Dog Friendly Tours in Holbrook, MA

There are 28 dog friendly tour within 20 miles of Holbrook. 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 Holbrook.

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
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
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
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
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
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
Winter Freedom Trail Walking Tour 'Winter Freedom Trail Walking Tour' is a pet-friendly Airbnb Experience hosted by Ellen. Head out on foot to walk a portion of the Freedom Trail. You will see and learn about the Old State House & the Boston Massacre, the Old Corner Bookstore & the Irish Famine Memorial & the Old South Meeting House - where the Tea Party started. Although dogs are allowed on the tour, they aren't allowed in the coffee shop and must be 25 lbs or less to enter the hotel. The experience lasts 2 hours and can accommodate up to 10 guests ages 8 and up. Parents may also bring children under 2 years of age. Rates start at $25 per person. See Details
Boston Ghosts Boston Ghosts is pet-friendly. Are you and Fido ready to take a trip through downtown Boston’s most haunted hotspots? The tours take place at 8pm every day of the week and last around an hour. Dogs are welcome on a leash, as long as they are well-behaved. See Details
The Boston Less Traveled Tour 'The Boston Less Traveled Tour' is a pet-friendly Airbnb Experience hosted by Johnny. You and Fido will be led on a guided tour through Boston and hear about the history of historic landmarks along the way. See historic sites such as Warren Tavern, Charlestown Navy Yard, Boston Harbor, Old State House, Faneuil Hall and much more! The experience lasts 2 hours and can accommodate up to 10 guests ages 18 and up. Rates start at $28 per person. See Details
Insider's Boston Walking Tours 'Insider's Boston Walking Tours' is a pet-friendly Airbnb Experience hosted by Bill. Explore every aspect of the city as you walk through 5 different neighborhoods. Your host will look after your dog if you want to check out the inside of any of the tour buildings. The experience lasts 3 hours and can accommodate up to 6 guests ages 10 and up. Parents may also bring children under 2 years of age. Rates start at $100 per person. See Details
Mount Washington Summit Adventure 'Mount Washington Summit Adventure' is a pet-friendly Airbnb Experience hosted by Drew. Leashed dogs are welcome to join their owners on this strenuous hike to the top of the tallest mountain in New Hampshire and the Northeastern part of America. The experience lasts 2 days and can accommodate up to 7 guests ages 18 and up. The activity level for this Adventure is strenuous. This hike is 10 miles up steep terrain and is challenging. Rates start at $300 per person. See Details
Boston's The Story of America Scavenger Hunt Tour Boston's The Story of America Scavenger Hunt Rout is pet-friendly. Walk from landmark to landmark to discover art, culture and history. Search plaques, statues and art to solve riddles that can only be found on location. If you can't find the answer, they'll guide you to the next location. Leashed pups are welcome to take part in this app-led hunt that can be completed at any time. See Details
North End Walking Tour 'North End Walking Tour' is a pet-friendly Airbnb Experience hosted by Ellen. Meet at the Boston Public Market, cross the Rose Kennedy Greenway and travel into the North End up Salem Street exploring the side streets as you go. There's plenty more of Boston to see on this tour, too. Leashed dogs are welcome in the outside areas of this tour. The experience lasts 2 hours and can accommodate up to 10 guests ages 8 and up. Parents may also bring children under 2 years of age. Rates start at $25 per person. See Details