My Denis Sullivan Sailing Experience: What to Expect Aboard the Historic Schooner
By
Lynn Celek
on
September 12, 2025
I spent four days sailing as guest crew on the Denis Sullivan. If you're considering the same, this guide covers:
Background on the Denis Sullivan
Sailing trips for students, adults, and volunteers, including special discounts for Milwaukee residents
My Boston-Gloucester guest crew experience
Unique highlights
What to expect on board: duties, food, sleeping, toilets, and showers, and more.
About the crew
Photo from Sail Training International
Background on the Denis Sullivan
What Is the Denis Sullivan?
The Denis Sullivan is a 137-foot, three-masted schooner modeled after 19th-century Great Lakes cargo ships. Below deck, it has 31 sleeping cabins.
Built in 2000 by volunteers and shipbuilders in Milwaukee, Wisconsin, the schooner was named after Captain Denis Sullivan, one of the longest-serving captains on the Great Lakes.
Where is the Denis Sullivan?
In 2022, Discovery World Museum in Milwaukee sold the ship to World Ocean School, a nonprofit based in Boston, Massachusetts. The goal was to ensure the vessel continued its mission as a floating classroom.
World Ocean School offers hands-on sailing education that teaches students teamwork, ocean ecology, and sailing skills. While many programs are for ages 12–19, there are also opportunities for adults to sail.
Sailing Trips on the Denis Sullivan
Educational Programs for Students
Day Programs – Five-day morning or afternoon sessions for 5th grade and up. Focuses on STEM and social-emotional skills.
Custom Live-Aboard Programs – Up to 18 students live aboard and sail.
Summer Programs – Middle and high school opportunities.
Winter Ambassador Program – Sail to the U.S. Virgin Islands, ages 16–19.
Thanksgiving on the Sea – Nine-day voyage from St. Croix to the Virgin Islands.
Visit the World Ocean School website to learn more about specific programs, destinations, and sail dates.
Volunteer Opportunities for Adults
World Ocean school welcomes adult volunteers.
Positions include:
Deckhand educator
Cook
Engineer
Volunteers can join voyages to destinations like the Virgin Islands.
Trips and Experiences for Adults
Walk the Plank Fundraiser – Brave souls leap into Boston Harbor.
Two-Hour Boston Harbor Sail – Perfect for those who want a short sailing adventure.
Southbound Transit – Sail from Norfolk, VA to Charleston, SC (check dates on the website).
Private Charters – Book the Denis Sullivan for special events.
Gloucester Schooner Festival – A highlight for Milwaukee residents, who can book this trip for just $50 (normally $700+ for non-residents).
Milwaukee residents should contact World Ocean School for other discounted trips.
My Experience as Guest Crew on the Boston-Gloucester Sail
Touring other tall ships during the Gloucester Schooner Festival Open House.
Quick Overview
This four-day adventure is tied to the Gloucester Schooner Festival:
Day 1: Depart Boston and sail to Gloucester.
Day 2: Dock in Gloucester and prepare the ship for festival events.
Day 3: Join the parade of tall ships and a schooner race. End with a community celebration.
Day 4: Sail back to Boston.
Meals and snacks are included, and guests may board the night before departure and stay the night of return.
The Details
Night Before
I boarded the Denis Sullivan the night before we set sail for Gloucester. If you arrive early, you’re responsible for your own dinner, but it’s a nice chance to settle in and get comfortable with the ship before the trip begins.
Day 1: Boston to Gloucester
We departed from the Moakley Courthouse Dock in Boston Harbor around 9 a.m. During the journey, the crew raised all sails to practice before the race. Guest crew were welcome—and encouraged—to help sail the ship throughout the trip.
We arrived in Gloucester in the afternoon and had free time to explore the town. Breakfast, lunch, and dinner were served on board, and we stayed docked overnight in Gloucester Harbor. We were free to go explore Gloucester that evening.
Day 2: Gloucester Schooner Festival
This was the only full day we stayed docked. Guest crew were divided into groups and given light tasks. Those on morning duty helped prepare the ship for the Open House with basic cleaning. A tent was also set up on shore with merchandise and information about World Ocean School.
The festival began at noon and ran until around 4 p.m. Some of us stayed on board to welcome festival visitors, while others staffed the tent and chatted with passersby. All meals were served on the ship, though I went into town for dinner with a friend. The evening was ours to spend however we liked.
Day 3: Parade of Sail and Schooner Race
We set sail around 9 a.m. to join the Parade of Sail, where dozens of tall ships circled Gloucester Harbor together. In the afternoon, we participated in the schooner “race.” With light winds, it wasn’t much of a race, but it turned into a beautiful day on the water.
That day we also had extra guests on board—people who had purchased day tickets to sail with us during the festival.
In the evening, there was a big ceremony and party for all participants, complete with free food and drinks. Our group later ended the night with a dance party on another tall ship docked nearby. It was a long day, but also one of the most fun.
Day 4: Return to Boston
We left Gloucester around 9 a.m. for a relaxed sail back to Boston, arriving in the afternoon. Once the sails and ropes were secured and a bit of light cleaning was done, guest crew were free to leave. I chose to spend the evening exploring Boston and stayed one more night on the ship. Breakfast and lunch were served on board, and dinner was available for anyone who stayed overnight.
Day 5: Departure
A light breakfast was served in the morning before I packed up, cleaned my bunk areas, and disembarked.
Tall ships gathering for the Parade of Sails.
Unique Highlights Aboard the Denis Sullivan
The final day sailing back to Boston had a relaxed pace, which made it a great time to try something new. Guests who wanted to climb the rigging were welcome to give it a go. The crew provided safety harnesses, so even if you’re nervous about heights, you could climb with confidence.
There was also the chance to take the wheel and steer the ship. It looks simple from a distance, but once you try it yourself, you realize just how much skill it takes to keep a schooner on course.
Me climbing to the top of the rigging of the Denis Sullivan.
What to Expect On Board
Learning the Ropes
You don’t need sailing experience. Guests can participate as little or as much as they want—hoisting sails, tying knots, or even steering the ship.
I’m not a sailor, so I started out 100% useless. I got to learn a few knots, roll a few sails, pull a few ropes. I left the ship feeling 80% useless. I was fine with this outcome. But, if you’re more proactive than me, you can definitely learn much more. The crew are there to teach you.
Me helping store the sails.
Festival Duties
Is There a Curfew?
What's the Food Like?
The food was simple, healthy, and tasty, with plenty of fresh fruit and salad available. The crew also made sure to accommodate dietary needs, including vegetarian and gluten-free options. I always felt well-fed, and there were snacks on hand between meals.
Adults are welcome to bring their own snacks as well, but they need to be labeled with your name and stored in the galley to avoid attracting pests.
Below deck dining area. Most meals were served and eaten on deck.
Sleeping Accommodations aboard the Denis Sullivan
Before boarding, I’ll admit the thing I worried about most was sleeping below deck. (I have a hard time sleeping in my own best most nights.) Thankfully, the experience was much better than I expected.
Each guest is assigned a bunk in the main cabin area. The crew is thoughtful about who goes where—older guests or those with physical limitations are given bottom bunks, while younger and more agile passengers are placed on the upper levels. There are no ladders, but I found it easy to climb up using the built-in ledges and benches.
The bunks come with a firm mat, sheets, and a pillow, and some even have extra padding for added comfort. I only had the standard setup, and I slept soundly each night. The mats have a slight lift at the head side. Between the mat’s lift and the provided pillow, I had plenty of head support.
We were told to bring a light blanket, though I noticed the ship had extras available for anyone who forgot. With only a sheet and my thin blanket, I stayed perfectly warm. (I was traveling in August.)
Each bunk has its own reading light, a small fan, and a dark green privacy curtain.
Your pack stays with you in your bunk, but there’s enough room along the edges of your mat to store items. There’s also a shelf that runs the length of the wall.
The ceilings are low, so if you’re forgetful like me, you’ll probably bang your head a dozen times. And it’ll hurt because this ship is SOLID. Nothing creaks or wobbles with the bunks.
I also recommend packing earplugs. Snoring is always a possibility in shared sleeping quarters, though I was lucky enough to have quiet bunkmates.
Overall, I found the bunks cozy, private enough, and surprisingly comfortable.
Bathrooms and Showers on the Denis Sullivan
The bathrooms—called “heads” on ships—were my second-biggest concern.
While Docked
While docked in Boston Harbor, guests can use the “shore head,” which is basically a hotel restroom just a minute’s walk from the dock. It’s open 24 hours. There’s also access to a shower a few minutes away, though it’s a single stall, so sometimes there’s a wait. I didn’t get a chance to use this shower due to the wait, but those that did said it was great.
In Gloucester Harbor, you can use the bathroom at the nearby restaurant if it’s open. Otherwise, you need to walk about 5 minutes to the Harbor Master building. There are restrooms open to the public. They also have a separate shower and bathroom area that can only be accessed by code. We were given the code, and I was able to shower here. The facility is nice and contains two showers in the women’s section.
On the Ship
On board the Denis Sullivan itself, there are three toilets and one shower available for guest use. Two of the bathrooms are located in the main sleeping quarters, and a third is in the pilot house. The pilot house toilet is the easiest to use—it looks like a regular toilet with a push-button flush. The other two are smaller, round marine toilets. To flush them, you need to close the lid to create a seal and then pump a handle several times. It takes a little effort to get used to, but it’s not difficult.
There’s one very important rule: absolutely no toilet paper goes down the toilets. Instead, you toss it into the small covered bins in each bathroom. If you forget and flush paper, the plumbing clogs quickly—as someone on my trip unfortunately proved. The broken toilet smelled pretty bad until it was fixed, but the other two stayed clean and odor-free the entire time.
The single shower on board was better than I expected. I actually had hot water, though the crew reminded us to conserve by turning the water off while soaping up and then turning it back on to rinse. They provided basic body wash and shampoo, but most people brought their own toiletries. I recommend also packing a quick-dry towel and a small mirror, since there aren’t good mirrors available in the ship bathrooms.
In short: the bathrooms and shower are functional, clean, and easy enough once you get the hang of the pump-flush system. They’re not luxury by any stretch, but for a working tall ship, they’re perfectly adequate.
Right: Pump marine toilet. Left: Shower below deck on the Denis Sullivan.
What's the Crew Like?
The crew were genuinely delightful. Since much of their work involves teaching kids and teens, they’re skilled at explaining anything you’d like to learn about the ship or sailing in general. Most of the crew are on the younger side, often volunteers or modestly paid staff, which means they’re there out of passion rather than obligation.
Our captain, Chris, was a highlight of the trip. He was funny, kind, and had exactly the look and energy you’d imagine a schooner captain would have. Sailing with him made the experience even more memorable.
Captain Chris
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