YESSAIL WEEK

DESIGNED

SAILING EXPERIENCES

Carefully curated sailing weeks, built around people, pace, and smart routes.​​

★★★★★
Rated 4.8/5 by guests who sailed with us

The Essentials of Your Journey

BASIC INFORMATIONS

Explore our most popular routes, destinations, and sailing styles — each week thoughtfully curated around people, pace, and place. From vibrant island-hopping adventures to laid-back coastal escapes, every itinerary is designed to balance discovery, connection, and effortless moments at sea.

CHOOSE YOUR PERFECT YACHT

OUR FLEET

From elegant sailing yachts and spacious catamarans to powerful motor yachs – each vesel in our fleet is carefully selected for comfort, performance and unforgettable time at sea.

The Art of Moving Differently

WHY SAILING

When the sails catch the wind, time stretches. Conversations deepen. The coast reveals itself differently – quiet bays, open horizons, real freedom. It’s in these unhurried moments that the sea reshapes your sense of distance, direction, and what truly matters.

RHYTHM

Sail at your own pace

Sail at a pace set by the wind — no rush, no noise, just presence.

PLACES

Access the unreachable

Reach bays and beaches only accessible by sea.

MOMENTS

Moments that stay

Quiet sunsets, open water, and memories that stay with you.

This is not transportation. This is presence.

Explore our curated sailing weeks, discover the routes, or reach out and start planning.

Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.

Mark Twain

Video experience

Video experience

A trip like no other.

Each yacht is its own world—your space to eat, sleep, connect and unwind. No schedules, no stress. Just the open sea, good people and the best stories you’ll ever tell.

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Those Who Know the Waters

MEET OUR SKIPPERS

Sailing is personal. These are the people who turn routes into experiences and weeks at sea into stories — bringing character, energy, and intention to every mile along the way.

Dado
Lead Skipper
12+ years sailing Greece. Explorer of wild islands and remote anchorages.
“I sail to find places where the sea still feels untouched.”
[Skipper name]
Skipper
Passionate about wind, waves and teaching people to sail.
“There is no better day than the one spent on the sea.”
[Skipper name]
Skipper
Adventurer, storyteller, island lover.
“I love showing guests the Greece only sailors know.”
★★★★★
RATED 4.8/5 BY GUESTS WHO SAILED WITH US

Sailed. Shared. Remembered.

EXPERIENCES

Every yacht and sailing route you see here has been experienced by real people. Their feedback, stories, and ratings shape the journeys we offer — week after week. We listen closely, refine continuously, and let genuine experiences guide every detail, so each new departure builds on the trust and memories of those who sailed before.

The sailing experince with YesSail and Dado was great. He did everything to make our vacation unforgettable. He took us to the hidden gems of Aegean Sea. Highly recommended.
Amazing vacation on the Greek sea with highly professional skipper and confortable and safe boat. I enjoyed the routes we took, breathtaking scenaries of Cyclades we visited, as well as funny and friendly people I met. To make long story short - this is a lifetime experience!
This summer, I went sailing for the very first time and honestly, it turned out to be one of the best decisions I’ve ever made. 😊 Not only did I discover the beauty of life at sea - crystal-clear water, quiet bays and sunsets that take your breath away, but I also had the chance to meet some truly amazing people. ❤️ There’s something special about sharing a boat with others for a few days. You bond quickly, laugh a lot, share stories over dinner and create memories that stay with you long after the trip is over. Dado, our skipper, was absolutely fantastic. He’s experienced, calm and clearly loves what he does. He made sure we felt safe, relaxed, and most importantly that we had fun. His knowledge of the sea and the islands made every stop along the way feel like a little hidden gem. If you're still hesitating, don’t! Just go for it. I didn’t know what to expect and I came back with a full heart, new friends and stories I’ll be telling for years. I already know where I’ll be next summer!

FAQ

WHAT YOU NEED TO KNOW

Our FAQ section is designed to give you clarity before you even step on board. From booking details and cabin arrangements to sailing experience, payments, and what to pack — we’ve gathered the most common questions and answered them with honesty and transparency. So you can plan with confidence, knowing exactly what to expect before your week at sea begins.

Q Do I need sailing experience?
No — beginners are fully welcome.
Q How many hours do we sail per day?
Usually 2–4 hours, depending on weather and route.
Q Do we sleep on the boat?
Yes — in comfortable, fully equipped cabins.
Q What should I pack?
Light clothes, swimsuit, towel and a soft travel bag. You’ll receive a full checklist after booking.
Q Who usually joins these trips?
Singles, couples, friends and adventurers — mostly 20s, 30s and 40s. In short: people who love the sea.

ASK us anything

REACH OUT TO US

Whether you’re ready to book or simply exploring your options, we’re here to help. Reach out with your questions, ideas, or plans — and we’ll guide you toward the sailing experience that fits you best. Every great journey begins with a conversation.