Cruising Made Simple & Joyful
We believe every moment on the water should feel effortless, so we handle the details while you soak in the views. From first hello to final goodbye, our friendly crew keeps things smooth, safe, and fun.
Whether you’re chasing a golden sunset or planning an all-day adventure with friends, we tailor each charter to match your pace and style. Relax, laugh, and leave the planning to us—we’re here to help you create memories that last long after you dock.
Crab Shack Cruise
$900.00 per trip (Max 6 Guests)
Join us for a fun day on the water with a private cruise leave Annapolis and stopping at a local favorite spot, Cantler’s, for some delicious lunch. After lunch, sail the bay and enjoy the sights with the breeze in your hair before we end the trip back at our home port. Our experienced Captains can help you enjoy the immersive experience with some light instruction. Come relax with us!
Custom Cruise Experience
$1,800.00 per day (1-3 day trips available)
Let our team help you realize your ultimate goals for a charter on the Bay. Whether you are looking for a trip to Baltimore with a slip on Fells Point to take in a game or the nightlife, a tour of quiet anchorages to star gaze and enjoy some quiet time, or a favorite destination like St. Michaels we can plan it all. The fee includes all the boat fees and our USCG licensed Captain but provisioning will be the guest’s responsibility. Let us plan your next adventure today!
Chesapeake Bay History Cruise
$150.00 per guest (Max 6 Guests)
Spend three hours on the bay hearing the fun facts and fascinating history of all our local landmarks and terrain features. Our knowledgeable captains will also point out any surprise wildlife along the way so keep your eyes peeled for dolphins and rays!
Chesapeake Bay Sunset Cruise
$150.00 per guest (Max 6 Guests)
Spend two hours out on the bay finding the perfect vantage point for your sunset photos! We provide a sparkling wine toast, but you are free to bring along any food or non-alcoholic beverages you would enjoy. Our Captains are not only experienced mariners they are also great amateur photographers as well so don’t be shy about asking for their help with the perfect shot.
Ready to Sail?
Send us a quick message, and we’ll chart the course for your perfect day on the water—no worries, we’ve got you covered!