Annapolis: Round Trip Cruise to St. Michaels

Traveling along Maryland’s Chesapeake Bay offers a delightful blend of scenic water views, historic towns, and maritime culture. This particular cruise from Annapolis to St. Michaels is a popular day-trip option for those looking to combine a boat ride with some charming sightseeing. While we haven’t taken it ourselves, the reviews and tour details give us plenty to recommend—and some considerations to keep in mind.

What we love about this experience is the scenic cruise itself, with its calming waters and picture-perfect vistas, and the chance to explore St. Michaels at your own pace—a small town packed with boutique shops, cozy cafes, and historic sites. The Chesapeake Bay Maritime Museum adds a fascinating educational element that enriches the trip.

One possible drawback? The short amount of free time in St. Michaels might feel a bit rushed for some travelers, especially if you want to fully enjoy the town’s offerings or have a leisurely meal. It’s best suited for those who enjoy a mix of scenery, quick exploration, and a touch of local history—ideal if you’re a fan of water-based outings combined with small-town charm.

Key Points

• Scenic Chesapeake Bay cruise offers beautiful water views and a relaxing ride.
• Self-guided exploration in St. Michaels allows flexibility and personal pacing.
• Educational visit to the Chesapeake Bay Maritime Museum enriches understanding of local maritime heritage.
• Affordable value with included cruise, museum admission, and a complimentary beverage.
• Limited free time in town may require prioritizing sights or skipping meals.
• Suitable for outdoor lovers, history buffs, and those seeking a laid-back day trip.

You can check availability for your dates here:

A Scenic Journey Across Chesapeake Bay

The most appealing part of this tour is undoubtedly the cruise itself. Departing from Annapolis, you’ll glide across the Chesapeake Bay on a vessel that’s described as well-managed, roomy, and easy to find—look for the red umbrella and Watermark ticket stand at the end of Annapolis City Dock. The two to two and a half hours each way on the water, accompanied by a complimentary non-alcoholic beverage, makes for a peaceful, visually engaging ride.

The water views are what you’d expect from a classic Chesapeake outing: wide-open skies, shimmering water, and the occasional sailboat or fishing vessel passing by. The boat ride’s serene pace and ample seating provide a comfortable way to unwind and enjoy the scenery.

Exploring St. Michaels at Your Own Pace

Once ashore in St. Michaels, you get around 3 hours of free time—enough for a quick walk through the town’s charming streets, some boutique shopping, or a relaxed meal. This flexibility is a major plus, especially for those who prefer to skip a guided tour and set their own rhythm.

The town itself is well-loved for its historic buildings, waterfront charm, and seafood spots. You might find it perfect for some casual strolling, photo opportunities, or popping into local galleries. But be aware that some reviews mention that the town can be seen in about 30 minutes if you’re quick, so prioritizing your interests is key if you want to make the most of that time.

Visiting the Chesapeake Bay Maritime Museum

The included admission to the Chesapeake Bay Maritime Museum is a highlight that sets this experience apart. The museum offers a collection of exhibits that showcase the area’s maritime heritage and culture—perfect for history lovers or those curious about Chesapeake’s water-based traditions.

The museum is accessible directly from the town and provides a good dose of educational content on the region’s fishing, boatbuilding, and maritime industries. Several reviewers praise the museum for its fascinating exhibits and excellent storytelling, making it a worthwhile stop that offers more depth than just sightseeing.

The Practical Side: Costs, Timing, and Comfort

At $157 per person, this tour offers solid value—especially considering the included round-trip cruise, museum admission, and beverage. The price is comparable to similar day trips, and the convenience of an all-in-one experience offsets the separate costs of transportation and admissions.

The tour is generally scheduled in the morning, making it an easy full-day activity. Keep in mind that parking is not included, so plan for potential fees at the departure point. Also, the boat trip is not suitable for those with mobility impairments or who are prone to seasickness; this is a water-based excursion that can be choppy depending on weather.

More Great Tours Nearby

What the Reviews Say

Real travelers’ insights help paint a clearer picture. Shirley gave a perfect rating, saying, “I enjoyed the trip very much. The captain explained what we needed to do. I would highly recommend this trip.” Debbie echoed this, praising the crew’s helpfulness and the “beautiful day.”

On the critical side, Julieta mentioned feeling overcharged—paying $157 when the actual ticket price is listed as $118—highlighting that travelers should verify prices and consider possible additional costs.

Paul found the vessel “nice, easy to find, and well-managed,” but noted that with only about 3 hours ashore, the visit felt a bit rushed—so if you’re looking for a slow, leisurely day, you might want to extend your stay or choose a longer trip.

Bradly’s review suggests that some might find the trip not worth a full day, considering how quickly St. Michaels can be explored. He recommends a longer cruise if you want a more relaxed experience.

Summary of the Experience

This cruise offers a practical blend of scenic water travel and small-town exploration. The boat ride prioritizes comfort and views, making it suitable for those who enjoy being on the water and want a straightforward journey. The visit to St. Michaels is flexible, fitting for those who like to explore independently rather than follow a strict schedule.

The museum visit adds educational richness that appeals to history enthusiasts or families interested in maritime traditions. The combination of scenery, culture, and a relaxed pace makes this a good choice for outdoors lovers, casual travelers, or anyone wanting an easy day trip from Annapolis.

Who Will Enjoy This Tour?

This experience is perfect for travelers who appreciate water-based excursions, scenic views, and small-town charm. It suits those looking for a family-friendly outing, history buffs, or anyone wanting a relaxing day combining boat travel and light exploration.

However, it might not be ideal if you prefer longer visits, full-day adventures, or accessible options—since the boat isn’t suitable for those with mobility challenges and the free time in town is limited.

FAQ

Is the cruise suitable for children?
The tour is generally family-friendly, but keep in mind that the boat isn’t suitable for unaccompanied minors or those with mobility issues. Kids who enjoy water views and small-town wandering will likely have a good time.

How long is the entire tour?
Including the boat ride, exploration time, and museum visit, the tour lasts about 7.5 hours, with the cruise itself taking around 2-2.5 hours each way.

What facilities are available onboard?
There is a full-service bar for purchase, and a complimentary non-alcoholic beverage is included. Seating is ample, and the vessel is described as easy to find and well-managed.

Are there any restrictions I should know about?
Yes, the tour prohibits weapons, smoking, vaping, alcohol, drones, coolers, and unaccompanied minors. It’s also not wheelchair accessible or suitable for those prone to seasickness.

Can I buy tickets on the day of the trip?
Yes, you can buy tickets at the dock, but there’s a small risk of sellout, so booking in advance is recommended. The price might be slightly higher if purchased last-minute.

What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund, offering flexibility if your plans change.

Does the route or schedule change?
Yes, routes and vessel assignments are subject to change based on weather or operational needs, which is common for water-based tours.

Final Thoughts

This Annapolis to St. Michaels cruise offers a well-rounded day of scenic water travel, small-town charm, and educational discovery. It’s an excellent choice for those who appreciate relaxing boat rides paired with independent exploration. The inclusion of the Chesapeake Bay Maritime Museum adds an enriching element that makes this trip more than just a scenic cruise.

The value for money, especially considering the museum admission and beverages, makes it an accessible option for a wide range of travelers. The trip’s main limitation is the short amount of time ashore, so if a relaxed, in-depth visit to St. Michaels is your goal, you might want to extend your stay or seek other options.

In essence, if you’re after a beautiful, laid-back day on the water with a taste of local culture, this cruise from Annapolis to St. Michaels could be just the ticket.

You can check availability for your dates here: