A happy beagle dog sitting on a wooden trail bridge in a lush green forest, with a woman kneeling behind it holding its leash. The woman is wearing sunglasses and a purple shirt.

Dog Walks

Life gets busy, and your dog still deserves a good walk. Whether you’re at work, out for the day, or off-island, we provide calm, consistent walks that give your dog fresh air, movement, and focused one-on-one attention. With their routine in place, your day can unfold a little more easily.

Which Walk Fits Your Dog Best?

Every dog is different! Choose the option that best matches your pup's personality.

🐾 My Dog Loves Other Dogs

Our Buddy Walks are designed for friendly, social dogs who enjoy walking with canine companions. Small groups make walks fun while encouraging confidence, enrichment, and good social skills.

Explore Buddy Walks

🌿 My Dog Prefers One-on-One Time

Solo Walks are perfect for puppies, seniors, shy or reactive dogs, or any pup who enjoys individualized attention and exploring at their own pace.

Explore Solo Walks

Low-stress, enrichment-focused walks for island dogs

We’re Fear Free Certified and experienced with a wide range of dogs, from easygoing companions to more sensitive or strong-willed personalities. Our walks are calm, structured, and tailored to your dog—naturally reinforcing good habits along the way.

Over time, many dogs become more relaxed, responsive, and confident on their walks with us. We focus on making each visit feel predictable, low-stress, and genuinely enjoyable—so your dog looks forward to their time outside.

Where We Walk

We offer weekly and as-needed walks primarily in Edgartown, Oak Bluffs, Vineyard Haven, and West Tisbury. For our up-island clients, we offer customized scheduling based on location, availability, and your dog’s specific care needs.

A cartoon-style illustration of a smiling man wearing sunglasses and a blue jacket holding three dogs on a dock by the water under a blue sky with clouds. The three dogs, of different breeds and colors, are sitting on the dock, looking happy with their tongues out.
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Solo Dog Walks & Visits

Personalized, one-on-one care designed around your dog’s energy, comfort, routine, and favorite way to explore.

Express Walk

$52 • 25 Minutes

A personalized neighborhood outing with one-on-one attention, gentle movement, and time to sniff and reset.

  • Great for everyday exercise and potty breaks
  • Ideal for puppies, seniors, and easygoing walkers
  • Tailored to your dog’s preferred pace
  • GPS tracking, photos, and a detailed visit report

Additional dog: +$6

Adventure Walk

$64 • 45 Minutes

An extended one-on-one walk with more time to explore, decompress, and enjoy the outdoors.

  • Great for active dogs and enthusiastic sniffers
  • Extra time for movement and enrichment
  • Helpful for dogs who thrive on routine and structure
  • GPS tracking, photos, and a detailed visit report

Additional dog: +$6

Journey Walk

$79 • 60 Minutes

A longer outing for dogs who are happiest exploring Vineyard trails, sandy roads, and peaceful outdoor spaces.

  • Pickup and drop-off included
  • At least 45 minutes spent exploring outdoors
  • Ideal for dogs who enjoy a change of scenery
  • GPS tracking, photos, and a detailed visit report

Additional dog: +$12

Quick & Evening Care

Shorter and meal-time visits for days when your dog needs a little extra support at home.

Relief Visit

$40 • 15 Minutes

A quick visit for fresh air, a water refresh, and a gentle break during the day.

  • Short leashed potty walk or supervised yard time
  • Fresh water and basic routine care
  • Best for dogs who do not need a full-length walk
  • Photos and a visit report included

Supper & Stroll

$56 • 35 Minutes

An evening visit combining a relaxed walk, meal service, and companionship before your dog settles in for the night.

  • Relaxed neighborhood stroll
  • Meal and fresh-water service
  • Ideal for late workdays, dinners, or evenings off-island
  • Photos and a detailed visit report included

Additional dog: +$6

New to Al Fresco Tails?

New Client Trial Walk

$55 • 30 Minutes

Your dog’s first visit gives us a chance to meet, learn their routine and walking style, and make sure our services feel comfortable for everyone.

A trial walk is required before ongoing walks, overnight care, or vacation pet-care services can begin.

Someone must be home during the scheduled arrival window for this introductory visit.

Additional dog: +$6

Ready to Get Started?

New clients can submit an inquiry below. Current clients can request services directly through Time To Pet.

New Client Inquiry Current Client Login

Walk Schedule

  • Days: Monday–Saturday

  • Hours: 8:30 AM – 6:30 PM

  • Service windows:

    • Morning → 8:30–10:30 AM

    • Mid-day → 11:30 AM–1:30 PM

    • Afternoon → 2:00–4:00 PM

    • Early Evening. → 4:30–6:30 PM

Buddy Walks

Our signature small-group walks for friendly, social dogs.

What Are Buddy Walks?

$46 • 25–30 Minute Walk

Buddy Walks pair your dog with a carefully matched group of 2–4 friendly dogs based on personality, walking pace, size, and play style.

  • Small groups of 2–4 dogs
  • 25–30 minute neighborhood walks
  • Thoughtfully matched walking companions
  • Trial walk required before joining a group
  • Perfect for dogs who enjoy canine companionship

Where Are Buddy Walks Available?

Currently available only to Downtown Edgartown residents.

Our Buddy Walk groups are built around neighboring dogs, allowing us to spend more time walking and less time driving.

Not sure if you're in our Buddy Walk Zone? Just submit a New Client Inquiry and we'll be happy to confirm whether your home is within our current service area.

