Trip Type : Small Ship Cruise
Greece Sailing Adventure: Cyclades Islands tour
Mykonos Santorini Greece Sailing Adventure: Cyclades Islands Trip
Sailing Sailing Greece Sailing Adventure: Cyclades Islands package

Greece Sailing Adventure: Cyclades Islands

Intrepid Travel Preferred
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
4.7 . Excellent
98%
Travel Style: A lot of free time, with very few inclusions. Ideal for independent and/or low-key travelers and cruisers. Relaxed
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: Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels. Value - 3 star
10 days
From: $ 1,603 $ 160 / day
Checking price

Overview

Highlights

  • The sight of a Santorini sunset can turn even the most hardened of souls into a romantic. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs
  • Sail across the Aegean Sea on a yacht and island hop through the picture-postcard Cyclades. Swim off the side of the boat and let the waves rock you to sleep each night
  • Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands, far away from tourists and the rest of the world
  • Step back in time among the Venetian architecture of Naxos and learn about present-day rural life with a daytrip to a country village
  • The chic isle of Mykonos invites you to embrace your hedonistic side with its boutique culture and thumping nightlife

Short Description

Give in to dreams of sailing the Greek Islands on this seafaring adventure around the renowned Cyclades Islands. Bliss out on Mediterranean waters, swim in turquoise seas, explore ancient towns and delight in fresh Greek food and culture. From laidback non-touristy islands like Small Cyclades to the vibrant holiday mecca of Mykonos, all holiday bases are covered on this eight-day sailing odyssey.

Small ship cruises usually have a max passenger count of 500. The primary purpose of these trips is to spend time off the vessel in local ports (e.g. Mediterranean) or experiencing nature (e.g Galapagos or Antarctica). Cabins can vary from budget to luxury.
Trip Type Small Ship Cruise
See all the highlights and popular spots on a classic tour.
Itinerary Focus Classic Highlights
Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Lodging Level Value - 3 star
Flights & Transport N/A
Start City Santorini
End City Santorini

Travel Theme

Sailing Small Ship Cruise

Destinations

Greece

Cities & Attractions

Mykonos Santorini

Activities

Sailing

No Single Supplement
See more
Find your perfect trip
A vast selection of trips on every continent, for every style. Thousands of itineraries from hundreds of trusted travel companies.
Save time
Use simple search and comparison tools to easily find the best trip. Don't sweat the logistics -- travel providers plan for you.
Save money
Book directly with the operator. Find inclusive packages for the best value and get access to amazing deals.
Travel confidently
Read unbiased user reviews, pick the company that fits your style, and connect with them directly. No worries, just memories.

Itinerary

Day 1 Santorini – Ios

Welcome to Greece. There will be an important 11 am group meeting today where you'll meet your skipper and shipmates. The first port of call is then the local supermarket to buy supplies for your trip as a group. If you have any special dietary requirements, please make sure you notify us at the time of booking so we can accommodate your requests. Consider arriving a couple of days early in order to enjoy lovely Santorini and its awe-inspiring caldera. Check out the range of restaurants, shops and bars in the island's capital, Fira. An absolute must is to take a walk along the caldera's rim to Firostefani, Imerovigli and Oia. This is a particularly memorable experience at sunset, but make sure you leave plenty of time so you aren't walking in darkness. Santorini's volcanic beaches are another must-see. Check out Red Beach or the black beaches of Perissa, Vlhada, Perivolos and Agios Georgios. The Orthodox Metropolitan Cathedral, Catholic Cathedral and Dominican Convent are worth a visit, as is Megaron Gyzi Museum. After the welcome meeting you'll set sail (approximately 5 hours) through Santorini’s caldera, cruising across the Aegean Sea to drop anchor at the island of Ios (the boat will stop at Manganari Beach along the way). Check out Hora's shops, restaurants and bars (a short walk from the harbour in Ios) which all come alive in the evenings. A visit to Panagia Gremiotissa (Church of the Virgin) offers beautiful sunset views from a hilltop. Notes: The beauty of sailing is that each day is unique and, while we have a destination to reach, if the weather changes or something takes the group’s fancy, we are flexible on the day's itinerary. The itinerary may be subject to change depending on weather. Your skipper will make the final call to ensure your safety at all times.

