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Enriching pets’ lives

on Martha’s Vineyard

Steady routines, dependable care, and happy pets.

Our promise: Loving care. Every visit, every stay.

Al Fresco Tails provides dog walking and in-home pet sitting for a wide range of animals—including dogs, cats, birds, and small pets—with a calm, behavior-aware approach. Each visit is tailored to your pet, supporting comfort, routine, and overall well-being.

Our services

A young person in a gray jacket and orange beanie sitting on a brown couch, hugging a large, happy Golden Retriever dog.

Whether you need weekday walks or a trusted sitter in your home while you’re away, we’re here to provide steady, thoughtful care every step of the way.

Learn more about us

  • "Heather and Cay were absolutely incredible with our golden retriever, Chico. They treated him like their own, from long walks and playtime to making sure he was settled in and comfortable at home. What really stood out was the level of care and communication. We got thoughtful updates, photos, and little details about his day that made us feel completely at ease. It honestly felt like Chico was on his own little vacation. They even caught that his harness wasn’t the most secure and helped us upgrade it, going above and beyond in ways you don’t expect. Couldn’t recommend them more. Chico already misses them!"

    - Luiz

  • "We highly recommend Cay and Heather at Al Fresco Tails. They are real pros who are knowledgeable about every facet of dog care, and it gives us peace of mind that they are so dependable and I never have to worry about whether or not they'll show up. Most important: they're kind and caring and funny."

    - Elizabeth

  • "We were so happy to know that our dog was in your care for the day. We had no worries about his welfare. We thank you and Boyd thanks you!"

    - Laura

  • "Cay and Heather are just wonderful. Before now I’ve never trusted anyone to walk my dogs. They are loyal, honest, reliable and hard-working. My dog Ruby loves them and just can’t wait for her walk days, they are the highlight of her week."

    - C.

  • "We just started using Al Fresco Tails for our dog Poppy this summer and I can’t say enough good things about them! They really care about Poppy and I can tell she loves her walks with them. Heather also sends the best updates and photos!"

    - Hope

  • "Al Fresco Tails is the absolute best! The owners are the nicest people and I trust them implicitly to take care of our dogs. They leave detailed, hilarious updates on their portal throughout the day and the dogs have SO MUCH FUN! And not for nothing, our house was cleaner when we came home than when we left it. Love them."

    - Anne

  • "Heather took such great care of our lab Murphy. It is clear she is a serious dog person who takes such joy in caring for pets. Their many walks and adventures during the day and fun routines in the evening were all captured in photo updates each day, letting us know just how much fun they were having and giving us peace of mind that our pup was in good hands!"

    - Peter

  • "My dog absolutely adores them—and so do I! From the very beginning, they’ve been kind, reliable, and incredibly thoughtful. I was a little nervous at first because my dog can be reactive, but Cay and Heather have handled her with so much care, patience, and confidence. It’s been such a relief to know she’s in good hands. They’ve also been a huge help to both me and my parents, especially when we’ve needed last-minute walks. Scheduling is super easy, and I always feel reassured knowing she’s getting exercise and love from people who truly care. I’m so grateful we found them—can’t recommend them enough!"

    -Kristine

  • "Heather and Cay provide an exceptional service. We are beyond thankful that our islander black lab has been under their care for many years. We’ve seen their services expand and respond to community needs and growth - we trust them implicitly with his care and also the care they provide our home. Their professionalism and communication is unmatched, and the love for the animals they care for is clear as the Vineyard Sound."

    - Erin

  • "Al Fresco Tails Pet Services are loved by my dogs, Juno and Pebbles! Cay and Heather take amazing care of them, whether it’s walks or house sitting when I’m away. My dogs always come home happy and well-exercised. A++ service!"

    - Deb

  • "We cannot thank Cay & Heather enough for taking such incredible care of Lolo. We really have no words to express just how grateful we are for their supremely loving, thoughtful, and kind care. Not only did we not have to worry if she was getting the basics, but we knew she was having an absolute ball!! 🎾 Lolo adores them both and definitely felt the love in return. Thank you x a million!"

    - Hillary

  • Close-up of a smiling black Labrador puppy with water on its nose, standing on a brick walkway near a marina with boats docked and a blue sky with clouds above.

    "The peace of mind that comes with their sincere, kind, clean, personal care and dedication means the world! Highest praise and sincere recommendation for all they do!"

    - Kim

  • "We loved all the updates, and we never worried for a minute about the dogs knowing they were in their care! We’re excited for our next Al Fresco adventure!"

    - Celia

  • "There is no one I would trust more to stay with or walk our dogs than Cay & Heather at Al Fresco Tails! We trust and recommend Al Fresco Tails to everyone that is considering their services. Always leave our house spotless and send tons of cute videos, pictures and updates on our girls. We sometimes joke Chowder and Riley like Cay and Heather more than us because they are that excited when they come to do an overnight or walk!"

    - Ashley

  • "Our pets are our family! We have been using Al Fresco Tails for 1 year and have had the best experience we could have ever asked for. Our beloved pets look forward to their walks and love provided by Al Fresco Tails. They are always willing to work with us when our needs change. Simply knowing Al Fresco will be there for you provides such a sense of security. You know your pets are being taken care of as if you were there. I would not go anywhere else. Highest recommendation I could give!"

    - Dave

  • "Reliable, trustworthy, and funny! The review of my dog’s walk and accompanied photos always brighten my day. I use their services routinely (standing weekly walks) but they were so helpful when I needed some last minute walks and were able to accommodate my requests. 10/10."

    - Kristie

  • "Their service is top notch: my house is always spotless when we return from a trip, and in addition to all the photos and notes sent to me from each visit/walk/overnight, there is a thank you note on my counter too. Bottom line, they are more expensive than the random petsitter who sleeps over at your home, but they are professional, intelligent, personable women who deliver what they promise with 100% priority to your pet, to your home, and you."

    - Cyndy

  • "FANTASTIC FANTASTIC FANTASTIC. We leave our two labs, 4 years old and 1 year old, and 6yo cat in their most capable hands. Just the best ever!!!"

    - Geoghan

  • "Truly stellar pet care service! Heather and Cay were quite patient with our anxious schnauzer, easing into the meet & greet, and getting him comfortable and happy on his walk! They’re meticulous about every detail, giving us full confidence and peace of mind when we were away from the pup! They also take the cutest pictures on the walks!"

    - Martha

  • "Just ask my Ivy Rose what she thinks about Heather and Cay. She has been one of their first pups since they started their business. She says: they really are softies. I have them trained to go my way, my pace, and give cookies on demand! We can’t say enough about Al Fresco Tails. We give them 10 paws!"

    - Sharon

  • "Al Fresco Tails walked my two Golden Retrievers several times this summer and we look forward to continuing to use their services. They took great care to give us a report with photos of the dogs’ adventures. The report also provided information on what happened on the walk and confirms that they did things like check the water bowl or check for ticks. They also made a point to figure out the best way for our two dogs to walk together with them. We have been very pleased so far and our dogs adore Heather."

    - Sarah

  • "Heather and Cay have always done a great job with our pets. They were able to take care of our aging beagles making us feel they were safe and well attended to. After we lost them, Heather and Cay have worked with us to help Tug Boat (a 3.5 year old rescue beagle) adapt to our home. They go out of their way to get information on his troublesome behaviors and have helped him to join our household. When they sit for us, we get loads of pictures and friendly notes."

    Carol B.

  • "We have been using Al Fresco Tails for the past year and they are amazing! I can’t say enough great things. They make sure our pups are well exercised and loved. They provide updates throughout the day when we are traveling and it puts my mind at ease. Heather and Cay are the best! We love them."

    Kelly R.

  • Close-up of a yellow lab wearing an orange and teal harness outdoors with trees and another dog in the background.

