Dog-Friendly Annapolis, Maryland Activities: Dog-Friendly Cruises on Annapolis Harbor

Dog-Friendly Annapolis, Maryland Activities

Dog-Friendly Cruises on Annapolis Harbor |  Cruises on the Bay℠  by Watermark®

Dog-Friendly Annapolis, Maryland Activities. We enjoyed a great dog-friendly cruise on the Annapolis Harbor thanks to Cruises on the Bay by Watermark. #raisingyourpetsnaturally
Dog-Friendly Annapolis Boat Cruise

Disclaimer: This post is sponsored by Extended Stay America. However, I will always offer my readers an unbiased and honest account of my experiences. Your trust is very appreciated, and never taken for granted. ~Tonya, Dexter and Nutter

During our dog-friendly vacation in Maryland, I knew I wanted to take Dexter on a boat ride. Dexter LOVES taking boat rides. I think there is something about the gentle rocking of the boat, the breeze in his ears and the scent of the open water that just mesmerizes Dexter.

While searching online for a dog-friendly boat cruise, I found Cruises on the Bay℠ by Watermark®. I messaged them about bringing Dexter aboard their boat, and they were very helpful and friendly in our conversations. With over 45 years of experience, this was the Annapolis dog-friendly cruise I wanted to take Dexter aboard.

Watermark’s cruises are pet-friendly as long as dogs are friendly and leashed, and the dogs cruise free of charge! The boat also had restrooms and a full bar and cruise mementos. I have to admit, I wanted to purchase a souvenir, but totally forgot.

Dog-Friendly Annapolis, Maryland Activities. We enjoyed a great dog-friendly cruise on the Annapolis Harbor thanks to Cruises on the Bay by Watermark. #raisingyourpetsnaturally
Dog-Friendly Annapolis Activities

While purchasing our ticket, the nice gentleman was telling me all about his Cavalier King Charles Spaniel. Everyone was very happy to see Dexter and Levi board the cruise ship. Our 40-minute narrated cruise left from the City Dock at 7 pm.

We sat on the upper deck to get the most out of our dog-friendly boat cruise. It was a sunny and warm evening, but the breeze cut down the heat and Dexter and I positioned ourselves in the shade. We learned so much of the area’s history listening to the narration while sightseeing the waterways of the Annapolis Harbor. Seeing the U.S. Navy Academy was a treat, too.

Dog-Friendly Annapolis, Maryland Activities. We enjoyed a great dog-friendly cruise on the Annapolis Harbor thanks to Cruises on the Bay by Watermark. #raisingyourpetsnaturally
Levi sleeping

Both Dexter and his travel buddy, Levi, enjoyed smelling the fresh air and looking around. Eventually, both dogs were lulled to sleep. Whether you are looking for dog-friendly things to do in Annapolis or want to leave Fido at home, Watermark has the perfect cruise for you! Plan a group trip, field trip, or private charter with their team of specialists. Tell them Dexter sent you.

Save 20% off 1-29 nights at Extended Stay America hotels with promo code MZ7RN. Book 10/1-10/31


Is your dog adventurous? Tell me in the comments.

Dog-Friendly Annapolis, Maryland Activities. We enjoyed a great dog-friendly cruise on the Annapolis Harbor thanks to Cruises on the Bay by Watermark. #raisingyourpetsnaturally
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92 thoughts on “Dog-Friendly Annapolis, Maryland Activities: Dog-Friendly Cruises on Annapolis Harbor

  1. My hometown does Dog day in the pool. The last day of the season they open the pool to all the dogs that want to come swim. After the day is over they clean the pool and close it down until the following summer.

  2. This is great! I’ve never heard of boat trips allowing dogs on before but I think they have just as much right as we do! The dog in the photos looks so happy to be on the boat – very cute!

  3. I had no idea there was such a thing as dog friendly cruises, how cool is that?! Glad you shared this, we have two doggies and now we know if we ever want to venture on a cruise, there are options!

  4. love this idea my daughter has no children yet but has a special spoiled pup. This little pup goes every where and does everything they would love this idea.

  5. I love that the cruise was dog-friendly, that is pretty sweet. Most places want your dogs to be service dogs in order to bring them along. This was great.

  6. I am happy to learn of these dog friendly boat rides! My fur child would love this. We have set up a small inflatable pool for him in the backyard so he can cool off when he needs to. Although I am confident he won’t jump into the water during a boat ride, the fresh air would really do him good.

  7. Dogs are my fav animals! They are super adorable and it’s great to see how many cities are having dog-friendly places! I definitely didn’t know about dog cruises tho!

  8. This is a great idea to do with your loved one. I wonder if our local lake allows this service. I would love to take our BellaPoo onto a local cruise. That would be awesome. Dexter is just adorable, oh my. I understand why the guy had to tell you about his dog. Dexter is a true conversation piece. 😉

  9. I hadn’t ever heard of a dog friendly cruise before so it’s cool that those actually exist! My dog is a 16 year old lab so I don’t know how well she would do on a cruise but I feel like I’d want to go on it just to pet everyone else’s dogs!

  10. Little Dexter on the boat sure made me smile. There’s nothing better than sunshine on your shoulders, the wind in your fur, and spending the day with the people you love so very much. Bonus, at the end of the day you’re bound to get some tasty treats and take a big nap! x

  11. Oh your dog is such a sweetheart, so cute!! Can you imagine that my neighborhood doesn’t even allow pets?! People continuously violate this rule though haha 😛

  12. So funny! Never in a million years would I have thought of taking a dog for a boat ride- but I would now. Sounds like fun.

  13. Excellent read, I just passed this onto a friend who was doing a little research on that. And he just bought me lunch since I found it for him smile Thus let me rephrase that: Thank you for lunch!

  14. The pictures are soo cute, and the dog seems so happy and enjoyed the tour! I have read your previous article and its always a success providing options for our pet-lover reader.

  15. Annapolis is one of my favorite places to visit. Down town and harbor is absolutely breathtaking. It’s good to know they have pet friendly cruises. You dog such a cutie. what bread is it ?

  16. I’ve never heard of this before but sounds like lot of fun not only for pooches but their humans as well. Definitely checking this out. Thank you.

  17. A few weeks ago it was national spoil your dog day – now dog friendly cruises. No wonder people talk about Americans and their dogs. My neph-doggie loves anything to do with water, I wonder if he would try to leap from the boat.

  18. omg, Dexter is adorable. What a great travel companion. I like to take my little dog with me as well and fortunately there are a lot of dog friendly places here in the Northwest. We even have ferries that the dogs are allowed on.

  19. I haven’t been to Maryland since I got my little dog but it’s time that I turned that around. Maryland is a great place to vacation at. I haven’t been to Annapolis yet but it’s on my bucket list.

  20. I honestly didn’t know there are boat cruises that allow a pet. That is awesome that you get to enjoy the boat ride with your dog. He loves it!

  21. This article made me miss my dogs so much! They aren’t with us now because we are moving to Hawaii soon but we will ship them out to us once we get settled! I hope there are fun things to do with them in Hawaii once we get there!

  22. This is awesome information about the Watermark’s cruises that are dog friendly. It looks like Dexter had a blast on the cruise. I have never thought to take my dog on a cruise but it does sound fund for the whole family. Thanks for sharing the information and your experience.

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