Black Friday•Organized tours worldwide  up to 70% OFF

Ends: 11 Nov, 2026

Switch to the app and book faster and easier!

Where?
When?
2
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

Where to?

Traveling when?

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

Who is travelling?

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
From
US $1,955 per person

Cyclades Islands Multi-Activity Adventure

7 days
•
Start and end in Athens
4.7 (9 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.
  • Two people jumping on a mountain overlooking the sea.
    View all

  • Absolutely perfect is the best way to describe our vacation with Trails Beyond. The service was impeccable.

    EricStathes•traveled in July5.0
  • 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.
  • Person kayaking near rocky cliffs.
  • Food on a table with a view of the sea.
    View all
From
US $1,955 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 departure month

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
Pay only 10% today. The rest is due 60 days before departure. Learn more

Best price guarantee Learn More

Plan your adventure:
Gold Operator
Trails Beyond
Hiking & Trekking
Conquer epic trails and breathtaking landscapes
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+

Explore our featured adventures

TourRadar earns higher commission on featured adventures here.

Image of a map showing the route of the tour

Itinerary

  1. Intro

    Introduction

  2. Day 1

    Piraeus to Naxos

    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
  3. Day 2

    Naxos

    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
  4. Day 3

    Naxos

    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
  5. Day 4

    Naxos to Santorini

    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
  6. Day 5

    Santorini

    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
  7. Day 6

    Santorini

    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
  8. Day 7

    Santorini to Athens

    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

Want to read it later?

Download this tour’s PDF brochure and start tour planning offline

What's Included

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

What's Not Included

  • Flights
  • Insurance
  • Optional
  • Additional Services

Operated by

Trails Beyond

Gold Operator
Rating
4.9 (97 reviews)
Response time
within 2 days
Response rate
100%
Cancellation policy
Learn more

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

Most recent
Most popular
Highest first
Lowest first

Sort by

Most Recent
Most Popular
Highest First
Lowest First
  • Jan5.0•May 2024
    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
  • Samuel5.0•November 2019
    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
  • Deborah4.0•October 2019
    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
  • Theresia3.5•June 2019
    Breakfast at the hotels could be improved, for instance fresh bread at the hotel in Santorini; some Greek...
    Show more
    • 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.
    • Sailing ship at sea with a backdrop of a hillside town.
    • Man standing on a boat near a turquoise sea and distant mountains.
    • People lounging on a black sand beach with umbrellas and sunbeds.
    Traveled in June 2019
  • Brogan5.0•July 2018
    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
  • amanda5.0•July 2018
    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
    • Women posing with ocean view and 'Santorini 2018' written.
    • Scenic cliffside village with white houses.
    • Wine glasses raised against a coastal backdrop.
    • Cyclades Islands Multi-Activity Adventure customer review photo
    • Two people jumping with a scenic ocean view.
    Traveled in June 2018
  • EricStathes5.0•July 2018
    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
  • Markella
    Markella5.0•May 2015
    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
  • Elena
    Elena5.0•May 2015
    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

Sign up or log in to access your TourRadar+ savings

Dates & Prices

Select departure month

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
Upcoming departures
Hurry, deals only available for a limited time!
Ends on 11 Nov, 2026
  • Instant Confirmation
    From Sunday
    21 Mar, 2027
    To Saturday
    27 Mar, 2027
    English
    From:
    US$1,948 per person
    Price based on Private Double Room
  • Instant Confirmation
    From Sunday
    18 Apr, 2027
    To Saturday
    24 Apr, 2027
    English
    From:
    US$1,948 per person
    Price based on Private Double Room
  • Instant Confirmation
    From Sunday
    9 May, 2027
    To Saturday
    15 May, 2027
    English
    From:
    US$1,948 per person
    Price based on Private Double Room
  • Instant Confirmation
    From Sunday
    19 Sep, 2027
    To Saturday
    25 Sep, 2027
    English
    From:
    US$2,071 per person
    Price based on Private Double Room
  • Instant Confirmation
    From Sunday
    10 Oct, 2027
    To Saturday
    16 Oct, 2027
    English
    From:
    US$1,948 per person
    Price based on Private Double Room

Want to read it later?

Download this tour’s PDF brochure and start tour planning offline

Why book with TourRadar?

    • Trusted and vetted operators
    • Rated excellent on
    • Best price guarantee
    • 24/7 customer support
    • Unlock exclusive TourRadar+ member savings

    To protect your payment and ensure your booking will be processed in United States, never transfer or communicate outside of the TourRadar website or app.

More benefits

What our customers ask about this tour

The content in our FAQ section is subject to change.
All questions
We couldn't find results
Try a different search term or ask a question to this adventure's experts
  • J

    Jen

    Asked on August 31st, 2026

    I am wondering about flights and when we should arrive on day 1 and when we should depart on day 7? Also, is there an included transfer from the Athens airport on day 1?

