Our story
About Annapolis Boat Experiences
How it started
Why I Started This
I've been sailing the Chesapeake Bay for years — Spa Creek, the Severn River, the Bay itself. At some point it became clear that the best way to share what I love about this place was to simply take people out on the water.
Annapolis is one of the great sailing cities in America. But most visitors never get past the waterfront restaurants and the shops on Main Street. The real Annapolis — the one that sailors know — is out on the water, looking back at the city from the Bay.
Every charter I run is private. Just your group, the boat, and a captain who knows these waters well. No strangers, no scripts, no rush. Just a genuinely good day on the Bay.
USCG Master
Credentialed Captain
Who you'll sail with
Captain Steve
I'm a USCG Master-credentialed captain based in Annapolis. I've spent years on these waters and know the anchorages, the tides, the best spots for a sunset, and the waterfront restaurants worth arriving at by boat.
My approach is simple: show up prepared, keep things relaxed, and make sure everyone has a genuinely great time. I've taken out first-time sailors, families with young kids, couples celebrating anniversaries, and groups of friends who just wanted a great afternoon on the water.
I operate two boats — a classic Nauticat 331 pilothouse ketch for sailing and longer outings, and a nimble 12-foot AB Oceanus RIB for shorter harbor cruises. Whatever you have in mind, we can make it work.
Our approach
What Sets Us Apart
Always Private
Every charter is exclusively yours. No shared boats, no strangers, no compromises on your experience.
Genuinely Local
Born and based in Annapolis. We know these waters, the tides, the anchorages, and the spots worth finding.
USCG Credentialed
Every trip is captained by a USCG Master-credentialed captain. Fully insured, properly equipped, safety first.
Flexible & Personal
No fixed itineraries. We tailor every trip to your group — your pace, your interests, your day.
Where we sail
Our Waters
We operate on Spa Creek, the Severn River, the Annapolis Harbor, and the broader Chesapeake Bay. Annapolis sits at the mouth of the Severn River where it meets the Bay — one of the most beautiful stretches of sailing water on the East Coast.
Depending on your trip, we might cruise past the Naval Academy, anchor in a quiet cove off the Severn, sail out to the Bay Bridge, or simply drift through Spa Creek and Ego Alley and watch the world go by from the water.
The Chesapeake Bay is a special place. We're lucky to call it home.
Ready to Get on the Water?
Reach out directly — Steve responds quickly and loves talking about the Bay.