CURRENT JOB OPENINGS
Tall Ship Windy - U.S. Coast Guard Master (Captain)
Tall Ship Windy is actively seeking individuals with 100-ton or above U.S. Coast Guard Merchant Mariner Master credentials. We are actively seeking a full-time Captain for April through September for Tall Ship Windy in Chicago. This individual will also have the opportunity to work October through March as a Captain in the U.S. Virgin Islands for Seas the Day Charters USVI. The qualified individual will have significant experience at the helm on vessels between 50 and 100 tons and must also possess a sailing endorsement on their credential. Tall Ship Windy and Seas the Day Charters offers excellent pay and benefits. As important, we offer a fun, exciting and flexible work environment with the chance to travel and grow with a leading maritime tour operator.
Tall Ship Windy - Senior Deckhands
HIRING FULL AND PART-TIME SENIOR DECKHANDS. The Senior Deckhand is responsible in ensuring that all crew are informed of the ship’s policies, the purpose of those policies and the critical nature of each crew persons supporting of those policies. The Senior Deckhand is the second in command and will act with integrity as a supporting conduit between the Captain and the crew. The Senior Deckhand will fulfill all duties and tasks delegated to them by the Captain. These duties and tasks will include bridge watches, harbor watches, anchor watches, administrative work, safety management, physical labor in cleaning, prepping, painting, repairing and maintaining of all surfaces and equipment. The duties and responsibilities also include but are not limited to operating the sails and rigging of Windy underway, maintaining Windy in good working order, ensuring safety of guests and fellow crew while sailing, performing storytelling and other artistic events and providing unique sailing experiences for guests. The Senior Deckhand oversees the preparation of the vessel for sea and berthing and briefs crew members on their deck duties at these times. When guests are on board they oversee and participates in deck operations in respect to guest activities. The Senior Deckhand must be familiar with all aspects of the vessel and be able to assume command if the Captain is absent or incapacitated. Tall Ship Windy offers crew quarters during season in Chicago which runs from mid-April through September. Additionally, qualified individuals are given the opportunity to work at our sister company, Seas the Day Charters in the U.S. Virgin Islands from October through March. Tall Ship Windy and Seas the Day Charters offer excellent pay and benefits. As important, we offer a fun, exciting and flexible work environment with the chance to travel and grow with a leading maritime tour operator.
Tall Ship Windy - Deckhands and Trainees
NOW HIRING BOTH EXPERIENCED AND THOSE WILLING TO LEARN. Outstanding deckhands provide the foundation of any well-run ship. They are integral to the success of any maritime charter. Tall Ship Windy is seeking both qualified deckhands with previous experience. For the right individual, Tall Ship Windy is also willing to hire deckhands in training. The deckhand will fulfill all duties and tasks delegated to them by the Captain and Senior Deckhand. Duties of deckhands generally include: 1) Perform sailing operations of the vessel under the supervision of senior crew and Captain of the ship. 2) Assist with dockside guest services and promotion of the ship’s excursions. 3) Other duties may include performing educational demonstrations, storytelling and attending and participating in promotional activities arranged by or on behalf of the Company. 4) Reasonable duties also may include assisting the Company in flexible job roles from time-to-time, including office work, maintenance projects, bartending and box office staffing. The Deckhand is responsible for cleaning and maintaining the exterior and technical spaces of the vessel to standards and procedures set down by the Captain and Senior Deckhand. The deckhand is to always be neat and in the correct uniform – worn correctly – and that proper routines and disciplines as described within the ship’s policies and standing orders are followed. The deckhand must have a full working understanding of all safety procedures and equipment. Tall Ship Windy offers crew quarters during season in Chicago which runs from mid-April through September. Additionally, qualified individuals are given the opportunity to work at our sister company, Seas the Day Charters in the U.S. Virgin Islands from October through March.
Seas the Day Charters USVI - U.S. Coast Guard Master (Captain)
Seas the Day Charters USVI is actively seeking individuals with 100-ton or above U.S. Coast Guard Merchant Mariner Master credentials. We are actively seeking full-time captains year round in St. Thomas, USVI. The qualified individual will have significant experience at the helm on vessels between 50 and 100 tons and must also possess a sailing endorsement on their credential. Seas the Day Charters USVI offers excellent pay and benefits. As important, we offer a fun, exciting and flexible work environment with the chance to travel and grow with a leading maritime tour operator.
