Ditch the car, bring the family & dog and make this beloved and restored 1920's bungalow in the desirable maritime community of Eastport yours for a weekend or longer. Enjoy the best of Annapolis with an easy one mile walk to Downtown, City Dock, Naval Academy, State House, etc. The Captain’s Quarters is a unique mix of old and new craftsmanship featuring wood floors (some that creak) covered in oriental rugs, wood furniture, and hand-picked antiques that all reflect Captain Paul’s style.

This is self entry - you will be provided the pinned code within a few days of your arrival.

Guests have full access to the entire first and second level of the home as well as the expansive back yard.

The Captain's Quarters has four Queen bedrooms and a full Futon sofa, but we think the home is best arranged for a group of eight or fewer. Uniquely, the Captain’s Quarters provides both a primary and secondary suite with full ensuite bathrooms; perfect for two families or accommodating the In-Laws. We pride ourselves in providing the best of green living with rooftop solar panels, permeable gravel driveway, energy efficient tankless water heater (NO Navy Showers!) composting, recycling, organic garden, fig & pawpaw trees, 2 fishponds, and environmentally friendly landscaping. We offer a single off-street parking spot with only two steps up to enter a spacious foyer to unload and rest at the end of your day’s journey. There is also plenty of free, on-street parking for extra vehicles. Ceiling fans, central AC and a private, fenced backyard with patio and grill, chiminea, lawn furniture, and plenty of shade trees add up to the perfect place to relax and entertain. The Captain’s Quarters provides complimentary wireless internet access, two smart TVs, two office spaces with desks and chairs for your teleworking needs, and numerous books to research sailing and the local area.

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.

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.