Get Your FREE Ultimate Weekend Packing Cheat Sheet!

Why You Should Take a Sunset Cruise in St. Michaels, Maryland PullOverAndLetMeOut
Picture of Anna Marie

Anna Marie

Why You Should Take a Sunset Cruise in St. Michaels, Maryland

St. Michaels, on Maryland's Eastern Shore, is a lovely and historic town. Travel there with PullOverandLetMeOut to find out why it's even more stunning from the water.
A woman sipping coffee outside
Hi, I’m Anna Marie. I’m a wife, mother, Irish dancer, and pug mom living in North Carolina. I also love to travel. Come along for the ride! If you see something you like, don’t be afraid to say, ‘Pull over and let me out.’

St. Michaels is located on Maryland’s picturesque Eastern Shore and while I’ve visited and written about it previously, I’d never seen this magical town on the other side of the Chesapeake Bay from the water. Now that I’ve had the pleasure of a nautical view of the historic port city, I can confidently tell you why you should take a sunset tour in St. Michael’s, Maryland.

Visiting St. Michaels, Maryland

Girl’s weekends offer some of the best and most memorable opportunities to see new things and places with good friends and lots of laughter. It can also afford the opportunity to view places from a new and different perspective. Our annual get-together was made even more special when my life-long friend and gracious hostess for the weekend, Sherri, suggested a sunset cruise.

My response to Sherri’s idea was an immediate, Ahoy!

The St. Michaels, MD lighthouse at sunset
The historic St. Michaels Lighthouse is a highlight of the Sunset Cruise

A Sunset Cruise of St. Michaels

This sounded like a lot of fun. So, on a crisp late September Saturday evening, my friends and I boarded a St. Michaels Harbor Shuttle Tour boat for a Sunset Cruise.

We met the boat and our skipper, Captain Joyce, outside the Crab & Steak Restaurant on Mulberry Street in the main port. We climbed aboard the boat where we learned the basics such as the location of the life jackets, cooler, and fire extinguisher as well as what to do just in case we needed to call in the Coast Guard. (Thankfully this was an extremely remote possibility) 

Captain Joyce of St. Michaels Harbor Shuttle Tours
Captain Joyce of St. Michaels Harbor Shuttle Tours.
sunset view from the back of a boat
Breathtaking views make a sunset cruise memorable.
PullOver Pro Tip picture

Are you traveling with your dog? In St. Michaels, many hotels, restaurants, businesses, and even local banks cater to dogs traveling with their owners, making the Eastern Shore town a haven for furry family members. And yes, the Sunset Cruise is dog-friendly too!


St. Michaels Harbor Shuttles began offering these tours in 2020, and they have rapidly become a must-do when visiting St. Michaels. Each tour lasts around an hour, is BYOB (bring your own beverages), drinks, food, and pets are welcome and costs $35 per person. In addition to quietly floating along Miles River and admiring the gorgeous harbor, we are blessed with a breathtaking sunset view at the moment the golden orb is putting on a brilliant display as it sinks behind the St. Michaels skyline.

a sailboat on the water at sunset
A classic sailboat at sunset.
St. Michaels, MD at sunset from the water
Stunning sunset!
The sun dipping behind St. Michaels MD
The gloaming at St. Michaels, MD

Seeing St. Michaels from the water

The fun doesn’t end the moment the sun dips below the horizon. While there is still a little light in the gloaming, Captain Joyce treats us to a tour filled with historic tidbits about the things we’re seeing. She regales us with the story of how the St. Michaels Lighthouse was moved to the Maritime Museum property in pieces.

She also shares the history of the old church that was there before St. Michaels was a town. As we coast along the water, we hear harrowing tales of cannonballs flying overhead during the War of 1812 and of how the townspeople outsmarted the British Navy.

Similarly, she takes us past the iconic Crab Claw restaurant and even points out the lovely inn where the movie Wedding Crashers filmed a wedding scene a few years ago. Each item she reveals sheds light on another fascinating aspect of the story of St. Michaels, Maryland.

The Crab Claw restaurant at sunset
The Crab Claw's history dates back to the 1950s
Inn at Perry Cabin in St. Michaels at sunset
Inn at Perry Cabin Resort as seen in the movie Wedding Crashers

Is a sunset cruise of St. Michaels worth it?

My friends and I had a great time sailing around St. Michaels at sunset. It’s a one-of-a-kind and enjoyable activity that has become a highlight of our time together this year.

The scenery, the history, the soothing calm of the water, and the camaraderie of life-long friends made this a magical and memorable itinerary item. And while I can’t guarantee you’ll enjoy the same blissful weather we were blessed with that Saturday evening, I can sincerely endorse a water view and sailing around St. Michaels, Maryland.

To quote the St. Michaels Harbor Shuttle Tours website, “You haven’t seen St. Michaels unless you’ve seen it from the water!”

St. Michaels Harbor Shuttle Tours

a group of women around a restaurant table
Post-Sunset Cruise dinner with life-long friends... PRICELESS!

Hey, Pinners! Pin this for later!

► Plan Your Trip To St. Michaels, Maryland, Now!

It makes it simple to plan your trip.   We’ve pre-filled the destination from the article and if there are multiple places mentioned in the article, we’ve put the one that is best used as your base to see all of the places mentioned.

Just select I’M STAYING and enter the travel dates and hit SEARCH.  It automatically uses the first place in the article.  

For a multi-day trip, if you stay near that location, you should be able to use it as your base.

Super simple.  Just click on the pencil and enter the name of any place mentioned in the story.  Or you can enter any address or even the name of a company if you are mixing business and pleasure.

Just click I’M DRIVING and you can see how long it will take, get driving directions and even rent a car if you need one.

Yes, we guarantee the best published rates on hotels.  Click on the link for BEST RATE 110% GUARANTEE for details.

Share your experiences  

Hey pinners, save this for pinning after your trip

After you get back from your trip, please use these images to post to social media or post your own photos.  Please tag us on your post #pulloverandletmeout
You can also use the social sharing links on the SmartTrip tool.
Paws for Purple Hearts logo

More stories you'll love reading!

Cover photo two pints of Guinness

What You Need to Know Before You Order That Pint of Guinness

Few beverages are as closely linked to a location as Guinness is to Ireland. Rich in heritage, the creamy dark stout is a daily staple at pubs and bars across Ireland and the world. Travel along with Pull Over and Let Me Out to the Emerald Isle and learn what you need to know before you order that pint of Guinness.

Read More »

Let’s Get Social!
Click below and join the conversation on social media

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top

FREE Access to Exclusive Travel Tips and Deals

Get the latest travel news, tips & information from!

Save on Membership with


don't leave empty-handed

Get your FREE Ultimate Weekend Packing Cheat Sheet

Happy Travels