    "It's so hard for us to leave our dogs behind, and I can honestly say that this was the most comfortable I have ever been with being away from them."

    - Evan

  • "They take such good care of the dogs and they are so thoughtful they even do tick checks and send you loads of pictures. It’s clear just how much they love and truly care about your dogs. I feel so grateful for them- like seriously they are a hidden gem that might be no-so-hidden quite soon."

    Shalei H.

  • Close-up of a black cat with yellow eyes, looking directly at the camera inside a home.

    "Al Fresco Tails excels at dog care BUT we've used their services for years for visits to our increasingly elderly cat. Am blown away by the difference compared to a kennel stay. While we're gone we're treated to daily reports AND photos. And we return home to calm, happy cat who got to spend the week at home instead of in a kennel. Al Fresco Tails delivers pet-owner peace of mind."

    Brenda H.

  • "Cay and Heather are wonderful caregivers and their communication is stellar - fabulous pictures and reports on our two dogs on a daily basis. When you have to travel, there is such comfort knowing your pets are being loved my such remarkable women. Highly recommend this service ❤️❤️ Quinn and Chilie agree!!"

    Marie L.

  • A happy, curly-haired dog with a black nose and open mouth standing on a woods trail.

    "Took wonderful care of my dog. Communication was excellent. House sitting, additionally, was a bonus and really enhanced the experience for my dog."

    Detta T.

  • "Their communication is stellar and responsive. We have been so impressed with their attention to detail and happy to find the house in great order and the dogs very happy upon our return. I know that both dogs miss them and they genuinely care about our pets. I can't recommend them enough."

    Mary H.

  • Close-up of a black dog on a beach, with sand and water in the background, wearing a green collar.

    "Their level of attention, professionalism, and genuine affection for our spirited 100+ pound canine boy, Oggie is off the charts!"

    Christopher C.

  • "Cay and Heather have lovingly cared for our lab Trudy many times over the past few years when she cannot travel with us. Trudy is now a senior citizen and we would not even consider leaving her under the care of anybody else. They are so incredibly responsible, reliable, and it is fun and comforting to get reports multiple times a day, complete with pictures. They have our highest recommendation!

    Jeff M.

  • A small, fluffy, light brown dog with a bandana around its neck, sitting on a gravel path near water, with a cloudy sky and lighthouse in the background.

    "One of the best parts of the experience were the updates that we received throughout Ruby's stay. It was clear that she was keeping busy and getting lots of love. We now joke about needing to make special trips to MV just so that Ruby can stay with her friends at Al Fresco again. We can't recommend them enough and look forward to many more visits in the future!"

    Halie C.

  • "Heather and Cay are amazing! They operate a very professional business, provide timely and clear communication, are very trustworthy and are extraordinarily reliable. As the owner of a small dog with some special needs, I am delighted by the care they provide. I always rest easy knowing that my dog is happy and safe in their care. Both my dog and I adore them!"

    Nancy G.

  • "They are the best!!! The dogs and we love them and their services. They care so much for the dogs and are part of our family. They are the only ones we have ever trusted enough to leave the dogs with so we can travel."

    Shannon S.

  • "Al Fresco tails takes such great care of our golden retriever Lambert, whether by daily dog walking or overnight stays when we go away. He absolutely loves them! I look forward to their adorable updates and photos. They are so professional and amazing! Highly recommend."

    - Lauren

  • "Al Fresco Tails is amazing! Cay and Heather go above and beyond, they are so professional and kind and my dog absolutely adores them. I could not ask for a better pet sitting/dog walking service!"

    Samantha M.

  • "I had Heather and Cay care for my pets while on vacation. They were fantastic. I loved all of the photos and stories they sent me about all my fur babies. I felt confident and secure knowing that my pets were being so well cared for. They are the best."

    Rose W.

  • "Beyond thrilled to have found Cay and Heather! I had been waiting years for a service like this on the Vineyard! Professional, reliable, and loving.....exactly what Posie and Pippa need!"

