Save To Wish List

Adding item to wishlist requires an account



A Learn-To-Sail Vacation

hosted by Whitecaps Sailing School
  • 7 Days
  • 2024: April - October
  • 101 / 103 / 104 / 114
Enjoy serene blue backgrounds and gorgeous Grecian views while learning to sail with Whitecaps Sailing School

Whitecaps Sailing stands as an ASA certified sailing school specializing in Mediterranean Sailing Adventures. Our overarching mission is to impart our deep-seated passion for sailing while guiding our students in acquiring the expertise and skills necessary to realize their sailing aspirations. Whether the goal is to gain sufficient knowledge for leisurely day sails or to become proficient charterers or liveaboards, we are dedicated to fostering the journey. Over the years, we’ve introduced numerous sailors to enchanting destinations like Croatia, Greece, Italy, Spain, Seychelles, and Brazil. For those whose native language is other than English, our instructors are fluent in Spanish, French, Greek, and Italian, ensuring a tailored and inclusive learning experience.

The Destination

Greece offers an idyllic setting for those wanting to learn to sail, with its rich maritime history, crystal-clear waters and diverse sailing conditions. The Greek islands, scattered throughout the Aegean and Ionian Seas, provide a stunning backdrop for sailing education, with their picturesque landscapes, charming villages and secluded coves. The gentle winds and relatively calm seas in many areas make Greece an ideal environment for novices to grasp the basics of sailing without feeling overwhelmed. Aspiring sailors can navigate through the Greek archipelago, honing their skills while exploring the unique culture and history of each island. With its combination of favorable sailing conditions and a vibrant maritime culture, Greece makes it an exceptional destination for those looking to learn the art of sailing.

The Sailing

Greece, a destination adorned with sunny weather, warm beaches, breathtaking landscapes, incredible cuisine, and, of course, renowned for its Greek hospitality, stands as the birthplace of democracy and the Olympic Games. This region boasts a wealth of history and culture.

Recognized for their favorable conditions, we have strategically chosen the Ionian Sea and the Saronic Gulf for our Learn-to-Sail Vacations. The mild weather, tranquil waters and line-of-sight sailing make these areas ideal for sailors of all levels. The abundance of islands not only adds to the picturesque scenery but also creates a more sheltered and protected environment, enhanced by well-established navigational aids. To complement this, the region also offers a robust tourism infrastructure, including marinas equipped with facilities and amenities specifically tailored to the needs of sailors, ensuring a smooth and delightful sailing journey.


Whitecaps Sailing offers a variety of 7-day live-aboard courses including : Basic Keelboat Sailing (ASA 101), Basic Coastal Cruising (ASA 103), Bareboat Charter Certification (ASA 104) and Multihull Certification (ASA 114).

· ASA 101-103-104 | 7-day Course
Basic Keelboat Sailing, Basic Coastal Cruising & Bareboat Cruising

· ASA 103-104 | 4-day Course (followed by 2 days of charter sailing)
Basic Coastal Cruising & Bareboat Cruising

· ASA 103-104-114 | 4-day Course (followed by 2 days of charter sailing)
Basic Coastal Cruising, Bareboat Cruising and Cruising Catamaran

· ASA 114 | 7-day Experience on a Cruising Catamaran
This 2-day class takes place during a flotilla when the lead boat is a catamaran.
*Cost in addition to the flotilla fee. Provisioning not included.


ASA 101-104 Greece live aboard courses are typically conducted on a Monohaul (38-49ft Bavaria or Jeanneau).
ASA 114 Greece live aboard courses are typically conducted on a Catamaran (40-45ft Lagoon or Bali).

Day 1

ARRIVAL AND SET SAIL. Meet at the Marina and provision with your instructor as part of the Bareboat Instruction. Departure will be around 17:00 for our first night on Meganisi Island, Vathi Marina.

Day 2
Fiskardo, Kefalonia Island

After breakfast, we set sail for the island of Kefalonia. We’ll point our bows toward the South and the charming village of Fiskardo. On the way, we’ll stop to enjoy lunch and a quick swim in the beautiful bay of Atherinos or Abelaki.

Day 3

Next, we head South from Fiskardo, sailing through the channel between Kefalonia and Ithaka towards the port of Sami (about 12NM) with the opportunity to visit Melissani and/or the Dragorati Caves.

Day 4
Vathi, Ithaka Island

Across from Sami is the island of Ithaka, the mythical home of Odysseus, and our next overnight stop. Here we will overnight at the main port of the island, Vathi, with its many customary Greek fish restaurants. At nearby Gidaki beach, swimming and snorkeling are favored activities among the enchanting ambiance.

Day 5
Vathi, Kalamos Island

We now leave Vathi for the island of Kalamos where, in the port of the same name, George will be waiting for us to help secure our boat before having dinner at his renowned restaurant. On the way to Kalamos, we will drop the hook near the tiny island of Formikoula for an afternoon swim.

