Annapolis: Round Trip Cruise to St. Michaels

If you’re considering a day trip from Annapolis that combines scenic views, charming small-town vibes, and a touch of maritime history, this Round Trip Cruise to St. Michaels might be just what you’re looking for. While I haven’t personally taken this exact cruise, the reviews and details paint a pretty clear picture of what to expect, and honestly, it sounds like a lovely way to spend part of your day exploring Maryland’s Eastern Shore.

What I really like about this experience are the stunning water views during the cruise and the flexibility to explore St. Michaels at your own pace. Plus, the inclusion of admission to the Chesapeake Bay Maritime Museum adds an educational element without extra hassle. The only potential snag? The trip’s duration and timing might feel a bit rushed for some, especially if you love taking your time once ashore. This tour seems best suited to those who appreciate a balanced mix of sightseeing, gentle travel, and local culture without spending too many days away.

This trip could be perfect if you’re looking for a straightforward, scenic escape from Annapolis that doesn’t require much planning. It’s especially good for travelers who enjoy being on the water, exploring small towns, or want an easy, well-organized day that combines transportation, sightseeing, and learning.

Key Points

• Scenic Chesapeake Bay cruise offers beautiful views en route to St. Michaels.
• Flexible exploration allows you to wander the village at your own pace.
• Includes admission to the Chesapeake Bay Maritime Museum, adding educational value.
• Comfortable seating and amenities make the boat ride relaxing.
• Cost at $157 per person provides good value considering the cruise, museum, and scenic experience.
• Not suitable for those with mobility issues or prone to seasickness.

You can check availability for your dates here:

The Itinerary Breakdown

The Cruise Crossing Chesapeake Bay

The trip starts at Annapolis City Dock, where you’ll find the meeting point marked by a red umbrella and Watermark ticket stand. With check-in happening 15 minutes before departure, it’s a smooth start, but arriving early is always a good idea to settle in comfortably.

The boat ride itself lasts about 2 to 2.5 hours each way, making it a leisurely journey. During this time, you’ll enjoy a complimentary non-alcoholic beverage, which is a nice touch that adds to the relaxing vibe. The views during the cruise are often praised—expect to see plenty of water, passing boats, and scenic Maryland shoreline. As one reviewer said, the ship was “nice, easy to find, and well-managed,” and the outdoor deck is perfect for soaking in the views.

Arrival in St. Michaels and Free Time

Once you arrive in St. Michaels, you’ll have approximately 3 hours ashore. The village is described as picturesque, filled with boutique shops, art galleries, and cafes. It’s the kind of place where you can casually stroll through the streets, pop into a few shops, or sit down for a seafood lunch. Keep in mind, some reviews mentioned the port time as feeling a bit tight—less than three hours means you’ll need to prioritize what you want to see and do.

Visiting the Chesapeake Bay Maritime Museum

Included in your ticket price is entry to the Chesapeake Bay Maritime Museum. This is a highlight for those interested in learning about local traditions, boat-building, and maritime history. The exhibits are said to be fascinating, offering insights into the area’s heritage that go beyond just pretty scenery.

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The Return Journey

After your time in St. Michaels, you’ll board the boat for the return trip. The views of the bay from this side are often praised for their serenity, making it a calming way to round out your day. Remember, the cruise route and vessel assignments can change, so be flexible if things shift unexpectedly.

What Travelers Say: Honest Feedback from Past Guests

The reviews give us useful insights. Shirley loved the trip, saying, “I enjoyed the trip very much. The captain explained what we needed to do. I would highly recommend this trip.” Clearly, knowledgeable guides and smooth management make a difference.

Debbie described the day as “beautiful,” praising the helpful crew members. That speaks to the friendly, welcoming atmosphere on board, which is key for a relaxing day.

Julieta’s only gripe was the overcharge—paying $157 when the listed price is $118—not ideal, but it does remind us to double-check prices or clarify before buying tickets.

Paul highlighted the easy-to-find boat and ample seating but pointed out that the time ashore is a bit rushed, especially if you want to include a full meal or visit the museum in depth. He suggests that making this a longer day might be better if you want to take everything in without feeling hurried.

