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Tails Of Boston At Tails of Boston we offer a variety of services to accommodate your busy lifestyle, and an opportunity to return your dog's unconditional loyalty and love. As a fully insured service provider, we offer safe, reliable and compassionate care for your canine companions. Tails of Boston provides services in the South End of Boston. Pets require companionship, physical and mental stimulation and the ever-important potty break. Many behavioral problems result from isolation, boredom and insufficient exercise.
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Tails of Boston is owned and operated by Heather Gay. Heather lives with her husband Bruce and a rescued greyhound named Ceylon. For many years they have volunteered as foster parents with Greyhound Options to help local Greyhounds find their forever homes. To date they have fostered over twenty greyhounds who have all been placed in wonderful homes in the Boston area.
Private leashed walk - A one-on-one jaunt through your own neighborhood. If you have an older dog, or a character with special needs, then individual attention in the middle of the day is just what your dog needs. Puppy walk - The perfect solution for the newest member of your family. We will stop by 2 or 3 times a day to let him out to explore his new surroundings easing his transition into your home.
Visit our Facebook page and like us there! You'll find photos of current and former clients, links to other pet care services in the South End, and much more. Yelp tends to hide older reviews unless you know how to look for them. Some of our reviews are listed below for your perusal. It will open up a new window where you will see all our archived customer reviews.
Reviews (7)
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Thomas H.
Jun 23, 2022
Highlights of Tails of Boston: 1. Heather - Extremely professional, trustworthy, and most importantly, very caring towards our dog 2. Great communication- daily text updates to let us know how the walk went and any issues that might have come up 3. Excellent web interface - the website allows for easy scheduling and weekly autopay options 4. Flexibility - We have a very dynamic work schedule, and Heather is extraordinarily accommodating with last minute changes and irregular days on a week-to-week basis Heather has been a huge blessing for our family, and we honestly don't know where we'd be without her.

When we first rescued our dog, he was extremely nervous around strangers. Unfortunately, as a two-career household, we had to figure out a dogwalking situation that would work for him. We went through several dogwalking programs who flat out told us no and went so far as to make us feel as if there was something wrong with our dog for being so fearful. Heather, on the other hand, was a relief from the moment she walked in the door.

She met our dog for about 15 minutes and was immediately confident that she could walk him. Her easygoing assuredness made us feel so much better about leaving him to go to work. Now he runs to meet her at the door and can't wait to go out with her. She's also been instrumental in bringing him out of his shell with other dogs - he has several friends through Heather that he walks with. Overall, Tails of Boston has been a tremendous benefit to our whole family, and we are so grateful to have Heather!
Alexa Callery
Jul 10, 2018
Heather and her team at Tails of Boston are terrific. We used them for dog walking 3-4 times a week in the South End and had a a great experience. Everyone was very professional and after every walk they sent me the route they took as well as a quick update on how our dog was. They are very responsive and quick to get back to you with any questions or changes.

They can help to reinforce any training that you are working on and will also let you know if your dog has gotten into anything while you were gone. I would recommend them to anyone looking for dog walking in the area.
Michael Gordon Penn
Nov 09, 2015
My Fido has been treated so well there in spite of his being a difficult rescue with issues around grooming. They have worked on him steadily allowing me to bring him in just to get closer to them at his own pace so it seems and we have made progress. Love it that he is cleaner and looking better for longer periods than he ever has! Grateful we are indeed about Tails!
Johanna M.
May 12, 2014
I was uncomfortable hiring Heather. I tried to negotiate a rate and she got very defensive and told me she was uncomfortable. I thought it was odd to not be able to discuss this openly with her. She sent a fairly nasty email and we decided to go our separate ways.
Tracy L.
Apr 01, 2013
Tails of Boston has been visiting with our dog for about two years now. Our schedules shift, and Heather is almost always able to accommodate a visit with our dog in the evening. She has also been extremely patient with our dog who is slow to warm up to new people. We are thankful for her services and would highly recommend her to others.
Rachel R.
Jul 09, 2012
Heather is fantastic! I work hard and travel frequently, so it has been great to have Heather's help with my wonderful new puppy. I signed up for the twice daily puppy walking -- it just makes me feel great that my dog is getting the attention she needs during the day. Heather has also boarded my dog when I travel. My dog has already been on so many adventures with Heather, and Heather even sends frequent photos of what fun they have been having. I spoil my dog and so does Heather! I would not hesitate to recommend her to anyone!
George C.
Oct 30, 2010
Heather is amazing! There is a reason why she has the only 100 percent approval rating among pet-sitters in the Boston area. When you are crazy about your cat, like me and my wife definitely are, it is refreshing to know that someone like Heather is around. Our cat is on the needy side, and to come home after a long trip to see him happy and healthy is beyond comforting.

You should book her without question. Ultimately with pet-sitters you are paying for peace of mind. You are paying to not worry. And you will never worry with this wonderful, incredible pet-sitter!