Fountaine Pajot Saba 50

The Latest News From Waypoints Annapolis



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

Category: Around Annapolis

Top Destination Highlight: Solomon’s Island

The Chesapeake Bay has no shortage of destinations on the more than 5,000 miles of coastline. The soft bottom and predictable winds make it one of the world’s top cruising destinations. When you plan your Spring 2020 charter on the Chesapeake, we highly recommend making Solomons Island a stop on your trip.

Solomons Island is a charming, working fishing village located where the Chesapeake Bay and Patuxent River meet. With a large selection of waterfront restaurants, shops, and historical maritime attractions, it has quickly become a favorite for our charters. From our home base in Annapolis, it’s best to sail to Solomons Island in two days. A good itinerary is stopping at Harrington Harbor on the way to Solomons Island and visiting St. Michaels on the way back.  … Read More

Category: Around Annapolis

Sunset Cruise on the Chesapeake

Sunset is one of the best times to be on the water. There’s no better chance to take it all in and enjoy nature’s beauty as the sky transforms from blue to shades of orange and pink. Sunset cruises are ideal for celebrating a special occasion, proposals, or just for fun. Cruising on one of our luxury yachts is truly an experience that will last a lifetime. 

Cruise Annapolis recently took the lucky winners of our Open House Raffle on a Sunset Cruise to Thomas Point Shoal Lighthouse. These guests had the opportunity to sail on our Saona 47, “Dark Star” with our fleet service manager, Mickey Lalor, as our accommodating and friendly Captain. The Fountaine Pajot Saona 47 easily accommodated our 12 cruisers in her many expansive living areas. With three levels of usable space, our cruisers had ample area to relax, mingle, and take in the gorgeous bay views. … Read More

Category: Around Annapolis

Top Destination Spotlight: Coastal Charm in St. Michaels

Once a colonial trading post, St. Michaels has become a popular waterfront tourist destination. The charming historic town on Mayland’s Eastern Shore has plenty of activities, sights, and restaurants to explore. With a little over 1,000 full-time residents and just 25 nautical miles from Annapolis, St. Michaels is the perfect charter trip getaway.

St. Michaels is home to several marinas including St. Michaels Marina and St. Michaels Harbour Inn Marina & Spa which both offer boat slips, refueling facilities and spas. Whichever marina you choose, it’s a great place to dock and start exploring the mainland. … Read More

Category: Around Annapolis, Charter Tips

The Ultimate Birthday Celebration: Chartering the Chesapeake

Birthdays are a milestone that deserve to be celebrated to the fullest! Most of us have a list of traditions on our special day: cutting cake, eating out with family and friends, opening up gifts…. but many of us would love to commemorate another trip around the sun with something special and unique. What better way to celebrate than being surrounded by friends and family aboard a private luxury yacht?

Recently, one of our Charter Experience Specialists did just that. Her trip was taken with a group of 6 aboard “Southern Accent” a Fountaine Pajot Astréa 42. With 3 cabins, 3 heads, and spacious outdoor and indoor living spaces, this yacht easily and comfortably accommodated the entire group. Amanda and her group of friends had quite the eventful trip from Thursday to Sunday:

… Read More

Category: Around Annapolis, Charter Tips

Make the Most Out of Your Bachelorette Party: Charter the Chesapeake

Bachelorette parties are a once-in-a-lifetime unforgettable experience that takes months of planning and deliberating to pull off. Whether you are organizing a bachelorette for a friend, family member or yourself, you want the experience to be truly special and memorable. 

Instead of hosting a typical bachelorette outing to a club or bar, consider treating your close friends to a party on the water on an award-winning yacht. Our personalized yacht experiences are in one of the best sailing destinations in the United States – Annapolis, MD, ‘America’s Sailing Capital’. 

Here are a few reasons why you should take your bachelorette to new horizons on a yacht charter: … Read More

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