Dog Friendly Tours in Chestnut Hill, MA

There are 38 dog friendly tours within 20 miles of Chestnut Hill. Use the links below to get an overview of each one, see pictures, print directions, and even read reviews from other dog owners. Coming from out of town? Get a discounted rate on pet friendly hotels in Chestnut Hill.

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 deCordova Sculpture Park and Museum
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
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
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
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
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
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
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
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
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
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
Learn and Practice Tarot in Witch City 'Learn and Practice Tarot in Witch City' is a pet-friendly Airbnb Experience hosted by Melissa. Well behaved pups are welcome at this workshop where you will learn the basic, hands-on structure of a Tarot deck and tips for building clear Tarot readings and how to use the cards to tap into your intuition. The experience lasts 2 hours and can accommodate up to 4 guests ages 16 and up. Rates start at $65 per person. See Details
Fun and Private Photo Shoot in Boston 'Fun and Private Photo Shoot in Boston' is a pet-friendly Airbnb Experience hosted by David. Create lasting memories with your pooch during this photo session. Be sure to contact your host prior to booking if Fido will be joining you. You will get to explore Boston Public Garden where your host will snap beautiful, candidly captured photos. You will receive 20 edited photos in three business days. The experience lasts 1 hour and can accommodate up to 4 guests ages 18 and up. Parents may also bring children under 2 years of age. Rates start at $129 per person. See Details
Secrets of Lexington and Concord 'Secrets of Lexington and Concord' is a pet-friendly Airbnb Experience hosted by Fred. Start the tour on Lexington Green, one of the best known landmarks of that fateful day when the American Revolution began and hear lesser known stories of the area. Leashed dogs are welcome in the outside portions of the tour, as long as the other tour members don't mind. The experience lasts 3 hours and can accommodate up to 3 guests ages 8 and up. Rates start at $36 per person. 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
Salem Ghosts Tours Learn about Salem's bewitching past with Salem Ghosts Tours. Canine companions are welcome on this Colonial Ghosts, LLC tour! Tours wind along cobblestone streets, through different sites around the city, each "spookier than the last." Salem Ghosts brands itself as a great way to see all of the main haunted attractions in Salem while getting a well-rounded view of the city and its history. Salem Ghosts welcomes leashed, friendly, quiet, and well-behaved pets for free. Advance reservation via Salem Ghosts' website or by phone is required for humans. Price and time vary by tour. See Details
Boston's Freedom Trail with Photos! 'Boston's Freedom Trail with Photos!' is a pet-friendly Airbnb Experience hosted by Nicholas. Dan and Nicholas will guide you through the Freedom Trail path around downtown Boston, Massachusetts. Dogs are welcome, as long as they can walk four miles. The experience lasts 2.5 hours and can accommodate up to 10 guests ages 5 and up. Parents may also bring children under 2 years of age. If you are over 21, I will recommend the best bars for lunch!. Rates start at $35 per person. See Details
Explore Boston's South End with Me & DV 'Explore Boston's South End with Me & DV' is a pet-friendly Airbnb Experience hosted by Ellen. You and your pooch will get to meet your host and her dog and take a guided walking tour of South End. Discover the brick townhouses, parks and gardens in a busy city, hear about the urban renewal, international scandal, Boston history, and more. The experience lasts 2 hours and can accommodate up to 10 guests ages 6 and up. Parents may also bring children under 2 years of age. Rates start at $22 per person. See Details
Boston Mindful Origami with OTA 'Boston Mindful Origami with OTA' is a pet-friendly Airbnb Experience hosted by Junko. With prior approval, your well-behaved pooch is welcome to join you at this workshop where you will learn basic folding for origami. One pack of origami paper is included and you will get to take home all of the pieces you create. The experience lasts 1 hour and can accommodate up to 6 guests ages 5 and up. Parents may also bring children under 2 years of age. Rates start at $25 per person. See Details
Quick Letterpress Printing Workshop 'Quick Letterpress Printing Workshop' is a pet-friendly Airbnb Experience hosted by Ted. Friendly dogs that get along with other pups are welcome to join you at this workshop where your host will give you an overview of the history and technology of letterpressing, and then show you how to use an antique Vendercook proofing press. You will then print your own notecards to take home. Please note that studio is small so larger dogs may not have a lot of room. The experience lasts 2 hours and can accommodate up to 6 guests ages 18 and up. Attendees should be comfortable with using hand tools and light machinery, using inks and solvents, and be able to carry medium loads (<20lbs). Rates start at $50 per person. See Details