Pet Sitting and Walking in Boston, MA

Choose the care schedule before comparing sitters

Write down feeding times, toilet breaks, exercise, medication, and how long you intend to leave your pet alone. Use that schedule to describe the job. For a walk, specify whether you want the caregiver to spend the booked time outdoors or include harness fitting, building access, and cleanup within that time.

For drop-in care, list the tasks you expect at each visit: food, fresh water, litter care, a toilet break, play, and a message confirming completion. For overnight care, ask for exact hours in your home and any planned daytime absences. Add separate daytime visits to the agreement if you need them.

Tell candidates about pulling, escape attempts, reactions to dogs, hiding, and handling sensitivities. Request a solo walk if you want the caregiver’s attention on your dog. If you consider group walks, ask about the other dogs, transport, introductions, and the procedure for separating dogs.

Set a route that follows Boston park rules

Boston Parks and Recreation requires dogs to remain leashed in city parks, except in designated Dog Recreation Spaces, and permits leashes up to eight feet. The department excludes dogs from children’s areas, including tot lots, play areas, sandboxes, ball fields, and other fenced areas described in its rules. Ask the walker to describe a route that respects those restrictions. [1]

The city identifies designated recreation spaces at Peters Park in the South End and DeFilippo Playground in the North End, among other locations. At Boston Common, the off-leash space rotates between lawn sections. If you approve off-leash activity there, instruct the walker to check the current signs before choosing a lawn. [1]

Give written permission before any off-leash outing. You can request leashed walks even where the city permits off-leash use. Ask the caregiver to carry waste bags and use a trash receptacle; the city requires cleanup and warns against putting pet waste in catch basins, which carry stormwater into waterways. [1]

Check handling, insurance, and backup coverage

Arrange a meet-and-greet with the person who will perform the care. Have them fit your pet’s harness, demonstrate the door routine, and repeat your feeding and medication instructions. Ask how they would handle a slipped leash, a missed visit, or a pet refusing food. Judge their answers against the instructions you want followed.

Ask for evidence of current insurance and an explanation of coverage for pets in their care and access to your home. If the provider advertises bonding, ask what it covers. Request references for care resembling your booking, such as medication visits or overnight stays, and ask who will substitute if the assigned caregiver cannot attend.

For medication, provide your veterinarian’s written instructions and ask the sitter to confirm they can perform the task. Agree on how they will record each dose and report a missed dose or refusal. Leave your veterinarian’s contact information, an emergency contact, transport instructions, and written authority for the care you approve.

Agree on weather changes and home access

Discuss weather changes before booking. The National Weather Service’s Boston report recorded 19 days with maximum temperatures of at least 90°F and 96 days with minimum temperatures at or below 32°F in 2025. Use those observations to plan questions about heat and cold contingencies, rather than as safe walking temperatures for your pet. [3]

Ask your veterinarian about limits appropriate to your pet, then agree on shorter outdoor breaks, indoor activity, or a change in timing when needed. Specify who decides to change the walk, how the sitter will notify you, and whether the booked charge changes.

Walk through the entrance procedure together. Show the sitter the lock, alarm, intercom, elevator or stairs, and the place where you keep supplies. Test access before you leave. Give the caregiver an approved alternative contact if they cannot enter, and agree on how they will return keys or stop using an access code after the booking.

Compare the complete booking charge

Request an itemized quote for your exact dates and care schedule. Ask candidates to state visit duration, number of visits, overnight hours, and charges for additional pets, medication, transport, holidays, or waiting for access. Check cancellation terms and the process for adding care if your return changes.

Compare offers using the same scope, including the tasks and time you expect at each visit. Keep municipal dog-license fees separate from the caregiver’s charge. Boston charges an annual base license fee of $15 for a spayed or neutered dog and $30 for an intact dog; account for that owner expense apart from your care budget. [2]

Boston annual dog-license fees

Match the booking to the care you want

Your hiring checklist

1. Write the feeding, toilet, exercise, and medication schedule.
2. Meet the assigned caregiver and demonstrate harness fitting and door handling.
3. Confirm solo or group walks, the route, and your off-leash instructions.
4. Test home access and name a contact for entry problems.
5. Leave veterinary instructions, emergency contacts, and treatment authority.
6. Agree on weather changes, visit updates, and substitute caregivers.
7. Get the full charge, cancellation terms, and return-delay arrangements in writing.

Frequently Asked Questions

Can my walker let my dog off leash in a city park?

Boston permits off-leash exceptions in designated Dog Recreation Spaces. Elsewhere in city parks, the department requires a leash and permits a length up to eight feet. Give the walker your own written permission or restriction, and require a current sign check for Boston Common’s rotating space. [1]

Does overnight sitting include daytime care?

Ask the candidate to define the booking. Write down overnight arrival and departure times, daytime absences, and any separate visits you want. Confirm feeding and medication times against those hours before accepting the quote.

Which documents should I leave for the sitter?

Leave veterinary contacts, medication instructions, emergency authority, and your dog’s identification details. Boston’s licensing application requires a current rabies certificate, so keep that document available for the handoff as well. Show the caregiver where to find the records. [2]

How should I compare two different quotes?

Ask both candidates to quote the same dates, visit lengths, tasks, and overnight hours. Compare the total charge and cancellation terms, then resolve differences in access time, medication, transport, backup coverage, and updates.