Annapolis Maryland Travel Guide

Annapolis, America’s “sailing capital” and at the same time the charming, small capital of the US state of Maryland, is characterized by its marina and its historic atmosphere and cityscape with historic buildings from the colonial era, small alleys and cobbled streets. Annapolis has a total population of 35,838.

The fantastic sailing boats, large and small yachts or motor boats in the port of Annapolis give the backdrop of the old town with its historic Capitol a special flair: here on the fascinating Chesapeake Bay, which is only separated from the Atlantic Ocean by narrow headlands, is the cradle of the Sailing and motor boating.

The charming city is a popular destination for tourists and, in addition to sailing and boat tours, offers numerous historical attractions such as the Maryland State House, the William Paca House and Garden and various museums. Annapolis is also home to the US Naval Academy – the American Navy’s cadet school, which can also be visited. The many shops on the main street invite you to go shopping.

Set sail on the Woodwind yourself

Sail towards the sunset:

The two schooners ” Woodwind ” and ” Woodwind II ” invite you to a special sailing adventure in the port of Annapolis . Every Wednesday evening, the two sister ships duel – very amicably, of course – at “Wednesday Night Racing” on the Chesapeake Bay. Sailing fans can try their hand at being a crew member.

In addition to the daily two-hour excursions, the more than 22-meter-long schooner “Woodwind” also offers private tours as a special experience.

Pirate adventure for kids

“ Pirate Adventures on the Chesapeake ” in Annapolis ensures family fun on Chesapeake Bay: Disguised as pirates, children can get excited about sailing and look for hidden treasures. The adventure begins when the crew pulls a message in a bottle out of the sea and meets the notorious pirate Pete. ( Pirate Adventures on the Chesapeake )

Thomas Point Shoal Lighthouse

Annapolis is home to the most famous screw-pile lighthouse in Maryland: the ” Thomas Point Shoal Lighthouse ” from 1875. The lighthouse is still in active use and is the only one of its kind in its original location off the coast of Annapolis. The building can only be reached by ship, which is why many boat tours to the city’s landmark are offered in summer.

US Naval Academy

For those interested in history, a visit to the US Naval Academy is also worthwhile , because the US Navy’s officers’ school with over 4,000 marines reflects an important piece of American culture and technical achievements. The marina and the many boutiques, art galleries and wine cellars in Annapolis are also worth a visit.

Shopping with an ice cream in hand

The ” Annapolis Ice Cream Company ” opened in the pretty capital of Maryland in 2004, right on the main shopping street, where antique and art dealers, specialty shops and boutiques line up. Owner Nancy Giera offers 36 flavors. Her specialties are the varieties “Apple Pie”, “Peanut Butter Oreo” and “Brownie Batter”. The guests prefer to sit down with their ice cream on the bench in front of the shop and watch the hustle and bustle on Main Street. In the shop itself, the many ice cream spoons painted by customers stand out on the wall. Only a small selection of around 1,000 pieces is shown here, the entire collection now amounts to almost 40,000 plastic spoons.

Chick and Ruth's Delly in Annapolis

Chick & Ruth’s Delly – An Annapolis institution

Since August 16, 1965, the diner has been serving classically pancakes or waffles with syrup, an almost confusing selection of sandwiches and other delicacies. A special spectacle for the visitors: every morning the guests and the staff swear the oath on the American flag.

With the neon advertising and the bright orange shop sign, Chick & Ruth’s Delly looks a bit quirky from the outside. And the inside is also colorful: the colors yellow and orange dominate, an American flag hangs from the ceiling and the furnishings seem to date from the time the shop was opened – a real American, personable diner.

“Keep it old-fashioned. Keep it original. ” Is the motto of owner Ted Levitt and his wife Beth, and obviously also their recipe for success. Since August 16, 1965, classic specialties such as pancakes, waffles with syrup, an almost confusing selection of omelets and sandwiches and many other delicacies have been offered here at reasonable prices. And celebrities like the governor of Maryland taste it too.

You don’t know cappuccino, but there is filter coffee as much as the guests like

Today the restaurant in Annapolis is a real institution and an integral part of the cityscape. It was founded by Ted’s parents Chick and Ruth, but Ted had to lend a hand at an early age. Breakfast is particularly popular with guests and is therefore served throughout the day. Fine coffee specialties such as latte macchiato or cappuccino are not known here, however, good old filter coffee is served. The refill is free, but the friendly wait staff regularly does their rounds with the words “Would you like some more coffee, honey?”.

“The Pledge” is the main attraction for many visitors

For lunch and dinner, burgers, pizza, steak, chicken wings or crab cakes, the specialty of the Chesapeake Bay region, are also on the menu. If you like it easier, you can have a soup or put together your own salad. But you don’t come to Chick & Ruth’s for a salad. Then rather for the supposedly largest milkshake in the world , which weighs a proud 2.6 kilograms (6 pounds).

The main attraction, however, is “ The Pledge ”: Many visitors to the city stop by to take a photo at breakfast when, since 1989, the patriotic employees and guests of the restaurant get up every day at 8:30 a.m. (Saturday and Sunday 9:30 a.m.) Put your right hand on your heart and swear the oath on the American flag.

“A real piece of Americana” and also popular with celebrities

Connie Del Signore, President and CEO of Annapolis & An Arundel County Conference and Visitors Bureau, congratulated Ted and Beth Levitt on their 50th anniversary : “Chick & Ruth’s Delly has become one of the landmarks of Annapolis, a real piece of Americana. For 50 years, generations of locals and visitors have come together in the restaurant, not just to enjoy the food. They come because of the camaraderie, because they have the feeling of sitting here with friends and dining – almost like at home. ”

Celebrities also appreciate this atmosphere: Marvin Mandel, Governor of Maryland from 1969 to 1977, ate his first breakfast the morning after his inauguration at the restaurant’s 1967 “Governor’s Booth” – a tradition that has been maintained by the state’s governors ever since is repeated.

The spelling of the word “ Delly ” in the restaurant name (instead of the usual Deli) is not a mistake: Chick Levitt chose this because it rhymes with “belly”. After all, Chick & Ruth’s stands for cheap and good food, and no guest should leave the restaurant hungry.