Thinking of Moving to Annapolis? Here’s Your Complete Guide to Chesapeake Bay Living

Thinking of moving to Annapolis or Anne Arundel County? This curated guide is your go-to resource for discovering what makes the Chesapeake Bay lifestyle so special. From can’t-miss holiday traditions and top-rated restaurants to family-friendly activities, wellness spots, and waterfront adventures, we’ve rounded up the best of local living to help you feel right at home. Whether you're relocating, purchasing a second home, or simply exploring the area, you'll find everything you need to live, dine, and thrive in Maryland’s capital region.

Mark Your Calendars for These Signature Annapolis Events & Festivals

Annapolis is known for more than just its waterfront charm—it's a city that celebrates all year long. From boat shows to holiday parades, these signature events and festivals are must-sees for anyone living in or moving to the area. Mark your calendar and join the fun!

• May Day: (May 1) May Day in Annapolis is a vibrant celebration of spring, where historic downtown comes alive with stunning floral displays adorning homes, shops, and storefronts. Stroll the brick-lined streets of the Annapolis Historic District and marvel at the creativity of hand-crafted flower baskets, a cherished tradition that draws visitors and locals alike. Don’t miss this iconic event, perfect for those exploring Annapolis' rich history, seasonal events, and picturesque charm!

• Commissioning Week: (May 14-23, 2025) Naval Academy graduation, a.k.a., Commissioning Week, is an electrifying celebration filled with parades, concerts, and the jaw-dropping spectacle of the Blue Angels soaring overhead. It’s a week of pride, tradition, and unforgettable moments! It’s called Commissioning Week because instead of graduating, the Midshipmen are commissioned into their service roles across the Navy and Marine Corps after leaving the Academy. (Blue Angels Practice Day – May 20, 2025 & Blue Angels Performance Day – May 21, 2025).

• Sherwood Forest Fireworks: (July 3) The Sherwood Forest Fireworks are a breathtaking Independence Day tradition that lights up the skies over the scenic Severn River, offering one of the most stunning displays in the Annapolis area. This annual celebration is a cherished event for locals and visitors, with vibrant fireworks reflecting off the water, creating a magical experience. This tradition always takes place the day before Independence Day on July 3, and is a must-see highlight of Annapolis' summer festivities, blending patriotic pride with the natural beauty of the Chesapeake Bay.

• Annapolis Rotary Crab Feast: (August 1, 2025) The Annapolis Rotary Crab Feast is a beloved summer tradition that brings together locals and visitors for a fun-filled afternoon of cracking Maryland's iconic blue crabs. Held annually, this community event offers an all-you-can-eat feast, featuring the freshest Chesapeake Bay crabs, complemented by delicious sides and local fare. Beyond the tasty seafood, attendees enjoy live music, raffles, and a lively atmosphere, all while supporting local charities through the Rotary Club's fundraising efforts. Whether you're a seasoned crab enthusiast or new to the experience, the Annapolis Rotary Crab Feast is the perfect way to savor the flavors of Maryland and soak in the festive spirit of the Chesapeake Bay!

• Maryland Seafood Festival: (September 2025) The Maryland Seafood Festival is a can’t-miss celebration of Chesapeake Bay cuisine, offering a mouthwatering array of fresh seafood dishes, from classic crab cakes to oysters and beyond. Set against the stunning backdrop of the Chesapeake Bay, this annual event combines delicious dining with live entertainment, family-friendly activities, and artisan vendors. Whether you're savoring local flavors, enjoying music, or taking in the coastal views, the Maryland Seafood Festival is a quintessential Annapolis experience for foodies and festival lovers alike!

• Annapolis Boat Shows: (Powerboat Show- October 2-5, 2025, Sailboat Show- October 9-13, 2025) A must-see for sailing and boating enthusiasts featuring luxury yachts, innovative marine technology, and signature Annapolis cocktails like the famous Painkiller, all set up along the bustling Annapolis harbor. The Annapolis Boat Shows, the first in-water boat shows in the U.S., continue to captivate boating enthusiasts and influencers from around the globe each year!

