Greece Sailing Adventure: 8-Day Island Explorer

Sailboat in Mykonos, Greece

What to expect on this itinerary

This 8-day Greece cruise through the stunning paradise of islands has been handcrafted for those in search of a laid-back approach to travel through the use of a comfortable sailing boat equipped with all the modern luxuries. The Greek archipelago has long attracted visitors with its historical legacy and pristine beaches. From Athens to Santorini, enjoy the breathtaking views and ancient ruins that make this location so unique.

Countries Visited

Greece

Places Visited

Athens, Poros, Kythnos, Mykonos, Delos, Sifnos, Karavostasis, Ios, Santorini

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Poros – A Stunning Seascape

A veritable paradise of sandy beaches, volcanic rock formations, and charming villages, the Greek archipelago offers visitors an excellent way to enjoy its abundant supply of history and rich culture while never straying too far from the comfort of a cabana or beautiful vista. You will embark into this charismatic seascape on your cruise today as you depart the port of Athens and make your way to the Agia Marina. Here, you can visit an ancient Greek temple before arriving at the southern section of the Saronic gulf and your destination for the day of Poros.

What's Included:

Cruise
Accommodation
Breakfast
Day 2

Kythnos – Perusing the Peloponnesus

Day 3

Mykonos – The Island of the Winds

Day 4

Paros – The Island that Time Forgot

Day 5

Milos – Milos' Volcanic Origins

Day 6

Folegandros – The Rugged Paths of Folegandros

Day 7

Ios – The Cycladic Islands

Day 8

Santorini – The Site of an Ancient Eruption

Trip Highlights

  • Stand in the shadows of the ancient ruins on Agia Marina, where visitors are greeted by the rustic ruins and scenic beauty of one of the island's best-preserved archaeological sites
  • Enjoy the quiet beauty of Hydra and explore its principal village where cars and motorized vehicles are forbidden
  • Witness the ample evidence of the oldest known Mesolithic settlement on the island of Kythnos, which time seems to have forgotten
  • Stroll along the picturesque paths of Mykonos and pay a visit to the beautiful balconies of the neighborhood known as Little Venice
  • Pay a visit to the original source of utility power on the Island of the Winds as you enjoy the historical perspective of Mykonos' iconic windmills
  • Visit the sacred ruins at Delos, which many still consider to be a spiritual center in addition to being one of the Mediterranean world's best-preserved archaeological sites
  • Survey the sights of a semi-submerged caldera from the slopes of Santorini, where, in the 16th-century BC, a massive eruption created the current island chain

Starting Price

$7,800 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

Verified Traveler Reviews

Based on 610 reviews

Greece Tour Review: Athens, Santorini, Mykonos, History, Culture, Tradition, Local Cuisine, Shopping, 8 Nights

If you're considering a trip to Greece, look no further than Zicasso. Our travel expert planned an unforgettable journey for our family; Athens, Mykonos, and Santorini, and every detail was executed with care, expertise, and passion. 

From the moment we arrived in Athens, we were immersed in the country’s warm hospitality. Our agent made sure we had the perfect balance of sightseeing and relaxation. The historical sites in Athens, like the Acropolis and the ancient Agora, were must-sees.

Mykonos is vibrant yet relaxed. The beaches were beautiful. Every meal on this trip was a highlight. Fresh seafood, local cheeses, olive oil, and delicious pastries—each bite told a story of Greece’s deep culinary heritage.

In Santorini, we were captivated by the island’s charm—whitewashed buildings, breathtaking sunsets, and the deep blue Aegean Sea. We visited traditional villages, giving us a glimpse into the rich cultural traditions that are still very much alive.

Throughout the trip, what stood out most—beyond the stunning landscapes and ancient history—was the friendliness of the Greek people. Their warmth and pride in their culture made every moment feel welcoming and genuine.

Our agent didn’t just plan a vacation—he created an experience rooted in history, tradition, and hospitality. I can’t recommend him and Zicasso highly enough.

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Greece Vacation Review: Naxos, Athens, Cuisine, Walking Tour, 10 Nights

Zicasso's travel company made our bucket-list trip to Greece come to life! They organised all our tours and transportation, worked with us to provide activities that were in line with our interests, and even gave detailed information on suggested itineraries for our free days.

Some highlights included the walking tour(s) of Athens, our trip to see Santorini, and the best steak I have ever had at a beach hotel in Naxos! Our only suggestion is that we went on a day tour to Delos which was self-guided. There is so much history there though that a guided tour would have been helpful. I would definitely recommend booking your tour with them!

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Greece Vacation Review: Santorini, Mykonos, Island Tour, Fishing Boat Trip, 12 Nights

Zicasso’s travel company was awesome. Our agent did a great job planning our trip experiences. The execution of all the private drivers and excursions was perfect. The trip planner tool was great to use, as we referenced it every day. The hotels, in-region airlines, and ferry reservations and tickets were all perfectly planned and delivered. Our many scheduled drivers were all on time and courteous. Our drivers were great drivers and scholars. They provided awesome restaurant and pub recommendations. 

We absolutely loved Santorini and the two excursions on that island. Both definitely exceeded our expectations. Our only excursion not rated five stars was the Jeep tour on Mykonos. Four of us were crammed into a closed, small Jeep and driven around the island with only a few stops. We were not taken to a top spot we heard about, which was the windmills and little Venice.  We rate that excursion zero stars for those reasons. 

All four trip participants agreed this was one of their best-ever vacations. We highly recommend this travel company for a great Greek vacation!

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Greece Tour Review: Athens, Naxos, Santorini, Crete, Cuisine, RIB Experience, Cooking Class. 10 Nights

Fabulous, Fantastic, Fun! We had an absolutely amazing 10 days traveling in Athens, Naxos, Santorini, and Crete. We were traveling with four 20somethings with varied interests. Zicasso's tour planner listened to my description of what we were looking for and created a masterpiece of a trip!

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Greece Tour Review: Athens, Mykonos, Santorini, Horseback Riding, Food Tours, 10 Days

We had a wonderful time in Greece. We spent 10 days there and went to Athens, Mykonos, and Santorini. The accommodations were great and the planned excursions were fantastic. The weather was perfect.

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Greece Trip Review: Athens, Santorini, Food Tour, Vineyard, 9 Nights

One of the best decisions I have made was booking my Greece trip with this Zicasso travel company The entire team was accommodating, responsive, and ensured a flawless trip. We stayed in Athens, Mykonos, and Santorini, having transportation provided to and from. The drivers, hotel partners, tour guides, and overall team were remarkable.

In Athens, I would highly recommend our guide for the Acropolis tour and our guide for the food tour. The Athens hotel was exceptional, right in the center of where you want to be.

In Mykonos, I would highly recommend the Jeep tour with our guide and the day trip to Delos and Rineia. Our stay at the hotel was beautiful.

In Santorini, I would highly recommend our guide and the driver for the walking tour and visit to a vineyard. The Oia boat company was great, serving up a fresh Greek feast right on board. The hotel suites were great, especially with the private hot tubs.

Overall, this was an exceptional experience, one we could not have gotten without our travel company. Our trip was planned in six weeks or less and the agents made the process so easy. Thank you!

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

30,000+ Verified Traveler Reviews