Book Now for a Summer Getaway on the Chesapeake Bay

It might be hard to get in the spirit of summer when there is frost on your car windows each morning, but summer dreams are right around the corner, and it’s time to start planning for your next vacation! Summer is often full of trips to the beach or a resort, but if you are ready to take your vacation to the next level, it’s time to book a charter with Waypoints Annapolis.

Take in Historic Annapolis

When you arrive at our base in the heart of Annapolis, you have high-end restaurants, shopping, and must-see historical sights, such as the United States Naval Academy, to visit before your charter begins. You will have some time to embrace this quaint, welcoming town while provisioning for your trip or sightseeing before you set sail. It will be the first of many amazing places to see on your luxury vacation.


Sailing the Chesapeake Bay

Annapolis is referred to as the Sailing Capital of the World. When you decide to book your charter, you will have endless choices of where to go and what to see along the 200 miles of the Chesapeake Bay. Whether you sail the North or South route, you will be delighted with the waterfront towns, secluded inlets, and all of the national landmarks along the way. When you sail South, you can take in many historical towns on the Eastern Shore of Maryland, including the quaint town of Oxford. You can continue up the Choptank River to check out Cambridge, one of the oldest towns in Maryland, with several must-see maritime museums. Cambridge Creek offers ample anchoring room for those looking for a protected spot to relax.

When you sail North, you can visit Rockhall for a day before making your way to the Baltimore Harbor. Baltimore’s Inner Harbor is one of the most visited features of the city. Both locals and visitors enjoy spending time at the shops, restaurants, and the National Aquarium when they get the chance. You can then set course for Chester River and make your way along Maryland’s Eastern Shore to towns like St. Michaels, with its delicious cuisine and welcoming atmosphere.

St. Michaels
Baltimore, Inner Harbor

No matter which route you take, you are sure to have an experience unlike any other. All you have to do is choose your yacht! Waypoints Annapolis has a full roster of amazing luxury yachts in its fleet that are ready and waiting for your next adventure.

Step Aboard Your Home Away From Home.

Fountaine Pajot Tanna 47

Booking your trip as early as possible allows you to pick the yacht of your choice during the dates that work best for you and your crew. Depending on the type of cruising you wish to do, you can choose from sailing catamarans, sailing monohulls, or powerboats.

New Fountaine Pajot Tanna 47s were added to the fleet this year. This Fountaine Pajot sailing catamaran was named Boat of the Year by Cruising World for 2023. With plenty of lounge areas to take in the Bay views, several cabins for comfortable sleeping, and smooth handling on the water, you won’t be able to resist chartering one of these beautiful yachts.

If you are ready to kick your adventure up a notch, a Dufour 430 sailing monohull, like Opportune Moment, is calling you. This sailing monohull has a dual helm cockpit, an electric swim platform, and all the luxury amenities you deserve. With several cabins, heads, and deck space for entertaining, you can enjoy sailing on the Bay and relaxing with a refreshing swim.

“Opportune Moment” – Dufour 430

If you are looking for speed, flexibility, comfort, and maneuverability, then a powerboat like Knot Home, a Jeanneau NC 33 is a perfect choice. The perks of a powerboat include being able to travel long distances in a shorter time frame allowing you and your crew to see more sights on your itinerary. Chartering a powerboat allows you to see the Chesapeake Bay in a whole new way. These are just a few of the stunning yachts our Annapolis Fleet has to choose from.

“Knot Home” – Jeanneau NC 33

Book Now! Your Summer Getaway Awaits You

While summer is still a few months away, bookings are open for charters with Waypoints Annapolis. Start planning your summer getaway today. Our Charter Experience Specialists are waiting to answer any questions or help you book the trip of a lifetime. Check out our fleet, view our sample itinerary, or book today