Greece Sailing Adventure
Airport We will arriving and departing from Athens.
The Cyclades (The Iconic Choice)
The Wind: This is the home of the Meltemi, a strong north wind that peaks in July and August. It can make for exhilarating sailing but also challenging swells.
The Vibe: White-washed houses, blue domes, and rugged landscapes. If the Meltemi, is making Sailing uncomfortable in the Cyclades we chose to sail
The Saronic Islands (The other good Choice)
The Wind: Generally much calmer and more predictable than the Cyclades. It’s protected by the Peloponnese mainland.
The Vibe: Lush greenery, neoclassical architecture, and charming harbor towns. It's much shorter distances between hops.
This trip offers the perfect blend of learning, adventure, and relaxation for sailors of all levels, in particular ASA 104 graduates. Ideal for people looking to build confidence and gain real cruising experience. Whether you want to sharpen your skills or simply soak up the sun, this adventure will leave you more confident, capable, and inspired to charter.
Greece is one of the premier cruising grounds in the world: beautiful, historic, and wonderfully challenging. Harbors here still capture the wild charm of the Mediterranean. Each day begins with a morning briefing and goal setting. You’ll work on chart reading, anchoring techniques, and scouting out the best spots to drop anchor. Spend time at the helm, fine-tune your sail trim. and experience the challenges of Mediterranean-style docking.
Experience Details
Trip Duration
12 days
Pricing
From $2900
June 29 - July 10, 2026
Next Dates
World class sailing through Greece
Friends + Family
Friends and family are completely welcome to join. They can kick back and enjoy the views from the boat, swim, snorkel, hike rugged islands with historic ruins, or explore local culture and cuisine. There will be ample time for everyone on board to enjoy the easy rhythm of life on the water and discover all the delights of Greece.
Meals & Shared Responsibilities
We sail as a team — and we eat as one.
Everyone participates in cooking, shopping, and cleanup.
When dining out as a group, we simply split the bill evenly.
The Boat
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Calila
The Jeanneau Sun Odyssey 439, a 44 ft cruiser 2011, comfortably accommodates up to 8 people, but for this trip we intentionally limit the group to 5 crew members plus myself — a thoughtful balance between comfort, fun, participation, and personal space.
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44 ft cruiser
4 cabins
2 WC
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3 Queen Cabins — comfortable and spacious
1 Small Cabin — two bunk beds
Saloon Berth — additional sleeping option
2 Bathrooms + 2 Interior Showers
1 Exterior Shower for post-swim rinse-offs
Plenty of room, plenty of comfort.
[ the journey ]More Details
Cancellation Policy
Before January 31, 2026:
Full refund minus a $125 administration fee.
After January 31, 2026:
Cancellations are not refundable.
However, if you must cancel, I will do my best to fill your spot with an appropriate replacement. If successful, I will happily refund your payment.
When you confirm your participation, you are committing to the trip and responsible for the agreed-upon price.
Trip Insurance
I highly recommend purchasing trip insurance to cover both the trip cost and your travel expenses. Life happens — insurance protects your investment.
Meet Your Captain
Captain Joerg “CJ” Chabowski
ASA Instructor • USCG Certified Captain
After my first sail in the Mediterranean in 2003, I discovered a lifelong passion for the sea. Greece quickly became one of my favorite cruising grounds. I’ve spent more than 35 weeks exploring its islands over the past 20 years, and also cruised in Spain, Italy, the Caribbean and British Columbia.
Currently, I am an American Sailing Association (ASA) instructor with Modern Sailing in the San Francisco Bay Area, as well as a U.S. Coast Guard–certified OUPV (“six-pack”) captain.
I live aboard my Ocean Alexander 48, Canto Del Mare, docked in Sausalito, California, where I sail and teach on the San Francisco Bay. I feel most at home on the water, constantly learning from the lessons the sea provides.
Credentials:
ASA 201, 203, 204, 218, 105, 106
USCG Captain (OUPV)
