Our Complete Cruising Guide to the Chesapeake Bay

14th May 2019

Annapolis, Maryland is quaint, peaceful and a little-known destination for world-class sailing.  With the 200-mile long Chesapeake Bay at its backyard, a downtown steeped in maritime history and home to unusual wildlife, Annapolis lives and breathes sailing. With nearly 12,000 miles of shoreline to explore, you could spend years sailing the bay and still find new places to visit whether you are sailing yourself or hiring a skipper.

We caught up with Erin Houpt, Head of Charter Sales and Brokers for Annapolis Bay Charters, to find out why our base in Annapolis, Maryland, is the heart of sailing in the United States. Annapolis Bay Charters merged with Dream Yacht Charter in 2011. Since then there has been a greater influx of international sailors around the Chesapeake Bay area, creating a vibrant sailing community with visitors from all over the globe.

Discover the Chesapeake Bay
Erin let us in on a little secret, the Chesapeake Bay is the pearl of Annapolis. It is so large and vast that it makes the perfect sailing ground, with the best months being May, June, September and October for weather.

Erin said: “You can  anchor while sailing around Annapolis and have the boat open at night while enjoying the friendly nightlife and general cheery atmosphere.

“Annapolis is popular for its central location and Baltimore is about an hour’s drive away. From there you can take a half-day or full day’s sail to visit the famous Baltimore Science Center and Baltimore Aquarium, as you look out over the glittering Harbour East Marina.

“With Annapolis’ proximity to some of the charming Chesapeake towns, you can access quiet little anchorages off St. Michael’s, Oxford, Cambridge, Herrington Harbour and Solomons Island. Spend a day sampling some of the freshest seafood, or even prepare it yourself after fishing, crabbing and visiting the Chesapeake Maritime Museum.”

Find out more about the Chesapeake Bay region.

Enjoy the hotspot for national and international sailing events
Erin said: “Over the last 10-15 years, racing events in Annapolis have sky-rocketed. Here is just a taster of the many activities you can get involved in. The region really has earned its place as the heart of the sailing community.”

Weekly races: Each year, more people participate in local and national regattas, alongside the local weekly races held every Wednesday, Thursday and Friday nights between April and August.

Boat shows: Annapolis hosts two national boat shows every year with one in the spring and one in the fall. The fall sees the largest in-water sailboat show in the US, and Annapolis was also chosen as the location for the J/22 World Championship regatta in 2018.

Regattas: In addition to national sailing events, the Annapolis Yacht Club hosts the NOOD regatta every year, a nine city sailboat racing circuit, which draws in droves of national tourists and sailing enthusiasts. During the summer season, Annapolis puts on a massive firework show for Independence Day, which sends locals and visitors to their boats for the best view.

Come and meet us at the Annapolis Fall Boat Show and catch up on how last year’s show went.

Explore the wildlife, community and nautical history
Annapolis is known as the location of the United States Naval Academy. During the summer season, blue angels fly above Annapolis in honor of the academy’s graduation, which tends to be one week before Memorial Day.

Erin said: “Ever since elementary school, I and fellow classmates would get pulled out of school and offices would shut down so locals could witness this riveting airshow from our boats.”

The local hotspots are as big a draw as the nautical history. On the Eastport side of Annapolis, Erin suggests:

  • Vin 909 for a laid-back evening sipping delicate rosés
  • For foodie lovers, the crab pretzel at Davis’ Pub is a must-try
  • In downtown Annapolis, Vida Taco Bar serves up some of the best fish tacos on the east coast

For those who want to take a look at wildlife instead of feasting on it, Annapolis is home to blue herons, blue crabs, rockfish and osprey. Osprey nests can be seen all over the bay in the summer. This special sight that can be witnessed on camera, as the local nature conservancies film the nests so you can watch the babies as they hatch.

Find out more about the  wildlife of the Chesapeake Bay.

Three ways you can sail Annapolis with us
Annapolis is unique for its last-minute charters and lack of sailing license restrictions. Here’s how you can explore on the water:

  1. Weekend sailing charters: Locals and east-coasters tend to book two or three-day weekend sails when the weather is clear and the sun is shining. Our base offers a two-day minimum for yacht charters. These are popular with families and large groups throughout the year for sailors wanting  bareboat yacht charters
  2. Skippered charters: You can still enjoy a sailing getaway in the region even if you do not have sailing experience. You can hire a skipper with our skippered charters.
  3. Short sailing trips: This year, Annapolis Bay Charters has teamed up with the Four Seasons Baltimore to offer two-hour happy hour cruises with their boat Vaughanderlust, a 2019 Bali 4.1. Docked at Harbor East Marina, the boat will also offer various chartering packages for longer sailing.

The Four Seasons Hotel Baltimore is on the edge of the marina and offers a luxurious retreat with a five-star spa and rooftop pool. It’s ideal for fabulous vacations with kids, romantic getaways and business stays. Enjoy miles of walkable waterfront, top restaurants and city landmarks all within easy reach. 


Discover more about our Annapolis fleet.

Find out more
Erin Houpt has been with Annapolis Bay Charters for over 11 years, so she knows everything about the area. For more information about sailing Annapolis, or to speak to other experienced team members, email us at infona@dreamyachtcharter.com or give us a call at 855.650.8902.