• Eastport Yacht Club Lighted Boat Parade: (December 14, 2025) The Eastport Yacht Club Lighted Boat Parade is a dazzling holiday tradition in Annapolis, where boats decked out in sparkling lights glide across the harbor, creating a magical waterfront spectacle. This must-see event perfectly captures the festive spirit and maritime charm of Annapolis during the holiday season!

• Tug of War: (First Saturday in November) A quirky Annapolis tradition, where Eastport and Downtown Annapolis battle it out in a lively, good-natured tug-of-war across the water, celebrating community spirit with plenty of laughs and local pride.

• Sock Burning: (Mid-March) Welcome spring by burning winter socks in a beloved maritime tradition, signaling the start of boating season with live music, seafood, and a community bonfire. Be sure to snag your tickets in January as this event is always a sell-out!

• Dinner Under the Stars: (Wednesday & Saturday – May – October) West Street transforms into an elegant al fresco dining experience with twinkling lights, live music, and exquisite cuisine from some of the best restaurants in the city.

• First Sundays: (First Sunday of the Month, May to November) A monthly celebration of local art, live music, and food vendors, where visitors can explore artisan markets, enjoy street performances, and discover hidden gems in downtown Annapolis.

Historic Adventures in Annapolis

Discover a city where the past meets the present, a Museum Without Walls: Annapolis is a vibrant blend of rich history and modern life. From the oldest state house in continuous legislative use to the birthplace of the US Naval Academy, this city is steeped in stories of democracy and innovation. Echoes of the Susquehannock tribes, who once fished the bay’s shores, remind us of the region’s deep roots. In Annapolis, history seamlessly intertwines with the present, creating an inviting atmosphere for all who wish to explore its legacy.

• Maryland State House: Stroll through the historic halls where George Washington once stood and resigned as Commander of the Continental Army, and explore the nation's oldest State House still in continuous legislative use.

• William Paca House & Garden: Tour the elegant Georgian mansion and its lush, restored gardens and learn about its namesake, William Paca, one of the four signers of the Declaration of Independence from Maryland. All four signers from Maryland had homes in Annapolis. Charles Carroll of Carrollton (Charles Carroll House), Samuel Chase (Chase-Lloyd House), Thomas Stone (Peggy Stewart House- closed to the public). All but the Peggy Stewart House remain open to the public.

• Hammond-Harwood House: Admire one of the finest examples of colonial architecture in the United States, designed by William Buckland, and said to have inspired Thomas Jefferson’s Monticello.

• United States Naval Academy: Tour the historic Yard, learn about Midshipmen life, and visit its Beaux-Arts designed campus at the mouth of the Severn River and the Chesapeake Bay, the crypt of John Paul Jones- Father of the American Navy, and its world-class nautical museum.

• Banneker-Douglass-Tubman Museum: Maryland’s only museum dedicated to African Americans from Maryland and historic and notable figures of the African Diaspora. The museum offers rotating exhibits and is a registered site on the International Underground Railroad Trail.

• Annapolis Tours and Crawls: History with a ghostly twist! Register for kid-friendly ghost tours, no matter the season, or opt for a haunted pub crawl or scandalous Annapolis ghost tour highlighting pubs and businesses with a haunted past.

Feasting in Annapolis and Anne Arundel County

From dockside crab houses to chef-driven fine dining, Annapolis serves up a vibrant culinary scene rooted in Chesapeake Bay tradition. Whether you're craving fresh-caught seafood, farm-to-table fare, or waterfront cocktails at sunset, there's something here for every palate.

Fine Dining Experiences in Annapolis

Indulge in the finest culinary offerings Annapolis has to offer, where world-class dining meets local flavor.

• InGrano (West Annapolis): Experience artisan bread and thoughtfully crafted dishes, made with passion and precision to elevate your dining experience in a cozy and intimate setting. 17 Annapolis St, Annapolis, MD

• Acqua al 2 (Downtown Annapolis): Savor authentic Italian cuisine with a contemporary twist, featuring tasting menus and premium imported ingredients that transport you straight to Italy. Don’t forget to secure a reservation for the subterranean speakeasy, Harold Black, for one of their signature nightcaps or delicious Espresso Martini! 236 Main Street, Annapolis, MD 21401

