Spending two perfect days in Annapolis


Many people think that the capital of Maryland is Baltimore. But it isn’t. The capital is the beautiful sailing town called Annapolis. With its 38,000 inhabitants, it is home to the U.S. Naval Academy as well, where 1,200 motivated students start off each year.

With an annual average of 20 degrees, it’s indeed the perfect location for both sailing and tourism.

Day 1: Historical tour

We suggest you spend the first day exploring the historic city’s downtown. Walking around is easy and the distances are short. You can go by foot if you like. All the historical sights are within close proximity. The U.S. Naval academy is a must see and its museum features stunning worthy items such as uniforms, weapons and flags. It can easily take up a whole morning to explore the story of the Navy. After that you might want to grab a bite – fish since you’re right at the bay. How about Mc Garvey’s Oyster bar? Only a short stroll away, they serve delicious seafood all day. Book your table in advance if you like.

Maryland State House is no further than a few minutes away and well worth a small visit. Being a Georgian house from the 18th century, it is still used as a State building and registered as a national historic landmark.

Paca House and Gardens, located in the very same area should be next on your list. Travel back in time and visit the historical house of one of the signers of the Declaration of Independence; William Paca. The gardens will leave you speechless and the interior will remind you of the prestige back in the days.

After this we’d say it’s time to get back to your hotel, freshen up, take a rest and head out for dinner. How does Metropolitan kitchen & lounge sound to you? Located at West street, it’s close to our O’Callaghan Annapolis hotel. Contemporary kitchen and sparkling cocktails.. chose from a wide choice!

There is a great choice of trendy bars in that area. Close your first day with a fine glass of red wine before heading back to sleep and gain energy for a fresh second day:

Day 2: Get to the beach

Having seen historical sights of Annapolis, today it’s time to get to the beach and explore what it has to offer. After all.. it’s a sailing capital. Chesapeake Bay is probably the most famous one of all and allows for long beach-walks. Don’t forget to bring along your camera to snap some pictures of the ships docking at the harbour.

Have a look at the screwpile off-shore lighthouse called Thomas Point Shoal Lighthouse (amongst others) while making the lighthouse cruise hosted by Watermark (leaving at the dock). The tour lasts 90 minutes but definitely is worth it. Book your tickets here.

Probably now it’s time for an ice cream at Annapolis Ice cream company. The Oreo or cookie dough taste are great and you would not want to miss that sweet experience.

Being back in the city centre, it’s time for some shopping. Main street and Maryland avenue are probably the best areas to find some treasures but also side streets are well worth a pit stop and you might be able to find something to bring home in a souvenir shop.

For dinner, there is only one option for us: O’Learys. Only a small cab ride from O’Callaghan Hotels, this is a popular place for another seafood night. Relax, enjoy and come back.


U.S. naval academy
U.S. naval academy

Obviously, time spent in Annapolis could never be enough as it’s such a gorgeous city but if we’d have to give you a plan, it would be this one. However, there is always space for some imagination of your own. Create your day as you like but keep in mind that these are sights you should have seen and restaurants you might want to try out.

See you soon!