Top Annapolis Water Tours

Cruise through history on the Annapolis Harbor & USNA Cruise. This narrated cruise offers insights into the U.S. Naval Academy and Annapolis' rich maritime heritage while enjoying stunning views of the Chesapeake Bay Bridge. Perfect for families and history buffs alike, this cruise is a cherished local tradition that uncovers the beauty and significance of this historic seaport. - Narrated cruise around Annapolis Harbor and U.S. Naval Academy - Learn about the history and significance of the region - Enjoy picturesque views, including the Chesapeake Bay Bridge

Sit back and relax on this up-close-and-personal cruise of Annapolis's waterways and scenic city shorelines on one of Watermark's 26-foot, open-aired vessels. Your captain will welcome you aboard for this intimate cruise from Annapolis Harbor and up Spa Creek, with stunning views of the U.S. Naval Academy, an abundance of boats of all size, a healthy dose of nature -- all with a recorded narration of historic facts and tidbits of Annapolis's colonial roots, its one-time ship-building might, and more.

Step aboard a classic vessel for a scenic Chesapeake Bay Bridge cruise. As you depart the dock in downtown Annapolis, you will pass along the seawall of the United States Naval Academy and out into open water. As you approach the Bay Bridge, keep an eye out for local wildlife, including osprey, eagles, rays, and even the occasional dolphin, while enjoying great outdoors sightseeing. Then, marvel at the twin spans of the bridge, one of the largest over-water structures in the world. Sit back and relax with a soft drink, beer, or wine available for purchase, and enjoy the sights on this 90-minute journey.

Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, boutique shops, and historic sites. Guests enjoy a complimentary non-alcoholic beverage during the cruise before spending around three hours ashore exploring the town before the return journey to Annapolis. Admission to the Chesapeake Bay Maritime Museum is included, making this sightseeing day trip an ideal way to experience Maryland's rich maritime history.

The Thomas Point Lighthouse is the most iconic lighthouse in Maryland. View this National Historic Landmark on a narrated cruise into the Chesapeake Bay. Not just for lighthouse enthusiasts, everyone loves it during this 1-hour-and-30-minute excursion that blends history, sightseeing, and the great outdoors into a memorable maritime adventure.

Explore the eerie side of Annapolis with the Spirits & Spirits tour, blending a captivating walking tour through the Historic District with a thrilling cruise on the haunted waterways. Listen to spooky stories from your Ghost Guide, uncover nautical myths, and indulge in beverages available for purchase during the cruise. Perfect for those seeking a unique blend of history and ghostly tales in a fun atmosphere. This tour is suitable for adults and private tours can be arranged upon request. - Combination of a guided walking tour and a scenic ghost cruise. - Hear chilling tales from expert Ghost Guides while exploring Annapolis's Historic District. - Enjoy a variety of beverages and snacks available for purchase once on the boat. - Tours available on select dates, departing from 188 Main Street, Annapolis.

We depart right from downtown Annapolis, putting you immediately in the heart of the waterfront, Spa Creek, Ego Alley, and the harbor scene without needing to travel to an outlying marina. Enjoy a customized experience tailored to your group with a USCG-licensed captain. Whether you want to cruise Spa Creek, sail the Bay, anchor for a swim, stop at a waterfront restaurant, or enjoy a sunset picnic, the classic teak-appointed Nauticat offers a refined and relaxed way to enjoy the water. Bring your own food and drinks or opt for catering to make your outing extra special. Enjoy a private boat experience with just your group and no crowds. Depart from downtown Annapolis, right in the heart of the waterfront. Choose from two vessels: the classic Nauticat 331 or the nimble AB Oceanus RIB. Suitable for family outings, casual celebrations, or intimate getaways. Flexible trip lengths and itineraries to match your preferences.