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 The Revolutionary Story Tour
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
Pet Friendly 2-hour Sail on Boston Harbor
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
deCordova Sculpture Park and Museum Get cultured alongside your four-legged friend at this Boston-area sculpture museum full of unusual pieces. Pets welcome on-leash. DeCordova fosters the creation, exhibition, and exploration of contemporary art through our exhibitions, learning opportunities, and unique park setting. 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
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 trail will lead you right to 16 of Boston’s most historic sites, so you don’t even need a map! 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
Dolphin Fleet of Provincetown Whale Watch Watch for whales with your pup in comfort aboard one of the Dolphin Fleet vessels. 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
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
Rock Stars of the American Revolution 'Rock Stars of the American Revolution' is a pet-friendly Airbnb Experience hosted by Ellen. Walk along the Freedom Trail and see the New & Old Massachusetts State House, Boston Common, Granary Burial Ground, King’s Chapel Church, Old & New City Hall, Old South Meeting House, Faneuil Hall & Quincy Market. The experience lasts 3 hours and can accommodate up to 14 guests ages 10 and up. Parents may also bring children under 2 years of age. Please arrive ten minutes before the tour start time If you are coming by Uber or Lyft make sure you find your way to 24 Beacon St - the meeting spot. Rates start at $39 per person. 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. Choose from a variety of 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
Waterfront Portrait Session 'Waterfront Portrait Session' is a pet-friendly Airbnb Experience hosted by Dani. Create lasting memories with your pooch at this photoshoot adventure. You will explore the beautiful beaches of Gloucester while your host takes portraits at several locations along the way. You will receive an online gallery within five days containing 25 beautiful photos with watermark, with the option to buy canvas ,albums, prints, etc. free of watermark. The experience lasts 1.5 hours and can accommodate up to 10 guests ages 18 and up. Guests should be comfortable walking in sand, getting a little sun, and have sun protection. Rates start at $75 per person. See Details
Must See Boston Walking Tour 'Must See Boston Walking Tour' is a pet-friendly Airbnb Experience hosted by Ellen. Your host will guide you and your pooch through major landmarks and you will get to hear about history and fun facts along the way. See Copley Square, the marathons finish line & Newbury Street, the oldest botanical garden and the oldest public park in America, the Massachusetts State House and civil war memorials, and more. The experience lasts 2.5 hours and can accommodate up to 14 guests of all ages. Rates start at $35 per person. See Details
Salem Historical Tours We are delighted to welcome leashed dogs on our Salem History, Witchcraft Trial, Movie and TV, and Haunted Footsteps tours. We are Salem’s Premiere Walking Tour Company and home to everyone's favorite, the Haunted Footsteps Ghost Tour – Salem’s original ghostly stroll. As the oldest established professional walking tour company in the Witch City, we deliver an array of historic themed strolls and special event tours providing an entertaining and informative interpretation of Salem's vast and varied history. Since 1997 we have enjoyed sharing Salem's unique history with the world. Step into the past with our knowledgeable and charismatic local guides and experience nearly 400 years of Salem's remarkable history. From storied architecture to our signature Haunted Footsteps Ghost Tour, Salem Historical Tours' numerous acclaimed tour selections represent the very best that Salem has to offer. 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 $30 per person. See Details
Sailing Adventure For Up to 6 People 'Sailing Adventure For Up to 6 People' is a pet-friendly Airbnb Experience hosted by Luciano. Explore Gloucester harbor and beyond aboard a very comfortable 36 foot Sailing Yacht with your small pooch. Dogs are welcome with prior approval. The experience lasts 2 hours and can accommodate up to 6 guests ages 8 and up. Parents may also bring children under 2 years of age. Guest should be able to board a sailboat and climb a boat ladder. Rates start at $75 per person. 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
Guided Night Photography Tour Cape Cod 'Guided Night Photography Tour Cape Cod' is a pet-friendly Airbnb Experience hosted by Timothy. Friendly pooches who can travel by crate while inside the host's vehicle are welcome on this experience. Be sure to contact host prior to booking for approval. You and your pooch will take a guided tour of Cape Cod, as you learn how to capture amazing night photos. All skill levels welcome. Participants will receive printed course material and a matted print of one of that night's locations. The experience lasts 5 hours and can accommodate one guest ages 18 and up (contact host for more people). You should be in generally good physical health capable of walking or standing for longer periods of time. Rates start at $350 per person. See Details
Salem's Witch Hysteria of 1692 'Salem's Witch Hysteria of 1692' is a pet-friendly Airbnb Experience hosted by Beth. You and Fido will visit several locations from the Salem Witch Trials and hear about the history and curses from that time, as well as the victims. 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. The experience lasts 1.5 hours and can accommodate up to 10 guests ages 2 and up. Rates start at $25 per person. See Details
Natal Chart Exploration 'Natal Chart Exploration' is a pet-friendly Airbnb Experience hosted by Adjovi. Fido is welcome to come along with your at this workshop where your host will explore your astrology natal chart with you and then dive into how each tarot card is associated with the details shown in your natal chart. Your host will then discuss all areas of life with you and future events through horary (predicative astrology). The experience lasts 2 hours and can accommodate up to 3 guests ages 18 and up. Rates start at $65 per person. See Details
Make a Spinner Ring in My Jewelry Studio 'Make a Spinner Ring in My Jewelry Studio' is a pet-friendly Airbnb Experience hosted by Maggie. Your pup is welcome to sit next to you during this experience where you will the basics of metal jewelry including measuring, hammering, forming and soldering to make your own spinner ring. All tools and materials are included. Please note the length of the class will require a patient pup by your side. The host also has two cats on premise, although they will usually hide if a dog is present. The experience lasts 4 hours and can accommodate up to 3 guests ages 18 and up. Rates start at $125 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
Pro-Photo Shoot in Historic Boston 'Pro-Photo Shoot in Historic Boston' is a pet-friendly Airbnb Experience hosted by Carlos. Create lasting memories with your pooch at this urban style photoshoot in historic Boston. Your host will guide you to locations such as Copley Square, Newbury Street, Public Gardens, Beacon Hill, and more while taking photos of you along the way. Be sure to wear comfortable shoes. You will receive a link to an online gallery of your photos in approximately 48 hours after your shoot. The experience lasts 1.5 hours and can accommodate up to 10 guests of all ages. No experience needed. Rates start at $150 per person. See Details
Insider's Walk Thru Historic Plymouth 'Insider's Walk Thru Historic Plymouth' is a pet-friendly Airbnb Experience hosted by Frank. You and your leashed pup will get an in-depth tour of Plymouth with a chance to see many of its historic landmarks. Wear comfortable shoes as you will be walking from site to site to see places including Pilgrim Hall, King's Highway, the 1820 Courthouse, Cole's Hill, Brewster Gardens, and many more historic sites and monuments. The experience lasts 2.5 hours and can accommodate up to 6 guests ages 8 and up. Rates start at $28 per person. See Details
Divination, Intuition, Tarot, Oracles 'Divination, Intuition, Tarot, Oracles' is a pet-friendly Airbnb Experience hosted by Diane. Step by step using oracles, cards, stones, tools, questions, and your intuition, uncover the energies flowing through and around you to intuitively unfold aspects of your life story. Dogs are welcome, but only in private sessions. The space is limited and prior approval is required. The experience lasts 1.5 hours and can accommodate up to 4 guests ages 18 and up. Guests need no prior experience. They should be open minded and ready to explore and practice finding the hidden signals and messages of life. Rates start at $44 per person. See Details