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Annapolis
Historic charm and scenic corners abound in Maryland's waterfront capital city.
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Pet-Friendly Things to Do in Annapolis, Maryland
Curated by
Jill Albino
Annapolis, Maryland is a idillic waterfront town with great food, history and plenty of things to do that are both fun and pet-friendly. I stayed in Annapolis for 4 months and fell in love with this beautiful town and the amazing pet-friendly community.
Local's Guide to History & Food in Annapolis, MD
Curated by
Jessica Rausch
I grew up in this unique waterfront town and still visit a few times a year. I love that Annapolis feels different during each season, but my favorite time of year is October, when you're surrounded by crisp air and autumn colors during the annual boat shows. There are plenty of great restaurants, bars and boutiques in walkable downtown, many with live music nightly. Don't miss out on getting live steamed blue crabs by the dozen — locals won't mind teaching you how to open and eat!
Dog-Friendly Getaway to Annapolis, Maryland
Curated by
Jamie Reynolds
Annapolis, Maryland, known for its historic charm and scenic waterfront, is a city that warmly embraces dog owners. With its abundance of parks, trails and pet-friendly establishments, Annapolis offers a plethora of activities for those looking to spend quality time with their beloved canine companions. In this guide, we will explore some of the best dog-friendly spots in Annapolis, allowing both residents and visitors to create memorable experiences with their furry friends.
A Food Lover's Guide to Annapolis, Maryland
Curated by
Kate Kempler
Situated on several large tributaries of the Chesapeake Bay, Annapolis is the capital of Maryland. It’s a quaint, historic city with lots of heart and personality. It’s perfect for a long weekend with the family, a girls trip for some good food and spa time or just a nice place to visit for a day if you’re staying in Baltimore or Washington, DC.
Weekend Getaway in the Sailing Capital of America: Annapolis, MD
Curated by
Nicole Todd
A weekend getaway in Annapolis, Maryland offers a delightful blend of quaint beauty, lively local culture and waterfront views. Nestled on the Chesapeake Bay, this charming town is perfect for a relaxing yet engaging escape.
Start your visit by exploring the cobblestone streets of the historic district, where colonial buildings (*1) and unique shops give you a glimpse into the past. You can stroll along the waterfront, where the scenic views of the harbor are breathtaking (I personally love the view during sunset) or take a leisurely boat tour to see Annapolis from the water.
History enthusiasts will appreciate a visit to the Maryland State House, one of the oldest state capitol buildings in continuous legislative use. The United States Naval Academy, where I had the pleasure of working in the past, is another must-see with its magnificent architecture and beautiful campus (also known as “the Yard”) overlooking the water.
For those who enjoy great food, Annapolis is a promising foodie haven. You can dine by the water at one of the many seafood restaurants, savoring local delicacies like crab cakes (or crab dips!) or oysters.
Outdoor enthusiasts can enjoy a variety of activities, such as biking along the water, kayaking and sailing. The city also offers beautiful parks like Quiet Waters Park, where you can enjoy art exhibitions and nature walks.
Overall, a weekend in Annapolis feels like stepping into a peaceful retreat with the perfect mix of history, modern charm, and nature. Whether you are there for relaxation or adventure, the city’s welcoming atmosphere will make it an unforgettable experience.
*1. Notable colonial buildings include:
1. Brice House
2. Maryland State House
3. St. Anne’s Church
4. The Hammond-Harwood House
5. William Paca House and Garden
Suggested Fora Advisors
See AllJill Albino
Adventurer who loves exploring and being on the move. I am a designer and mother of three – and four if you include the pup! My family and I share a passion for traveling, design and eating at the best restaurants.
Jamie Reynolds
A passion for adventure and putting together amazing experiences through meticulous attention to detail. Entrepreneur with a background in sports and athletics administration. The more I travel, the longer my bucket list gets.
Jessica Rausch
A luxury resort architect and designer, a lifelong hotel junkie and a culture enthusiast. Based in Florida with roots in the Northeast, Hawai'i and Australia.
Melissa Wood
A DC local and long time travel planner for friends, I am excited to curate a DC experience for you that only a local can provide. Whether you are looking for a tour of the monuments or the wineries in Virginia — I am skilled at finding the best deals and experiences for everyone!
Kate Kempler
Maryland-based travel enthusiast who loves the challenge of planning the perfect trip.
Nicole Todd
Bilingual travel advisor with a diverse professional background and a sharp eye for detail. I design personalized, high-touch travel experiences — from refined getaways to bespoke luxury escapes — for clients seeking meaningful and memorable journeys.