Winter Ambassador Voyage
Make unforgettable memories during your winter break aboard tall ship Denis Sullivan this year. Come aboard our 137’ wooden schooner as we sail throughout the Virgin Islands. This program is designed to allow young sailors and aspiring sailors ages 14-18 to step outside their comfort zones, make new friends, and see new places - all within a supportive learning community.
Sail the Caribbean This Winter — Your Adventure Awaits!
Watch a Program and see YOURSELF onboard
Your greatest winter ADVENTURE starts here
Winter Ambassador Voyage
Island-Hop by Tall Ship: Sail by day, anchor by night, and chart your own course through the Caribbean. (Exact itinerary to be determined based on the best winds and weather!)
Hands-On Sailing Skills:
Learn to crew a tall ship, navigate, hoist sails, and take the helm — all alongside professional mariners.
Epic Shore Excursions: In past voyages, students have:
Climbed historic lighthouses
Kayaked in glowing bioluminescent bays
Snorkeled vibrant coral reefs
Played kickball on the beach followed by ice cream parties!
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December 27, 2026 - January 02, 2027
Students will board the boat in St Croix on the 27th and then leave the ship on the 2rd
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$2,700 per student
This covers all food, board, instruction, and program activities aboard our iconic tall ship.Worried about the cost?
Don’t be. We offer generous need-based scholarships and are committed to making sure that no student is turned away due to financial circumstances. -
Students will embark from St. Croix, USVI on an unforgettable journey, sailing through the US and Spanish Virgin Islands
Dive into crystal-clear waters as you snorkel in vibrant reefs, paddle through magical bioluminescent bays, and visit historic lighthousesescription
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For high school students ages 14–18
Step aboard the schooner Denis Sullivan and sail alongside a professional crew — including a U.S. Coast Guard–certified Captain, Cook, Mate, Engineer and a team of Deckhand Educators.
Ready to set sail?
No experience is necessary — just bring your curiosity, teamwork, and a sense of adventure!
Application deadline November 1st
Stay Connected!
While you're away living your adventure, your family and friends can follow along! Our online Ship’s Log and “Where’s Denis Sullivan?” tracker will keep them updated on your journey across the islands.
The Denis Sullivan
The Denis Sullivan
Denis Sullivan is a 137’ wooden schooner owned by World Ocean School. She is our newest ship and is the sister ship to our schooner Roseway. She was built in 2000 in Milwaukee, WI after nearly a thousand people donated a million hours to complete her construction. She was built as the flagship of the State of Wisconsin and now makes her home with World Ocean School in Boston and St. Croix.
Life Aboard Denis Sullivan!
As a Winter Ambassador, you will get a taste of life aboard a tall ship - which means you'll live just like our professional crew members! You'll sleep in single bunks in our "Main Hold" compartment and get clean by soaping up and jumping into the ocean (or rinsing off with buckets if you're not in the mood for a swim!). When it’s time to eat, our cook will keep you nourished with three meals per day.
Each day, you will be part of a Watch Group, a group of 5-7 students who rotate through “watches” which are onboard activities related to sailing the ship. Your Watch Group will be led by Watch Leaders, our experienced deckhand educators. Learn more about Watch Rotations below!
Joining you will be 12 professional crew including a Coast Guard Licensed Captain, Mate, Deckhand Educators, an Engineer, and Cook.
The Ambassador experience immerses students in onboard living, sailing, and nature. Students' cell phones and any other technology are stored away for the duration of the voyage.
Watch Groups
Aboard a tall ship, your watch group is your home base—a group of 5-7 students with two or three crew members acting as your Watch Leaders. You'll rotate through all kinds of activities with your watch group while you're on board.
Chores
Everyone helps keep things clean aboard Denis Sullivan—all students participate in chores like washing dishes after meals and scrubbing Denis Sullivan's deck with the saltwater fire hose!
Daytime Rotations
While you sail, you and your group will rotate through three stations:
Active Watch
When you are on Active Watch, it means that your group is responsible for all aspects of sailing the ship, from steering and sail handling to completing hourly boat checks.
Seamanship Lessons
During Seamanship Lessons, your watch leaders will teach you a little bit of everything you need to know to be a sailor - knot-tying, shanty-singing, navigation, and more!
Reading & Reflection
Reading & Reflection is for taking a break from the action of the ship - time to read a book, write in your journal, draw the sunset, or just watch the ocean go by!
FAQS
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Definitely not just chores! Life aboard Denis Sullivan is full of fun and unforgettable moments.
You'll sail in small teams or watches and bond with your crew through shared challenges and wins.
Off-watch, enjoy board games, movie nights, sea shanties, guitar sessions, and stargazing.
Onshore adventures might include climbing a lighthouse, shucking oysters, snorkeling a reef, or ice cream sundaes after kickball.
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You absolutely belong here — just as you are.
We welcome every personality type: quiet thinkers, bold leaders, and everyone in between.
The ship runs on teamwork and respect, not popularity or extroversion.
You’ll be encouraged, supported, and appreciated—and you might even surprise yourself.
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Nope!
Most students come aboard with no sailing experience at all.
Our crew will teach you everything you need to know—step by step.
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Students will be surrounded by a professional, caring, and experienced crew.
10–15 full-time staff including a USCG-certified Captain, Mate(s), Cook, Engineer, and Educators
2:1 student-to-crew ratio ensures constant supervision and support
Staff provide hands-on mentorship and create a safe, inclusive learning environment
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Yes — we’re committed to accessibility for all families.
Full and partial scholarships available, especially for students from Boston, St. Croix, and Milwaukee
Just indicate your need in the application and we’ll guide you through the next steps
Don’t let cost stop you—if you’re excited to join, we want to help make it happen
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We’ve got you covered.
Our registration process collects important health and dietary info so we can prepare in advance
A full-time Cook and Medical Officer ensure all students are safe, supported, and well-fed
Have a concern? Reach out anytime—we’re happy to discuss accommodations
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Absolutely.
Students gain confidence, responsibility, leadership, and teamwork
Real-world learning supports subjects like science, math, and history
Exposure to maritime careers (and potential sea time for certifications!)
Stand out on applications by showing initiative, resilience, and hands-on experience