Things to do in Talbot County, Talbot County: The Best Boat Tours & Water Sports

Covid: Yes we are open! Sail Selina II Boat Tours sails daily from St Michaels MD April-Oct. limited to just 6 guests for a personal experience of the history of sail. Built in 1926 during the Great Gatsby era, climb aboard go back in time when yachtsmen enjoyed the elegance of freshly varnished mahogany and brightly polished brass. Available on a per person basis or private charter, we offer day sails, Champagne Sunset Cruises, moonlight sails, sailing lessons, wine tasting and beer tasting excursions, small weddings, engagements, birthdays & anniversary celebrations. Once we cast off lines we tour the harbor and enjoy the sights that dot the shoreline of our quaint little seafood town. Hear the stories of the historic boats on display at the Chesapeake Bay Maritime Museums, and see where the movie "Wedding Crashers" was filmed. Once we leave the harbor we go out into the Miles River, put up the sails and follow the wind. Guests are invited to participate or simply sit back relax.

The classic yacht Lady Patty departs three times daily for the beautiful Chesapeake Bay from Tilghman Island, MD, just twelve scenic miles past St Michaels, MD from April 1 through October 31. Lady Patty is a 45' sailing yacht built in 1935 for offshore racing. She carries over 1000 square feet of sail and is USCG inspected for 16 passengers. During charters beer, wine and drink service is offered. We specialize in Champagne Sunset Sails. Don't settle for sailing in the rivers and harbors. Join us aboard the only sailing vessel in the area that sails on the open Chesapeake Bay. Come sail away aboard the classic yacht Lady Patty.

Each May through October, the Chesapeake Bay Maritime Museum’s 1920 buy boat Winnie Estelle takes passengers out with our docents and volunteer Captain and crew to get out on the water and experience some of the Chesapeake's most beautiful scenery and wildlife along the Miles River and St. Michaels Harbor. The 45-minute, drop-in public cruises are available Fridays through Mondays, May through October, and depart from CBMM on the hour from noon to 3:00 p.m. Before coming to the Chesapeake Bay Maritime Museum, Winnie operated as a workboat on the lower Chesapeake for more than 50 years, carrying seafood and produce to market across the Chesapeake Bay. In the 1970s, she made Belize her port of call, where she operated as an island trader, carrying lumber from Honduras to Belize, and later as a charter boat for divers. In 2012, she was returned to the Chesapeake Bay by Michael Whitehill of Centreville, Md. In 2014, Winnie Estelle joined CBMM’s floating fleet of historic boats, which includes the 1955 skipjack Rosie Parks and the 1889 nine-log bugeye, Edna E. Lockwood, which is now under historic restoration. Now, Winnie Estelle takes passengers out for drop-in public cruises, ecology tours, student and adult education tours, private charters, and weddings. Tickets for drop-in cruises aboard Winnie can be purchased online at CBMM's website or at the CBMM’s store or welcome center the day of your visit. Tickets are available at $10 for non-members, $5 for CBMM members, $3 for non-member children ages 6-17, and free for member children ages 17 and under, and for all children ages five and under. General museum admission is additional for non-CBMM members, with general admission good for two consecutive days. All cruises are weather-dependent, with limited boarding and availability subject to change. CBMM is located in the historic district of St. Michaels and is within walking distance of several restaurants, boutiques, other attractions, and inns reviewed on TripAdvisor. Established in 1965, the Chesapeake Bay Maritime Museum is a world-class maritime museum dedicated to preserving and exploring the history, environment and people of the entire Chesapeake Bay, with the values of relevancy, authenticity, and stewardship guiding its mission. Serving nearly 70,000 guests each year, CBMM’s campus includes a floating fleet of historic boats and 12 exhibition buildings, situated in a park-like, waterfront setting along the Miles River and St. Michaels’ harbor.

30 and 60 minute boat cruises exploring the history, ecology, and folklore of St. Michaels, MD. The shuttle also serves as a water taxi to the area providing dock to dock (or boat to dock) service. All tours are BYOB, can accommodate up to 13 guests, and pets are welcome. Tour times are flexible to fit the needs of your group.

Imagine taking in the beauty of the Miles River and St Michaels on a replica of a 1930's steam ship called "The Patriot". We help you become familiar with the area as we cruise upon the beautiful Miles River, part of the Chesapeake Bay Estuary which is the largest in the Western Hemisphere. Learn about our local beginnings, view historic homes and wildlife, and watch local watermen harvest clams, oysters and the famous Chesapeake Bay Blue Crab during their respective seasons.The PATRIOT offers more than the historical scenic cruises for which it is famous. Four daily cruises are scheduled as well as evening charters for a variety of events. Let our captain and crew cater your small intimate affairs with close friends, family reunions, corporate events and more! Relax while you and your guests enjoy beautiful views along the Miles River that change with the seasons. Check our Patriot Cruises website for availability.

FLoating Crab Feasts, Private Charters, Group Tours on the 49 passenger Express Royale. We offer destination managment services, teambuilding and day and overnight itineraries for groups of 25 or more.

Come and experience the exhilaration of gliding silently through the water while witnessing the natural scenic beauty of the Bay and the many creatures that thrive in it's waters. Osprey, great blue heron, bald eagle, geese, ducks, and white tail deer. A variety of different waterway trails await paddlers of any level experience.

Offering annual boat slips as well as transient slips with special focus on yacht clubs & groups. We are also the areas largest purveyor of outdoor recreational rental equipment. Renting WaveRunners, Jet-Skis, Pontoon Boats, Fishing Boats, Crabbing Boats, Sailboats, Stand-up Paddle Boards, Kayaks, Canoes, Bikes, Crab/Fishing Gear. We provide personal instruction. All safety equipment and activity gear is included with your rental.