• Osteria (Downtown Annapolis): Delight in traditional Italian flavors fused with local Annapolis ingredients, creating an unforgettable fine dining experience in a charming atmosphere in the heart of downtown Annapolis. 177 Main Street. Annapolis, MD 21401

• O’Leary’s Seafood Restaurant (Eastport): A true local favorite, O’Leary’s serves expertly prepared seafood in an elegant, relaxed setting, perfect for a memorable night out in the charming neighborhood of Eastport, close to the water’s edge. 310 3rd St, Annapolis, MD 21403

• Lewnes' Steakhouse (Eastport): Renowned for its top-tier steaks and seafood, Lewnes’ offers a classic, upscale dining experience in the heart of Eastport, perfect for those craving exceptional quality and white glove service. 401 Fourth St, Annapolis, MD

For a laid-back and authentic Chesapeake Bay Dining Experience:

• Dock Bars & Crab Houses: Embrace waterfront dining at iconic spots like The Point Crab House and Cantler’s Riverside Inn, where you can enjoy fresh Maryland crabs and refreshing cocktails while soaking in stunning Chesapeake Bay sunsets. Arrive by boat for the ultimate Chesapeake Bay dining experience!

Whether you’re craving gourmet Italian fare, international influences, fresh seafood, or a relaxed waterfront experience, Annapolis offers unparalleled dining experiences for every taste and occasion.

For Man's Best Friend

Annapolis is a true paradise for pets, offering plenty of ways to explore the Bay together. From paddle boarding with your pup to cruising Spa Creek on the Water Taxi, this pet-friendly town welcomes four-legged family members with open arms.

• Waterfront Walks: Enjoy scenic strolls along Spa Creek or explore Quiet Waters Park, featuring a dedicated dog beach where your pup can splash around and enjoy the water. Capital SUP also offers paddleboarding playdates with your pup, seasonally, May- October.

• Pet-Friendly Patios: Many downtown restaurants, including Federal House, Iron Rooster, and Preserve, offer welcoming outdoor patios where pets are invited to relax and enjoy the vibrant atmosphere. Doggie menus and water bowls are also on the menu for man’s best friend!

• Yappy Hours & More: Join the fun at local breweries and parks, where Yappy Hours are designed specifically for dogs and their owners to socialize and unwind in a dog-friendly setting. Don’t miss Forward Brewing, a brewery where pets are welcome outdoors, Quiet Waters Park Dog Park/Dog Beach, Great Frogs Winery, and the Naval Academy—where leashed pets are welcome on the grounds—and Watermark Cruises and Water Taxi! Capital SUP even offers pup-friendly meet-ups for paddles and brews!

From waterfront walks to dog-friendly dining and social events, Annapolis offers plenty of opportunities for pets and their owners to enjoy the best of Maryland’s capital city by the Bay!

Pet Grooming

Maryland Elite Dog Spa – Mobile Dog Grooming: Consider this mobile grooming service to keep your pet looking fine and fresh! There is no need to bring your precious pet to the groomer when they come to you! Contact Form

Veterinary

Bayside Animal Medical (Tica’s Pick): Bayside Animal Medical Center is a full-service veterinary hospital that provides gentle and compassionate care for its patients and their owners. Its professional and dedicated staff offers top-quality preventive, medical, surgical, and dental services for the highly valued patients.

Kid-Friendly Adventures in Annapolis

Annapolis is packed with exciting activities that the whole family will love. From pirate adventures to historical tours, there’s something for every age group:

• Pirate Adventures of the Chesapeake: Let your young adventurers set sail on a thrilling treasure hunt aboard a real pirate ship. This interactive, fun-filled experience brings the excitement of the high seas to life, complete with water cannons and pirate costumes as you search for Pirate Pete on the high seas!

• Naval Academy Tours & Football Games: Immerse your family in the rich traditions and excitement of Midshipmen life at the U.S. Naval Academy. Explore its historic campus with a guided tour and catch a thrilling Navy football game for an unforgettable family outing.

• Museums & Gardens: Enjoy a day of learning and exploration at the Annapolis Maritime Museum, where hands-on exhibits bring the area's maritime history to life. The waterfront museum in Eastport also offers summer camps for kids from kindergarten through 9th grade! Or take a peaceful stroll through the William Paca House gardens, offering a tranquil retreat perfect for all ages.

