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Suggested Itineraries

Annapolis NOW side bannerSituated in the heart of the Chesapeake Bay, Annapolis is of one of the East Coast's most treasured cities. With an abundance of history, a thriving arts district, tons of family-friendly activities, unique shopping destinations, and even more things to do on the water, it's the ideal location to get the full Chesapeake Bay experience. 

With so much happening in Annapolis, we've lined up a few suggested itineraries for you browse through. Feel free to mix and match to build a multi-day itinerary and get the most out of your visit to Annapolis.


Suggested Itineraries

Family Fun in Annapolis

Looking for something to do with the whole family? We've got you covered. Bring the dog along, too! Annapolis has a ton of things to choose from to satisfy everyone in the family. Get out on the water. Grab a bite to eat outside with the pup lounging under the table. Become pirates for a few hours. Hop on a tour and learn about our historic city...more

The Chesapeake Experience

Experiencing the Chesapeake is all about getting your feet wet, tasting its flavors, and learning about its history. Here in Annapolis, the Chesapeake is on full display in all its glory...more

Annapolis History

Annapolis is nothing if not historic. Transformative historical icons such as Jefferson, Franklin, and Washington have wandered Annapolis’ brick streets, frequenting many of the still-standing taverns and buildings in town. Streets lined with 18th-century homes, historic buildings-turned-museums, and centuries-old taverns and pubs make Annapolis a history buff’s paradise...more

Artistic Annapolis

Enjoy exploring art in new cities? Then Annapolis is for you. Consistently ranked as one of the country's top 25 arts destinations, Annapolis is home to over 20 art galleries, along with performing arts studios and live music venues...more

Girls' Weekend in Annapolis

We all need a getaway once and a while. So, grab the girls and head to Annapolis for the weekend. Filled with shopping and dining options, fun activities and a great nightlife, Annapolis is the perfect place to get away with your gal pals for a few days...more

The Annapolis Countryside

Cross over the South River Bridge from downtown Annapolis and, almost immediately, things start to feel different. The traffic dwindles, the pace slows, and you soon find yourself in the beautiful, pristine Annapolis Countryside, where much of what you'll witness appears as if time has stood still for hundreds of years...more

Baltimore, Annapolis, D.C. Weekend

Why not cross off three great cities while visiting Annapolis? A short drive away, Baltimore, Annapolis, and Washington D.C. offer a great, three-day travel experience. Fly into BWI Thurgood Marshall Airport from anywhere in the country, and get your trip started...more

Annapolis Adventure

Seeking a little adventure while visiting Annapolis? We have you covered. From adventures out on the Chesapeake Bay to high-flying, adrenaline-filled activities and tours, there's something to take care of your thrill-seeking needs...more

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Annapolis & Anne Arundel County Conference & Visitors Bureau

26 West Street, Annapolis, MD 21401

Phone: 410.280.0445   Fax: 410.263.9591
Toll-free from the U.S. 888.302.2852

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