Bed and Breakfast & Inns

1747 Georgian House Bed & Breakfast

This Georgian colonial, built in 1747, is one of the oldest residences in Annapolis and hosted many signers of the Declaration of Independence. All rooms have private bath, TV and high speed internet ...

Pub & Bar

1747 Pub at Reynolds Tavern

Cellar pub that once served as the kitchen and hat shop when during the 18th century. Full service Pub, restaurant with a step back in history. Daily Happy Hour, attentive service and great food! Live...

Events & Festivals

Across The Bay 10K

** Due to mandatory maintenance on the Chesapeake Bay Bridge, the 2019 Across the Bay 10K will be a Virtual Run.** A virtual run is a race you will complete in your own time and place – around y...

Specialty Shops

Alpaca International

Ladies and Gentleman clothing made from the finest Alpaca wool in the world, featured in the flagship store located at 206 Main Street in the heart of Annapolis. Along with shops in Park City, Utah an...

Events & Festivals

Annapolis Arts District

The Annapolis Arts District is comprised of unique venues, bars, and restaurants with local artists experienced in an array of media, experience Annapolis from the flip side of the looking glass. From...

Events & Festivals

Annapolis Arts Week

The eight-day event provides a snapshot of the depth and breadth of Annapolis’ thriving arts and entertainment scene. The celebration is anchored in part by the plein air painting event, Paint Annap...

Boating

Annapolis Bay Charters Inc.

Annapolis Bay Charters is the original sailboat rental business in the Chesapeake Bay area. Enjoy a sailing charter vacation in and around the breathtaking coastal waters. Our agents help you choose t...

Events & Festivals

Annapolis Book Festival

Every year, more than 3,000 people attend the community festival that celebrates the beauty, power, passion and excitement of the written word. The Annapolis Book Festival brings nationally renowned a...

Events & Festivals

Annapolis by Candlelight

A crisp autumn evening is the perfect time to walk through one of the historic neighborhoods of Annapolis. The experience is even better when the doors to some of the homes are open and you are invite...

Kayaking & Paddleboarding

Annapolis Canoe and Kayak

Canoe and Kayak sales and rentals. Expert staff and large inventory on hand. Try before you buy from our floating dock in Eastport directly across from Ruth's Chris Steak House....

Sports Outfitters

Annapolis Canoe and Kayak

Canoe and Kayak sales and rentals. Expert staff and large inventory on hand. Try before you buy from our floating dock in Eastport directly across from Ruth's Chris Steak House....

Events & Festivals

Annapolis Cup Croquet Match

The “Johnnies” and the “Mids” vie for the coveted Annapolis Cup during this annual rite of spring. The croquet match brings together two starkly different institutions for an event Sports Illu...