Annapolis offers endless fun for families with kids, providing opportunities for adventure, history, and relaxation all in one beautiful waterfront city.

Outdoor Recreation in Annapolis and the Chesapeake Bay

Life on the Chesapeake Bay provides endless opportunities for outdoor adventures, allowing you to immerse yourself in the beauty of this iconic waterfront destination. Whether you're looking for relaxation or excitement, there is something for everyone on the water:

• Sailing & Yachting: Set sail on the tranquil waters of the Chesapeake Bay by chartering a private boat or joining a local sailing club. Explore the stunning coastline, picturesque islands, and hidden coves while enjoying a day on the water. Annapolis is known as the "America’s Sailing Capital," making it the perfect destination for those looking to experience world-class yachting.

• Annapolis Sailing School: This sailing school offers an incredible introduction to sailing for all ages. As one of the country's oldest and most respected sailing schools, it provides hands-on lessons in a relaxed and family-friendly environment. Whether you’re a beginner looking to gain confidence on the water or a seasoned sailor refining your skills, the school offers courses tailored to every experience level.

• Fishing & Crabbing: Embark on a guided fishing or crabbing expedition for an authentic Chesapeake Bay experience. Whether you're casting a line for striped bass, catching blue crabs, or just enjoying a day on the water, fishing and crabbing are a beloved local tradition. Explore the bay’s rich marine life and create unforgettable memories with family and friends.

• Paddleboarding & Kayaking: Discover the serene creeks, coves, and marshes of the Chesapeake Bay with paddleboarding and kayaking. These peaceful water sports are ideal for exploring the bay’s hidden beauty at your own pace. Paddle through quiet waterways, surrounded by nature, and take in the stunning scenery of this iconic waterway.

From sailing and yachting to fishing, crabbing, and paddling, the Chesapeake Bay offers an unparalleled setting for outdoor recreation. Whether you’re an experienced adventurer or a casual explorer, these activities provide a perfect way to enjoy the bay's natural beauty while making lifelong memories.

Everyday Essentials

Living in Annapolis is a smooth experience, thanks to the wide range of high-quality services, shops, and wellness options throughout the city. Whether you’re searching for fresh groceries, a luxurious spa day, top-notch medical care, or premier fitness facilities, Annapolis has everything you need. Below, you will find a curated list of essential businesses catering to residents and newcomers who want to embrace the Chesapeake Bay lifestyle. Here are some of our tried-and-true favorites.

Groceries

• Graul’s Market

• Whole Foods

• Fresh Market

• You will also find discount grocery retailers Trader Joe’s, Aldi, and Lidl in locations across the county.

Salon & Spa

• Salons:

• Crea Hair Studio

• Hudson and Fouquet

• Spa & Massage:

• Sadona Salon

• Nails:

• Bella Nails

Health & Wellness

• Fitness Centers:

• Evolutions

• Life Time Fitness

• Yoga & Meditation:

• Tina Lanzoni

• Pickleball:

• Annapolis Pickleball League

• Life Time Fitness

• The Put Away

• Golf & Sailing Lessons:

• Annapolis Sailing School

• The Preserve at Eisenhower Golf Course

Healthcare

• Primary Care:

• Maryland Primary Care Physicians

• Dental:

• Drs. Lee, Bonfiglio, and Vesley

Boat Maintenance

• Pelorus Yacht Management

Make Your Move to Annapolis and the Chesapeake Bay

Whether you're drawn to Annapolis' walkable downtown, its rich historical charm, or the endless outdoor adventures on the Chesapeake Bay, this vibrant region offers the perfect blend of modern luxury and timeless beauty. From sailing on the bay to dining by the waterfront, family-friendly activities, and a pet-friendly lifestyle, Annapolis and Anne Arundel County truly embody the Chesapeake Bay lifestyle.

Ready to immerse yourself in this idyllic setting? Discover your dream waterfront property today and start living the life you've always dreamed of, surrounded by the natural beauty, rich history, and unmatched lifestyle that only the Chesapeake Bay can offer. Let us help you make that dream a reality—contact the Brad Kappel Team today and take the first step toward living your best life on the Chesapeake.