Boat & Bougie

Aug 17 - 24 2024


Boat & Bougie

August 17 - 24 2024

Book your trip

Private Cabin
Private Cabin

Private Cabin

A private cabin includes a double bed, private bathroom with shower, a/c and closet space. This can be for one or two people. For one person the price is $4,750, for two people in one cabin in one bed the price is $2,750 per person.


Pay with a deposit of $687.50/pp.


Sail the Greek Islands

Adventure in Greece
Fitness and Adventure Holidays

Sail the Greek Islands

There's 1,000's of islands in Greece; why not hit them all up on our way from Athen to Porto Cheli? The tiny ones, big ones, sexy ones and even the secret knotty ones (get it..)? We're here to climb every hill top, taste every island's local wine, eat fresh fish, olives and feta, swim in all the hidden coves and snorkel all the sparkling blue corners we can find. Our fleet of catamarans will be our home for the next week. Built for cruising the coasts in the calm warm waters of the Mediterranean, each luxurious cabin has their own bathroom, closet, and air conditioning. On the deck, there are more than enough cushions for everyone to lay out on, shaded areas for your siesta and water-sports equipment for your adventure. Everyday, we'll be sailing in the late mornings to a different port or bay, adventuring on each island, and exploring where the best gyros and drinks at night. Expect luxury, serenity on the calm waters, salty workouts and some serious party vibes all at the same time for a whole 8-days!

fun for daze



Fly into Athen's airport (AIA) and meet us at Alimos Marina by 3pm where you'll board your catamaran! We'll get to know each other and our floating home, safety first! Now typically, on charters we sleep in port the first night, but we're eager and going to set sail as soon as possible around 2 hours before sunset. We head towards our first island: Poros. Once we arrive, we jump in the crystal clear waters, do a little swim workout, and have our first family meal together!



We'll let you guess what the fastest way to wake up is, hint hint it involved jumping into the warm waters of the Mediterranean. After our work, and huge breakfast on deck we'll explore the island before beginning our journey to Spetses, one of the most beautiful towns you'll see on our sail week. Remember though, only the mad men sail against the wind, so be up for change! An adventurous spirit is all you need, be open to exploring Greece's majestic islands and open waters. 



We'll explore the cute cafes of this town after our morning workout on an empty beach and then stock up for our next sail to Porto Heli. 

This is a busy town, we'll take some time to explore it but will probably find a nice cove nearby to set up for the night! Secluded empty beaches all to ourselves is how we like things!



It's time to sail to the magical island of Hydra and explore the famous town!

We have the best lunch spots, the best view points for you next gram moment (and with our photographer, it's gonna be next level), and all the spots that make this place magic in store for today! 



After the morning workout and breakfast we'll make our way to Epidavros where we'll explore by hiking beautiful viewpoints and grab lunch in one of the oldest towns around the area. We'll take a journey to cliff jumping spots only accessible by boat and take our time to enjoy what the magic of Greece really is while sipping a cocktail overlooking an unreal sunset. 



Beyond our usual exploration, workouts, snorkeling and afternoon beers, we're going to explore Dokos. This is where we'll take on a great hike for majestic views and then back on the boats we're going to play our famous 'boat crawl' where each boat sets up a party for everyone else... this will be one of your favorite nights of the whole trip!



It's our last day exploring the beautiful hidden coves and beaches. We'll be visiting Agistri on our way back towards Athens! Here we'll have our last full day together, maybe ride some ATVs if you're up for it! After our land adventures and exploration we'll sail back to Athens and have our last dinner together on deck where we'll have our famous awards ceremony and dance party (among many other surprises)!



We wake up on the boat for the last time, say our thank you's to our captains and make our way out of the port. But don't worry this isn't goodbye, this is just the beginning of a beautiful friendship. 

There are no airport transfers; head into Athens for a day of exploring or to the airport for your flight. 

experience it all


  • Catamaran Accomodations
  • Air Conditioning
  • Full Fitness Programming
  • 4 Dinners
  • 3 Lunches
  • 7 Breakfasts
  • Ocean Kayak
  • Stand Up Paddle Board
  • Water Toys
  • Guided Tours
  • Beach Games
  • Daily Aperol Spritz
  • Unlimited Catamaran Drinks
  • Sunrise Dokos Hike
  • Themed Parties
  • SYB Welcome Package
  • Photographer + Videographer
  • Services of SYB Adventure Leaders


  • International Flights
  • Alcoholic Beverages at Restaurants
  • Airport Pickup/Dropoff
  • 3 Dinners on the Island
  • Travel Insurance
  • Medical Insurance
  • Lunches on the Island
  • Tips for your Captain



cool stuff people said




Live a life that’s impossible to forget, I know I am #greece #sybgreece



“We meet so many people in life, but we connect to the heart of very few” @surfyogabeer #sybgreece



Sunset whites, and a 66.6% chance of resting bitch face. Saved by @trishbird_ …as always 💕



"The breath of life is in the sunlight and the hand of life is in the wind." - Kahlil Gibran #sybgreece #surfyogabeer @surfyogabeer 📸 @martin.straschnoy (& extra shoutout to @mantaszvinas )



Gone sailing #SYBGreece

trip faqs



What about sea sickness?

