Other
    • Trails BeyondOperator•Written July 2016

      Some of the activities included are: hiking, horseback riding on the beach, daily sailing cruise from Naxos to the Small Cyclades, wine tasting and hiking in Santorini, sailing cruising with a catamaran in the caldera of Santorini and of course swimming and cultural activities. Then there are optional activities such as sea kayaking and scuba diving.

Can’t find the answer to your question?
Reach out to the experts at Trails Beyond with your enquiry, they usually respond within 1 day.
From
US $1,992 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Save and compare this adventure

Best price guarantee Learn More

Plan your adventure:

Good to Know

Tour ID: 79203

  • Currency
    €
    Euro
    Greece
  • Plugs & Adapters

  • Vaccines
    • These are only indications, so please visit your doctor before you travel to be 100% sure.
    • Hepatitis A - Recommended for Greece. Ideally 2 weeks before travel.
    • Hepatitis B - Recommended for Greece. Ideally 2 months before travel.
  • Visa
    • Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
    • Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
  • Payment information
    • For any tour departing before June 20th, 2026 a full payment is necessary. For tours departing after June 20th, 2026, a minimum payment of 10% is required to confirm your booking with Trails Beyond. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 60 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
    • Some departure dates and prices may vary and Trails Beyond will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Trails Beyond" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
  • Cancellation Policy
  • Accessibility
    Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.
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Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec