Waypoints Annapolis Corporate Charter Outing

Corporate Charter on the Chesapeake Bay

Looking for a unique way to bond as a team? Elevate this year’s corporate outing with a charter aboard a privately-owned, meticulously maintained monohull or catamaran. NCA, Inc. chose Waypoints Annapolis for their corporate event, spending two days and one night on the Chesapeake Bay.

The majority of this group had no prior sailing experience, so they hired captains who navigated the Bay for them while they relaxed and mingled aboard. They rented four of our luxury monohulls, accommodating 21 people in total.

NCA, Inc. Team

Besame Mucho

“We chose to use monohulls for our trip and were really pleased by how spacious and comfortable they were. Each boat held about six to eight people, allowing our team to easily fit among the four boats with plenty of room to spare. The downstairs part of each boat felt like an apartment,” said recruiter Chelsea Markle.

Traveling from out-of-state, most of the team was able to take advantage of our free parking spots (two per boat), with the remainder using convenient street parking nearby.

On their first night, the team explored Downtown Annapolis, enjoying seafood at O’Brien’s Oyster Bar. The next morning, they met early at the Waypoints Annapolis dock and then set sail to St. Michael’s. They brought their own groceries with them and enjoyed charcuterie, finger sandwiches, and chips during their first sail.

NCA, Inc. Team

When the team docked in St. Michaels, they spent the day at the free public pool at the St. Michaels Harbour Inn. “The staff was extremely accommodating and they had amazing frozen drinks which were a great way to cool off after a long day on the boat”, said Chelsea. That evening they explored the quaint, charming town of St. Michaels and ate dinner at Foxy’s Harbor Grille – a restaurant with a beachy vibe where they enjoyed crab cakes, mussels, and burgers. Foxy’s gave them an entire room to themselves and even invited their captains.

Foxy’s Harbor Grille
Foxy’s Harbor Grille

“We fell in love with St. Michael’s. It was a cute, small-town that reminded me of the show Gilmore Girls. Our only regret was that everything in town closed early since it was the middle of the week, so I wish that we had explored the town more during the day,” said Chelsea.

Big fans of the movie Wedding Crashers, the group traveled to see the house where the movie was filmed. “I think that was one of our favorite parts of the trip,” said Chelsea.

Between stops, the group swapped boats so they could maximize their time with the entire team. They also did a group raft-up, tying multiple boats together allowing them to easily hop from boat to boat. A few Waypoints staff members even took a boat out themselves to take pictures of the team jumping off of the boats and enjoying some fun in the sun.

Summer Salt and Opportune Moment
Waypoints Staff

Chelsea described their adventure as a 10/10. “There is a 100% chance that I would recommend Waypoints to my friends and family. The Waypoints team was so friendly during the entire process. They truly made the experience even more enjoyable.”

At Waypoints Annapolis, our goal is to offer a one-of-a-kind way of cruising. Each of our catamarans and monohulls is equipped with high-quality linens, generators, air-conditioning, ice makers, watermakers, and all of the comforts of home, making your corporate event an unforgettable experience.