Money in Greece

Your Captain!

Food & Drinks

What happens if the weather goes crazy?

Fitness Programming

Cultural Tours

Photography & Videography

Travel & Medical Insurance

The Location

Safety in Greece

Full Guide

Please arrive to Athens International Airport (AIA) by 2pm on August 17th so you can have enough time to get to the port to meet us for our departure at 4pm. If you miss this, no problem we can have a speed boat or find a ferry to help you catch up. 

NYC Friends: We recommend taking the nonstop United flight departing August 17th at 5:35 from EWR and arriving August 19th to ATH at 10:10am. 

Recommended depart is anytime convenient on August 24 as we won't have transportation to the airport.

NYC Friends: We recommend taking the nonstop United flight departing August 24th at 12:15pm from ATH.

Our home will be a fleet of luxury catamarans! These cats are sexy and have a spacious deck; they're extremely stable and are the best way to see the islands in luxury comfort! On the deck, there are more than enough sun cushions for everyone to lay our, hammocks to nap on and water-sports equipment. 

Naturally, safety is number one, so upon boarding, we will go over all the essential aspects of keeping us safe aboard, but then let the fun as we head off into the Aegean Sea! 

We rec bringing along motion sickness bracelets from Amazon if you're known to have issues with the motion in the ocean. Additionally, non drowsy dramamine has been a fleet favorite. However, we use 50+ ft catamarans (with A/C) instead of sailboats because of the large pontoons make it a smoother ride.

You NEED EUROS for this trip! Greek Islands and much of Greece do not accept USD or foreign currency. We suggest you play it safe and withdraw Euros while at home to avoid being stressed. In Greece, most ATMs charge a withdrawal fee, so we offer that if you fear you may spend more, bring a little extra cash to avoid any additional fees. We suggest bringing about €300 to €400 to use at bars and a few of our dinners, but otherwise, we've got you covered! 

For reference, the average price of an alcoholic drink is €10. Most Greek Islands we are going to will have ATMs. However, the proximity and location to where we will be located is unclear. We urge you to prepare and withdraw cash before the start of the trip!

Our catamarans come with an amazing, experienced and fun boat captain to take care of our squad the entire week. We spend a lot of time with them and by the end, they feel like a part of our family. Be prepared to learn a few Greek words and go on some wild dingy rides from boat to boat. We ask that each guest brings cash to tip your captain at the end of the week. Ever seen below deck? If so, you know how it goes. 

We hope you're a feta lover, because the Greeks seem to put this stuff in EVERYTHING. We'll either be pulling up to port cities and enjoying amazing dishes at local restaurants are having family meals on our ship home. Either way, you'll be going home dreaming of your meals. 

Alcohol is included on the boats, drink until you can't float, but up to you when we're out and about. 

Don't worry, that's why we've got our local captains to guide us through any winds and storms. It's all about going with the flow -- life's better when it's spontaneous. We'll still be hitting the sexiest spots in Greece rain or shine. 

After a late night, you may not want to wake up and join us for a workout, but we highly suggest it! Included in your trip, the bootcamps and yoga sessions keep us energized. There is nothing better than waking up with the sunrise and sweating with your new friends! Our world-class trip leaders know how to start your day the best way, with a good workout to prime us for a day of adventuring. 

This experience is included in trip fees. 

Greece is the land of ancient artifacts, so obviously, we will be seeing some really old ish. We will be perfectly mixing culture with once-in-a-lifetime adventures and fitness.

These experiences are included in trip fees. 

No need to whip out your phone or camera at any point throughout this trip because we have got you covered. We will have a professional photographer and videographer joining us on this trip to capture every moment. These will be the best travel photos and videos you will ever get; your friends better be ready for a photo dump out of their wildest dreams!! *Drone shots included* 

We highly recommend you get travel and/or medical insurance. This is just for emergencies or unforeseen circumstances. 

We convene in Athens. Fly into Airport Eleftherios Venizelos (AIA) to begin our adventures together! We will explore the Aegean Islands in the Aegean Sea, which is an elongated embayment of the Mediterranean Sea between the Balkans and Anatolia. 

We head directly from Athens to our first island, Kythnos, which has over 60 miles of coastline! From Kythnos, we head to the iconic Mykonos to explore the city streets, ancient ruins, temples, theatres and villas, all while experiencing world-famous DJs dancing the night away. Mykonos leads us to our next destination, Syros, known for its hiking and cliff jumping - don't worry, we will get to experience this firsthand! After a bustling few days, we had to Kea to unwind and soak up the sun. And finally, we return to Athens and fly out of AIA. 

Greece is an incredibly safe country for tourists to visit. Greek cities and islands are trouble-free for the most part, BUT there can be some petty crime & theft, primarily in central touristy parts of Athens. 

The catamarans will have safes for us to leave our valuables in, and we suggest leaving all important items in the safe while we are out exploring - but maybe keep your Yeezys and nice jewelry at home!




Adventure with your best friends you haven't met yet!



Cancelled trips will hold as credit if notified up to 28 days prior.



We are inclusive. Fitness and adventure belongs to everyone.