20/20 Chesapeake and Annapolis Charters & Rentals: 
'The Feeling of a True Tropical Island Getaway'
1/2 Day / Full Day / Sunset Cruises / Overnight B & B


Ahoy, Welcome to the Wave!

We offer memorable sail and powerboat charters for families & friends seeking a private Chesapeake getaway. Our daily voyages, Sunset Cruises, BYOB! Happy Hour Fridays, Overnight B & B, 12 Guests-2-Boat-Raft-Up Parties and specialty charters are a fantastic way to celebrate birthdays, anniversaries and any celebration. Cruises include crew, food, water sport activities and non-stop entertainment. Located in Edgewater Maryland, 5 miles south of Annapolis, the 'Sailing Capital of America'; close to Washington D.C. & Baltimore.

Cruise Safe. Cruise Chill. Cruise the Wave.



Crewed Charters & Rentals

Cruise with us on either or both our 43' sailboat & 34' powerboat.
Rent 20' Bow-rider without captain. 

BYOB! and dine with us!

Bring your own bottle and order from
our delicious Maryland seafood menu.

Fun experience

From 3 hours Sunset Cruise to 22 hours 
Overnight Boat & Breakfast. Enjoy Watersport fun,
food, byob! and come chill on da island.