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. 

Please note: the site may show a waitlist even when spots are still available.

Feel free to reach out by phone, text or click the ask question button — I'd love to hear from you! Before signing up, I do ask that we have a brief phone call first. I know it's an extra step, but speaking with each participant beforehand helps me ensure the trip is the right fit for everyone involved.

C: 510-504-3692

Airport:

We will arriving and departing from Athens.

Cruising:

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.

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.

ASA Instructor • USCG Certified Captain

It started with one sail in the Mediterranean in 2003. Now I live on a boat. These

things happen.

Greece grabbed me early and hasn't let go — 35+ weeks of island hopping over 20 years, plus detours through Spain, Italy, the Caribbean, and British Columbia (where the scenery is stunning and the water is aggressively cold).

I'm an ASA sailing instructor with Modern Sailing on San Francisco Bay and a USCG-certified OUPV captain, which is a lot of acronyms that basically mean: I know what I'm doing out there, and I am legally allowed to prove it.

Home is my Ocean Alexander 48, Canto Del Mare, moored in Sausalito. She's a better address than anything I ever rented on land, and she never once raised the rent.

Credentials:

• ASA 201, 203, 204, 214, 218, 216, 101, 103, 104, 105, 106, 114, 116

• USCG Captain (OUPV)

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.

• 44 ft cruiser

• 4 cabins

• 2 WC

Cabins & Layout

• 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.

https://sailboatdata.com/sailboat/sun-odyssey-439-jeanneau/

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.