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Right Outside Downtown Annapolis! A 10 minute Uber ride! Great for Stadium events, the holidays, or exploring the downtown bars!
Welcome to Annapolis, a gem of the Chesapeake Bay known for its rich maritime heritage, charming cobbled streets, and vibrant cultural scene. Nestled by the water, our sailboat is anchored in an area that truly captures the heart and soul of this historic town.
Natural Beauty: The serene environment surrounding the sailboat is a nature lover's dream. Expect to be greeted by ospreys soaring overhead, playful ducks wading by, and the occasional splash of fish in the waters. The nearby trails are perfect for morning jogs or evening strolls, offering breathtaking views of the bay.
Proximity to Attractions: you are so close you can hear the music!
Outdoor Activities: For those seeking an active stay, the area boasts a plethora of bike trails, a fenced-in dog park for your furry friends, and a nearby golf course to test your skills.
Downtown Annapolis: A trip to downtown Annapolis is a must. Here, you'll find quaint shops, delicious eateries, lively bars, and an array of events and festivals that keep the town buzzing year-round. People love moving the sailboat to downtown Annapolis for a unique experience amidst the hustle and bustle.
Accessibility: Free public parking ensures that guests driving to the location have a hassle-free experience. The Annapolis city webpage has parking options for downtown!
Additionally, the town's public transportation and easy road access mean exploring broader Annapolis and its neighboring areas is a breeze.
In essence, the neighborhood combines the tranquility of waterfront living with the excitement of town life, ensuring guests have a multifaceted experience. Whether you're seeking relaxation, adventure, or a bit of both, Annapolis promises not to disappoint.
Annapolis is known for its diverse culinary scene. Here are some general examples of restaurants that are close by:
Cantlers Riverside Inn: Renowned for its fresh seafood, Cantlers is a must-visit for guests. Whether you crave crab cakes or oysters, this local favorite is easily accessible by kayak or dingy from the sailboat.
Carrol's Creek Cafe: Offering waterfront dining with views of the Annapolis harbor, Carrol's Creek Cafe specializes in seafood and contemporary American cuisine.
Pusser's Caribbean Grille: If you're in the mood for tropical flavors, Pusser's offers Caribbean-inspired dishes and drinks, with a waterfront setting to enhance the experience.
Vin 909: For those who appreciate farm-to-table dining and artisanal pizzas, Vin 909 in Eastport might be a great choice, known for its unique blends of flavors and cozy atmosphere.
Iron Rooster: Perfect for breakfast or brunch, Iron Rooster serves up classic comfort food with a Southern twist. Enjoy their signature homemade pop-tarts or dive into a hearty breakfast plate.
Mission BBQ: For barbecue enthusiasts, Mission BBQ offers mouthwatering ribs, brisket, and more, served in a patriotic-themed atmosphere.
Chart House: Situated on Spa Creek, Chart House offers premium seafood, steaks, and a fine dining experience with stunning waterfront views.
Middleton's Tavern: A historic gem in downtown Annapolis, Middleton's offers a mix of traditional American fare and seafood. With its colonial charm, live music, and reputed ghostly inhabitants, it provides both a culinary and cultural experience. Also a frequent stop for George Washington and the oldest pub in Maryland! The whiskey piano bar upstairs is great!
Davis' Pub: Tucked away in the historic maritime district of Eastport, Davis' Pub offers an authentic Annapolitan experience. Known for its laid-back atmosphere and classic pub fare, it's a favorite among both locals and visitors. The menu features a mix of seafood and traditional pub foods, with crab dishes being particularly popular. The setting is unpretentious, with a dive-bar feel that's rich in character and history. It's a great place to enjoy a cold drink, tasty meal, and soak in the local culture.
These are just a few examples, and the neighborhood likely offers a range of other dining options to suit various tastes and preferences. Whether you're looking for a quick bite, a romantic dinner, or a casual meal with friends, Annapolis's culinary scene is sure to satisfy.

Navigating Annapolis and its surrounding areas is both convenient and enjoyable, offering a diverse range of transportation methods tailored to your adventure.
By Foot: Downtown Annapolis is pedestrian-friendly, allowing you to explore its historic streets, shops, and landmarks at a leisurely pace. Many attractions are just a short walk away.
Water Taxi: A top choice for travel between waterfront locations, the water taxi provides not only a mode of transport but also scenic views of the Chesapeake Bay. It's a delightful and efficient way to move around the city.
Kayaks: For those eager to paddle their way through the waters, we offer 2 kayaks available for rental. It's a unique and fun way to explore Annapolis from a different perspective and can be especially invigorating during the early mornings or sunset hours.
Dingy Details:
9-foot Dingy when not cold Included with your Airbnb stay, this dingy is equipped with a battery-powered 4hp electric motor, ideal for brief journeys between the sailboat and shore.
14-foot Dingy Rental: For guests seeking longer excursions, during spring and summer months, we offer a day rental for a 14-foot dingy powered by a 25hp gas motor. This is perfect for trips downtown or some offshore fishing.
Public Transportation: Annapolis's reliable bus system is an affordable option for those wanting to traverse longer city distances without the fuss.
Biking: Annapolis's bike trails are a treat for cyclists of all levels. Whether you're looking for a rigorous ride or a leisurely cycle, the city's paths have something for everyone.
Driving: For those with vehicles, free parking is available near the sailboat's location. Do keep in mind that traffic can get busier during events or peak seasons.
Rideshares and Taxis: Uber, Lyft, and local taxi services ensure direct and speedy transport for those times you want to get somewhere without delay.
With so many transportation options on offer, getting around Annapolis is both an adventure in itself and a means to further exploration. Whatever your preferred mode, the city awaits with open arms!