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
Island hopping · Aegean Sea Professional skipper included Seychelles · Indian Ocean All skill levels welcome Cyclades · Greece From €800 per person Steady trade winds year-round Island hopping · Aegean Sea Professional skipper included Seychelles · Indian Ocean All skill levels welcome Cyclades · Greece From €800 per person Steady trade winds year-round

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.

Why sail with us

Built around people, not packages

Every week is carefully designed so you spend less time worrying and more time living. Whether you're a first-timer or seasoned sailor, we've got you covered from start to finish.

Learn more about us
Expert skippers
Every boat comes with a professional, experienced skipper who knows these waters inside out.
Small groups
Max 10 guests per boat. Intimate, personal, and easy to make lifelong friends.
All inclusive
Boat, skipper, fuel, safety gear and route planning — everything is handled for you.
Rated 4.8/5
Over 500 guests have sailed with us and left reviews that speak for themselves.

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.

Sailboat · up to 8 guests
Nautitech 46
from €1,202
Nautitech 46
View boat →
Sailboat · up to 6 guests
Beneteau 51.1
from €1,599
Beneteau 51.1
View boat →
Catamaran · up to 12 guests
Lagoon 42
from €18,000
Lagoon 42
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Monohull · up to 10 guests
Bavaria 46
from €1,497
Bavaria 46
View boat →
Nautitech 46
View boat →
Beneteau 51.1
View boat →
Lagoon 42
View boat →
Bavaria 46
View boat →

SUBSCRIBE TO OUR NEWSLETER!

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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.”

Sailed. Shared. Remembered.

EXPERIENCES

Real feedback from real guests – shaping every journey we offer.

★★★★★

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.

Mirjana Trobok IT Designer
★★★★★

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!

Marina Andjelic Economist
★★★★★

Sailing can be a beautiful experience, as well as a horrible one. I give much more thought to whom will I give my trust when choosing a sailing agency than when looking for a hotel or a mainland trip arrangement. Happily, with YesSail you need to search no more. They provide excellent organisation and significant experience. They are client oriented, ready for creative solutions, and the allover atmosphere is very friendly. Sailing with YesSail is always a Yes!

Deni Doo Facebook Review
★★★★★

Sailing with YesSail has been an amazing life experience, and Dado, our skipper, is nothing short of incredible, fantastic, amazing, and dedicated. If you are into visiting hidden coves, beaches, salty waters, or getting dirty with volcanic mud, this is definitely the trip for you! Dado thank you for taking us to these amazing places and sorry for your lack of sleep from our late nights!

Stefan Pavlovic Facebook Review
★★★★★

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!

Marina Andjelic Photographer

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.