Dog Friendly Tours in Massachusetts

Taking the dog out for a walk takes on a new meaning when you’re on vacation in Massachusetts. After all, there are tons of sights to see, and smell, around every corner. Browse our dog friendly tours in Massachusetts 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 Dog Gone Sailing Charters
Dog Gone Sailing Charters You don't have to leave your furry family members behind as you enjoy the experience of sailing on Cape Cod Bay with Dog Gone Sailing Charters in Provincetown, MA. Choose from a variety of dog-friendly trips including whale-watching trips, shrimp sails, sunrise and sunset sails. Dogs of all sizes are welcome aboard and Captain Ro has life vests in all sizes for the pups, too! There is no fee for dogs to sail. See Details
Pet Friendly Dolphin Fleet of Provincetown Whale Watch
Dolphin Fleet of Provincetown Whale Watch Watch for marine life with your pup in comfort aboard one of the dog-friendly vessels of Dolphin Fleet of Provincetown Whale Watch. Enjoy the 3-4 hour cruise from Provincetown, MA in the centrally-heated and air-conditioned interior cabin, or spend your time on the sundeck and walk-out platform. Well-behaved, leashed pets are welcome at no extra charge. Reservations are recommended. See Details
Mahi Harbor Cruises Enjoy a day on the water with Mahi Harbor Cruises in Salem, MA. This tour company offers pet-friendly cruises for well-behaved dogs. You and Fido can hop on the Harbor Cruise and enjoy a daytime boat trip around the harbor. Dogs are also welcome on the Sunset Cruise. Please note that cruises are seasonal. See Details
SeaSalt Charters SeaSalt Charters offers private whale watching and fishing trips in Cape Cod out of Provincetown, MA. This pet-friendly tour company is owned and operated by the Avellar family, pioneers of whale watching on the East Coast. Parking is available nearby in the MacMillan Pier parking lot. See Details
Charles River Canoe & Kayak Charles River Canoe & Kayak is a dog-friendly kayak rental business with a location in Boston, MA, that lets you bring Fido out on the water. They may even have a canine life jacket available for your pup to wear (size dependent). Hours vary by location, but the season runs from May through mid-October. See Details
Explore Salem with a Local 'Explore Salem with a Local' is a pet-friendly Airbnb Experience hosted by Beth. Walk and talk throughout this tour and visit about 20 locations around the city. Discuss the Salem Witch Trials of 1692, as well as the Golden Age of Sail and Salem's role in the Revolutionary War. The experience lasts 2 hours and can accommodate up to 20 guests of all ages. Please remember there is a good amount of walking during this tour with little or no seating or restroom options along the way. Salem is an old city, and some areas may have uneven bricks or cobblestones. Rates start at $30 per person. See Details
Bay Lady II Sailing Tours Fido is welcome to join you in the company of Captain Bob Burns and the crew of the pet-friendly schooner Bay Lady II as it sails across Provincetown Harbor and into Cape Cod Bay. Daytime and sunset sails are available, and reservations are required. See Details
Witch City Walking Tours Since its beginning, Witch City Walking Tours have given thousands of tours to visitors from all over the world. Rated as the top walking tour in Salem, taking a tour with Witch City Walking Tours is like taking a tour with good friends. You will get the inside scoop on the true history of this rich and diverse seaport, learn about the infamous 1692 Witch Trials hysteria, and visit off the beaten path locations. Dogs are welcome on most tours; prices start at $25. See Details
Count Orlok's Nightmare Gallery Monster Museum Leashed dogs are welcome to visit Count Orlok's Nightmare Gallery Monster Museum in Salem, MA. This pet-friendly, wax museum experience offers a delightful creepy journey through exhibits featuring over 60 life-sized, realistic reproductions of classic horror movie characters. See vampires, werewolves, zombies and more, all created by Hollywood special effects artists. It is recommended that you arrive at least 10 minutes before your reserved time slot. See Details
Witchwood Tours Leashed dogs are welcome to join you on a pet-friendly tour with Witchwood Tours in Salem, MA. You and Fido can join a Mushroom Witch on a short, guided walking tour where you will learn about local lore, plant usage, history and mushrooms. See Details
CityView Trolley Tours CityView Trolley Tours is a pet-friendly attraction in Boston, MA. Your leashed furry friend can hop aboard the streetcar to explore downtown by your side. Please refer to their website for information on the seasonal hours of operation. Note that CityView Trolley Tours only allows dogs up to 18 lbs to join you in this excursion. See Details
New Bedford Whaling National Historic Park Bring Fido along for a visit to New Bedford Whaling National Historic Park. Located in New Bedford, MA, this pet-friendly historic destination offers one-hour walking tours from May to October. The tour will bring you up and down cobblestone streets past restored whaling mansions, the custom house and the Seaman's Bethel, made famous in the novel Moby Dick. Leashed dogs are allowed in the garden area, but pets are not permitted inside the park visitor center. See Details
Island Spirit Kayak Island Spirit Kayak welcomes your dog to join you on a pet-friendly kayaking adventure in Oak Bluffs, MA. You can choose to explore on your own with a rental or join others on a tour. In addition to rentals, Island Spirit Kayak offers paddle board yoga, sunrise kayak tours, sunset and moonlight paddles, kid's kayak adventures, full moon trips and more. They even offer doggie PFDs in all shapes and sizes! See Details
Gale Force Bikes You and your pup can enjoy a bike ride together with a bike and pet-friendly trailer rental from Gale Force Bikes in Provincetown, MA. They are generally closed from November through March, but please check their website for up to date information. See Details
Dog Friendly City Tours Dog Friendly City Tours invites you and Fido to learn about Boston's pet and animal stories on this fun and informative 75-minute tour that covers a 1-mile area. You'll be amazed by the tales that link pets and animals with Ben Franklin, the Industrial Revolution, Salem Witch Trials, Alexander Hamilton, and more. Don't be offended if Fido doesn't seem to be listening; Fido will be overjoyed with the opportunity to explore new territory with you. Visit their website for pricing and availability. See Details
Freedom Trail Fido can walk in the footsteps of America’s founding fathers by following the pet-friendly Freedom Trail through downtown Boston, MA. All you need to enjoy this free attraction is your dog’s leash and a good pair of walking shoes. The 2.5-mile red brick trail leads right to 16 of the city's most historic sites. See Details
The Witch House at Salem The Witch House at Salem is a dog-friendly museum for small pups that can be carried. This was once the house of Judge Jonathan Corwin and is the only structure still standing in Salem, MA, with direct ties to the Salem Witch Trials of 1692. Be aware that strollers are not permitted in the museum. See Details
Edgartown Lighthouse Edgartown Lighthouse in Edgartown, MA, is pet friendly. Hike along the beach and enjoy spectacular views of Edgartown Harbor, Chappaquiddick and Cape Cod with your furry friend. See Details
The Mount, Edith Wharton's Home The Mount, Edith Wharton's Home, is a dog-friendly venue in Lenox, MA. The famous novelist loved dogs, and as such, Fido is welcome to join you on the grounds as long as they remain leashed. Visit and see the home that Edith Wharton designed herself, right down to the sunken Italian garden. See Details
Young's Bicycle Shop Dogs are welcome to join you at Young's Bicycle Shop where you can get pet-friendly Jeep or bike rental to explore the beautiful island of Nantucket, MA. You can rent a Burley trailer that attaches to their bicycle rentals so Fido can ride along safely. See Details