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Sappho: A Private Hudson River Sailboat Tour with Vintage Vibes

Hoboken is home to some of the most beautiful architecture, expansive parks, and must-try restaurants that the area has to offer. Some say that it’s the perfect balance between hustle and bustle city life and coveted small-town vibes. While we’re out and about, enjoying what this small but mighty city has to offer and trying to make the most of its spoils, there’s a unique opportunity to both embrace the city lifestyle and experience nature to its fullest – a luxury sailboat tour that sails right out from Hoboken Shipyard Marina. This isn’t just any boat or any tour: Sappho is a vintage sailboat that boasts the charm of the 1900s while offering a special experience fit for the times, a private tour of the Hudson River’s best views. Perfect for any special occasion including proposals, graduations, family gatherings, or a GNO, Sappho is the perfect activity for a memorable staycation. Read on to learn more about Sappho located in the Shipyard Marina at 1301 Sinatra Drive, including the history of the vessel, what it’s like to tour on it, and more.

Meet the Team

sappho

^ Captain Sean

Sean Meszkat is the Captain of Sappho. Originally from Merrick, New York, Sean now lives in Clinton, New Jersey. As the Captain, Sean is in charge of every aspect of the boat, including maintenance and scheduling all charter tours. Sean, a lifelong sailor, explained, “I was intrigued with sailing as a youngster. My first experiences with sailing started when I was eight years old on my sunfish boat. As most cities have a common sport, sailing in Merrick, NY was like baseball is to Hoboken.” Sean has been sailing boats in the Hudson River for 12 consecutive seasons, teaching sailing lessons, and giving tours in New York Harbor.

Sean’s favorite part of being Sappho’s Captain? “Meeting and interacting with the people on my tours. People are awed by the beauty of the Harbor and the view of the City from the water. I love to share that experience with them. It never gets old!”

Max Reo is the Sailing Director of the Hoboken Sailing Club and also Sappho’s Co-Captain, which means he assists with leading the tours. He grew up in Fanwood, NJ, and has called Jersey City home for the last three years. Max told us, “The fact that we are building a staple for the community is my favorite part. The Hudson River is Hoboken’s backyard. However, it is sometimes difficult to access all of the educational and recreational opportunities the River provides. We are easing the barrier for the community and adding value and accessibility to the waterfront.”

Read More: Fun Water and Outdoor Activities in Hoboken + Jersey City

sappho

^ Mark, Yasmin, + Sean

Mark Stehli is the Manager of the Shipyard Marina. Growing up on the north shore of the Long Island Sound in Westport, CT was where Mark developed his love for sailing. A Hoboken resident for over a decade now, Mark continues to fuel his passion for sailing through his work at the Hoboken Sailing Club. He oversees the docks, tours, the Hoboken Sailing Club, and the Hoboken Sailing School. “It is an honor and a privilege to be a part of building something special for our community. My favorite part is sharing the joy that people feel when they are developing their skills and having the experience of being out on the majestic Hudson River.”

Yasmin Coto is the Assistant General Manager of the Hoboken Sailing Club and a Hoboken native. She is in charge of managing contractors, engineers, vendors Security of Piers 11-12, and assists with accounting. Yasmin also assists in maintaining the structure of the docks and building Pier 12 as well as plans the Sailing Club’s events. “Working at the Sailing Club is more than just a job to me. Growing up on Hudson Street and always being intrigued by the docks makes working here now that much more special to me.”

As for her favorite part, Yasmin shared, “The roles, duties, experiences, and meeting people, in general, has become quite an experience. It helps one see the full picture of growth in its entirety. I appreciate and respect it. Next season my favorite part will most likely be sailing. Until then, I enjoy it when I have the opportunity of being a passenger on the sailing boat.”

History of Sailboat + Design

sappho

Sappho is a classic 44’ Cherubini sailing yacht designed by John Cherubini of Cherubini Yachts. The vessel is a time capsule in itself, as the design and craftsmanship of the boat date back to the 1920s.

There are only 35 Cherubini 44s in the world, one of which, Silhouette, has won the Marion Bermuda Race three times. The race is a 645-mile ocean race that begins in Buzzards Bay off Marion, Massachusetts, and finishes off of St. Davids Head, Bermuda.

Sappho Sailing Tours

Sappho’s lines are an ode to classic themes in American sailboats including the clipper ships, Chesapeake Bay bugeyes, and some designs of L. Francis Herreshoff, especially Ticonderoga and Mobjack, the team explained to us.