Ask About Buddy Walks

We're always looking for opportunities to expand Buddy Walks into new neighborhoods as interest grows.

Every Walk Comes With Peace of Mind

Gear Up

Every walk includes premium harnesses and leashes, doggie waste bags, hand-picked treats, and safety vests during hunting season—thoughtful details for your dog’s comfort and your peace of mind.

Track the Fun

GPS tracking and detailed time logs give you full visibility into your dog’s walk—so you can relax knowing every moment of their outing is safe, accounted for, and full of joy.

Adventure Updates

Personalized updates with photos and detailed notes give you a glimpse into your dog’s daily excursions, capturing every joyful moment and memory.

  • "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.

  • "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.

  • "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.

  • "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 Labrador puppy with a happy expression, on a red brick surface near a marina with boats and blue water, under a partly cloudy sky.

    "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.

  • "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.

  • Close-up of a black dog with a green collar on a sandy beach near the water, looking directly at the camera.

    "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.

  • "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.

  • "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.

  • "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.

A woman wearing sunglasses and a purple t-shirt taking a selfie with three dogs outdoors under green tree foliage. The dogs include a black and white Australian Shepherd, a brown and white Beagle, and a large fluffy black and gray dog, all smiling with their tongues out.

Walks, Their Way

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.

Dog Walking FAQ

  • We schedule dog walks within flexible time windows to give each pup plenty of attention and adventure. Here are our typical walk windows:

    • Morning Refresh: 8:30 AM – 10:30 AM

    • Midday Break: 11:30 AM – 1:30 PM

    • Afternoon Adventure: 2:00 PM – 4:00 PM

    • Evening Reset: 4:30 PM – 6:30 PM (May-Oct)

    While we can’t guarantee an exact time, we’ll always aim to fit your dog’s walk within the requested window.

  • We can’t guarantee exact times because of the number of pups we care for and the need to plan efficient routes. Walks happen within service windows (like 8:30–10:30 AM or 2:00–4:00 PM), which helps us keep every visit calm, fun, and stress-free for your dog.

  • We get this question a lot! Yes, we can walk a friend’s dog staying at your home, as long as we have vaccination records in advance. Your friend can simply email us the records and we’ll be ready to go!

  • Each walk includes leash time tailored to your dog’s needs, enrichment opportunities (like sniffing, exploring, or practicing familiar behaviors), and a little love and routine care — like fresh water and towel-drying when needed. We bring our own force-free gear, including a comfortable harness, leash, poop bags, and treats (unless you'd prefer we use yours). After every visit, you’ll receive an emailed walk report with GPS and time tracking, a few photos, and a personalized update.

  • We walk in most Vineyard weather — yes to mist, light rain, wind, and flurries, but we may shorten or reschedule walks during extreme heat, heavy rain, snow, or dangerous conditions. Your dog’s safety is always our top priority.

  • Unfortunately, no. Due to parking, access, and scheduling limitations, we are unable to provide services for pets staying aboard vessels or requiring pickup and drop-off at docks, marinas, or ferry terminals.

    Our services are best suited for pets staying in homes, vacation rentals, and other accessible accommodations on Martha's Vineyard.

  • For safety reasons, we don’t use prong collars. Don’t worry — we’ll bring our own harness for your dog so walks stay safe, comfortable, and enjoyable.

  • Once you’re set up in our system, you can request walks through our online Client Portal anytime. First-time clients will be scheduled for a trial walk to assess comfort and fit — we ask that someone is home during this first visit so we can meet your dog and make sure everyone feels good moving forward.

  • Yes! Pups on a weekly walking schedule enjoy lower rates as well as wider scheduling availability — perks not available to clients who book walks on an as-needed basis.

  • We recommend booking walks at least 48 hours in advance, especially during holidays and busy seasons.

  • Both! We work with clients who need consistent, weekly walks and others who book as-needed. Let us know what works best for your schedule.

  • We offer a few perks for recurring clients and our VIPs, but we don’t sell bulk packages. Our focus is on consistent care, not locking anyone into something that might not suit their dog long-term.

  • The VIP Program is our way of thanking the clients who trust us with their pets year after year. VIP clients enjoy lower rates, priority scheduling, access to all visit windows, credits that never expire, and waived after-hours fees.

    VIP Program invitations are extended to select established clients, and clients with a standing walk schedule automatically qualify.

  • All clients are required to use autopay through our secure Client Portal. Billing happens at the time of booking unless you’re on a recurring weekly schedule — in that case, billing occurs at the end of your scheduled week. Autopay makes everything smooth and stress-free, so you don’t have to worry about missing a payment.

  • You can pay by credit card, debit card, or bank transfer through our secure and easy-to-use Client Portal. Tips can be added manually or set up automatically.

    • Cancel by 8 AM → No fee, and you will receive a credit for a future walk (expires one month after payment unless you’re a VIP — VIP credits never expire).

    • Cancel after 8 AM → Full walk fee applies.

    • Reschedule at least 2 hours before your walk → No cancellation fee!

    We understand plans change, and we do our best to be flexible while keeping schedules fair for all pups.

  • Yes! Up-to-date vaccinations are required for all dogs before starting services to ensure the safety of everyone on our walks.

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

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What Makes Us Different

We don’t just walk dogs — we build relationships. With a focus on canine well-being and positive reinforcement, we walk with your dog’s body and brain in mind. You can expect consistent walkers, real-time updates, and the kind of care we’d want for our own dogs.

Premium home stays in your home, where your dog feels safest and most at ease.

More than just dog walking

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