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Greece Flotilla Greece Flotilla Greece Flotilla Greece Flotilla

Continue the seafarers' tradition of thousands of years with an Aegean adventure under sail. Experience the colorful, the quiet, the famous, the historic and the exotic – all in two weeks. You'll travel through time in a world of ancient ruins, modern resorts and ageless wonders.

Crystal-Clear Waters And Timeless Cultures

The Aegean has a wealth of natural beauty that defines the Mediterranean. Inside the Saronic Gulf is a necklace of islands surrounded by the Gulf's protective headlands. Predictable winds and line-of-sight navigation make it an excellent area for relaxed sailing. Exhilarating open water sailing awaits you to the southeast in the islands of the Cyclades; famed for white houses, blue windows and narrow paths full of flowers

The Cyclades

This is the finest sailing with open-water passages and stunning anchorages. Volcanic craters formed most of these islands, so you’ll anchor on buoys or tie “Med Style” to quays throughout the region. Sail to the charming island of Kea with its small village perched atop the harbor. Continue east and visit the island of Syros. Don’t miss a stop in famous Mikonos with its whitewashed buildings and trendy clubs. Sail south to Naxos, los and Paros, where you’ll pass in the shadows of white chalk cliffs. Paros is an island of plantations, palm trees and historic monasteries. Also, be sure to check out the great beach cafes. Naxos boasts windmills, churches and the remnants of the Temple of Apollo. Don’t miss the opportunity to arrange a day trip to Santorini, often called the most beautiful island in the Aegean. In Sifnos, anchor in the port with charming Cliffside villages and take a gondola up the top for an unforgettable view. Sail to Serifos past a rocky coast cut with deep coves and great beaches. Here, you can walk among ancient stone formations that resemble human figures.

OCSC’s Flotillas

If you haven’t been on a flotilla before, here’s how it works. OCSC reserves several boats for the location and holds a series of planning parties to explain the details and answer questions from anyone who is interested. Some members choose to reserve a whole boat with their friends and family; some hook up with other singles or couples to form their own boat; a third option is to charter a cabin on a boat skippered by an OCSC Instructor. These planning meetings are the best way to decide which option works best for you. We suggest that you use them to meet potential shipmates, other skippers, and the OCSC personnel who will be leading the flotilla.

Flotilla charters are ideal for first-time skippers since OCSC helps in cruise planning, introduces individuals to others interested in sharing a yacht, and sends an experienced ‘group leader’ along. The security in this type of ‘buddy-boating’ is one reason for flotilla-style chartering, but the ease of participation, sailing with lots of friends made at the planning parties and multi-boat get-togethers in the evenings make any charter that much more enjoyable.

How to Get Involved

There are three ways to get involved. You can charter your own yacht, let us help you hook up with other members and sailors, or book a cabin on an OCSC Flotilla Leader’s yacht.

  • Option 1: With a small deposit (appx. 15%), you may reserve a boat with your friends or family, or reserve a boat and let us help you find crewmates. 
  • Option 2: If you want to go but need to hook up with others on the flotilla, we will help you meet some other sailors to join a boat or set up a crew.
  • Option 3: If you like the idea of learning more while you relax, consider reserving a cabin on one of the OCSC Flotilla Leader yachts. All OCSC flotilla leaders are qualified sailing instructor with years of cruising experience. They make wonderful skippers, and are perfectly willing to make the experience for you as educational as you like. In addition to your share of the charter, you have only an additional skipper fee to pay: $450 per person, double occupancy, or $900 per cabin. If you come as a single, we will work to help you find a cabin mate or you can pay for a full cabin for privacy.
Giving Back to the fragile environment we cherish

Since it’s founding, OCSC has been committed to environmental protection. We have always felt that especially since our business is built on enjoying nature, we are compelled to support organizations that work as guardians for all of us. Part of our approach has been to focus our efforts and appreciation on areas that we are privileged to visit on our bareboat flotillas.

To help this end your participation in our flotilla includes an additional contribution of $50 per person. The funds we collect are donated to an environmental protection initiative in the region we visit.

Yachts range in size from 40–49 feet.

Dates and Leaders
Start End Leaders

September 12, 2020

September 26, 2020

Anthony Sandberg

Retail Rate Member Rate

From $3668 per person

From $3668 per person

Price is based on double occupancy cabin in a OCSC Skippered Catamaran. You can charter your yacht, please call for details.

OCSC Members & Repeat OCSC Adventurers save 5%!