She can sustain speeds over 12 knots, almost 50 percent above theoretical hull speed because of her narrow design and sharp bow.

sappho

The “bow” up top allows for the perfect NYC version of the iconic Titanic “I’m flying” scene. Not only is it a special feature because we are able to live out of dreams of reenacting the beloved Rose and Jack, but most sailing yachts don’t actually have that feature, making Sappho that much more special.

sappho

(Photo credit: Hoboken Sailing Club)

Passengers will be blown away (no pun intended) by the stunning wood details throughout the vessel. The salon boasts delicate blue velvet cushions on the built-in seating along the sides of the boat with stain glass window detail above it – an Instagrammable moment if there ever was one. There’s even a quaint room at the far end of the boat with a bed and small glass ceiling cut-out for passengers to stargaze.

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Locals can book a tour during the sailing season that runs from April through mid-November. Sappho is owned and operated by the Hoboken Sailing Club.

About the Tour + Experience 

sappho

(Photo credit: Hoboken Sailing Club)

The tour costs $750 for a total of six passengers and is a three-hour sail down the Hudson River and throughout the famed New York Harbor. Passengers can enjoy stunning up-close views of the Manhattan skyline, the Statue of Liberty, and more.

What might be the best part of the Sappho experience is that the team will work with you to create the itinerary that you want for your adventure, while adhering to safety and weather guidelines. This means you have an opportunity to adjust and customize your tour to your liking – a major highlight!

Captain Sean and Co-Captain Max are very kind and are willing to answer any questions passengers may have, as they have a wealth of knowledge about sailing locally. They’re also happy to step in as the in-house photographers if needed! The pair definitely add to the charm of the Sappho experience.

As for what it feels like when she’s in her element, Sappho can reach up to 12 knots under sail with just the slightest bit of heel, Captain Sean explained. Feeling the wind in the sails as Sappho glides along the harbor is truly one of a kind experience.

sappho

There is open-air seating on deck, either in the cockpit or on the cabin top.

Passengers are encouraged to bring their own snacks and beverages as the boat is stocked with ice, cups, a refrigerator, and a permanent folding table built into the bed of the boat. There are two small bathrooms, a mini galley (kitchen), and a salon for passengers to make the most of the experience when enjoying their food below deck.

If you’re not sure what to pack as snacks, fret not, there’s a booking option that includes a curated platter of Hoboken famed mutz, fresh Italian bread, and rose wine.

Sappho offers all of the luxuries without sacrificing any of the comforts. In short, she is a strong, expertly crafted, fast, comfortable sail.

See More: Fun Boating Adventures to Try Along the Hudson River

Things to Note Before Boarding

sappho

(Photo credit: Hoboken Sailing Club)

A few tips before you board Sappho from the Captain himself:

  • It’s important to bring clothing based on the weather. A light wind jacket comes in handy as it’s chillier on the water than on land.
  • Sneakers or closed-toe shoes are the best option for the boat so that you are able to maintain balance and avoid any stubbed toes when moving about.

Note: Under extreme weather such as rain or excessive wind, tours will be canceled and rescheduled. Guests will work with the Sappho team to determine a new tour date that works for everyone.

About the Hoboken Sailing Club + School

hoboken sailing club

Hoboken Sailing Club was started in 2016, and the Sailing School was launched a few years later. Despite this recent renaissance, the Mile Square actually has an illustrious history of boating. The Stevens family was significantly involved in the New York Yacht Club, which opened its initial clubhouse, established in 1845, right here in Hoboken.

The Hoboken Sailing Club is geared towards mariners who already have steady sealegs. Such sailors can join under an individual membership ($1,250 per season) or as part of a family package ($1,875 per season). The club is as much fun on land as by sea, often hosting awards ceremonies and other social events at the private Pier 12.

hoboken sailing club

For those who are brand new to the sport, Hoboken’s Sailing School is a great place to start. The program is a two-day course that consists of a classroom component in addition to technical, on-the-water instruction. To learn more about the Hoboken Sailing Club and school, see here.

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Written by:

Victoria is HG's Associate Editor and Social Media Coordinator for the Hoboken Historical Museum + Fire Department Museum. She is a fourth-generation Hoboken native, BNR in the Mile Square, and Jersey City. Through playing softball in town for fourteen years, playing the trumpet for the Hoboken High School Redwings Band, and graduating from New Jersey City University, these two cities have a special place in her heart. When she isn’t Style Assisting or volunteering at Symposia Bookstore, she’s exploring everything the Concrete Jungle has to offer. You can catch her at art exhibitions, local festivities, traveling, diving into a new book, thrifting, or indulging in some form of arts and crafts.