Seas the Day Charters USVI - Charter Crew
For those that want a fun atmosphere while enjoying the crystal blue waters of the Caribbean, a charter crew position with Seas the Day Charters USVI is for you. We are seeking experienced crew who desire full-time positions in the U.S. Virgin Islands.
Meet our LEADERSHIP team
Hope Stawski, Founder and President and Director
Hope Stawski is a customer service and marketing executive with significant management experience in both the hospitality and technology industry. Hope oversees the day-to-day operations of Amphitrite Digital and has been critical to the establishment of our award-winning customer experience programs. Hope also leads the management team in the recruitment of world-class talent for each of our tour activity operator companies.
Hope was born and bred in Fort Worth, Texas with a passion for understanding the world through diverse cultural mores, delicious foods and succulent wines. Her talents have taken her across the globe, traveling both professionally to share her skills and acumen with others and personally to hone her culinary talents and to create a life tapestry from ethnic mosaics. Always with a welcoming smile and friendly fist bump, she’s most at home on the bow of a boat singing the Songs of the Sirens or conversing with the dolphins.
Rob Chapple, Chief Executive Officer and Director
Rob Chapple has a strong track record delivering results by leading and motivating top-performing customer focused business and client teams across global cultures and customer bases. His experience as an executive leader of large teams and serving Fortune 100 organizations, combined with his roles in start-up and growth stage companies where he created and scaled sales, marketing and customer operations, provides an extensive foundation of managing teams that create predictable and profitable growth.
Rob is accountable for all day-to-day operations, at the corporate function and each line of business, and his responsibilities include planning and managing the teams to meet and exceed the goals of Amphitrite Digital and its portfolio of businesses and operations.
Rob is an avid sailor, first learning how to sail while living in Australia and then furthering his qualifications through the Royal Yachting Association while living in the U.K. Rob is a father to three wonderful adult children and he is based in Atlanta, Georgia with his wife.
Scott Stawski, Executive Chairman and Director
Scott Stawski is a seasoned technology executive with over 25 years management experience, most recently as Chief Revenue Officer for DXC Technology (formerly Hewlett Packard Enterprise Services) he was responsible for more than $6B in annual revenue. Scott is responsible for the strategic planning and growth of the company and Amphitrite Digital's digitally enabled sales and marketing programs. He has also been instrumental in building out the company’s overall digital operating platform.
Scott is an avid lover of the beach and the sea and holds his U.S. Coast Guard Merchant Mariners (Captain) license. He has a love of history and completed his Masters at Harvard University.
Patrick Mullett, EVP of Operations and Director
Pat Mullett is a seasoned hospitality executive most recently VP of Operations for Margaritaville Caribbean Group responsible for the opening and management of Jimmy Buffett’s Margaritaville restaurant chain in the Caribbean. Pat is responsible for the day-to-day operations of our charter vessels including Captain and Crew scheduling, training and our repair and maintenance program.
Pat is originally from upstate New York and has had the opportunity to live throughout the Caribbean. When not working, which is rarely, you will find Pat and his lovely wife Teresa traveling the world.
Captain Rick Stage, General Manager of Windy of Chicago LTD
Rick Stage is a USCG licensed 100-ton Master Captain who has lived in Chicago with his wife Amy since 2001. He is a self-taught sailor who got hooked after going for a sail with a friend on a 19’ Lightning sailboat while on vacation in 1994, and he bought his first sailboat two weeks later. Captain Rick believes that sailing takes a weekend to learn and a lifetime to master.
After moving to Chicago, Captain Rick bought his first keelboat with his brother and learned to sail in the vast unforgiving playground wilderness next door to the Windy City - Lake Michigan. In 2008 he was invited to crew in the Chicago Race To Mackinac and has been racing north every summer since. In 2012 he purchased his J/35 Alpha Puppy and started offering sail charters to the public while still finding time to skipper a full racing program, reaching the podium in competitive buoy races like the Colors, NOODs, and Verve. Captain Rick loves to sail in the Caribbean with friends turning a week of February into a week of summer. However, his true passion is offshore racing in the Mac, and the Single Handed Race to Mackinac sponsored by the Great Lakes Singlehanded Society with section wins in both.
