Sailing the Greek Islands
May 23-30, 2026

$6,400 Per Cabin (1-2 persons)
Early Dolphin price $5,900 till March 12, 2026
Dive Now

An Exploration of the Greek Islands

Price Includes: Pick-up / Drop-off from Airport, Double Occupancy Cabin, Breakfast and snacks on board.
Price does not include: Airfare, lunch, dinner, alcoholic beverages, hotels, ground transportation, admission to temples and museums.

Sail with Ray and Nina

The sea has always been a mirror for the soul. With each island rising from the blue, something within us awakens. Stripped of distraction, guided by wind and horizon, we remember an older rhythm—one where discovery is inward as much as it is across the map.

Here, nourishment is sacred. Greek cuisine unfolds as a ritual of color, earth, and sea—sun-ripened olives, wild herbs, fresh catch, and meals shared slowly, as they have been for millennia. Each dish carries the wisdom of place, simplicity, and devotion to life.

Like the Argonauts before us, we return not as we departed, but changed—bearing a quiet treasure discovered not at the edge of the world, but in the depths of ourselves.

The Argonauts Journey to the Authentic Self

This voyage begins the way the Argonauts once began theirs—not in haste, but in trust. They set sail in search of the Golden Fleece, though the real treasure was never the prize, but the remembering of who they were beneath duty and destiny. In that same spirit, we sail to rediscover the part of ourselves that is innocent, joyful, and delightfully unburdened—the part that knows how to laugh, wander, and feel at home in the world.

Days unfold at the pace of wind and water. We wake anchored in a quiet coves, turquoise sea stretching in all directions, the sun rising as if just for us. Mornings invite coffee or tea, swimming in crystal-clear waters, and the radical act of doing absolutely nothing—unless, of course, you feel called to do something. Divine play is encouraged; schedules are not.

As the sails rise, those curious about sailing can join Ray in learning the ropes and feeling the quiet intelligence of wind and helm. Others may choose the equally sacred path of sunbathing, napping, or perfecting the art of gazing at the horizon. Along the way, we share a leisurely Greek brunch—golden honey, thick yogurt, walnuts, olives, island cheeses, and olive oil so good it feels like a blessing from the gods themselves.

We arrive gently into ancient harbors where whitewashed houses tumble toward the sea, islands that have welcomed sailors, poets, healers, and dreamers for thousands of years. Evenings unfold with fresh, vegetarian-friendly meals, long sunsets, and laughter carried on the Mediterranean breeze. This is not a journey to become someone new, but to remember who you were before life got complicated—playful, connected, and in quiet conversation with the divine through sea, sky, and salt air.

Ray Crist

Ray is a licensed captain since 1992 and has since sailed the Greek islands in the Mediterranean, Aegean Sea, and the Ionian. He owned a sailing boat and lead retreats in the Caribbean and the Virgin Islands. As a native Greek he knows all the Greek island ports, secluded coves, swimming sports as well as restaurants and the great places to shop on all the islands. You are in for treat as Ray is a connoisseur of gourmet food, healthy living and will guide you into a deep relaxing experience!

Nina Crist

Nina is an avid sailor and since 2017 has sailed the Aegean, the Ionian as well as the Virgin Islands. She is a master Tai Chi teacher with over 20 years of experience in teaching martial arts, outdoor adventures, and wilderness survival. Nina and Ray have explored the Greek Islands, the ports and coves of the mainland as well as the Virgin Islands.

"Our sailing boat "Golden Eye" was our magic way to escape the cold winters of the Berkshires"

Ray and Nina Crist

Since 2017 Nina and Ray have been leading sailing retreats together in the Mediterranean, the Ionian and the Aegean Seas, as well as the Caribbean and Virgin Islands! They share from their heart, and their passion for sailing and life.

“At sea, the soul remembers what the mind forgets: how to trust, how to play, and how to be free.”

Walk with Ray and Nina through cobblestone narrow roads discover the best restaurnts, shops, boutiques, and galleries

"Let food be thy medicine and medicine be thy food" Hippocrates

Taste the pure ingredients born of a rich in mineral land, showered by the mediterranean sun and salty breeze.

FAQS

To ensure your comfort, safety, and to fully enjoy your trip it is essential to have with you a few things you may need and know more about your trip:

Click to hide text

Arrival/Departure

The price included pick up and drop off at the airport - how is this handled and scheduled as we may all be coming in from different locations?
We have a taxi service from the airport to the marina at 11:00 am
Please verify arrival/departure times.
You should be arriving at the marina at 1:00 pm on the day of departure. We arrive back at the marina at 5:00pm Friday. Check out time is Saturday at 9:00am (You can stay on the boat or book a hotel room for that night (not included) )
Are there lodging options you would recommend in Athens to use before or after the trip?
Hotels.com and AirB&B are two good sources to find places to stay
Are you offering the week-long land tour in Athens this year? If so, is it the week before the sailing tour?
Working on the dates for that and will let you know as soon as we have the trip online.

Luggage

How much room is there for luggage in each cabin on the boat? What do you recommend we limit ourselves to?
Space is limited on the boat! Please use a duffel bag so it is easy to store.
Is there off-boat luggage storage options for those who are planning to extend their vacation beyond the week?
There is a luggage storage room and we can also leave a couple of suitcases in my car that is in the marina

Bathrooms/Showers

Please explain the setup - when we will have access and what to expect.
5 cabins - 3 bathrooms. Two cabins have their own bathrooms and the 3 back cabins share a bathroom.
Are towels provided? Soap and/or Shampoo, etc.?
Towels and hand soap are provided. Bring your shampoo or any other cosmetics you like to have.
What is the typical flow of the day - will we generally return to the boat to clean up/change for dinner? Or is it more casual than that?
Wake up swim sail, arrive at a new island swim, go out to explore, change at night go out to a restaurant.

Boat Security / General Internet Questions

What - if any - are the internet capabilities
Slow internet on board through my cell phone and good internet in some ports where we get WiFi from the Cafes
General boat security - is it wise/safe to have computers/passports/phones or other valuables left on the boat during the day?
Your valuables are your responsibility. We ask you to be mindful of how you store/hide any valuables when we are all off the boat. Generally, boats are safe. In my 40 years of sailing, I have never had someone come on board to steal.

Money

Is there much need for cash?
Exchange 500 Euros at the airport. Most places accept Visa and Master card (no one accepts American Express)
Is the currency Euros?
Yes
What is the price of a typical dinner?
Most dinners cost $10-$20 If there is more wine and drinks that can go up to $40 / per person
What customary tipping practices should we be aware of?
1-5 Euros is considered a very good tip

General Preparation

Seasickness - how often does this affect your guests and what do you recommend we bring to prevent/treat it?
We rarely get people who get seasick Usually, the weather is nice and we do not get waves. We have Peppermint drops and ginger that help.
What is the typical flow of the day regarding structured vs. free time? Are we all together all day or do we get to an island and explore on our own?
Think of your time here as a time to relax and enjoy. Most of the time is free time. We offer a 20-minute Tai Chi practice for anyone interested. Most of the time the team is together and there are also opportunities for you to explore on your own, or even choose to have dinner alone...
How long do we typically sail each day?
3-4 hours with maybe one day of 6 hours (Weather depending)
Do we need to prepare for rain?
Have a light rain jacket more for sea spray than for rain.
How should we plan to dress?
Mostly casual. Have one dress-up option for a night out to town.
Is there access to laundry?
Some islands have laundry. But you will probably not need it.
Any recommended must haves? i.e. particular shoes, sunscreen, waterproof bags, backpacks, etc?
Shoes with white soles, sunscreen, hat, sunglasses

Sailing the Greek Islands May 23-30, 2026