Water Taxi


Cruise & Dine

Sailing with us means you have the choice of our catered delicious menu and BBQ on your yacht, but don’t forget there are some really nice restaurants and bars on the Chesapeake Bay and Annapolis region you have to try out as well! Each and every restaurant has a different feel and a wide variety of foods. The major anchorages around the Chesapeake Bay offer several bars and restaurants to choose from.

Allow our crew aboard Island Chill Irie Vibes 34' powerboat to take you to selected dock-bars & restaurants and try Maryland's blue crab, oysters, blue fish and rock fish. The list is long, but below we have gathered a selection of some of our friends.

Islan' Grill Kitchen Catering Menu

Water Taxi Rates

  • 2hr drop-off to restaurant with captain: $500
  • 3 hr sunset cruise with crew: $650
  • Half day charter with crew: starting at $585 - $800
  • FREE fuel surcharge included in final cost.



Click to check out restaurant's info and website. If your desired restaurant is not on the list below, please give us a call (410) 212 4476.


Watertaxi: Irie Vibes 34' powerboat takes 6 guest.

Annapolis-coconut-joes-Southriver-Pier-Oyster-Bar-Waterfront island-seasonal-outdoor-seafood-American

The Pier - Oyster Bar & Grill

Address: 48 S River Rd S, Edgewater, MD 

Address: 910 Kentmorr Rd, Stevensville, MD 

Sam's on the Waterfront

Address: 2020 Chesapeake Harbour Dr E, Annapolis

Annapolis is also home to charming, bricked streets lined with one-of-a-kind houses, lighthouses, marinas, shops and restaurants. Below are a few places we recommend visiting when you visit Annapolis and the Chesapeake Bay.