Day 2 Amorgos

Sail to the rugged island of Amorgos (approximately 4 hours). This is the stunning location of Luc Bresson's film, 'The Big Blue'. Stop for a swim at Paradisi Beach before continuing along the coast to the port of Katapola. The restaurants, cafes and bars along the waterfront are an excellent place to relax and enjoy views of classic Cycladic windmills and an old Venetian castle. You might like to explore the ancient Minoan Settlement or drive up to the spectacular 11th-century monastery, Moni Hozoviotissis, for beautiful views of the Aegean Sea. Also worth a visit is the village of Hora, sitting high up in the rocky mountainside. Stroll through the labyrinth of stone laneways and Byzantine churches surrounding the town square. The Amorgos Archaeological Collection is housed nearby in Gavros Tower.

Day 3 Small Cyclades

Cast off and sail to the Small Cyclades this morning (approximately 4 hours). This group of islands boast quaint fishing villages, clear waters and beautiful beaches. While all of these islands once harboured communities in ancient times, the middle ages saw this reduced to just pirates and goats. Today, only Koufonisia, Iraklia, Schinoussa and Donousa have permanent residents, with the largest population said to be around 300. In the evening, perhaps sample fresh seafood in a waterfront taverna and sit back to enjoy the peace of the Mediterranean.

Day 4-5 Naxos

Today you'll make your way to the largest Cycladic island of Naxos. There’s the option of taking a day trip around the island, but you can always stay behind and relax. The island’s best beaches are to the south, where water sports are also on offer. Perhaps hike up to the old Roman Catholic neighbourhood of Kastro, where winding laneways, mansions and churches all retain a medieval feel. While here, stop by the Roman Catholic Cathedral in the square, and the nearby Archaeological Museum which is housed in the former Jesuit School of Commerce. Take an optional trip to the countryside to observe rural life, see one of the oldest temples in Greece and enjoy lunch in the hills at a family tavern. Get a taste of the local brew with a shot of Kitron (best described as a lemon liquor). In the evenings, indulge in the vibrant nightlife of Hora.

Day 6 Syros

Sail to the island of Syros (approximately 4 hours), dropping by the Bay of Gaidharos along the way for a swim. Known for its relaxed atmosphere and neo-classical architecture, Syros’ neutral role during the Greek revolution made it a safe haven for the persecuted. Perhaps catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleyways (the views of the Aegean are stunning from up here). Sample authentic Greek food and culture in the capital of Syros and the Cyclades, Ermoupoli, and check out the magnificent town hall in the main square.

Day 7 Mykonos

In the morning, raise anchor and set off on a short cruise (approximately 3 hours) to an island packed with beauty and glamour, Mykonos. With a history of around 5,000 years, the island is said to be named after Apollo's grandson. It was also the mythological base for a deadly battle between Zeus and the Titans, their giant petrified bodies forming the rocks of the island. Browse the chic galleries and boutiques in town, examine the unique architecture of the Church of Panagia Paraportiani or relax on one of the island’s white beaches. In the evening, perhaps wander down to Little Venice, where colourful wooden balconies hang precariously over the sea – the ideal spot to sit back with a cocktail and enjoy an Aegean sunset. Afterwards, join in the fun of Mykonos’ notorious nightlife.

Day 8 Sifnos

Set sail for the island of Sifnos, known for its production of high quality ceramics. The island's bare hills belie fertile valleys of wild juniper, terraced olive groves and almond trees. The beach in the main port of Kamares is one of the best on the island and the ideal place to swim. Wander among the whitewashed houses, churches and chapels of the village of Apollonia, which is the capital of Sifnos. The Museum of Popular Art displays old photographs, textiles, costumes and pots. Climb up the headland to enjoy panoramic ocean views and see the medieval architecture of the fortress of Kastro.

