New clients start with a trial walk. This visit takes place while you’re home so your dog can get comfortable with us, and we can learn their routine before any house or pet sitting.

We’d love to help! To make sure everyone is comfortable, house and pet sitting is offered to clients whose dogs we’ve already met through walks or trial visits. If you’re new, start with a trial walk first — then we can chat about house or pet sitting tailored to your dog.

Yes — in a limited capacity. While most of our services are based on Martha’s Vineyard, we occasionally take a small number of off-island sits each year, including Rhode Island. Off-island sits follow our standard rates, with limited availability and longer stays preferred.

If you’re interested, feel free to reach out and we’re happy to see if it’s a good fit!

We ask that all clients provide at least 48 hours’ notice for house or pet sitting. For new clients, we require at least two weeks’ notice so we have time for a trial walk or visit and can get to know your dog. This helps us ensure a smooth, happy experience for everyone!

Absolutely! We care for pets year-round here on Martha’s Vineyard—whether it’s sunny summer strolls, cozy winter visits, or holiday adventures. The only exceptions are a few short breaks each year when we take time off. We always notify current clients at least two months in advance so you can plan your pet’s care with confidence.

From tail-waggers to purring pals—and even fish, birds, and hamsters—we love keeping a variety of pets happy and cared for. We don’t handle exotic pets like reptiles or snakes, but we can happily point you to local experts if needed.

We’re a small, family-run team—just Cay and Heather—so every visit feels like it was made just for your dog. Cay is a certified Family Dog Mediator, and together we use positive reinforcement and the LEGS approach to understand your pup’s unique personality and needs. Plus, we’re both pet CPR certified, bonded, and insured, so you can relax knowing your furry friend is in safe, capable hands.

We do more than walks—we create adventures. Whether it’s sniffing out hidden trails on Martha’s Vineyard, splashing on the beach, learning new skills, or enjoying cozy one-on-one time at home, our visits are designed to keep dogs happy, confident, and fully engaged. And because it’s just the two of us, we’re flexible, reliable, and excellent communicators, keeping you in the loop every step of the way.

We get to know your dog through a combination of your input and observations during your dog’s first walk. We design activities that match their energy level, social comfort, and preferences—whether that’s a beach adventure, group exploration, or quiet snuggle time.

Once you’re set up in our system, you can request services 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 pets and make sure everyone feels good moving forward!

For new clients, we ask for at least two weeks’ notice so we have time to set up care and get to know your pet. Regular clients can usually book with a minimum of 48 hours’ notice, though more time is always appreciated—especially around holidays and busy seasons.

We provide regular updates with photos, notes, and highlights from each visit—emailed directly to you and available anytime through the Time to Pet app. Every visit is time-tracked and GPS-tracked, so you can see exactly where your dog has been and how they spent their day. For our pet sitting packages, you’ll receive a minimum of three updates per day, giving you peace of mind and a front-row seat to all the fun.

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!

Our approach works best for dogs who are comfortable with new people and environments. For very shy or anxious dogs, we may not be the right fit, as our services focus on active, enrichment-based visits.

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.

All our pricing is now available right in your client account under the Scheduling area. Just log in to see rates for walks, trial visits, and house or pet sitting—everything you need to plan your dog’s adventures with us!

We offer cool perks for our weekly clients and VIP members, 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.

Payment timelines vary by service. Some services are billed on the booking date, while pet sitting packages require a deposit at booking and the remaining balance two weeks before care begins. If you’d like a full copy of our payment policies, we’re happy to provide one upon request.

You can pay online through our secure and easy-to-use Client Portal. We don’t accept cash or checks. Tips can be added manually or set up automatically.

We’re trained to handle common pet emergencies and will contact you immediately if something arises. Our protocol is to first call you, and if we can’t reach you, we’ll contact the emergency contact on file. Because we cannot transport pets or make medical decisions, having at least one emergency contact is required. In the rare event that neither contact can be reached, we will continue to monitor your pet and take steps to keep them safe while trying to reach someone.

Yes! Just reach out, and we’ll be happy to send you a complete copy of our payment and service policies.

Who needs a big company when you’ve got us? Just two humans, lots of love, and a knack for making dogs feel understood, happy, and enriched. Your pup will always see familiar faces, not a new walker every week!