Ship
-of-
Fools

Name: Ship of Fools
Start: 2027-05-22
End: 2027-05-28
Location: St. Vincent & The Grenadines

May 22-28, 2027

ST. VINCENT & THE GRENADINES

A CELEBRATION OF THE GRATEFUL DEAD

They taught us that a show could be a pilgrimage and the fans could be a family. They built a new way of gathering, where the music was central, the people were paramount and every day was a new adventure. Now, we’re carrying that spirit to the tropics.

CATAMARAN SAILING

Set sail four times during the week, with each sail ranging from 1.5 to 4 hours.

LIVE MUSIC

You’ll get up-close-and-personal with world-class musicians as they play unique sets.

DAILY ACTIVITIES

Dive or snorkel along beautiful reefs, explore tropical islands and relax on the beach.

Artist Lineup

Grahame Lesh ➤

With the entire catalog running through his veins, Grahame Lesh is Grateful Dead royalty, but his ability to breathe new life into the music is what truly captivates audiences. He’s a torch-bearer and multi-instrumentalist who takes fans on sonic adventures with Midnight North and The Terrapin Family Band, in addition to his highly acclaimed solo releases.

Holly Bowling ➤

With unparalleled piano skills, Holly Bowling would make waves in any genre but lucky for us, she honed her talents as a world-class musician by focusing on the Grateful Dead songbook. She’s sat in with nearly every major player in the jam scene and her solo shows are nothing short of a religious experience.

ANDERS BECK ➤

With a style that balances thoughtful improvisation with reckless abandon, Anders Beck may be the only dobro player in the universe who’s shared a stage with Bobby, Phil, Billy and Mickey. His improvisational skills are central to the psychedelic soundscapes created at Greensky Bluegrass shows, and as the Music Director for Rhythm & Sails, they’ll most definitely be central to this experience.

TRAVIS BOOK ➤

Travis Book was put on this earth to play and sing music. Onstage, he’s joyous, mischievous and groovy, but mostly he’s just an incredible talent. His bass playing with The Infamous Stringdusters has earned him one Grammy (so far), but it’s his work in Falco & Book Play Garcia that guarantees the inaugural Ship of Fools won’t sail without him.

Mark Morris ➤

A multi-instrumentalist powerhouse, Mark Morris is the front man of his band Rapidgrass and has taken his talents around the globe. He’s a human jukebox and a musician’s musician. All of your favorite artists love him and he’s welcomed onto any stage in the world with open arms.

“ THIS MUST BE HEAVEN
‘CAUSE HERE'S WHERE THE RAINBOW ENDS ”

AN ALL-INCLUSIVE EXPERIENCE

Licensed
Skippers

Private
chefs

Queen
Cabins

Private
Bathrooms

Daily
Performances

Unlimited
Beverages

Daily
Meals

Ground
Transport

Full Gallery

HEADS AGREE, IT’S THE BEST THING EVER.

This was one of the best vacations we ever did. If you get an opportunity to go, take it. The people, from the organizers to the crew and the other guests, become your family. Here we are a month later and still can't stop telling people about it.

- Jim B.

Wow! I was told this would be a trip of a lifetime and that was so true. I had the best time. Amazing people, food, music, adventure and time to relax... Thank you for every detail that the crew executed to the highest level.

- Alyse B.

“I was concerned my expectations would exceed the experience but it was just the opposite! The ships, the islands, the ocean, the music but most of all the people, were so far above my expectations I cannot explain.”

- Todd S.

“An unforgettable experience with Rhythm and Sails! From the moment we stepped aboard, we were treated to first-class service, breathtaking views, and a truly unique atmosphere that blends sailing, great music, delicious food and fun people with Caribbean vibes.”

- Ralph Reda

“Unbelievable trip. The scenery, the sailing, the food, the music, and most of all the people made for one of the best trips of my life.”

- Josh Emery

“The mingling of musicians with guests is such a treat and the settings where music is played is absolute bliss. I highly recommend the scuba diving day trip and snorkeling with sea turtles and rays. I can’t wait to return for another epic trip with Rhythm & Sails!”

- Alli Jones

This trip really changed my perspective on vacations. All other vacations I've taken pale in comparison. I don't think you can find anything else close to this.

- Brian Ray

Best travel experience ever! The music was so good, the boats were clean, comfortable and air conditioned, the people I met on the trip are now my best friends, and the boat chef was incredible!

- Jamie Cox

Second year attending this awesome life experience! Everything is so well organized, the crew is amazing, and the other attendees are of like mind and soul, it creates a great community. I will be attending again and again.

- Mark Luna

From the highly curated adventures to the most beautiful scenery, this is the experience of a lifetime! Whether you are a sailing aficionado or never stepped foot on a boat, this trip has it all. The musicians added such an awesome aspect to the trip that made it the most magical experience. When can I go back?!

- Colleen McGarity

SAINTS OF CIRCUMNAVIGATION

Your long strange trip begins on the main island of St.Vincent. Just a 4-hour flight from Miami, it serves as the gateway to the beautiful Grenadine Island chain, which is far less busy than other Caribbean destinations.

Throughout the week, we’ll sail around the beautiful archipelago and you'll get a chance to meet the locals, stroll the white sand beaches and sample the unique flavors that each destination has to offer.

BOX OF ANSWERS

How do I reserve a spot on the trip?

Cabins are limited and you can inquire for availability using the form at the top of this page. We'll set up a time to chat, answer any questions you have and get you placed in a luxurious cabin for the trip of a lifetime. Cabins must be booked in full (2 people). If you're a solo traveler, reach out to us and we'll let you know if there are any other solo travelers looking for a roommate.

Is the trip all inclusive? How much does it cost?

Yes. The trip includes all of the following:

Ground transportation between SVD airport and Blue Lagoon Marina on the day of arrival/departure
Single spot in double occupancy cabin
Snacks, water and n/a beverages on the boat
Unlimited beer, wine and cocktails on the boat
Towels, linens and wash cloths
Access to auxiliary boat for transfers from yacht-to-yacht or yacht-to-shore
Access to stand up paddle board
All mooring, marine park, cruising and docking fees

Payment plans start with just $975 down and the total cost of the trip is $8,970 per person. Unlike crowded commercial music festivals or standard cruises, Rhythm & Sails limits attendance to provide an intimate and exclusive voyage. By bundling premium chef-prepared meals, an open bar, custom ground logistics and daily private concerts, we ensure a seamless, world-class experience from the moment you land.
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What’s not included in the price?

Airfare
Trip Insurance
Food or beverages purchased on shore
Ground transportation before arrival day or after departure day

What kind of food can I expect to eat on the boat?

You can expect to eat a variety of fruit, eggs and protein for breakfast. Sandwiches and charcuteries for lunch, and fresh fish, proteins, and vegetables for dinner. We're happy to accommodate dietary restrictions and allergies and we'll ask you for that info after you book your trip.

Can I request specific food or drinks on the boat?

We're happy to entertain any requests and fulfill them as best we can but please note that not all brands or categories of food and beverage are available in the area.

How many people are on each boat?

Depending on the model and layout of the boat, there will be between 8 and 12 people on each one, with 6 or 8 being guest spots.

How often do the artists play on the trip?

The artists will play a minimum of one show each day of the trip, with the possibility of impromptu sessions along the way.

Can I be on the same boat as my friends?

Yes, subject to availability. If you would like to be on a boat with your friends, or reserve a private boat for your group, please inquire using the form on this page or by contacting us at info@rhythmandsails.com.

Won't You Come With Us?

INQUIRE NOW

Ship -of- Fools