Bradly was less impressed, feeling that the trip wasn’t worth a full day because St. Michaels is small and can be seen in about 30 minutes. His experience underscores that this trip is best for those who genuinely enjoy boat rides and small-town charm, rather than those hoping to explore extensively.

The Practical Details

Duration and Timing

At 7.5 hours total, including the cruise, time ashore, and museum visit, this is a full-day experience but not overly long. Most trips happen in the morning, which makes it suitable for those who want to fit in other activities later in the day.

Price and Value

At $157 per person, the trip includes the cruise, one non-alcoholic beverage, and museum admission. While some reviews mention paying more than the listing price, the overall value depends on your interest in water travel and maritime culture. For many, the scenic cruise combined with museum access makes this a fair deal, especially when considering the convenience of an organized tour.

Accessibility and Limitations

It’s important to note that this experience isn’t suitable for those with mobility issues, wheelchair users, or anyone prone to seasickness. The vessel is accessible for wheelchairs, but check with the provider for specific needs.

Additional Considerations

• Parking fees are not included, so plan accordingly.
• The boat route and vessel can change, which might affect your experience slightly.
• Drinks and snacks are available for purchase onboard, so if you want more than the complimentary beverage, bring cash or cards.
• The full-service bar on board offers additional options for those interested.

Who Should Consider This Trip?

This cruise is perfect for water lovers, history buffs interested in maritime traditions, or anyone wanting a relaxed day exploring Maryland’s scenic shoreline and charming village. It’s especially good if you’re traveling with a group that appreciates comfort, scenic views, and a touch of culture without a strenuous itinerary.

If you’re looking for a full-day sightseeing adventure with lots of museums or activities, this might feel a little limited. However, if your goal is to enjoy a peaceful boat ride and a charming town with some learning thrown in, this trip hits the mark.

Final Thoughts

This Round Trip Cruise to St. Michaels is a solid option for travelers seeking a seamless, scenic escape from Annapolis. The boat ride offers beautiful views, and the free time in the village allows for a relaxed exploration of one of Maryland’s most picturesque spots. The inclusion of the Maritime Museum adds a layer of interest for those curious about local watercraft and history.

While the journey might feel rushed for some, especially if you want to spend more time eating or browsing, the overall experience seems well-managed, friendly, and enjoyable. It’s a good choice if you want a straightforward, comfortable way to enjoy Maryland’s Chesapeake Bay area without too much fuss.

For those who love a calm water cruise combined with small-town charm, this tour can create some nice memories—just be sure to plan your day to maximize your time ashore.

FAQ

Is the cruise suitable for people with mobility impairments?
Not really. The experience isn’t designed for those with mobility issues, though the vessel is accessible for wheelchairs. Check with the provider if you have specific needs.

How long is the total trip?
The entire experience lasts about 7.5 hours, including the boat rides (about 2-2.5 hours each way), and approximately 3 hours ashore in St. Michaels.

What’s included in the price?
Your ticket covers the round-trip cruise, a single complimentary non-alcoholic beverage, and admission to the Chesapeake Bay Maritime Museum.

Can I buy drinks or snacks on board?
Yes, there is a full-service bar for purchase, and additional snacks or drinks are available for extra cost.

What is the meeting point?
Look for the red umbrella and Watermark ticket stand at Annapolis City Dock. Arrive 15 minutes early.

How flexible are the cruise routes?
Routes and vessel assignments may change without notice, so stay flexible and check with the operator if you have specific questions.

Is this a family-friendly trip?
It’s generally suitable for adults and older children, especially those who enjoy boat rides. However, it might not be ideal for very young children or those prone to seasickness.

What about weather considerations?
Since the trip is mostly outdoors, check the weather forecast and dress appropriately. Bad weather could lead to route changes or cancellations.

If you’re after a laid-back day on the water with a touch of local charm, this cruise could be a highlight of your Maryland trip. Just plan accordingly, and you’ll likely come away with some lovely memories.

You can check availability for your dates here: