Dog Walks

Our walks are all about letting your pup explore, sniff, and enjoy the neighborhood at their own pace. Whether they’re a power walker or a slow-and-steady sniffer catching up on “pup news,” we follow their lead every step of the way.

Each walk is a blend of social time, exercise, and exploration—tailored to what makes your dog happiest!

Personalized Solo Adventures

Got an active pup who’s bouncing off the walls while you’re stuck at work? We’ve got you covered! Our one-on-one walks are packed with adventure, exercise, and a whole lot of love. Whether your dog’s zooming through the island’s trails or strutting their stuff on the sidewalk, they’ll be soaking up attention and burning off all that extra energy (so your shoes stay safe!).

And don’t worry—after each outing, we’ll send you a full “pupdate” with pictures, so you can see exactly how much fun they’re having (hint: it’s a lot). Street swagger? Check. Trail cred? Double check. Happy, tired dog? Absolutely!

Why Choose Us?

  • Dog-Centered Experience: Your pup sets the pace and decides the adventure. Whether it’s a quick jaunt or a leisurely sniff session, we’re here to match their energy and curiosity.

  • Guaranteed Time Outdoors: Every walk starts with a 30-minute minimum, ensuring your dog gets the exercise and mental stimulation they need.

  • Simplicity for You: No complicated options—just one reliable, flexible service designed to fit your dog’s needs.

  • Safety First: From weather adjustments to personalized attention, we prioritize your pup’s health and happiness every step of the way.

Availability:

Daytime Walk Windows:

  • 8am - 11am

  • 11am - 2pm

  • 2pm - 5pm

Available Monday - Saturday

Rate: $56

Length: Minimum 30 minutes, up to 60 minutes

Additional dog: +$10 per dog

Weekend fee: +$10

Trail Buddies Daycare

Give your dog a daycare experience like no other with Trail Buddies—where every day is an adventure! We believe dogs thrive when they’re out exploring the world, and with Trail Buddies, your pup won’t be cooped up in a facility. Instead, they’ll join us for all scheduled walks, enjoying the great outdoors and making new furry friends along the way.

No stuffy daycare rooms here—just fresh air, exciting trails, and plenty of tails wagging! Your dog will come home each day feeling happy, fulfilled, and ready to relax after a day of fun and exploration.

Why Choose Trail Buddies?

  • Active, Enriching Days: Your dog gets to explore new environments, stay active, and socialize with other dogs.

  • No Crowded Facilities: We take the daycare experience outdoors, giving your dog the freedom to roam and play.

  • Personalized Attention: Your dog gets the care and companionship of their walker throughout the day.

Is Trail Buddies Right for Your Dog?

If your dog loves adventure, enjoys socializing with other pups, and thrives in active environments, Trail Buddies is the perfect fit! Whether your dog has boundless energy or simply needs a break from the ordinary, they’ll get to experience a day that’s stimulating and fun. Dogs must be over a year old, spayed/neutered, and dog-social on leash.

Availability & Schedule:

  • Available Monday through Friday (March - November)

  • Pick-up: Between 8 am - 11am

  • Drop-off: Between 11 am - 2 pm or 2 pm - 5 pm (full day)

Rates:

  • Single half-day session: $75

  • Single full-day session: $89

A Friendly Reminder: At Al Fresco Tails, we’re committed to using only gentle, positive methods with your pets. We don’t use equipment like pinch, choke, or shock collars. Please have a comfortable, non-aversive collar or harness ready for your dog’s first walk. If you’d like tips on choosing the best gear, just let us know—we’re happy to help!

Fear-Free Care

Every pet sit with us is Fear Free Certified. We prioritize your pet's comfort and happiness, ensuring a stress-free experience during each visit. Trust our certified pet sitters to provide gentle, compassionate care tailored to your furry companion's needs.

Book Services Easily with Time to Pet

  • 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.

  • 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.

We offer premium pet sitting and house sitting services

More than just dog walking

  • "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 M.

  • "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 R.

  • "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 Z.

  • "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 H.

  • "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 O.

  • "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 C.

  • "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 K.

  • "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 S.

  • "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 K.

  • "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.

  • "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 S.

  • "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.

  • "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 N.

  • "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.

  • "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.

  • "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.

  • "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.

  • "The ladies of Al Fresco Tails are absolutely wonderful. My dog gets so excited when they see them walking to the front door, and he cannot stop smiling. Not only do I know my dog loves these ladies, I know the ladies care so much for my dog. They send a detailed message via their app after every walk/visit. I know my dog is well taken care of and loved by these truly professional and loving ladies."

    Jessica M.

  • "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 M.

  • "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.

  • "Oreo loves her time with Cay and Heather! I love that I get a report and pictures with every visit. I can see Oreo smiling with them. Oreo was 13 weeks old when we rescued her. She started once-a-day walks and in a few weeks was a pro with leash walking! It was Heather and Kasha who trained her to do this and other basic commands. They are dependable and caring. We feel lucky to have Al Fresco Tails taking care of Oreo!"

    Catherine 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 B.

  • "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 C.

  • "Not just for dogs! Our cat loves Al Fresco Tails 😻. And so do we! Heather takes great care of him. She sends adorable photos and updates that make us feel at ease. Cay is organized and helpful making scheduling and billing easy. We’ve been trusting them with our cat since they first came to the island. They are both extremely professional, detail oriented, conscientious, and great communicators."

    Heather D.

  • "Cooper and I love Al Fresco Tails! On those occasions where life gets in the way of a good walk with the dog, I am grateful for Al Fresco Tails. The booking app couldn't be easier and I love the reports and pictures from his adventures."

    Stefanie C.

  • "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 L.

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Let us take the leash, so you can take a break!