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 deCordova Sculpture Park and Museum
deCordova Sculpture Park and Museum Get cultured alongside your four-legged friend at deCordova Sculpture Park and Museum in Lincoln, MA. Leashed dogs are welcome to explore the unusual pieces with you. This 30-acre, dog-friendly park is the largest of its kind in New England and is home to over 60 large-scale, modern, and contemporary sculptures. Exhibits are constantly changing, making each visit to the park unique. Admission fees apply but Fido is free to explore. 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 the centrally-heated and air-conditioned interior cabin or spend your time on the sundeck and walk-out platform. Well-behaved pets are welcome on-leash at no extra charge. Reservations are recommended. See Details
Dog Gone Sailing Charters You do not 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
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 10 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 $25 per person. See Details
SeaSalt Charters SeaSalt Charters offers private Whale Watching and Fishing trips out of Provincetown, MA., in Cape Cod. SeaSalt Charters is owned and operated by the Avellar family, pioneers of Whale Watching on the East Coast. 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 Bay Lady II as it sails across Provincetown Harbor and into Cape Cod Bay. The direction of the 2-hour sail is determined by the wind and will either take you towards the bluffs of Corn Hill or around Long Point Light to the tip of the cape. Daytime or sunset sails are available. Call for reservations. 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
Walking Tour of New Bedford Whaling National Park A guided walking tour of the Historic New Bedford Whaling District. The one hour tour is free and takes place several times a day in the summer months. The tour will bring you up and down restored cobblestone streets past restored whaling mansions, the custom house and the Seaman's Bethel made famous in the novel Moby Dick. See Details
Island Spirit Kayak Island Spirit Kayak welcomes your dog to join you on a kayaking adventure--whether you 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
Freedom Trail Fido can walk in the footsteps of America’s founding fathers by following the Freedom Trail through downtown Boston. 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, dog-friendly trail will lead you right to 16 of Boston’s most historic sites, so you don’t even need a map! See Details
Edgartown Lighthouse A nice hike out to the lighthouse in Edgartown Harbor. See Details
The Witch House at Salem The Jonathan Corwin House in Salem, Massachusetts, known as The Witch House, was the home of Judge Jonathan Corwin and is the only structure still standing in Salem with direct ties to the Salem witch trials of 1692. The spooky house was built between 1620 and 1642. The Witch House at Salem is open 10am to 5pm. See Details
Young's Bicycle Shop Dogs are welcome at Young's Bicycle Shop where you can get pet-friendly Jeep and bike rentals in Nantucket. Young's also rents a dog-friendly Burley trailer that attaches to their bicycle rentals so Fido can ride, too! There is no additional fee for your dog; check the website or call for a quote. See Details
Steamship Authority Ferries Leashed dogs are welcome on the pet-friendly Steamship Authority Ferries in Nantucket, MA. Dogs can ride free of charge but must be cleaned up after and leashed. Pets are not allowed in food service areas, on passenger seats or on tables. Prices vary by trip; check their website for current schedule of fares. Dog owners should arrive thirty minutes prior to sailing time. Reservations are not required. See Details
Steamship Authority Ferries Leashed dogs are welcome on the pet-friendly Steamship Authority Ferries in Hyannis, MA. Dogs can ride free of charge but must be cleaned up after and leashed. Pets are not allowed in food service areas, on passenger seats or on tables. Prices vary by trip; check their website for current schedule of fares. Dog owners should arrive thirty minutes prior to sailing time. Reservations are not required. 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
Hy-Line Cruises Fido can take to the water on Hy-Line Cruises. Leashed dogs are allowed on board all island-bound ferries, except for the Captain's View section on its Nantucket High-Speed ferry Grey Lady IV. Dogs are not allowed on the furniture. Pets ride for free, however, human fare varies by tour. Dog owners can visit Hy-Line Cruises' official website for departure times and to make a reservation. See Details
Cape Air Cape Air is pet-friendly! Fido can take to the skies on one of its Cessna 402 flights. Only one pet per aircraft may be booked confirmed space. Multiple pets from the same family can be on the same aircraft; however, due to space or weight constraints, the passenger and pets may not be accommodated on any particular flight. Cape Air charges a $30 fee per animal, each way, and reservations are recommended as pets are approved on a first-come, first-served basis.

For information on whether your dog qualifies to fly without a kennel, check out Cape Air's official website.
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Endeavor Sailing Excursions Endeavor Sailing Excursions welcomes your pup to join you on their private charters. Chartered adventures last 1-1.5 hours. Up to 14 passengers can be accommodated on the boat and guests are welcome to bring aboard food and beverages.
See Details
The Revolutionary Story Tour 'The Revolutionary Story Tour' is a pet-friendly Airbnb Experience hosted by Mike. Tour the major landmarks of Boston on the Freedom Trail and learn about the history of the city. Dogs may have to be kept outside or carried in burial grounds. The experience lasts 3.5 hours and can accommodate up to 12 guests ages 10 and up. Children are allowed - it's just not the kids version of history. Rates start at $55 per person. See Details
2-hour Sail on Boston Harbor '2-hour Sail on Boston Harbor' is a pet-friendly Airbnb Experience hosted by Caitlyn, Grant and Emilio. Head off for a 2-hour sail on historic Boston Harbor with your host. Dogs are welcome on private tours and on tours where the other guests don't mind. The experience lasts 2 hours and can accommodate up to 4 guests of all ages. Minors should be accompanied by a parent or guardian. Rates start at $35 per person. See Details
Escape Room & Exclusive Backstage Tour 'Escape Room & Exclusive Backstage Tour' is a pet-friendly Airbnb Experience hosted by Marie. Your well-behaved pooch is welcome to join you on a private experience to escape the room in a given amount of time. You will need to solve puzzles along way in order to solve the game and escape the room! If bringing Fido along, you must book a private experience. Contact host prior to booking. The experience lasts 1.5 hours and can accommodate up to 10 guests ages 14 and up. Players under 16 must be accompanied by an adult. You MUST PLEASE call ahead if you would like to bring kids younger than 14 and dogs. Rates start at $39 per person. See Details
Lobster Charter, Catch & Cook 'Lobster Charter, Catch & Cook' is a pet-friendly Airbnb Experience hosted by John. Jump aboard the Christina Marie for a Lobster Charter with your pooch. Dogs are welcome if owners bring their own life jackets with them on board. The experience lasts 3 hours and can accommodate up to 4 guests ages 8 and up. This charter can only be booked with a minimum of 4 guests. Please contact for special arrangements. Rates start at $150 per person. See Details
Bloodlust: of Victorian Boston 'Bloodlust: of Victorian Boston' is a pet-friendly Airbnb Experience hosted by Michael. Explore this quaint post-Civil War suburb with its architectural gems that tourist rarely get to see. Then, delve into the concerns of the people who lived here, their art, science, politics and stories of true crime. Dogs are welcome on a leash. You'll even have the opportunity to stop by a dog park along the route. The experience lasts 2 hours and can accommodate up to 10 guests ages 13 and up. Due to the graphic nature of some of the true crime stories, this tour is recommended for ages 13 and up. There will be some detailed discussion of violence and murder. Rates start at $24 per person. See Details