Captain's Quarters - Eastport!

Escape to this one-of-a-kind, restored 1920s bungalow in Eastport’s sought-after maritime community, perfect for a cozy family getaway. Leave the car behind and enjoy a relaxing one-mile stroll to Downtown Annapolis, City Dock, the Naval Academy, and the State House. The Captain's Quarters blends historic charm with modern comfort, featuring wood floors, oriental rugs, warm wood furniture, and unique antiques—plus plenty of maritime decor reflecting Captain Paul’s nautical style.

Upon arrival, enjoy a smooth contactless check-in experience. While we’re not available 24/7, we’re here to assist you virtually through the app you used to book your stay. Feel free to reach out with any questions or needs—we’ll respond as quickly as we can!

The neighborhood around this home in Annapolis is a charming and peaceful area, offering a perfect blend of suburban tranquility and close proximity to the heart of the city. Boucher Ave is tucked into a quiet residential section, with tree-lined streets and well-kept homes that give it a welcoming, community feel.

You’re just a short drive away from the bustling downtown Annapolis, where you can explore the historic waterfront, stroll along the vibrant Main Street, or enjoy a meal at one of the many excellent restaurants. The iconic Maryland State House and the U.S. Naval Academy are also nearby, offering plenty of cultural and historical sights to explore.

If you’re looking to relax outdoors, you’ll appreciate the proximity to several parks, including the scenic Broadneck Park and the Chesapeake Bay, where you can enjoy boating, fishing, and beautiful views. Additionally, there are plenty of local shops, cafes, and eateries to explore right in the area, giving you plenty of options to experience the local vibe.

Whether you’re in town for a weekend getaway or a longer stay, the neighborhood offers a peaceful retreat with easy access to everything Annapolis has to offer.

Guests will have access to the home by keypad entry. The code changes with every guest.

Welcome to The Captain’s Quarters! As you enter, you’ll step into the main room, filled with quirky character and maritime decor. You’ll find a desk stocked with interesting reading materials and maps, a drum set for some musical fun, and a full futon sofa and an armchair, offering extra seating or sleeping space. To the left of this main room, you will enter into the second living room area, perfect for reading or enjoying small gatherings. This space features another futon bed and armchair, and it flows effortlessly into the dining room, which is seamlessly connected to the fully equipped kitchen.

From the kitchen, a sliding door opens to the side yard and backyard, revealing a private outdoor oasis. Here, you'll find an organic garden, fig and pawpaw trees, two small ponds (one in the front), and eco-friendly landscaping. The fenced-in yard offers a patio with a grill, chiminea, lawn furniture, and plenty of shade trees, making it an ideal spot for relaxation or entertaining.

Inside, the layout continues, which is adjacent to the second living room, with a first-floor Queen bedroom that features an attached bathroom with a shower for added convenience. Upstairs, you’ll find three additional Queen bedrooms, each providing a restful retreat. The Captain’s Quarters offers both a primary and secondary suite, each with its own ensuite bathroom—perfect for two families or accommodating in-laws.

Captain Paul is passionate about green living, and the home is equipped with rooftop solar panels, a permeable gravel driveway, an energy-efficient tankless water heater (no Navy showers here!), and a commitment to composting and recycling. For your convenience, there’s a single off-street parking spot just a few steps from the entrance, with ample free on-street parking for additional vehicles.

Inside, you'll enjoy ceiling fans, central AC, and complimentary wireless internet. The home also features two smart TVs and two office spaces, each with desks and chairs—ideal for anyone working remotely. And for those interested in sailing or curious about the local area, there are lots of books to explore, covering everything from sailing to the local culture!

As mentioned above, most Annapolis destinations are within walking distance, however, if you want to experience travel the way the locals do - Eastport residents fully utilize the Water Taxi!

The Captain's Quarters is just a three minute walk to the water taxi pick up spot @ South Annapolis Yacht Center (750 Boucher Ave.). A beautiful and entertaining ride takes you directly to the Annapolis City Dock with a few other dockside (and potentially boat side) pickups along the way. Don't forget to ask your Captain for his or her recommendations and local info.

This is unique and exciting addition to your trip - a MUST on your to-do checklist!

As mentioned above, most Annapolis destinations are within walking distance, however, if you want to experience travel the way the locals do - Eastport residents fully utilize the Water Taxi!

The Captain's Quarters is just a three-minute walk to the Water Taxi Pick Up Spot @ South Annapolis Yacht Center!
(750 Boucher Ave.)
A beautiful and entertaining ride takes you directly to the Annapolis City Dock with a few other dockside (and potentially boat side) pickups along the way. Don't forget to ask your Captain for his or her recommendations and local info.

Early Check-In & Late Check-Out Policy
We offer early check-in and late check-out upon request, subject to availability.
One hour is complimentary
However, a fee applies as follows:
• Early Check-In before 3pm for an additional fee of $50 to be paid before check -in
• Late Check-Out after 12pm for an additional fee of $50 to be paid before check-out
Please request in advance so we can confirm availability. Thank you!

We kindly advise you and your guests to provide your own charcoal and kindling wood for the Chiminea located on the patio. Grill tools are conveniently stored in the small dock box. Additionally, you are also encouraged to feed the fish in the back pond, using only small amounts of fish food provided on the patio shelves. Your cooperation is greatly appreciated.