    Flights / Transfers
    • Trails BeyondOperator•Written August 2026

      On day1 the ferry departure is usually scheduled around 07.30am-08.00am, so you can be on time in Naxos and start the itinerary. That means that your arrival in Athens should be either very early in the morning on the 11th of Oct or one day before on the 10th of Oct and have a pre-tour accommodation in Athens too. For any extra stay or transfer we will be glad to assist you. On day7, we usually arrange a ferry departure at late noon time (5,5 hours journey), so you can enjoy breakfast at your hotel and have some free morning time to explore Fira town, purchase any souvenirs you may want or enjoy an optional activity of your choice before we board the ferry back to Athens. Upon arrival in Athens at Piraeus port, you may head to Athens int. airport to catch your flight which should be ideally booked from 21.00pm onwards. Otherwise, the most less time consuming option is to pay a little more money and fly from Santorini to Athens.

    • J

      Jen

      Traveler•Written August 2026

      For the meeting day on Oct. 11, will there be a shuttle from the airport or pre-accomodation hotel to the Piraus port, or are we responsible to get there on our own? If I did the ferry back to Athens, would there be a transfer to the airport?

    • Trails BeyondOperator•Written August 2026

      On day1 both arrival transfer from Athens int airport and pre-tour accommodation are not included in the package. In any case, you may catch the metro (Blue line) and head to Athens centre or Pireaus port depending on your travel plans (9€ ticket per person). If you need a private taxi transfer the price will be 55€ in total from Athens int. airport to Athens centre (hotel drop off) and 60€ in total from the airport to Piraeus port. We can also suggest hotels in Athens that we cooperate with where you can stay one night before the tour starts. The group meeting will be on the 11th of Oct directly at Piraeus port to catch the ferry to Naxos. On day7, upon arrival in Piraeus port there is not a complimentary transfer to the airport. However, we can arrange it for you with a private taxi (60€ in total) or you can also grab the metro and head to the airport (Piraeus-Athens airport /Blue Line/ 9€ pp, routes every '36 min).

      • J
      2 more answers
  • 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 2 days.

Good to know

Tour ID: 79203

The practical details for your trip across Greece: money, plugs and flexible ways to pay, all in one place.

Have a question? Chat with a travel expert

  • Pay in installments

    Spread the cost in interest-free biweekly installments of $88.

  • Deposit only

    Book now with just a 10% deposit. The remaining balance is due 60 days before departure.

  • € - Euro

    You’ll encounter Euro in Greece.

  • Plug types C, F

    You’ll need an adapter for these sockets in Greece.

  • Currency

    €
    Euro

    Greece

  • Plugs & adapters

    As a traveler from USA, Canada, England, Australia, New Zealand, South Africa you will need an adaptor for types C, F.

    • Type C

      Used in Greece

    • Type F

      Used in Greece

  • Visa

    Whether you need a visa depends on your nationality and how long you stay. We can’t process visas for you, but here’s a quick indication for this trip.

    This is only an indication. Visa rules depend on your passport, trip length and purpose. Always confirm with the official embassy or consulate before you travel.

  • Payment information

    Pay now
    A 10% deposit
    Balance due
    60 days before departure
    Installments
    Interest-free, every two weeks
    Currency
    USD
    Booking fee
    None

    Book now with just a 10% deposit and pay the rest later. The remaining balance is due 60 days before departure, charged automatically to your card, or you can split it into interest-free biweekly installments of $88 at checkout. Everything is charged in USD, and TourRadar never adds a booking fee. Any trip departing before January 4th, 2027 will need to be paid in full at checkout.

    Accepted for Trails Beyond tours

    • Visa
    • Maestro
    • Mastercard
    • American Express
    • PayPal

    TourRadar does NOT charge you an extra fee for using any of these payment methods.

  • Cancellation Policy

    Cancellation terms may vary per tour. Please check for the full cancellation policy here.

    Checking the cancellation terms for this tour…

    Your money is protected. TourRadar is an authorized agent of Trails Beyond, and we handle payments so you don’t have to. Payment is securely transferred to the operator based on your departure date.

  • Insurance

    Our travel protection from our award-winning partner, XCover, means you and your travel companions can book with peace of mind knowing there’s protection available in case your trip doesn’t go to plan. At checkout you will be able to select between different options in case you or the tour are eligible for insurance. In case no option is available, you are always able to purchase travel insurance outside of TourRadar.

    Checking which travel protection options are available for you…

  • Best price guarantee

    Found a lower price for the same tour elsewhere? We work directly with every tour operator, so we can match it.

    How it works

    1. Find a lower price

      Spot the same tour cheaper on another site or agency.

    2. Send us the quote

      Contact us before you book.

    3. We match it

      If the quote qualifies, you book with us at that price.

    Your quote needs

    • Same tour and operator
    • Same start and end dates
    • Same number of travelers
    • Same inclusions and destinations
    • Same booking and cancellation terms, in the same currency
    • A link to the site or agency offering it

    What doesn’t count

    • Quotes issued more than 24 hours ago
    • Cash back or loyalty program rebates
    • Itineraries that are similar but not identical
    • Similar tours run by a different operator
    • Bookings already confirmed on TourRadar

    Every new booking also counts toward your , which unlocks extra savings.

  • 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.

  • People also viewed

From
US $1,955 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 departure month

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
Pay only 10% today. The rest is due 60 days before departure. Learn more

Best price guarantee Learn More

Plan your adventure:

Earn while you share

With TourRadar RISE, you can earn commission when someone books a tour through a link you share — like this one.

Video from Trails Beyond

  • Western Europe Travel Guide

Keep Exploring Greece

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