Customer Service – Schooner Woodwind

(Annapolis, MD)

The schooner Woodwind operation in Annapolis is entering an exciting new chapter as part of 59º North Sailing. While this is a shore-based, customer-facing role rather than a sailing position, it plays a critical part in delivering the experience our guests remember long after they leave the dock.

As we work to more closely align Woodwind with the broader 59º North Sailing operation, this role may gradually expand to include similar customer service, reservations, or administrative responsibilities on the 59º North side of the business. We’re looking for someone who enjoys being the hub of activity, takes pride in great service, and is comfortable juggling details in a fast-paced waterfront environment.

You’ll be the first point of contact for many of our guests — setting the tone, answering questions, and helping ensure that each sailing day runs smoothly for customers, crew, and dock staff alike.

Customer Service Responsibilities

Serve as the first impression for Woodwind customers; greet and assist guests with an alert, enthusiastic, and outgoing approach
Act as the front-line contact and concierge for visitors by answering questions about the local area and providing directions to the dock
Sell tickets by phone and in person for Schooner Woodwind sailing cruises using reservation software
Answer incoming phone calls and respond to customer emails
Accept docking reservations for the small wharf-side marina
Communicate daily schedules and activities to dock staff and crew
Perform computer, administrative, and clerical duties as needed
Complete daily and weekly inventory checklists
In emergency situations, be willing to adapt normal duties to help secure business property, assets, and/or vessel safety

Background & Experience

Prior experience in customer service, hospitality, or retail is required
Experience with reservation or booking software is helpful
Friendly, professional, and safety-minded demeanor
Boating knowledge or an interest in boating is a plus, but not required

Qualifications

The successful candidate will demonstrate:

Excellent oral and written communication skills
Basic computer skills and comfort working with internet-based software
Ability to use multi-line phone systems
Local area knowledge, or willingness to learn quickly
Ability to lift, bend, and carry 10–15 lbs to access overhead and floor-level storage

Compensation

Customer Service pay is commensurate with experience, with an hourly wage within an established range. A work commitment incentive is available for qualified employees.

Additional Perks

Ability to bring friends and family aboard the Woodwind vessels when seats are available
Employee discounts at the restaurant at the Annapolis Waterfront Hotel

To apply online, click on the "Apply for Job" button below. If you prefer to download an application and mail or fax to us, you may download a PDF application.

Download a PDF Employment Application

Schooner Woodwind & Woodwind II are identical 74-foot sailing yachts available for public sailing and private charter departing from the Annapolis Waterfront Hotel.

Schooner Woodwind also manages and maintains the 360 feet of wharf side dock space (available for transient dockage) on behalf of the Annapolis Waterfront Hotel.

Since 1993 the Woodwinds have been a family-owned and operated company.

Offsite Office: 1930-A Lincoln Drive, Annapolis, MD 21401 (Monday-Friday, 9-5)
Onsite Office & Boats: 80 Compromise Street, Annapolis, MD 21401 (Everyday April 15-October 31)
Phone: (410) 263-1981
Fax: (410) 280-6952
Email: info@schoonerwoodwind.com
Web: www.schoonerwoodwind.com

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