Captain Rick joined the Amphitrite Digital family as General Manager of Tall Ship Windy at Navy Pier in 2023 and nowadays you’ll meet him on the Windy dock overseeing everyday operations. Guests aboard Tall Ship Windy may even be lucky enough to meet him at the helm as they sail on Lake Michigan.
Captain Jason Frisbey-Jones, General Manager of Paradise Adventures Catamarans and Watersports
Jason Frisbey-Jones is a USCG licensed 100-ton Master Captain with endorsements and over a decade of experience in the maritime industry. At Paradise Adventures in Panama City Beach, Florida, Jason is responsible for leading all day-to-day operations for the company and a full team of captains, crew and supporting dock, island and kiosk staff.
Born and raised on the coast of the Gulf of Mexico, Captain Jason's lifelong passion for the ocean has been the driving force behind his successful career. From a young age, he felt a deep connection with the sea, and his love for sailing and exploring new waters only grew stronger over time. Captain Jason's extensive travels have taken him to breathtaking destinations around the world.
Working in locations from Fort Lauderdale and Key West in Florida, to Hawaii and New Zealand, he has navigated a wide range of challenging environments and honed his skills at the helm and as a leader. His commitment to maintaining the highest standards in the industry has earned him a reputation for professionalism and excellence.
Captain Holly Payne, Assistant General Manager of Seas the Day Charters USVI
Holly Payne is a USCG licensed 100-ton Master Captain with years of maritime experience, including more than a decade at the helm navigating the waters of the Virgin Islands. She is a leader, responsible for the company’s operations and ensuring captains, crew and support personnel enjoy working as part of an exceptional team as they continue to be a top charter company in the Caribbean.
Captain Holly’s maritime career began on The Arabella, a 160-foot schooner, where she sailed in and around the New England Waters and to the Caribbean. Before joining the Seas the Day Charters USVI team in 2021, she was a freelance captain where she gained extensive knowledge of the US and British Virgin Islands, from both land and sea.
When Holly isn’t out boating for fun, you’ll find her remodeling and renting properties on St. Thomas and St. John or giving tours to friends and family of the beautiful islands we call home.
Captain Hope Sholtes, Director of Guest Services
Hope Sholtes is responsible for the guest experience across the Amphitrite Digital portfolio and has played a key role in implementing the 5-star standard of service that brings our guests back for a day, a week and a lifetime of experiences. Hope started her career in the Amphitrite Digital family as a first mate and then a captain at Seas the Day Charters in the US Virgin Islands. She spent those years developing a thorough understanding of what it takes to make the guest experience seamless, consistent, memorable and scalable. Her tan might be fading as she spends her time strategizing instead of snorkeling, but her passion for the maritime industry and creating lifelong memories is unwavering.
Hope is originally from California and after 5 years of enjoying the year-round warm weather in the Virgin Islands, she now resides in Charleston, South Carolina with her husband Tucker and their black lab puppy, Stout. When not working, you can find Hope camping, traveling and looking for every opportunity to watch the sunset from
a boat or the beach.
Sonni Pank, Director of Marketing
Sonni Pank leads the marketing efforts for Amphitrite Digital and each of its companies. Sonni has an extensive advertising and hospitality background across multiple industries, along with hands-on experience in the maritime industry. She champions brand management and ensures cohesion and efficiency across the various digital technology platforms the company employs. These behind-the-scenes efforts are the first step to ensuring all guests across the Amphitrite Digital portfolio have the best day of vacation.
Originally from the farmlands of Upstate New York, the cold winters and name “Sonni” never seemed to align, so she followed her dreams and the setting sun to the West Coast, landing in San Diego, California. There, she felt the Pacific was too cold and menacing so again she followed her sun, this time to the Caribbean which led right to the doors of Amphitrite Digital’s Seas the Day Charters USVI. With the wind in her sails and always up for an adventure, on her days off you’ll now find Sonni exploring the Gulf Shores in the Florida Panhandle.