Annapolis: Round Trip Cruise to St. Michaels

A Relaxing Day on the Chesapeake: Annapolis Round Trip Cruise to St. Michaels

Imagine sailing across the Chesapeake Bay, feeling the breeze and soaking up views of Maryland’s water-loving landscapes. That’s what this Round Trip Cruise to St. Michaels promises — a leisurely trip that combines scenic beauty, charming town exploration, and a bit of history, all wrapped into a neat 7.5-hour package.

What we love most about this experience are the stunning water vistas, the opportunity to explore a picturesque historic village at your own pace, and the educational aspect of the Chesapeake Bay Maritime Museum. It’s a relaxed way to enjoy Maryland’s eastern shore without the hassle of driving or planning multiple stops.

One thing to consider is that the timing can feel a little rushed — with less than three hours ashore, some may find it tight to see everything they want. Still, if you’re looking for a day of gentle exploration, this trip fits the bill.

This experience is perfect for history buffs, water lovers, and those seeking a laid-back escape from city life. Whether you’re visiting Annapolis and want a taste of nearby maritime charm or planning a scenic day trip, this cruise offers good value and memorable views.

You can check if your dates are available here:

Good To Know

• Scenic Chesapeake Bay Views: The cruise offers beautiful vistas that capture the essence of Maryland’s waterway charm.
• Flexible Exploration: You can explore St. Michaels at your own pace, with ample time for shopping, dining, or wandering through historic streets.
• Educational Experience: Admission to the Chesapeake Bay Maritime Museum enriches your visit with insights into the region’s maritime culture.
• Comfortable Journey: The vessel is described as well-managed, with ample seating and a relaxing atmosphere, plus a complimentary non-alcoholic beverage.
• Cost and Value: At $157 per person, it’s a reasonable price considering the included museum entry, scenic cruise, and the potential for a lovely day out.
• Potential for Rushed Visit: With under three hours ashore, some may feel the time is a bit tight, so planning ahead is advisable.

The Details of the Day: What to Expect

The day begins with a meeting at Annapolis City Dock, marked by a red umbrella and Watermark ticket stand. From there, you board the vessel for a roughly 2 to 2.5-hour cruise across the Chesapeake Bay. During the boat ride, you’ll be offered a complimentary non-alcoholic beverage, which makes the journey more pleasant and refreshes your palate for the scenic views ahead.

Once in St. Michaels, you’ll have around three hours to explore this charming historic village. Known for its boutique shops, art galleries, and fresh seafood, the town is perfect for a relaxed stroll. Many visitors appreciate the opportunity to browse local stores, enjoy a coffee or snack, or simply soak in the waterfront atmosphere.

The highlight of the visit is the Chesapeake Bay Maritime Museum. The admission is included, so you can wander through exhibits that showcase the area’s maritime traditions, boats, and artifacts. One reviewer mentioned that the museum’s displays offer fascinating insights, which help deepen your understanding of the region’s nautical past.

The return trip offers another scenic cruise back to Annapolis, giving you more water views and a chance to unwind before concluding your day. The schedule feels well-paced, although some reviews suggest that the short time ashore may feel rushed for those wanting to do more than just a quick look around.

Comfort, Convenience, and Practicalities

The boat itself is described as “nice” and “well-managed,” with enough seating to find a comfortable spot for the journey. If you prefer outdoor views, the upper deck is a good choice for water immersion and photos. A full-service bar is available on board for purchases, and some reviews noted that while the bar isn’t extensive, it provides enough options for a drink or snack.

Accessibility is limited, as the tour isn’t suitable for people with mobility impairments or wheelchair users. Seasickness could also be a concern, given the boat’s open water route, so travelers prone to feeling queasy might want to prepare accordingly.

Parking at Annapolis is not included, so plan for additional fees or arrive early to secure a spot. Check-in begins 15 minutes prior to departure, so arriving promptly is advised.

An Honest Look from Reviewers

The majority of reviews are positive, highlighting the knowledgeable crew and beautiful views. For instance, one guest appreciated the captain’s explanations, noting, “The captain explained what we needed to do,” which enhanced the overall experience.

Another reviewer called the trip “amazing” and praised the crew’s helpfulness, calling their service “very nice and helpful.” This underscores the importance of a friendly, informed crew to make the trip enjoyable.

However, some feedback points to the value for money, with one guest feeling overcharged — paying $157 when the ticket price was $118. This suggests that some travelers might want to shop around or buy tickets at the dock if they’re okay with the risk of a sellout.

The short time in St. Michaels was another point of critique, with one guest saying it felt “rushed” and suggesting a longer stay would improve the experience. Still, many see it as a good quick escape rather than an in-depth visit.

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The Balance of Cost and Experience

$157 per person is a fair price considering what’s included: a scenic cruise, museum admission, and a charming village visit. It’s a relaxed, all-in-one package that’s especially valuable for those who prefer not to plan multiple stops or drive between locations.

If you’re someone who enjoys water-based sightseeing, discovering local maritime culture, or simply relaxing on a boat, this trip offers a lot of bang for your buck. Just keep in mind the time constraints — if you love to explore every corner of a town, you might find the allotted hours a little limiting.

Who Will Love This Tour?

This cruise suits travelers looking for a peaceful day out with beautiful water views. It’s ideal for history and maritime enthusiasts eager to learn more about the Chesapeake Bay area. The included museum visit adds educational value, making it a good choice for families, couples, or solo explorers.

It’s perfect for those who prefer guided yet flexible experiences, with enough free time to wander and enjoy the scenery. However, if you’re after a long, leisurely exploration or have mobility issues, this might not be the best fit.

Final Thoughts

The Annapolis Round Trip Cruise to St. Michaels offers a delightful slice of Maryland’s eastern shore. It’s a well-organized, scenic outing that balances water views, local charm, and cultural insights with a manageable schedule. The combination of a comfortable boat ride, a historic village, and a museum makes it a well-rounded choice for a day trip.

While it’s not without minor drawbacks — mostly related to timing and accessibility — the experience delivers good value, especially if you’re keen on scenic water travel and a taste of local history. It’s best suited for those wanting a relaxed, scenic escape rather than a full day of sightseeing.

If you’re in Annapolis and craving a peaceful, water-centric day, this cruise could be just what you need to enjoy Maryland’s maritime side.

Frequently Asked Questions

How long is the overall trip?
The entire experience lasts about 7.5 hours, including the cruise to and from St. Michaels and the time spent exploring the village.

What is included in the price?
Your ticket includes the round trip cruise, one complimentary non-alcoholic beverage, and admission to the Chesapeake Bay Maritime Museum.

Is there any food available onboard?
Yes, there is a full-service bar where you can purchase drinks and snacks, but it’s not included in the ticket price.

Can I buy tickets at the dock?
Yes, some guests mentioned that tickets are available for purchase at the dock, which might offer a slight discount, but beware of the risk of the cruise selling out.

Is this tour wheelchair accessible?
No, the tour is not suitable for people with mobility impairments or wheelchair users.

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

This cruise from Annapolis to St. Michaels offers a gentle yet memorable way to enjoy Maryland’s scenic waterways and charming towns. It’s a worthwhile option for those craving a relaxing day, scenic views, and a touch of maritime history—all in one easy trip.

You can check if your dates are available here: