Join us on this incredible sailing adventure in a professionally guided flotilla in Greece
Take the helm at one of our 2027 adventure sailing trips
Sail through the breathtaking Ionian Sea in the Mediterranean on a guided flotilla adventure, earning your ASA 103 & 104 Bareboat certification while exploring Greece’s most enchanting islands. Or come along cruising on a fully catered trip, no sailing experience required. We’ll be leaving from Lefkada.
Navigate between lush, emerald-green isles, anchor in serene bays with crystal-clear waters, and discover charming seaside villages rich in Greek culture and history.
Aboard S/V Beleza, refine your sailing skills with hands-on instruction, while S/V Oasis offers a skippered and catered experience for those seeking a more relaxed journey.
We have 2 trips scheduled in Greece in 2027. Come for cruising or get certified. Either way, you’ll have a fantastic time!
May 8-15, 2027
Come to get certified (ASA 103/104)
Join me on a beautiful Beneteau Oceanis 41, “Beleza” and get your 103 and 104 ASA certifications
Or come along for a relaxed cruising experience- professionally captained and hosted s/v “Oasis”
Join Captain Michail Soutos with onboard Stewart and Hostess Sophia of Oasis Sailing, who bring years of experience sailing and great local knowledge of the waters and Islands in the Ionian Sea and Archipelago.
Rates:
S/V Beleza: $5,000 per cabin for one person (second person in cabin $600) Certifications available
S/V Oasis: $5,000 per cabin for one person (second person in cabin $600) Cruising only
Bunk Cabin (one person only) $3,200
Ready to Sail Greece?
Spots on both voyages are limited, and I want to make sure each one goes to someone who’s genuinely ready for it. The process starts with a short application form — it takes about 10 minutes and helps me understand your sailing background and what you’re hoping for. From there, I’ll reach out personally to set up a conversation. If we both feel it’s a great fit, I’ll send you the details to secure your spot with a deposit.
This is not a sign-up link. It’s the beginning of a real conversation.
Certification Trip in Greece
“I came to Greece with Captain Berry to earn my ASA 103 and 104. What I didn’t expect was how much I’d learn about myself. There were moments of real challenge — riding out a ” Medicane” at the dock on the Ionian Sea, navigating tight harbors, working through crew dynamics in close quarters. But every time I felt out of my depth, Berry’s calm, clear instruction helped me find my footing. By the end of the week, I wasn’t just certified — I was a sailor. Greece was the perfect classroom: stunning, unforgiving, and absolutely unforgettable.”
— Certification Crew, o/b Beleza
Sept. 4-11 2027
Come to get certified (ASA 103/104)
Join me on a beautiful Beneteau Oceanis 41, “Beleza” and get your 103 and 104 ASA certifications
Or come along for a relaxed cruising experience- professionally captained and hosted s/v “Oasis”
Join Captain Michail Soutos with onboard Stewart and Hostess Sophia of Oasis Sailing, who bring years of experience sailing and great local knowledge of the waters and Islands in the Ionian Sea and Archipelago.
Rates:
S/V Beleza: $5,500 per cabin for one person (second person in cabin $600) Certifications available
S/V Oasis: $5,500 per cabin for one person (second person in cabin $600) Cruising only
Bunk Cabin (one person only) $3,500
Ready to Sail Greece?
Spots on both voyages are limited, and I want to make sure each one goes to someone who’s genuinely ready for it. The process starts with a short application form — it takes about 10 minutes and helps me understand your sailing background and what you’re hoping for. From there, I’ll reach out personally to set up a conversation. If we both feel it’s a great fit, I’ll send you the details to secure your spot with a deposit.
This is not a sign-up link. It’s the beginning of a real conversation.
First Time Coastal Cruising
“I had never sailed on open water before this trip. My first moments at the helm — wind in the sails, the Greek coastline sliding by — genuinely changed something in me. Berry has a rare gift: she makes you feel competent before you realize you’ve become competent. I left with my certifications, a new love for sailing, and a handful of people I’ll call lifelong crew. If you’re wondering whether this trip is for you — it is.”
— First-Time Offshore Sailor, o/b Beleza
About Captain Berry
USCG Captain | ASA Certified Sailing Instructor
With over 50 years of sailing experience, I have navigated offshore waters of the North Sea and Atlantic, near-coastal passages in the Salish Sea and San Juan Islands, and inland waterways, including rivers and lakes. For the past 25 years, I have been actively sailing on the Columbia River, balancing both racing and cruising.
As a USCG-licensed captain and a certified ASA instructor in ASA 101 (Basic Keelboat Sailing), ASA 103 (Coastal Cruising), ASA 104 (Bareboat Cruising) and ASA 105 (Coastal Navigation), I am passionate about sharing my knowledge and helping others gain confidence on the water. Whether racing, cruising, or teaching, my goal is to cultivate skill, safety, and a deep appreciation for the art of sailing.
I have sailed with Mike and Sophia in Greece among the Ionian Islands twice, and as a “cold weather” sailor I truly enjoyed the warm hospitality Mike and Sophia offered as well as their sense of adventure to discover white beaches, turquoise bays, and quaint villages.
About Captain “Mike”
Michail Soutos is the Owner of Oasis Sailing, which is a small, boutique, local charter operator based in Lefkas Marina, Greece, dedicated to providing quality sailing experiences in the islands of the Ionian Archipelago.
As a professional captain, Mike has been operating in the area for the past decade, He knows all the highlights and hidden gems, and has collaborators and friends everywhere.
Mike and Sophia provide a personal service from the minute you step on the boat until the time you disembark the boat.
Cruising Trip Greece
“What I’ll carry home from this trip is harder to put in a logbook. Falling asleep on deck to the sound of waves. The simplicity of meals made fresh in a small galley. The way time slows down when you’re anchored in a quiet Ionian bay with nowhere to be. Happy at the Helm created something rare — not just a sailing trip, but a week that reminded me what actually matters. I’d go again without a second thought.”
— Cruising Crew, o/b Oasis
Questions? I’ve got some answers!
Will I be certified to skipper my own monohull charters after this trip?
YES! Not only will you be learning all of the aspects of preparing for, planning for, and running a trip like this – you will actually be doing exactly that! This is a fully hands on participation based trip and class.
You will also be developing your “resume” (sailing log) which the charter companies look at together with your certifications. Furthermore, you will be able to reference this trip directly with Oasis Sailing for your next charter as they will recognize you’re having not only achieved your ASA Certifications but also have done so on one of their boats!
What is the cost of these adventure trips?
Each charter class is very unique and pricing is based on several factors including the boat being chartered; the location and area being sailed; the season the charter is being booked; and the duration of the charter.
Therefore pricing will be reflected in the specific charter listing. Please see rates for each trip above.
How do I book?
Since these are highly specialized and carefully developed adventure learning opportunities we prefer to discuss your goals and desires directly with you!
Start with filling out the “I’m Interested” form. Then I will contact you for a short conversation. If we both think this is a good fit for your sailing/adventure goals and you’re ready to sign up, I will send you details and terms for payment. We request a non-refundable deposit of 30% of cost trip to hold your reservation.
Does every guest that is coming have to certified?
Not at all! Beleza will be skippered by Berry Kruijning with instruction as noted and and Oasis will be for pleasure cruising with no certifications required.
Are the certifications included in the cost?
Yes. This is a fully certified ASA course and upon completion you will be given formal certification from the American Sailing Association. This and all curriculum materials are included in the cost of the class.
What else is included in the cost?
The captains, boats; fuel; boat associated costs (moorings, fuel, etc) are included as well as all of your certifications and curriculum for your American Sailing Classes. Welcome dinner on Sunday. Provisioning for breakfasts and lunches and some dinners aboard (as well as beverages- alcoholic and non-alcoholic) are also included.
On Beleza the crew will be helping with provisioning as part of the learning experience. Oasis is fully catered and Sophia will cook lovely Greek food for you.
What’s not included are your travel costs; any ashore activities you should choose to partake in, dinners ashore (3-4 evenings); and any specialized personally desired provisioning such as special snacks, etc.
When to board and where?
You will be boarding the boat the evening before your charter begins at 1700hrs on Saturday allowing everyone to settle in nicely and be prepared for cutting loose the next morning from Lefkada Marina on Lefkada. If you are on Beleza (certification), you will spend the afternoon before boarding on provisioning in Lefkada.
Visualize | Book | Plan | Go
I know from experience that these trips fill up fast. Click the “I’m Interested” button on this page (above) to get the planning started.
Embark on an unforgettable sailing adventure with Happy at the Helm, in partnership with Island Sailing School and Oasis Sailing through Greece’s breathtaking Ionian Islands, where you’ll explore picturesque villages, crystal-clear waters, and secluded bays with expert guidance and top notch instruction.