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June 22-29, 2024 

Greece Ionian Islands Flotilla CruiseDelightful Shared Cruising Surrounded by Greek Mythology

On this magical cruise you sail along Greece’s Ionian Coast and tiny islets steeped in history. In every port Greece’s fabled culture, delicious cuisine, beautiful villages, and fun nightlife tempt you to come back for more – as do beautiful sandy beaches, mythological sites, soaring cliffs and lush green mountains. Cruising this storied land takes you to imposing ruins of medieval fortresses while enjoying modern-day culture and quay-side dining in local tavernas with delightful wines.Greece Ionian Islands Flotilla Cruise

Beautiful Coasts, Spectacular Mountains, Brilliant Blue Seas

Cruising from Lefkas in the Ionian Sea is truly a fantastic “see-the-world-under-sail” experience! Bordered by the Ionian Sea, named after the Greek nymph Io, this delightful cruising destination offers comfortable sailing to picturesque towns along the coast and high in the hills, fishing villages packed with iconic fishing skiffs, colorful tiled homes, humble and grand churches and monasteries.Greece Ionian Islands Flotilla Cruise

The Cruise Starts in Lefkas

Lefkas, also known as Lefkada, is an island in the Ionian Sea on the west coast of Greece, connected to the mainland by a long causeway and floating bridge. Known for its magnificent mountain backdrops, this island is a photographer’s dream destination, especially inland where hill villages with bright terracotta roofs and whitewashed stone nestle in lush pine forests. There is so much to do here we highly recommend you arrive a few days before the cruise to explore.Greece Ionian Islands Flotilla Cruise

You Get to Sail on Monohulls!

For an exciting, traditional sailing experience, our reserved fleet of monohulls provides the ultimate sailing adventure in these fabled waters! The fleet you board in Lefkas consists of Sunsail 44’, 47’ and 52’ cruising yachts built by Jeanneau, all with four cabins and lots of deck space, and twin steering wheels for great control and visibility under sail. We cannot guarantee which yacht you will be assigned. Offshore has the Jeanneau 440 (44′) and Jeanneau 479 (47′) in our teaching fleet in Florida. We love these boats!Greece Ionian Islands Flotilla Cruise

Beyond Lefkas to the South

There are three main islands beyond Lefkas, that you are likely to visit on this cruise. Your cruise leaders will choose the final itinerary after discussion with the Sunsail base manager before you arrive. Here are some possible highlights:


Called “heaven on earth,” Meganisi is a small island opposite the port of Hydri on Lefkas, known for its untouched beaches and emerald waters. Two attractions here include the small fishing village of Vathi and Papanikoli Cave where submarines hid during World War II.


This mythical island is famous as the home of Odysseus (Ulysses), hero of the Homeric poem Odysseus, where faithful Penelope waited patiently 20 years for her husband to return from the Trojan War. Odysseus Palace is a top historical landmark, with 3,000-year-old ruins and archaeological digs. Ithaca also has beautiful bays and beaches, some pebbly, some sandy. The capital, Vathy, dates back to 1500 AD, with alleys to explore, colorful hillside houses, sidewalk cafes, shops, live entertainment and spectacular sunsets.


The 2001 film Captain Corelli’s Mandolin was set here, on the largest of the Ionian Islands. Kefalonia is known for its emerald-green mountains, sparkling waters and dazzling beaches. Drogarati Cave and Melissani Lake are dramatic sights. Mount Ainos National Park is great for hiking if there is time, but if not, scenic villages with historic treasures and wonderful dockside dining beckon.Greece Ionian Islands Flotilla Cruise

Lefkas Highlights

  • The Castle of Agia Mavia (shown here) dating back to 14th lonia century, built to guard the channel between Lefkada and the Greek mainland
  • Porto Katsiki, one of the best beaches backing onto gorgeous cliffs
  • Panagia Faneromeni, a monastery of spiritual significance with an Ecclesiastical Museum where hundreds of religious objects are preserved; plus a nearby Maritime Museum
  • Dimosari Waterfalls on the east side of Lefkas near Nidri reached by a 15-20 minute winding gorge trail
  • Mylos Beach, a “hidden Jewel” south of Agios Nikitas village, accessible by boat or a walk around the village, known as a kite lovers paradise
  • Vassiliki, a traditional fishing village, with great restaurants and coffee bars, also an exceptional windsurfing spot
  • Cape Doukato (also known as Cape Lefkatas) with a 19th century lighthouse perched on awe-inspiring cliffs, with breathtaking panoramic views
  • Church of Agios Ioannis Antzoussis, the oldest and most intriguing church in the area, built in 65 AD by the Franks; Apostle Paul is said to have preached here 2000 years ago
  • Lefkaditiki Gi Winery near Nydri, for exceptional reds and whitesGreece Ionian Islands Flotilla Cruise



2024 Ionian Package Costs are a True Bargain

Note: The original VISA requirement to take effect in 2024, has been delayed until 2025. At that time, US Citizens will need to obtain a VISA prior to traveling to Greece. This is an online process taking only a few minutes, for a nominal fee, approx. $8.00. View details.

