Best Things To Do In Annapolis

 I knew very little about Annapolis before our driving trip began. Our east coast driving trip had already taken us to Raleigh, Norfolk, Virginia Beach, Ocean City, MD and Rehoboth Beach, DE.

One thing for sure when visiting the Washington DC area is to make a stop in Annapolis –dubbed the sailing capital of the world.

Located in the heart of Chesapeake Bay, the area is rich with historical landmarks, maritime adventure, and excellent shopping. Annapolis also features some of the best places to eat on the east coast. 

The best things to do in Annapolis, MD: Dubbed the “sailing capital of the world” Annapolis is home to great sailing adventures, historical landmarks, the U.S. Navel Academy, delicious lobster rolls, fantastic restaurants, excellent shopping and so much more. #sailing #maryland #usatravel

Downtown Annapolis

Sailing in Chesapeake Bay

One of the main reasons we decided to travel to Annapolis was to get out on the water for some sailing. After some research, we discovered the Schooner Woodwind, which is a wooden, 74-foot schooner that gave us a true sailing experience.

The captain let us raise the sails and steer the boat, and enjoy dolphins jumping out of the water right next to the boat.

The Woodwind II was used in the filming of the 2005 classic Wedding Crashers. Check out the boat in this clip from the movie.

Here is our proud captain.

Woodwind II

I look right at home behind the wheel.

Skipper Dave

Our 2-hour cruise sailed by these places:

  • United States Naval Academy
  • Annapolis Harbor
  • Chesapeake Bay
  • Scenic views of Annapolis skyline
  • Severn River

Enjoying the sail

We saw some beautiful yachts in the harbor. Would like to get out on a ride with one someday.

Owned by the Baltimore Raven’s owner, this yacht called Checkmate is currently for sale for a cool $16,400.00.

Checkmate yacht

The crew of the Woodwind II was well versed on the history of the area and how it has played a key role in the history of our country. This trip is well worth it!

Annapolis Boat Show

Annapolis Boat Show

These boat shows have been an Annapolis tradition since 1970.

The 1970 debut of the United States Sailboat Show in Annapolis, Maryland marked a new concept — the first in-water sailboat show in the country.

Today the Annapolis Boat Shows has an unsurpassed reputation for offering the most comprehensive boating exhibitions in the industry.

Each of the 4 boat shows throughout the year gives boaters the unique opportunity to board and inspect virtually every new model on the market, make side-by-side comparisons, and talk to industry representatives about all aspects of buying and owning a boat.

In addition, you can shop from a vast display of boating products and services — everything from financing and insurance to electronics and foul weather gear.

It’s always a fun and informative day exploring boats and boat supplies.

Annapolis Yacht

Places To Eat

1. The Boatyard Bar & Grill

There is no shortage of places to eat in Annapolis and we visited a few of the best dining spots during our few days here.

Our first stop was for some great crab and seafood at the Boatyard Bar & Grill – voted the #2 bar for sailors in the U.S.

Boatyard Bar & Grill

Founded in 2001, The owner’s vision for the Boatyard was to celebrate the Chesapeake Bay lifestyle and other places that Chesapeake Bay sailors and fishermen frequent such as Key West.

We found the food to be excellent. Our meal consisted of calamari, oysters, a fish fry, and a crab sandwich.

Crab Sandwich

Crab Sandwich

Oysters Rockafeller

If you want your seafood fix, The Boatyard is the place to visit.

2. Mason’s Famous Lobster Rolls

Mason's Lobster Rolls

During our road trip to Maine, I did eat lobster but never did eat a lobster roll. I was happy to find Annapolis had a Mason’s Famous Lobster Roll.

The classic lobster roll is served chilled with mayo and butter. The Connecticut roll is served warm with butter. I opted for the Connecticut.

Lobster Roll

Lobster Roll

This was one of the best sandwiches I’ve ever eaten.

Well worth stopping in on your visit to Annapolis.

3. Iron Rooster

This cozy eatery serves breakfast all day. The made from scratch dishes put a new twist on traditional comfort food.

Their signature item is called the Housemade Roostart. Made fresh daily and served warm, these homemade pop tart feature a different flavor each day.

We ordered the apple and the chocolate oreo.

Apple Roostart

Chocolate Oreo Roostart

4. City Dock Coffee

Located right next door to the Iron Rooster, City Dock Coffee is a great place to grab a cup of excellent coffee, enjoy some bakery, people watch and watch what’s going on in the marina.

City Dock Coffee

Great Place To Stay

A great place to stay in downtown Annapolis is the Historic Inns of Annapolis which is comprised of three landmark buildings in the heart of all the action.

The newly renovated Governor Calvert House, the Maryland Inn, and the Robert Johnson House and within walking distance to downtown Annapolis, the Maryland State House, the US Naval Academy, restaurants, marina, and shopping.

We stayed at the Governor Calvert House which combines old world charm and modern touches. A very comfortable place to stay for a long weekend.

Governor Calvert House

Governor Calvert House

We spent only 1-1/2 days in Annapolis but you could easily make it a 3-day trip. We ran out of time, but I would have liked to have toured the US Naval Academy and explored more of the shops and restaurants.

Planning a Trip To Annapolis

For even more tips and information when planning a trip to Annapolis and Chesapeake Bay visit their website. You can also receive a Visitors Guide in the mail.

We can’t wait to go back!

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The best things to do in Annapolis, MD: Dubbed the “sailing capital of the world” Annapolis is home to great sailing adventures, historical landmarks, the U.S. Navel Academy, delicious lobster rolls, fantastic restaurants, excellent shopping and so much more. #sailing #maryland #usatravel

he very best of Annapolis, MD awaits your next visit: Visit the U.S. Naval Academy, great sailing adventures, historical landmarks, the Maryland State House, delicious lobster rolls, fantastic restaurants, excellent shopping and so much more. #sailing #maryland #usatravel

The best food & fun things to do in Annapolis, MD: Dubbed the “sailing capital of the world” Annapolis is home to great sailing adventures, historical landmarks, the U.S. Navel Academy, fantastic restaurants, tasty lobster rolls, crab sandwiches, excellent shopping and so much more. #sailing #maryland #tusaravel

About the Author David

David Kluge is the founder of the Global Travel Boss blog. He loves helping Empty Nesters & Midlife Adventurers create more freedom, travel more, travel smarter, explore destinations, and for less money. He is a travel activist, small business advisor, avid Green Bay Packer fan, and has a Caribbean soul he can barely control.

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