    -Brooke

  • "I love Al Fresco’s service! They are extremely reliable and take excellent care of my dogs. I highly recommend their service!"

    Andora A.

  • "Phenomenal service. I could not feel more comfortable leaving my fur kids in their caring, capable hands. They are awesome!"

    Paige G.

  • "Tanzie had a wonderful time while staying with Al Fresco Tails! She had a perfect mix of fun outdoor adventures and warm snuggles on the couch." 🐕❤️👍

    Mackenzie N.

  • "Cay & Heather are the best dog sitters ever! I feel so comfortable leaving my dog with them. My dog has some special issues, so it has always been worrisome to leave him in the care of others, but Al Fresco Tails has always done an amazing job! They are very professional, give great updates and stay in touch. I absolutely recommend Al Fresco Tails!"

    Hilary G.

  • "Al Fresco Tails took care of our dog for a week, during which time he obviously enjoyed himself to the point that his greeting on our return was more like “Oh hey, you’re back. Where’s Heather?”

    - Chip

  • "I only wish there were more stars to give them! Our dogs just love Cay and Heather and they are incredibly reliable! Thank you both for such piece of mind."

    - DJ

  • "Al Fresco Tails did an incredible job ensuring that we could have our cake and eat it too on our wedding day by allowing our furry family to be involved when it was their time to shine. They also took amazing care of them while the humans partied the night away. I could not recommend Al Fresco Tails more for any bride who wants their fur-babies involved in their big day. We knew our pups were in great hands, and that peace of mind allowed us to have the best night of our lives! They were amazing in coordinating and working with other vendors as well."

    - Sarah

  • "The team at Al Fresco Tails is great! Cay was so responsive and communicative in helping me set up a profile and confirm services as well as checking in afterwards. Heather was early to our evening pet sitting and patient in greeting our extra large and slightly anxious doodle! She also sent us updates throughout the evening so we knew our dog was safe and all was well. I'm excited to use Al Fresco moving forward for pet sitting and more while we're on the island and would definitely recommend them!"

    -Julia

How it works

A woman in a purple shirt kneeling on the grass, petting a large dog, with another woman smiling in the background on a patio, surrounded by green bushes and trees.

Just a few simple steps to total peace of mind

  • Tell us about you, your pets, and the care you need.
    We’ll use this info to set you up in Time To Pet and send your client portal invite.

  • Once your portal is activated, you’ll be able to complete your profile, add your pet’s vaccination records, and a payment method. We’ll review everything and reach out by email to schedule a New Client Trial Walk.

  • Think of it as a first date… but for dog walking!
    We’ll arrive within your preferred 2-hour window, meet you and your pet(s), go over the important details (entry instructions, leash setup, routines, etc.), and then head out for a short walk so we can get to know your pup. Once we’re back home and everyone’s settled, we’ll confirm next steps with you.

  • Most pets are ready to jump right into regular visits after their New Client Trial Walk. If your pet seems especially shy, fearful, or unsure during the first visit, we may recommend a Solo Trial Visit (with you out of the home) to help them build confidence and ensure everything goes smoothly before ongoing care begins.

Get started

Easy & Intuitive Scheduling, Guaranteed

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  • When we arrive at your home, we come prepared with all the details you've shared with us. Time to Pet enables us to securely store your client information, providing you the flexibility to update your online profile whenever necessary. Our commitment to you is delivering personalized care, every single time.

  • Prepare to receive an adorable report capturing your pet's time with us, featuring heartfelt photos, GPS tracking, and a delightful story of our shared moments. Each report card is conveniently saved in Time to Pet, creating a cherished collection of precious pet memories at your fingertips.

  • Stay connected with us while you're on the move! Request our pet sitting services or drop us a message right from your client portal. For a seamless experience, we highly recommend using our dedicated app for all your pet care needs

  • Once we've confirmed your service request, an invoice is instantly generated and accessible through our app. Time to Pet relies on Stripe for secure credit card processing, ensuring full PCI compliance for your peace of mind.
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