Mutts Adventure in Annapolis, Maryland
- Luie Boone
- Aug 10
- 6 min read
This vacation destination is a part of our third series of blog posts titled Rover Ready.
When Luie Boone heard Chesapeake Bay, he thought his hoomans said Cheesecake Bay. Unfortunately, Annapolis, Maryland is not nestled along Cheesecake Bay, but rather Chesapeake Bay. Regardless, he'll be getting a cheesecake or two on his vacation to Annapolis. It is a historic waterfront city, which offers the perfect mix of walkable charm, maritime character, and open-hearted hospitality for both people and their pups.
Annapolis is widely celebrated as one of the most dog-friendly cities on the East Coast. The locals frequently agree! The moment you arrive, you and your pup can enjoy scenic strolls along Ego Alley and the City Dock. From cobblestone streets to shaded promenades overlooking the harbor, the entire downtown feels thoughtfully designed for dog lovers.
The adventure continues just a short drive away at Quiet Waters Park, which is one of the area’s most beloved destinations for canine visitors. This expansive public park features wooded trails, large fenced-in dog areas, and even a designated dog beach. At the dog beach, your pup can splash in the waves and roll in the sand. For more active outings, you can rent a paddleboard or kayak through Capital SUP, which allows dogs to tag along as you explore the calm inlets and coves of the Chesapeake.
If a relaxing boat ride is more your speed, several of the local harbor cruise companies and water taxis welcome well-behaved dogs aboard—some even for free! This gives you the chance to take in panoramic views of sailboats and historic architecture from the water.
When it’s time to eat, Annapolis offers a wide range of dog-friendly dining spots. Many restaurants in Eastport and the downtown district have spacious patios and outdoor seating areas that not only allow dogs but go the extra mile with water bowls, treats, and attentive service for four-legged guests. Places like Rams Head Tavern, Davis’ Pub, and Reynolds Tavern are some of the popular favorites!
Annapolis supports dog parents with practical resources like boarding, daycare, and grooming services if you need a break or want to explore a non-dog-friendly spot... just don't tell your pooch you're going on adventures without them. Luie Boone would get a severe case of FOMO. Instead, just distract them with spots like Dogwood Acres Pet Retreat, which offer luxury-level care just minutes from the city. It'll give the hoomans peace, when they want to balance sightseeing with pet comfort.
Whether you're planning to wander the quiet historic streets, share a seafood dinner on a sunny patio, or let your dog romp freely at a Chesapeake beach, Annapolis promises an easygoing, tail-waggingly, wonderful vacation.
Paws Rest Here
Luie Boone paw-selected this perfect vacation rental for your stay in Annapolis, Maryland. Check it out below!
Rental Name: Contemporary Waterfront Oasis
This rental has 4 bedrooms with 4 beds and 4.5 baths.
Photos courtesy of Annapolis Accommodations
It features the following amenities:
Waterfront home
Breathtaking views of the South River
Resort-style pool with lounge areas
Landscaped backyard with deck and dining area for six
Grill
Multiple outdoor entertaining areas, including garden seating
Private dock with direct access to the South River
2 kayaks provided
Minutes from Downtown Annapolis
What does Luie Boone think of this rental? He woofed:
From what I've overheard, a vacation to Annapolis, Maryland, sounds like a dream for all of us. Annapolis is known as one of the most dog-friendly cities on the East Coast, which means that I’ll be welcome just about everywhere. My hoomans keep talking about a house right on the water, with a big backyard and a pool. There’ll be many long dinners outside on the deck. I’ve already claimed my spot under the table—crumb patrol. It has four bedrooms and a huge kitchen. Outside, there’s a sculpture garden to sniff and a dock perfect for sunset watching. They also mentioned bikes, kayaks, a piano, and something called a pool table. All I know for sure is that I plan to be wherever the fun is. I don’t know exactly when we’re leaving, but I’m all set. My leash is packed, Sally (my toy squirrel) is ready by the door, and I’ve claimed my spot in the back seat... even though I deserve shotgun. I always go where they go!
Paws Venture Here
Quiet Waters Park
Your pup will love Quiet Waters Park. There’s a path that leads right down to the beach. Although the beach is small, there is enough room that allows dogs to run off leash. Your pup is also welcome to join you on the park's dog-friendly trails.
Watermark Journey - Cruises on the Bay
Here, you can cruise with your four-legged friend on most public cruises. Fees do vary by person and tour, but Fido rides for free. Cruises are informative, affordable, and a great way to explore the waters of Annapolis!
Broadneck Park
At Broadneck Park, your best friend is welcome to enjoy a stroll with you on the walking trail around the park. There is also an on-site dog park! Luie Boone can't wait to make some friends that aren't just his toys.
Helen Avalynne Tawes Garden
This is a five-acre garden, which includes a forest typical of Western Maryland, a stream, and an Eastern Shore peninsula. The barrier-free garden in the park contains pleasant ponds and a raised planter with lots of different plants You can wander with your pooch around the trails and let them sniff all the smelly plants!
Greenbury Point Conservation Area
This conservation area is one of the last remaining natural areas at the mouth of the Severn River on the Chesapeake Bay. This is a popular public destination for nature lovers, runners, anglers, and dog walkers. Bring your best buddy!
Broad Creek Park
The Broad Creek Park is a 91 acre natural area park situated on Broad Creek, which is a tributary of the South River. There are approximately 5 miles of natural surface trails that are open to hikers, runners, nature lovers, and their canine companions.
Jonas and Anne Catharine Green Park
This park has recreation space where two-and four-legged friends can explore. It's located along the Severn River, and its amenities include a picnic area, a fishing pier, restrooms, and a beach for boat launching!
Federal House Bar & Grill
At this bar and grill, you can enjoy fish tacos, crab-stuffed flounder, and a wide selection of draft beers from across the country! Luie Boone's hooman dad will love all the beer. They also have dog-friendly outdoor tables with water bowls and even a special dog menu for Fido! Luie Boone will be ordering it all!
Luie Boone's Pet Peeve about
Annapolis, Maryland
There's just so much to love about this vacation destination, but there's one thing that's got Luie Boone's leash in a twist. He woofed:
My hoomans say Annapolis, Maryland, has it all: water, boats, and lots of good smells. I was already excited, but then I heard at the dog park that it’s nicknamed Naptown and obviously, I thought, “Wow, a city named in honor of dogs like me who take napping very seriously!” But, no, that's actually not the case. It turns out that nickname has nothing to do with dogs. Instead, it has something to do about music history and people thinking the town used to be quiet, slow paced, and boring! That’s not napping! Clearly, no dogs were consulted on this misleading nickname choice. Us dogs are the true napping legends... after kitty cats, of course. We nap in the sun, in the car, on laps, and under tables. Basically, we nap anywhere that looks slightly soft or slightly warm. We live the nap life proudly, every day! And before anyone says it—no, I don’t want to hear my brother, Tobi the cat, say it’s about catnaps. He naps on top of the TV stand and acts smug about it. Who cares? That’s not talent. That’s just cattitude! Anyway, I still want to go to Annapolis. But now I’ve got a mission. Do you want to know what it is? Well, it's to represent all napping dogs everywhere! I will proudly snooze in every shady and sunny spot that I find. Annapolis may not have been named after dogs, but by the end of my vacation, it’s going to wish it had been!
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