of contracts returned with payment within 48 hours
increase in transient dockage

Pain Point

Spending significant time manually processing contracts / payments.


Switching from first-come first-serve to advanced reservations and automating requesting / collecting contracts with Dockwa.

Menemsha Harbor Uses Dockwa to Automate Paperwork and Boost Reservations

Marina management can be hectic, especially when you’re in a summer hotspot for boating activity.

Ryan Rossi is the Harbormaster for the town of Chilmark on Martha’s Vineyard. His role includes vessel movement within the town’s waterways, as well as being the marina manager for the Menemsha Harbor.

Menemsha Harbor is a unique and desirable destination for summer boating traffic and is home to many multi-generational fishing families. They run a mix of contracted slips alongside a thriving business with transient boaters.

Like many other busy marinas, Menemsha Harbor would often find themselves chasing paperwork and operating off a largely manual system. Frustration with this was a catalyst for change.

The “Old Way” of Operating

Ask Ryan about the everyday operations for Menemsha Harbor, and he raises two key areas that had administrative headaches: seasonal contracts and transient bookings.

“All of our seasonal contracts for residential slips and private mornings were done through paper forms in the mail,” he says. “So everything would get sent out through the mail on November 1st, and it had a deadline to return your signed contract and your form of payment by January 15th of each year.”

The team at the harbor found they’d spend a lot of time tracking people ahead of the deadline to ensure their contracts and payments went through on time. Ryan adds, “This was very hard to manage because things would get lost in the mail. It was hard to maintain communication with the contracted customers because the only way of contacting them would be by phone, email, or through the mail. It made things difficult.”

A closer in arial photo of Chillmark Harbor showing boats docked and a busy marina.

Transient Slip Bookings

Transient bookings during the busy seasons represented another set of challenges. The slips in the harbor are different widths, so they must make the reservations of those slips based on booking an appropriate slip width. Transient boaters would typically have to call the harbor at 7 am on arrival day to try and secure space to fit their vessel. Of course, space was not always available, so boaters had difficulty planning. They would generally only know their plans on the day of their journey.

For Menemsha Harbor, this meant they weren’t always maximizing their opportunities to rent space to transient boats. Many people prefer to be able to plan ahead, so Menemsha would often miss out on their business.

Introduction to Dockwa

Ryan and the team first came to Dockwa to find a solution that would improve their transient booking system. They found that the online reservation system through Dockwa created a streamlined solution for them and their customers. Instead of 7 am phone calls, customers could make a reservation request online, which the harbor team could then accept or decline.

“It has definitely streamlined the process for us,” Ryan says. “After one season of the transient interactions, we decided that it would be good to bring everything into Dockwa because of the seamlessness of the use of the program.” The convenience included bringing all the harbor’s contracted residential and private mooring customers into the program.

Using Dockwa, Menemsha had 30% of contracts returned with insurance registration information and payment within 48 hours. This represents a huge time saving, compared to the old mail-in system.

How was the transition for them? “The support was fantastic,” says Ryan. “We're a very unique harbor, so our reservations have to be based on slip width. They were able to tailor the program uniquely to Menemsha Harbor to fit our needs.”

Ryan says they found the help desk to understand their business and how to genuinely help. “I can contact someone from Dockwa, from the support team just by clicking on the feature in Dockwa. If I have any type of issue with a certain reservation or anything within the system, I can just chat with them, and their support team is on it within a matter of minutes,” he says. “They're very responsive; they understand the struggles that we have as a marina and are very, very capable and responsive in helping with those problems.”

Revenue certainly increased just after one season of using Dockwa

Ryan Rossi
Harbormaster - Town of Chilmark

Slashing Office Paperwork

Managing filing and paperwork had been time-consuming under the harbor’s previous paper-based system. Ryan describes concerns such as losing paperwork or contracts in the mail. However, Dockwa has transformed that system, allowing Ryan and the team to slash paperwork and locate critical information and documents easily.

“It really just makes things a lot more organized for me,” says Ryan. “That's probably the biggest benefit to us - having everything in one centralized location, that we don't have to worry about misplacement of documents, or losing payments or, you know, missing checks or anything like that.”

Dockwa also helped Menemsha Harbor to streamline communication, especially with transient boaters. “One of my favorite features of Dockwa is the chat feature,” says Ryan. ‘It allows us to communicate with the transient boaters easily just by sending a chat message to determine what their ETA might be to the marina or if we have any questions regarding their boat specifications.”

The chat feature has allowed Ryan to reach boaters reliably to communicate critical information. “A lot of boaters, when they're sailing or steaming, I can't just reach out and call them all the time. So I'll send them a Dockwa message, and when they get that message, they can usually get back to me in a timely manner and let me know what their ETA might be to the vessels so that we can coordinate where we're going to station our personnel and when people are going to arrive so that we don't end up with too much to handle at once,” he says.

Improving the Customer Experience

How have customers felt about the move to Dockwa? Ryan describes how they initially experienced resistance, particularly from transient customers used to their old system. “But after putting it in place and going through one season, the customer satisfaction was very good,” Ryan says.

You just need to see customer reviews of Menemsha Harbor to understand the level of satisfaction. With predominantly 5 star reviews on Dockwa, Menemsha is offering a warm welcome and efficient service that has customers coming back for more.

The most significant benefit for transient customers is that they no longer have to call at 7 am on their planned arrival day to try to book a dock. Those customers can now plan their trips according to their reservations rather than having to make last-minute plans when space is unavailable.

Customers with seasonal contracts also had an improved experience since the introduction of Dockwa. With all their contract and payment details filed electronically, they no longer had to worry about missing contract deadlines due to missing paperwork.

Growing the Business

Ryan and the Menemsha Harbor team found some additional benefits to the business from shifting to Dockwa. Firstly, they experienced an increase in awareness of the harbor among boaters.

“Being able to have a reservation-based program certainly opened up more opportunities, and it increased the awareness of our marina to different customers that weren't otherwise aware of it before,” Ryan says.

Dockwa’s marina management software offers a built-in network of hundreds of thousands of boaters. Menemsha Harbor benefits from leveraging the platform to boost visibility and awareness among boating communities.

Another benefit was an increase in revenue since the introduction of Dockwa in 2019. “Revenue certainly increased just after one season of using Dockwa,” says Ryan. Financial reports from the City of Chilmark indicate that the revenue from transient dockage grew by over 500% within a year of introducing Dockwa.

Chillmark Harbor arial photo on a nice day showing the beautiful blueish clear water and the marina.

Streamlining to Success

For Menemsha Harbor, upgrading from its paper-based system to Dockwa’s cloud-based marina management system has delivered a streamlined process and successful business growth. They’re spending less time on paperwork and more time on essential harbor management activities. Importantly, their customers are happy with the change and are reaping the benefits.

If any other marinas are sitting on the fence, wondering if it’s time to change to Dockwa, Ryan says: “It's just something that has evolved into a much easier system for us, for my staff, for my staff, for everyone. Just the organization alone is enough reason to use this program for any marina.”

Dockwa Knows Marinas

30% of all Dockwa employees are former marina operators.