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Cruise Annapolis is Now Waypoints Annapolis®

Annapolis, Maryland, September 22 — Established yacht charter company Cruise Annapolis has announced its corporate name change to Waypoints Annapolis®, effective September 22, 2020. The company will continue providing full-service bareboat and captained charter vacations on the historic Chesapeake, and its headquarters will remain in Annapolis, Maryland.

The company has been a member of the Waypoints® charter network since the network’s founding in 2017. The name change reflects the continued growth of Waypoints®, which offers top-notch charter experiences at premier sailing destinations throughout the United States and the Caribbean. … Read More

Category: Around Annapolis, Charter Tips

Why Charter Local? Annapolis is the Sailing Capital of the U.S.!

The Chesapeake Bay is the largest estuary in the U.S., offering so many options to the sailor and boater. From amazing sails under the magnificent Chesapeake Bay Bridge, exploring the many inlets, dropping anchor in a quiet cove, watching the stars at night, or sailing by the famous Thomas Point Lighthouse.  

Not to mention, the many ports you can visit. Starting with Annapolis, you have the U.S. Sailboat Shows in the Spring and Fall, Blue Angels practice and main show during Commissioning week, and the historic treasures of downtown Annapolis to explore. Next is St.Michaels, a short day sail away with plenty to do, including a visit to the Chesapeake Maritime Museum, a tour of the local winery, and shopping. The local hotels on the water offer dockage and free use of the pool for those hot summer days. Oxford, Solomons, and Deale are other quaint little towns that offer a nostalgic feel and are known for their romantic destinations. If you are more into the big city life, Baltimore is close and easily reachable by boat.    … Read More

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Category: Charter Tips

Choosing a Powerboat for Your Chesapeake Charter

Experience the thrill of a powerboat charter trip on the Bay. See more of what the Chesapeake Bay has to offer when you book a high-performance cruising yacht, with the option to take the helm yourself*, or with a Cruise Annapolis provided Captain. Below we explore the reasons why you should choose a powerboat for your next trip:

Powerboats Perks:

 

Speed
Have the need for speed? Look no further! The engine power of a powerboat allows you to zip around quickly and see more of the Chesapeake Bay. This gives you more relaxation time and less time underway. … Read More

Category: Charter Tips

Monohull or Catamaran? Picking the Right Boat for Your Chesapeake Charter Vacation

When planning a sailing vacation, the first step is deciding what kind of yacht you’d like to charter. Your selection will either be a catamaran or a monohull. So what is the main difference between catamarans and monohulls? One is not necessarily better than the other, it depends on what your needs are for your trip. Whichever one you choose, the Chesapeake Bay offers forgiving conditions with a soft bottom, gentle and predictable winds, and multiple charming harbors across the bay. Below are some of the advantages and features of chartering a monohull versus catamaran: … Read More

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