Day 9 Folegandros

Sail towards the tranquil island of Folegandros this morning. Named after the son of a former King of Crete, Folegandros has suffered a long history of colonisation and occupation like many of the surrounding islands. In the port of Karavostasis, the pebbly beach or a waterfront taverna are nice places to relax. Take a stroll through the island’s capital of Hora, one of the oldest villages in the Cyclades. The area in and around the Kastro is the most striking. In the evening wander up the hill to the pretty Church of the Panagia, an excellent vantage point to view the sunset.

Day 10 Santorini

Bid farewell to the open water as you sail back through the caldera and drop anchor in Santorini. You should arrive by approximately 11 am, after which time you are free to go. If you plan to depart today, please don’t book a flight earlier than 4 pm in case the boat’s arrival is delayed due to weather conditions.

Availability

Checking price
Price From $ 1,603
Price Per Day: $ 160 per day
Check Availability
Checking price
Start DateFinish DateBase PriceDeparture GuaranteedAvailability 
May-31-2019Jun-09-2019$ 1,659Yes1 spots left Reserve
Jun-10-2019Jun-19-2019$ 1,693Yes2 spots left Reserve
Jun-20-2019Jun-29-2019$ 1,719Yes1 spots left Reserve
Jun-30-2019Jul-09-2019$ 1,689Yes4 spots left Reserve
Jul-10-2019Jul-19-2019$ 1,704Yes3 spots left Reserve
Jul-20-2019Jul-29-2019$ 1,711Yes6 spots left Reserve
Jul-30-2019Aug-08-2019$ 1,783Yes1 spots left Reserve
Aug-09-2019Aug-18-2019$ 1,603Yes3 spots left Reserve
Aug-19-2019Aug-28-2019$ 1,603Yes8 spots left Reserve
Sep-08-2019Sep-17-2019$ 2,210YesSold Out Reserve
Sep-18-2019Sep-27-2019$ 2,020Yes11 spots left Reserve
Sep-28-2019Oct-07-2019$ 2,020Yes6 spots left Reserve
May-09-2020May-18-2020$ 2,020Yes11 spots left Reserve
May-19-2020May-28-2020$ 2,020Yes11 spots left Reserve
May-29-2020Jun-07-2020$ 2,020Yes11 spots left Reserve
Jun-08-2020Jun-17-2020$ 2,020Yes11 spots left Reserve
Jun-18-2020Jun-27-2020$ 2,020Yes11 spots left Reserve
Jun-28-2020Jul-07-2020$ 2,020Yes11 spots left Reserve
Jul-08-2020Jul-17-2020$ 2,020Yes11 spots left Reserve
Jul-18-2020Jul-27-2020$ 2,020Yes11 spots left Reserve
Jul-28-2020Aug-06-2020$ 2,020Yes11 spots left Reserve
Aug-07-2020Aug-16-2020$ 2,020Yes11 spots left Reserve
Aug-17-2020Aug-26-2020$ 2,020Yes11 spots left Reserve
Aug-27-2020Sep-05-2020$ 2,020Yes11 spots left Reserve
Sep-06-2020Sep-15-2020$ 2,020Yes11 spots left Reserve
Sep-16-2020Sep-25-2020$ 2,020Yes11 spots left Reserve
Sep-26-2020Oct-05-2020$ 2,020Yes11 spots left Reserve
See more

Check Current Availability, prices, specials with Intrepid Travel.

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.

Ask Our Destination Experts

Clark Norton
Email Us

Stride Featured in

Stride Feature In

3,163 Intrepid Travel Travel Reviews & Ratings

98%
4.7 out of 5 (100+ reviews)
Excellent 2,356
Great 625
Average 101
Disappointing 37
Terrible 39
Value
4.7
Guide
4.7
Activities
4.7
Lodging
4.7
Transportation
4.7
Meals
4.7

Greece Sailing Adventure: Cyclades Islands

Write a Review

The trip met all expectations, was a

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
The trip met all expectations, was a lovely, pleasant experience, the skipper was knowledgeable and competent.