  • $4,195 single in a private cabin
  • $3,695 per person for two sharing a cabin

Up to $500 Discount for Qualified Offshore Grads!

  • If you earned US Sailing Basic Keelboat certification with Offshore Sailing School, you may deduct $300 per person.
  • If you earned US Sailing Bareboat Cruising certification, you may deduct $450 per person.
  • If you have both Bareboat Cruising certification and the IPC, International Proficiency Certificate, you may deduct $500 per person. 

Offshore Sailing School grads with US Sailing Bareboat Cruising certification need to apply for their US Sailing International Proficiency Certificate, in order to charter and skipper in Mediterranean countries, such as Greece.

Offshore Grads with US Sailing Bareboat Cruising CertificationGreece Ionian Islands Flotilla Cruise

  • $3,695 single in a private cabin with OSS/US Sailing Bareboat Cruising Certification
  • $3,195 per person if sharing a cabin, for both individuals with OSS/US Sailing Bareboat Cruising Certification and an IPC

Your Ionian Flotilla Cruise Package Includes: 

  • 7 nights in a private or shared cabin on one of the flotilla yachts, assigned in advance by your cruise leaders
  • Starter pack of provisions and bottled water
  • Welcome meet and greet party and dinner first night of trip
  • Gala group dinner ashore during the cruise or at end of cruiseGreece Ionian Islands Flotilla Cruise
  • Commemorative Colgate Sailing Adventures® Greek Islands Flotilla Cruise shirt and hat
  • Wi-Fi aboard your yacht
  • Full fuel and water tanks upon departure, no need to replenish fuel upon return
  • Comprehensive e-book prepared by Offshore, to help you plan your trip
  • Guidance by expert cruise leaders Nate and Heather Atwater, with the fleet throughout the cruise

Contributing to the Boat Kitty

As with any Colgate Sailing Adventures® Flotilla Cruise, crew on each boat contribute equally to a kitty to cover shared costs during the cruise, usually starting with $100 per person. To discover Greek fare and the hospitality of those who live there, you and your crewmates enjoy shopping the local markets for goodies to share aboard. And you will definitely want to head ashore to dine in seaside and inland tavernas most nights.Greece Ionian Islands Flotilla Cruise

Who Can Participate on a Colgate Sailing Adventures® Flotilla Cruise?

If you are an Offshore Sailing School graduate with Bareboat Cruising Certification (OSS 104/114) or higher, and love sharing sailing adventures with likeminded sailors, this cruise is for you!  If you took OSS 101 or OSS 102 you are also welcome, as well as those with equivalent sailing and cruising experience (based on a sailing resume you provide).




Why is a Sailing Resume Required?Greece Ionian Islands Flotilla Cruise

You must fill out the Sailing Resume at the same time you sign up, with a deposit or full payment. As soon as you are accepted to participate, a complete guide for this trip will be sent providing all you need to know to prepare you to sail in this glorious sailing area.

All Colgate Sailing Adventures® flotilla cruises are hands-on activities that require unaided mobility on the yacht you live and sail on, and on the dinghies you must board to go ashore and back to the boat, regardless of how choppy the seas and harbor waters might be. So, you must complete a Sailing Resume before you can be confirmed on this trip. There are many questions and all of those questions including information about medical or physical conditions that may hinder your full participation must be answered. Only the cruise leaders and Offshore management see these resumes.

Designated Skippers and Designated MatesGreece Ionian Islands Flotilla Cruise

Greece requires two people on each boat have an International Proficiency Certification (IPC). A designated Skipper and Designated Mate will be assigned to each boat based on completed Resumes and possession of the IPC. It’s very easy to obtain if you have Bareboat Cruising Certification! Learn how to get it here.

Your Cruise Leaders

Heather and Nate Atwater are your guides as you discover this Ionian region under sail. They have led Colgate Sailing Adventures® Flotilla cruises for many years and they, too, must have your completed resume in order to assign crews to each boat and choose the designated “skipper and mate” from information you provide on the resume. When you are ready to book, please print, fill out and email the form in the link provided and send it to Ionian Islands Flotilla Cruise

How to Get to Lefkas

The best way to get to Lefkas is via flights from Athens International Airport (ATH) to Preveza-Aktion Airport, located on the Greek Mainland 45 minutes (50 Euros) from the Sunsail base. To find the best flights from your home base to Athens, and connecting flights to Preveza, we  recommend you call the Moorings/Sunsail travel service (866-649-2003) as they have tremendous experience in helping sailors get to Sunsail and Moorings destinations. Check your passports now! They must be valid for six months after your return home.

Sign Up for this Ionian Islands Flotilla Cruise NOW!

Because of pent up demand for monohulls among Offshore Sailing School cruising enthusiasts, the 19 cabins available will fill quickly.