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Experience a scenic Chesapeake Bay cruise from Annapolis to St. Michaels with museum visits, historic village exploration, and a relaxing 7.5-hour day trip.

A round-trip cruise from Annapolis to St. Michaels offers an engaging way to enjoy Maryland’s picturesque waterways. For $157 per person, this 7.5-hour excursion combines a relaxing boat ride with free time in the charming historic village of St. Michaels and admission to the Chesapeake Bay Maritime Museum. The tour departs from Annapolis, featuring a scenic journey across Chesapeake Bay with a complimentary non-alcoholic beverage onboard.
While the cruise’s duration and the museum visit provide a well-rounded experience, it’s worth considering that the 3-hour port stay can feel a bit tight for some travelers, especially those wanting to explore the village and museum thoroughly. Nonetheless, this trip suits visitors seeking a mix of water views, local history, and light exploration.
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The cruise begins at Annapolis City Dock, where travelers find the Watermark ticket stand under a red umbrella. Check-in occurs 15 minutes before the scheduled departure. This location is easy to find, and the boat is generally well-managed and comfortable, with ample seating options.
The round-trip voyage takes about 2 to 2.5 hours each way, offering beautiful views of Chesapeake Bay. The departure is typically scheduled in the morning, allowing plenty of time for your day on the Eastern Shore. Travelers can reserve their spot with the option to pay later, providing flexibility to fit this trip into wider travel plans.

The boat ride across Chesapeake Bay features notable scenery, with expansive water views that showcase Maryland’s maritime landscapes. A complimentary non-alcoholic beverage enhances the journey, and the vessel offers a full-service bar for purchase, giving options for those wanting additional drinks.
The watercraft’s design includes both indoor and outdoor decks. The upper outdoor deck provides a more immersive experience, perfect for snapping photos or simply soaking in the breeze. Indoor seating offers comfort if the weather is less cooperative.
Weather conditions and vessel schedules can lead to route changes or boat substitutions, but these are typically communicated clearly. The ride itself is approximately 2 to 2.5 hours each way, making the journey scenic yet manageable for most travelers.
Once in St. Michaels, you’ll find a walkable, charming village filled with boutique shops, cafes, and historic sites. The 3-hour port stop allows enough time to stroll along its picturesque streets, explore art galleries, and enjoy a casual meal or snack.
Known for its fresh seafood, St. Michaels offers various dining options, while the local shops provide unique souvenirs. Most attractions are within walking distance, but the limited timeframe may make it necessary to prioritize your interests, especially if planning to visit the Chesapeake Bay Maritime Museum.
More Great Tours NearbyIncluded in the tour is admission to the Chesapeake Bay Maritime Museum, which offers fascinating exhibits on the area’s water-based history. Visitors can explore displays that highlight the maritime industry, boat-building traditions, and local ecology.
The museum’s location is conveniently situated in the village, making it a popular stop for those interested in maritime culture. The exhibits are designed to educate and entertain, providing context and stories that bring Maryland’s water heritage alive.
The cost of the tour is $157 per person, covering the round-trip cruise, a complimentary non-alcoholic beverage, and museum admission. Additional purchases on board include drinks from the full-service bar and snacks, which are not included in the ticket price.
Parking fees are not included, and travelers should plan accordingly. The meeting point at Annapolis City Dock is straightforward to find, and the cruise is wheelchair accessible. However, it’s important to note that the tour is not suitable for people with mobility impairments or those prone to seasickness.
The duration of 7.5 hours means travelers should be prepared for a full-day outing, with check-in starting 15 minutes prior to departure and the trip usually scheduled in the morning.
While the experience offers a delightful combination of scenery and culture, some reviews highlight that the free time in St. Michaels can feel somewhat rushed, with less than 3 hours ashore. This limits the opportunity to fully explore the village or visit the museum without feeling hurried.
Plus, the length of the trip may not appeal to those seeking a leisurely, multi-day experience or travel with mobility challenges. Seasickness can also be a concern for sensitive travelers, and the boat’s schedule and route are subject to change due to weather or operational reasons.
This cruise offers a balanced taste of Maryland’s Eastern Shore and Chesapeake Bay, but several similar experiences exist, including harbor cruises, guided tours, ghost walks, and electric boat rentals. These options, available through providers like Watermark Journey, often focus on specific themes or activities, making this particular cruise ideal for those wanting a scenic water journey combined with a brief village exploration.

The Annapolis to St. Michaels cruise is a practical and enjoyable way to experience Maryland’s scenic waterways and historic village life. The $157 ticket covers the boat ride, museum access, and a beverage, making it a good value for a full-day outing.
While the port time is somewhat limited, the trip’s highlights—stunning views, maritime exhibits, and charming streets—are well worth it. This tour suits travelers who appreciate water views, local culture, and history and are comfortable with a full day of activities.
For those looking for a relaxing, scenic escape with manageable logistics and meaningful local experiences, this cruise provides a memorable way to enjoy Maryland’s Eastern Shore.
What is the price of the cruise?
The full cost is $157 per person, including the boat ride, a non-alcoholic beverage, and museum admission.
How long is the entire tour?
The total duration is approximately 7.5 hours, with about 2-2.5 hours of cruising each way and around 3 hours ashore in St. Michaels.
Where does the tour depart from?
The cruise departs from Annapolis City Dock, at a location marked by a red umbrella and Watermark ticket stand.
Is the tour accessible for travelers with mobility issues?
Yes, the tour is wheelchair accessible. However, it is not suitable for those with mobility impairments, and some walking may be involved during the port visit.
What is included in the ticket price?
The ticket covers the round-trip cruise, the admission to the Chesapeake Bay Maritime Museum, and a complimentary non-alcoholic beverage onboard.
Can I buy drinks and snacks on board?
Yes, a full-service bar offers additional drinks, and snacks are available for purchase.
What should I know about the timing?
Check-in occurs 15 minutes prior to departure, and the cruise is generally scheduled in the morning.
Is the route or vessel subject to change?
Yes, vessel substitutions and route changes are possible at any time, often due to weather or operational needs.
Is this tour suitable for children or families?
While the data does not specify age restrictions, the full-day nature and restrictions on minors suggest it is best suited for older children or families comfortable with boat travel.
How long do I have in St. Michaels?
The 3-hour stop provides time for sightseeing, shopping, and dining, though it may feel limited for those wishing to explore more extensively.