I picked this trip due to the

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
I picked this trip due to the itinerary of seeing numerous islands in a short time, and I had the freedom to be able to do that, getting to most islands by early afternoon.

It's a very unique trip I have

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
It's a very unique trip I have ever done. Small group is nice, and it's more relax.

Great trip leader, brand new boat

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
Great trip leader, brand new boat

I was very pleased with everything.Besides it

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
I was very pleased with everything.Besides it is the 2nd time I travel with intrepid

Intrepid continues to provide an authentic yet

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
Intrepid continues to provide an authentic yet affordable experience. My kind of travel.

Details

Group Size:

Small Group - 24 max

Maximum Number of People in Group: 11

Accomodations

Overnight boat (9 nts)

Guides

On this trip you will be accompanied by one of our skippers. Your skipper's role involves taking charge of the sailing, the safety of the vessel and safety for all passengers on board. Skippers all hold a Yacht Master Offshore license or higher and have completed an intense training and review process before sailing with us. They are also fully qualified in CPR and First Aid. The aim of the skipper is also to take the hassle out of your travels by organizing the overall operation and smooth-running of the trip, managing trip logistics and coordinating the kitty (where applicable). Your skipper will provide information on the places you are travelling through, offer suggestions for things to do and see, recommend great local eating venues and introduce you to our local friends. While not being guides in the traditional sense you can expect skippers to have a broad general knowledge of the places visited on the trip, including historical, cultural, religious and social aspects.

Additional Information:

Finish point

  • Akrotiri Hotel Beachfront Restaurant
  • Akrotiri Area, Ακρωτήρι
  • Akrotiri
  • Santorini
  • 847 00
  • GREECE
  • Phone: +30 2286 081375

Trip ID#:

intrepid-ZSRV

Similar Trips

See all similar trips
×
Great Choice!

Now, Unlock Member Savings

Our Stride Select trips allow you and your travel companions to save up to $700. You wouldn’t want to miss that, right?

or
or
Provide email and password

With your FREE membership you get to:

  • Save up to $700 per person!*
  • Access private deals and offers
  • See personalized trip recommendations
  • Save favorite trips
*See Member Savings Program details
Already a member?

We respect your privacy and take great care to protect your information. By joining you agree to our Privacy Policy and Terms of Use.

×
×
Sign in to Save Trips
Welcome back! We're so happy to see you. ? Forgot Password?
Don't have an account? Join
  • Bookmark trips you like
  • Share with your travel companions
  • Track price changes
  • Access private discounts on trips you save
×
Sign in to see your results

TripFinder is a member-only feature. Don’t worry, it’s free!

With a membership you:

  • Save up to $700 per person!*
  • Access private deals and offers
  • See personalized trip recommendations
  • Save favorite trips
*See Member Savings Program details
×
Activate your free Stride membership

Just use the email address and password provided in the email we sent.

? Forgot Password?

With your free membership you:

  • Save up to $700 per person!*
  • Access private deals and offers
  • See personalized trip recommendations
  • Save favorite trips
*See Member Savings Program details
×
To Follow, sign in or sign up (it's free) ? Forgot Password?
Don't have an account? Join
member benefits
First name is required!
Last name is required!
First name is not valid!
Last name is not valid!
This is not an email address!
Email address is required!
This email is already registered!
Please enter valid email address
Password is required!
Enter a valid password!
Please enter 6 or more characters!
Please enter 16 or less characters!
Passwords are not the same!
Terms and Conditions are required!
Email or Password is wrong!
Please select the captcha checkbox!
Please select the valid captcha!
Something went wrong! Try again later!

x
x
Download your brochure

Enter your email to get the "" brochure.

x
Brochure successfully sent!

We've sent the "" brochure to . Check your inbox!