Dog Friendly Tours in Maryland

Taking the dog out for a walk takes on a new meaning when you’re on vacation in Maryland. After all, there are tons of sights to see, and smell, around every corner. Browse our dog friendly tours in Maryland below for the scoop on self-guided walks, driving tours, and group tours that both you and your dog are sure to enjoy.

Pet Friendly Private VIP Sail Annapolis By Water
Private VIP Sail Annapolis By Water 'Private VIP Sail Annapolis By Water' is a pet-friendly Airbnb Experience hosted by Susan. There is no better way to see Annapolis than by the water on this 54 foot sailing yacht. If you're planning on bringing your pooch, make sure you bring a life vest for your dog. The experience lasts 2.5 hours and can accommodate up to 6 guests ages 5 and up. Rates start at $330 per person. See Details
Pet Friendly Come Sail With Us!
Come Sail With Us! 'Come Sail With Us!' is a pet-friendly Airbnb Experience hosted by Steve. Join this group experience around Baltimore Harbor and the Patapsco river. Leashed dogs are welcome with prior approval. The experience lasts 2 hours and can accommodate up to 6 guests ages 18 and up. Rates start at $75 per person. See Details
Watermark Journey - Cruises on the Bay Cruise with your four-legged friend aboard a Watermark yacht! Friendly dogs on leashes are welcome on most public cruises, except for the following: Fireworks Cruises, Blue Angels & Thunderbirds Cruises, Live Music Cruises including WRNR Rock ‘N River Cruises, and Cruises to Festivals in St. Michaels (WineFest, OysterFest, Watermen’s Festival). Cruises start at $19 per adult and $6 for children. Fido rides free. See Details
Sunset Sail with Wine and Cheese 'Sunset Sail with Wine and Cheese' is a pet-friendly Airbnb Experience hosted by Steve. Enjoy a beautiful sunset on the water. After a short safety briefing, head out into Baltimore Harbor to take in the sights of the city from the best vantage point. Dogs are welcome on private tours. The experience lasts 2 hours and can accommodate up to 6 guests ages 18 and up. Guests should be able to climb up and down three steps without a railing and have moderate balance on moving platforms. Rates start at $125 per person. See Details
Learn to Sail: Intro to Sailing 'Learn to Sail: Intro to Sailing' is a pet-friendly Airbnb Experience hosted by Steve. SeaAffinity uses sailing and water related experiences to challenge youth and adults, including those impacted by disabilities, to develop life skills and realize their potential. Leashed dogs are welcome with prior approval. The experience lasts 2 hours and can accommodate up to 5 guests ages 12 and up. Rates start at $100 per person. See Details
Cruises on the Bay by Watermark Baltimore Cruise with your four-legged friend aboard a Watermark yacht! All cruises are pet friendly (for well-behaved, leashed dogs)--dogs ride for free! See Details
Baltimore Ghost Tours Bring Fido along as you explore some of Baltimore's most spirited haunts with Baltimore Ghost Tours. Enjoy the Original Fells Point GhostWalk or the Mount Vernon GhostWalk while your costumed guide (a community actor) tells you all the rumors, lore, and ghostly history about the tour area. Pets must be leashed and well-behaved while on the tour. See Details
Hampton Historical Site Your pet can join you on-leash at the beautiful historic environs of this Towson park. See Details
Waterfall & Hike w an Outdoor Educator 'Waterfall & Hike w an Outdoor Educator' is a pet-friendly Airbnb Experience hosted by Liz. Hike at your pace along each trail and learn about local surroundings, take pictures, and enjoy a snack. Leashed dogs are welcome. The experience lasts 4.5 hours and can accommodate up to 10 guests ages 6 and up. Parents may also bring children under 2 years of age. Participants should wear a good/supportive sneaker or shoe, water and snacks as needed. Rates start at $65 per person. See Details
Patriot Boat Cruises This is a wonderful water tour of historic St. Michaels by water, and it docks right by the Chesapeake Bay Maritime Museum, which is also dog-friendly! We even got to take a photo of our dog, "steering" the ship with his paws on the wheel! We love to take our dog everywhere, and we highly recommend this tour. See Details
McClintock Distilling Co. McClintock Distilling Co. welcomes dogs to join their owners for tours and tastings of gin, white whiskey, and vodka. Located in downtown Frederick, limited parking is available at the distillery and additional parking can be found at the Carroll Creek Parking Garage at 44 East Patrick Street. McClintock Distilling Co. is open for tastings and tours Thursday and Friday from 4 pm until 8 pm, and on Saturdays and Sundays at noon until 8 pm. See Details
Street Style Baltimore 'Street Style Baltimore' is a pet-friendly Airbnb Experience hosted by Violesia. You and Fido will be guided through fine boutiques on Antique Row. The experience includes style advice, exclusive discounts and light refreshments at some shops, a glass of wine, a signature gift to take home and more! Please note that Fido may not be welcome in all the shops; contact host prior to booking. The experience lasts 3 hours and can accommodate up to 8 guests ages 18 and up. Rates start at $85 per person. See Details
Fells Point Thrift Shop & Food Tasting 'Fells Point Thrift Shop & Food Tasting' is a pet-friendly Airbnb Experience hosted by Violesia. Contact host before booking if looking to bring your pooch along; prior approval is needed. You and your pup will be guided along the streets of Fellspoint where you will be introduced to thrift and vintage shops. Guests of this tour will receive shopping incentives and giveaways. Please note that dogs may not be allowed to enter some shops. The experience lasts 3 hours and can accommodate up to 8 guests ages 18 and up. Rates start at $69 per person. See Details
Explore the Ruins of Seneca Quarry 'Explore the Ruins of Seneca Quarry' is a pet-friendly Airbnb Experience hosted by Garrett. Make your way along unpaved trails to view the ruins of Seneca Quarry, notable for producing the distinctive red sandstone used for the Smithsonian Castle and many other D.C. buildings. Dogs are more than welcome and your host suggests letting pups go off the leash on deer trails. The experience lasts 2.5 hours and can accommodate up to 15 guests ages 18 and up. People must be comfortable with an off-road hike on deer trails and be able to stand for the entire tour. During the experience, you will ascend one steep hill. Rates start at $30 per person. See Details
Chesapeake Bay Charters Come experience the splendor of the Chesapeake Bay on board a 40 foot sailboat. Private sailing adventures from 2 hours and up to two weeks are available for the whole family including Fido. Available services include but are not limited to: Dinner cruise to local restaurants,Nearby lighthouse cruise, Night sailing, Romantic sunset cruise, Beach cruise, Thomas Johnson Bridge cruise, or Introduction to sailing, sail handling, and helming. Owner/Operators are USCG licensed captains with over 20+ years of combined sailing experience. They strive to provide you and your family with a personalized private experience that will be remembered for years to come. See Details
Antietam National Battlefield Antietam National Battlefield is pet-friendly. Dogs are welcome to join in the fun as you step back in time at the historical battlefield. The site is situated on fields among the Appalachian foothills near the Potomac River, giving visitors a great area to walk their dogs. Stone arch Burnside's Bridge and a field hospital museum are also located there. Antietam is open every day of the year from 9am to 5pm. See Details
Sail Selina II Boat Tours Sail Selina II Boat Tours welcomes canine companions! Sail Selina II asks that pets wear booties or be in a carrier, such as a bag or basket so that the ship's varnished surfaces do not get damaged. There is a $100 fine if Fido gets loose. The tour group's sailing schedule, rates, and other offerings vary by trip, so dog owners should check its website for further information and to book. See Details
West Virginia River Relaxation 'West Virginia River Relaxation' is a pet-friendly Airbnb Experience hosted by Andrew. Enjoy a leisurely day on the South Branch of the Potomac River with your pooch in a kayak. Dogs who are comfortable in the water, as long as you bring their life vest. The experience lasts 6 hours and can accommodate up to 4 guests ages 10 and up. Guests under 18 must have a life vest. Rates start at $60 per person. See Details
Haunted Harbor Tours Haunted Harbor Tours is a dog-friendly walking tour in Annapolis. Aloysius Martin is the owner and operator and the soul tour guide on the Maiden Voyage Walking Tour. He only tells stories that are confirmed by court records, land records and the archives of newspapers and congress, making the interesting tales even more eerie to hear as you walk the streets together. Dogs get spooked for free, but humans have to pay a $20 ticket price, which is a steal if you like a good scare. The tour is ninety minutes in length and are held at 8pm and 10pm daily. See Details
Baltimore's Inner Harbor & Outer Sights Scavenger Hunt Tour Baltimore's Inner Harbor & Outer Sights Scavenger Hunt Tour is pet-friendly. Walk from landmark to landmark to discover art, culture and history. Search plaques, statues and art to solve riddles that can only be found on location. If you can't find the answer, they'll guide you to the next location. Leashed pups are welcome to take part in this app-led hunt that can be completed at any time. See Details
Baltimore Ghosts Baltimore Ghost Tours is pet-friendly. Join your guide to experience the darker side of Baltimore. This haunted walking tour will take you to famous locations across the Fell's Point neighborhood. You'll visit the Fell Family Cemetery, as well as the last bar Edgar Allen Poe visited before his death, along with several other creepy spots. See Details