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.
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.
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Steamship Authority Ferries
Leashed dogs are welcome on the pet-friendly Steamship Authority Ferries in Hyannis, MA. Pups 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. While dog owners should arrive 30 minutes prior to sailing time, reservations are not required.
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Hy-Line Cruises
Fido can take to the water on pet-friendly Hy-Line Cruises in Hyannis, MA. 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.
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Cape Air
Cape Air in Nantucket, MA is pet-friendly! Fido can take to the skies on one of its Cessna or Tecnam 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. 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 pet-friendly private charters in Nantucket, MA. Chartered adventures are located at Slip 1015 and 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. Dogs must be leashed at all times.
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Salem Trolley
Salem Trolley is a dog-friendly, narrated tour through historic Salem, MA. Your friendly pup is welcome aboard on this 8-mile trip past the Charter Street Burial Ground, the House of the Seven Gables, Witch Dungeon Museum, Salem Witch Museum, and Chestnut Street, considered one of the most beautiful streets in America. Portions of their trolleys are ADA accessible; please call ahead upon arrival.
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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 4 hours and can accommodate up to 10 guests ages 2 and up. Parents can also bring children under 2 years of age. Children are allowed - it's just not the kids version of history. Rates start at $76 per person.
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2-Hour Sail on Boston Harbor
'2-Hour Sail on Boston Harbor' is a pet-friendly Airbnb Experience hosted by Caitlyn 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.
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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 $44 per person.
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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.
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Bloodlust: Mysteries of Victorian Boston
'Bloodlust: Mysteries 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 30 guests ages 11 and up. Parents can also bring children under 2 years of age. Due to the graphic nature of some of the true crime stories, this tour is recommended for ages 11 and up. There will be some detailed discussion of violence and murder. Rates start at $34 per person.
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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 30 guests ages 2 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 $54 per person.
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Back Bay to Beacon Hill Walking Tour
'Back Bay to Beacon Hill 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 $48 per person.
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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.
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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 2.5 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 $450 per group.
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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.
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Explore Salem with a Local
'Explore Salem with a Local' 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 $30 per person.
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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.
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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.
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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.
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