There’s nothing as cool as walking the docks at the Annapolis Powerboat Show, kicking tires and dreaming about the adventures you could have on the Chesapeake. But if this experience leaves you with a feeling of wanderlust, or wander-boating, have no fear: there are great ways to get on the water and explore Annapolis Harbor and the Chesapeake Bay during the show without owning your own vessel.
Nautiste’s Champagne and Oyster Sail
Nautiste, generally known for their luxury yachting experiences, are offering a cruise curated by Michelin-starred chef and sommelier Troy Knapp. Enjoy a 1.5-hour cruise aboard the all-electric vintage 1976 Bruno & Stillman Downeast-style motor yacht, savoring freshly shucked local oysters and exquisite Champagne as you take in the stunning waterfront views. Prices are set at $149/per person.
Hint: If you’re visiting the Annapolis Sailboat Show next week, Nautiste offers a similar cruise during that show on Cru Classé, a 47’ Jeanneau Sun Odyssey sailing yacht.
Darling Charters
If you’re interested in a private experience, Darling Charters offers a gorgeous picnic boat straight from Martha’s Vineyard and now operational on the Bay. It’s a stylish, elegant way to experience Annapolis, with a charter captain happy to show you around places you’d never find by foot. The Darling can seat up to 6 and starts at $800 for two-hour cruises.
Miss Anne II by Watermark.
If you want to cruise the harbor in an intimate, funky setting, the Miss Anne II is your dream boat. Stocked with plenty of snacks and drinks, the 24-foot cozy launch can take up to 22 passengers and is great for exploring the more residential areas of Annapolis’ creeks. Tickets start at $25/person.
The Schooner Woodwind
One of the most beloved Annapolis experiences is a trip aboard the Schooner Woodwind, a 74-foot wooden schooner that stops traffic and makes even the crankiest boaters smile. With three two-hour cruises each day, the Woodwind offers both public and private tours of Annapolis and the greater Chesapeake. Prices start at $75 per person.
Waypoints Charters
If you’re looking for something more than a simple hop around town, Waypoints Charters offers the Knot Home: a Jeanneau NC33 motor yacht that allows you to get the full experience of living on the Chesapeake. You don’t have to worry about weather with the beautiful 360-degree views from the comfort of your cabin, and entertaining in style is on point. Prices start at $2,600 for the day, and $5,100 for the week (so you can stay for the Sailboat Show).
Annapolis Sailing School
Speaking of the Sailboat Show … if you are sailing inclined, the Annapolis Sailing School offers sailboat rentals in their fleet of 24-foot Rainbows, which were specifically designed to manage the Chesapeake waters.
Pricing starts at $158 for a day of sailing, but budget a 30-minute check-out sail with the ANSS team who will help you navigate the best waters for your trip.
