Just pack your bags and we’ll take care of everything else.

  • Day 1: Set sail from Annapolis to St. Michael’s. Learn the lines with Captain Michael on our first day of sailing.

  • Night 1: After checking out the Chesapeake Bay Maritime Museum and doing a little shopping, return to the boat for Tiki Night! Enjoy an array of tropical-inspired small bites paired with classic tiki cocktails. Our Painkiller is the perfect post-sailing remedy!

  • Day 2: Set sail from St. Michael’s to Wye Island for a private anchorage protected by a nature preserve. Enjoy swimming (we’ll bring the inflatables!), paddle boarding, or explore the preserve on our outboard dingy.

  • Night 2: Settle into our quiet cove with our Taste of the Chesapeake. Our crab cakes and rockfish are sourced locally and served with seasonal vegetables. Finish the dinner with Chef Jackie’s to-die-for cheesecake.

  • Day 3: Set sail from anchorage to Harrington Harbor South. Enjoy the marina’s vast amenities in this quaint cruiser’s getaway.

  • Night 3: Bourbon and Steak Night. Sit back and sip with us as we taste five bourbons alongside an assortment of snacks that will compliment our spirited collection before diving into a three-course steak dinner.

  • Day 4: Set sail from Harrington Harbor South to Oxford. Get a scoop of ice cream from the notorious Scottish Highland Creamery - arguably the best ice cream in Maryland.

  • Night 4: Get spicy with Taco Night. Our boat-made salsas and guacamole are accompanied by delightful jalapeno-garlic chicken and chipotle-braised short rib. Wash it all down with our fresh-squeezed margaritas.

  • Day 5: Set sail from Oxford back to Annapolis.

Our five-day all-inclusive excursion is recommended for 4-6 guests based on the availability of catamarans. Please contact for pricing.

Excursion dining includes our fully-loaded coffee bar, breakfast, lunch, an afternoon snack, dinner, and dessert. We’ll provision all water, coffee, tea, and any requested non-alcoholic beverages. A full bar will be provided to accommodate most cocktail requests. Please advise Captain Michael of any specific dietary restrictions or preferences during your consultation. Our all-inclusive package includes a 45-foot sailing catamaran, dockage, fuel, captain, and first mate/chef. Gratuity is not included.

The above itinerary is a sample and will be tailored to you and your guests’ specific requests during your consultation with Captain Michael.