Day 6
Spilia Bay, Maganisi Island

Our main attraction today will be Papanikolis’ Cave on the south side of Meganisi Island. On the way, we will pass Papageorge’s Cove, another great swimming hole. Our stop for the night will be Spilia Bay on Maganisi island where we will have time to visit the small village of Spartochori and savor another delightful Greek dinner.

Day 7

On the way back to Lafkada, we will encounter more opportunities for sailing and swimming. Perhaps even a stop at Skorpios Island, the home of the late Onassis. Finally, before heading back to base, we’ll savor one more onboard lunch while taking in the scenic views.

At base, you will have the option to stay on board for the night should you choose (Disembark by 09:00).

Day 1
Alimos Marina, Athens

ARRIVAL AND SET SAIL. Meet at the Marina. Provision with your instructor as part of the Bareboat Instruction. Next, we set sail for nearby Aegina, where we will spend the night and enjoy dinner at a local taverna.

Day 2
Cape Sounion

Off we go to Cape Sounion to visit the temple of Poseidon. Here, we’ll drop anchor for the night and dinghy into shore to indulge in a delectable dinner at a local taverna.

Day 3
Poros Island

Today’s adventure takes us to Poros, a journey of approximately 28NM. May Poseidon’s blessings favor us during this maritime venture. Our night in Poros offers another opportunity to indulge in the distinctive local flavors at one of the enchanting waterfront tavernas.

Day 4
Methana Peninsula

Today will be a short sail, aiming for the peninsula of Methana. Even without a scientific background, this Island’s origin name is easily discernible. The volcanic peninsula features thermal spas where, after a hike to the volcanic crater, you can soothe your well-worked muscles in healing mineral waters. Wrapping up the day, we’ll overnight in the nearby fishing village of Vathy.

Day 5
Ancient City of Epidavros

Next, we set sail for Epidavros, where an onshore excursion beckons, presenting a chance to delve into the wonders of the ancient city. This port of call provides an excellent opportunity to tour the acclaimed Temple of Asklepius and its iconic theater, the largest and best-preserved amphitheater in Greece.

Day 6
Moni Island

As we make our way back towards Athens, we’ll spend the night on Moni Island, near Aegina, where freely roaming peacocks and deer provide captivating photo opportunities. We’ll cap off the day with dinner on board, surrounded by the breathtaking scenery.

Day 7
Alimos Marina, Athens

Today marks the final day of our journey. As we head back to base, you’ll have the opportunity to relish in the mesmerizing deep blue Mediterranean waters, surrounded by the awe-inspiring views of Greece with one more day of sailing, swimming, and snorkeling.

At base, you will have the option to stay on board for the night should you choose (Disembark by 09:00).

*Itineraries are subject to change due to weather or other circumstances beyond our control.


I have had the pleasure of going on two flotillas with Captain Jean and Mila, Croatia and Greece, I fell so hard in love with sailing I decided to get my 103 and 104 certification through Whitecaps Sailing School. Happy to say I learned so much and passed feeling capable and empowered to sail my own boat. This is a school I would recommend if you’re interested in learning to sail and beyond.
Prestley (Georgia)
I had a wonderful time living on the boat and learning about sailing. Best of all, i got my ASA certificates 101-103-104 so I can be my own skipper in the future. The sailing instructor is very knowledgeable and gave us a lot of good information about sailing. We had just the right amount of studying time and hands-on exercises with the boat. Loved sailing so much, I joined Med Sailing Adventures Croatia flotilla a few months after my certifications.
Jason (New Hampshire)

The best sailing school experience I have ever had! I previously received my sailing 101/103 and 104 certifications bud didn’t feel confident in my sailing abilities and decided to join Capt. Jean and Mila with Whitecaps Sailing (Med Sailing Adventures) for a week in Croatia for a refresher course. Capt. Jean’s sailing experience and expertise brought me up to another sailing level! I had so much fun and learned so much about sailing, I decided to bring our whole family and some friends on their organized flotilla last year in Greece. With their local connections, we were able to get into the best docking spots and restaurants. We plan on going on a sailing trip every year with them!

Penny (Florida)



All-inclusive 7-night ASA Group Charters (Saturday – Saturday):
From $3950 USD per person
*Minimum Students 2, Max 6

All Courses (with the exception of 114) Include :
Private Cabin with Private Head (for each student/couple), Breakfast & Lunch Daily, 2x Dinners on Board, Use of the Yacht, Study Material, Testing & Certification, Docking Fees and Refueling.

Please complete the form below if you have questions or would like to make a reservation.

You may also email us directly at info@whitecapssailingschool.com or call us at +1 941-258-8890.

    Full Name*
    Telephone Number*
    Email Address*
    Your Enquiry*