🐾
Neighborhood Walk
A relaxed stroll for stretching legs, taking care of business, and investigating every interesting smell.
30 minutes · $28
$25 per walk when booking 2+ private walks per week
Thoughtful dog walking · SE Portland
Good days start outside.
Familiar faces. Thoughtful routines. Happier dogs. Personalized neighborhood walks with time for good sniffing, little discoveries, and the things that make each dog feel at home in the world.
Small by choice. Personal by nature. · Established 2019
How we can help
Care built around your dog.
Whether your dog looks forward to a familiar weekly routine or needs an occasional walk, there's room to explore at their pace. All private walks are tailored to your dog's comfort, energy, and interests.
🌿
Adventure Walk
A little more time to wander, explore, and follow your dog's curiosity. The perfect middle ground.
45 minutes · $38
$35 per walk when booking 2+ private walks per week
☀️
Journey Walk
A full hour of unhurried outdoor enrichment, tailored to your dog's pace and preferences.
60 minutes · $48
$45 per walk when booking 2+ private walks per week
A little consistency goes a long way. Schedule two or more private walks each week and enjoy $3 off every walk that week. Prefer to keep things flexible? As-needed bookings are always welcome! Private walk rates include up to two dogs from the same household. For three or more, an additional fee may apply depending on your crew's needs.
Better together
Buddy Walks.
Does your dog have a bestie down the block? Our 30-minute Buddy Walk brings two compatible dogs from separate nearby households together for a shared outing.
Dogs who already know each other are ideal, but we're happy to arrange a careful introduction for two friendly pups. No forced friendships!
30 minutes · $20 per household
Each household is invoiced separately. Buddy Walks are arranged by request and aren't eligible for the recurring discount.
Walks that fit your week.
- Recurring weekly walks — a familiar face and a reliable routine, even just once a week
- As-needed walks — a helping hand when your schedule gets busy
- Weekends by request — occasional walks when availability allows
Regular hours: Monday–Friday, 8 AM–4 PM.
A little more wonder
Time to stop and sniff.
Walks aren’t a race around the block. We follow the interesting smells, notice the little things, and let dogs experience the world at their own pace.
The Al Fresco difference
Familiar faces. Thoughtful routines. Happier dogs.
We're intentionally small. That means consistent, relationship-based care rather than a revolving door of unfamiliar walkers.
Kind, force-free care
We prioritize gentle, low-stress handling and never use prong, choke, or electronic collars.
Time to stop and sniff
We notice body language, make space for exploration, and adapt each outing to the dog in front of us.
Photos & updates
After each walk, you'll get a report and photos through Time To Pet, with GPS tracking for completed walks.
Easy online scheduling
Request walks, see upcoming visits, and send messages through your Time To Pet client portal.
Owner-led care
You'll know who's on the other end of the leash. Cay is your primary Portland walker.
Personalized routines
From senior dogs to sensitive souls, we take time to learn what makes each dog feel comfortable.
A little extra care
Occasional overnight care.
Need someone to stay with your pup? We occasionally offer overnight care in your home for dogs who are a good fit. Availability is limited and arrangements depend on your dog’s needs, routine, location, and our walking schedule.
Have a trip coming up? Reach out through Time To Pet and we can see whether it’s a match.
Offered selectively; pricing is discussed individually.
Meet the humans behind the leashes
Hi, we're Cay and Heather.
We started Al Fresco Tails on Martha's Vineyard in 2019 because we wanted dependable dog care to feel personal, thoughtful, and genuinely connected.
After seven years of walks, muddy paws, and friendships, we've brought that same spirit to Southeast Portland. Today, Cay is your primary walker, while Heather remains an important part of the business we built together.
As a Certified Family Dog Mediator, Cay considers the whole dog — their needs, experiences, environment, and way of seeing the world — and makes room for them to simply be a dog.
Certified Family Dog MediatorThe best part of our day
Little adventures. Very good company.
A walk around the block can be a whole world of discovery. We love being along for the ride.
The Al Fresco way
Small by choice. Personal by nature.
Your dog's people. And yours, too.
There's something special about becoming part of a dog's everyday world: the greeting when they recognize your footsteps, the familiar sniffing spot that still needs a thorough investigation, the moment a shy dog decides you're their person.
Those little things are the heart of Al Fresco Tails. We don't try to squeeze as many visits as possible into the day. We build lasting relationships with dogs and the people who love them.
One more sniff? Always.
Where we wander
Your neighborhood dog walker, on two wheels.
Based in Richmond, we travel to our canine clients by bike. Keeping things local means more time with dogs and less time in traffic.
Core neighborhoods: Richmond, Sunnyside, Hosford-Abernethy, Creston-Kenilworth, and nearby parts of Buckman and Laurelhurst.
By request: Kerns, North Tabor, and South Tabor, depending on the address and schedule.
Neighborhoods are approximate, not guaranteed coverage boundaries. Ask if you're unsure whether you're in range.
Our little corner of Portland
Regular areaBy request / nearby
Curious whether your home is within biking distance? Send your neighborhood or nearest intersection and we'll let you know.
Request an account ↗Illustrative neighborhood guide, not a street-level coverage map. Availability depends on your address and our schedule.
Kind words
Loved by dogs. Trusted by their people.
A few kind notes from the families who made our Martha's Vineyard chapter so special.
★★★★★“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
★★★★★“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
★★★★★“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
Let's get acquainted
Good company, on both ends of the leash.
Tell us about your dog, their favorite things, and where you live. We'll see whether we're a good fit for a walk — or many walks to come.
Request an account ↗Already a client? Log in to Time To Pet ↗
Monday–Friday · 8 AM–4 PM · Weekend walks by request
New clients can request an account through Time To Pet; existing clients can log in to schedule and message.
Already use Time To Pet with another pet care provider? Please log out of that account first, then come back here and select Request an account to get started with Al Fresco Tails.