20 - 27 AUGUST 2016 //


Click here for details


Oh hi. Meet YACHTLEGEND. We are the epitome of luxury fleet yachting. We're here to change your life.


Fleet yachting entails a group of sailing yachts, each berthing about 10 people, traveling together as a fleet from location to location on a pre-determined route for seven days and seven nights.


With a professional skipper guiding each yacht, crews learn to sail with old friends while invariably making new ones. It's no stretch to say that life perspectives and capacities for love and emotion are expanded. Typically, legends are born.

It’s the fleet of like-minded individuals that makes these trips mind-blowingly fun. At YACHTLEGEND, we provide everything you need to live life as a legend for one flat price with luxe amenities and events delivered seamlessly in style. 



Your 30s Are Just Your 20s With Money: 5 Reasons To Look Forward To The Next Decade

"While many people may believe that one’s 20s are the most important years to invest in oneself, the arguments are flawed. They usually go something along the lines of “find yourself, love can wait, prepare now, push your limits, retire at 40.”

Utilize your 20s so you can retire at 40? Wtf happened to our 30s?"

Read More on EliteDaily.com



Probably fair to mention that we at YACHTLEGEND created this company for ourselves. At our core, we want to pull on some rigging, unfurl a genoa, and generally embody yacht as a verb–freedom, curiosity, and audacity oozing from our pores. We'd like you to join us. There’s no better time to learn how to sail and no better way than via fleet. Become a legend.



Are you a discerning young-professional travel hound with some money to spend on yourself and your legacy? Then yes.



The best offer we can make you on YACHTLEGEND is the fleet itself. That's right. The most valuable thing we can deliver is something we can't really control. The people. A whole bunch of them.  Just like you.

Was summer camp about archery and trail mix? Of course not. It was about all the friends who seared that indelible image in your mind of what it means to be a part of something.

Well, YACHTLEGEND's about the same thing. But we know we gotta keep you fed and watered, so here's how we do it:  



•  Our yachts are stocked with food, locally-sourced beer and wine, and non-alcoholic beverages for the entire week.

•  Fabulous snacks, meals, and drinks are prepared daily (even hourly) onboard by YACHTLEGEND skippers and hostesses.


•  Every day, we offer you sailing, sunning, and other maritime activities that will make you feel like a child again.


•  Amazing full-fleet group dinner reservations are pre-arranged at select restaurants along our route, heartfelt speeches included.


•  We show you the way to dance parties, yacht clubs, and other nighttime hot spots in cities that lie in our path.

•  YACHTLEGEND builds a beautiful, relaxing beach picnic replete with s'mores and endless stars above.


•  The YACHTLEGEND price of admission secures your berth on the yachts for seven days and seven nights with all on-water expenses covered for you as a member of the fleet.


•  We place a professional, certified skipper on each yacht offering hands-on sailing instruction, safety supervision, and legend-making guidance every day.  

•  We place a professional hostess on every yacht whose raison d'être is keeping your cup full and mind at ease, including on-board cleaning throughout the week.

•  We never rest on our laurels. Supplies are restocked by YACHTLEGEND crew periodically throughout the week.


•  All marina mooring fees and yacht fuel consumed on the trip are included, de rigueur. You will never be asked to pay for necessities out-of-pocket.



We set sail and let the wind decide where to go and when to return. But for our scheduled world we set some points to fit everybody`s calendar. 
We'll visit some of the most beautiful spots around the Balearic Islands off the coast of Spain, the Greek Islands and the romantic coast of Turkey, or the Island of Ibiza that never sleeps. As we skip along the southern coast of the islands and cruise through the gorgeous archipelagos, you’ll experience the Mediterranean's natural beauty, learn to sail, catch up on sun, and party your heart out. Head to our route page for all the details: Route


We're operating fantastic 50- to 56-foot luxury sailing yachts for one fine-looking flotilla. We inspect all YACHTLEGEND vessels first-hand in their home marinas before chartering, and all of our yachts were built in the last 1-4 years, so these puppies are sexy, slick, and legit. Visit our booking page to see the entire flotilla.


"Why I originally decided to join YL, I have no idea.  But within the first few hours, it became a living euphoria with this magical high that lasted for a week straight! This trip was one of the few things in my life that I have bought that actually made me feel richer!!"    

          - Lisa Ptasinski, YL 2013 alum 

Read More Customer Testimonials 

Stay in touch.  Join our mailing list.

Name *

Follow us on Instagram, Facebook, and Twitter.