Leaving Your Dog with a Pet Sitter for the First Time: A Complete Guide

Choosing a trusted dog sitter or boarder

Leaving your dog with a pet sitter for the first time can be an emotional experience. Whether you’re going away for a weekend, taking a longer holiday or simply need someone to care for your dog while you’re at work, it’s completely normal to wonder how they’ll cope.

The good news is that with a little preparation, many dogs settle well into a familiar routine with a trusted pet sitter. Staying in their own home can be reassuring, especially for dogs who enjoy familiar surroundings, established routines or quieter environments.

This guide explains how to prepare your dog, what information to leave, how to help your pet sitter provide the best possible care and what you can do to make the experience as stress-free as possible for everyone.

If you’re still deciding which type of care is best, start with my “Choosing the Right Dog Care: A Complete Guide.

Why Preparation Matters

Dogs are creatures of habit.

They often feel most comfortable when their daily routine remains as familiar as possible. Even confident dogs may notice when their owners are away, while puppies, rescue dogs and older dogs may find changes in routine more noticeable.

Preparing in advance helps your pet sitter understand your dog’s normal habits, making it easier to keep life predictable while you’re away.

Good preparation also reduces the chance of misunderstandings, forgotten instructions or unnecessary stress during your absence.

Is Your Dog Ready for a Pet Sitter?

Every dog is different.

Some dogs settle quickly with new people, while others need more time to build trust.

Your dog may benefit from home pet sitting if they:

  • Enjoy their home environment.
  • Prefer familiar surroundings.
  • Find boarding kennels overwhelming.
  • Are older and enjoy a quieter routine.
  • Are recovering from illness or injury.
  • Have established medication routines.
  • Are rescue dogs who value consistency.

If your dog struggles with separation anxiety or complex behavioural concerns, discuss these openly with your pet sitter before confirming any booking.

Being honest helps everyone prepare appropriately.

Arrange a Meet and Greet First

Before leaving your dog with anyone, arrange a relaxed meet-and-greet.

This gives your dog the opportunity to meet the person who will be caring for them while you’re still present.

A meet and greet is also the perfect opportunity to discuss:

  • Feeding.
  • Medication.
  • Walking routines.
  • House access.
  • Emergency contacts.
  • Veterinary details.
  • Behaviour around people and other dogs.
  • Sleeping arrangements.
  • Favourite toys.
  • Daily routines.

For more advice, read Preparing for a Meet and Greet.

Preparing Your Home

One advantage of using a pet sitter is that your dog can stay in familiar surroundings.

Making your home easy to manage allows your pet sitter to focus on caring for your dog rather than on finding equipment or instructions.

Before you leave, make sure your pet sitter knows where to find:

  • Dog food.
  • Treats.
  • Food and water bowls.
  • Leads and harnesses.
  • Towels.
  • Bedding.
  • Medication.
  • Cleaning products.
  • Spare poo bags.
  • Spare leads if you have one.
  • Contact details for your vet.

If there are any rooms you’d prefer your dog not to access, explain this clearly beforehand.

Information Your Pet Sitter Needs

Providing clear information helps your pet sitter keep your dog’s routine as normal as possible.

InformationWhy It Matters
Feeding routineHelps avoid digestive upset and keeps your dog’s day familiar.
MedicationEnsures medication is given correctly and on time.
Veterinary detailsEssential if emergency treatment is needed.
Emergency contactSomeone who can make decisions if you’re unavailable.
Walking routineHelps maintain familiar exercise habits.
Behaviour around other dogsAllows walks to be planned safely.
Favourite toysHelps provide familiar enrichment.
Sleeping routineGives consistency and reassurance.
Allergies or dietary needsHelps prevent accidental exposure to unsuitable foods.
Household routinesMakes visits smoother for everyone.

For a more detailed guide, read What Information Should You Leave for a Dog Walker?

Helping Your Dog Feel Comfortable

Dogs don’t understand holidays in the same way we do.

What helps most is consistency.

Simple things can make a big difference:

  • Keep feeding times as normal as possible.
  • Leave your dog’s usual bedding where it normally stays.
  • Leave favourite toys available.
  • Stick to familiar walking routes where practical.
  • Leave familiar enrichment activities.
  • Avoid changing food just before you travel.
  • Let your pet sitter know about any recent changes in behaviour.

Many dogs find familiar smells reassuring, so resist the temptation to wash bedding immediately before you leave unless necessary.

Before You Leave: A Simple Checklist

Before You GoWhy It Helps
Leave enough food for the entire booking plus a little extra.Prevents unexpected shortages.
Clearly label medication.Reduces the chance of mistakes.
Leave written feeding instructions.Keeps routines consistent.
Check that keys work properly.Prevents access problems.
Leave emergency contact details.Helps if you’re unreachable.
Leave your vet’s details.Saves valuable time if needed.
Explain any behavioural quirks.Helps your pet sitter plan appropriately.
Leave cleaning supplies.Useful if accidents happen.
Charge automatic feeders or water fountains.Avoids equipment failing while you’re away.

House Sitting or Boarding?

Many owners wonder whether a pet sitter or boarding kennels would be the better choice.

There isn’t one answer that suits every dog.

The table below highlights some of the differences.

Home Pet SittingBoarding Kennels
Dog remains in familiar surroundings.Dog stays in a dedicated boarding facility.
Routine can often remain similar.Dogs adapt to the kennel’s routine.
Useful for dogs who enjoy home comforts.May suit sociable dogs comfortable with change.
Can be helpful for older dogs or those with established routines.May suit dogs already familiar with kennels.
Reduces travelling for many dogs.Requires transport to and from the kennels.


It is also important to remember that any boarder needs to be licensed by the council

If you’re still deciding, read House Sitting vs Boarding Kennels – Which Is Best for Your Dog?

Common Mistakes to Avoid

Most first-time bookings go smoothly, but a few simple mistakes can make life more difficult than necessary.

Try to avoid:

  • Leaving too little food.
  • Forgetting medication instructions.
  • Not testing keys beforehand.
  • Changing your dog’s routine immediately before you travel.
  • Forgetting to update emergency contact details.
  • Leaving no written instructions.
  • Assuming your pet sitter already knows your dog’s habits.
  • Introducing new foods or treats just before you leave.

A little preparation now often means a much more relaxed experience for everyone later.

Green Flags and Red Flags When Choosing a Pet Sitter

Not every pet sitter works in the same way, and that’s perfectly normal. However, there are some positive signs that can help you feel more confident, as well as a few warning signs that suggest you should ask more questions before making a decision.

Green FlagsRed Flags
Arranges a meet and greet before the first booking.Wants to start caring for your dog without meeting you first.
Asks detailed questions about your dog’s routine, health and behaviour.Shows little interest in your dog’s individual needs.
Is happy to explain how visits work and answer your questions.Gives vague or unclear answers about their service.
Discusses emergency procedures and asks for your vet’s details.Has no clear emergency plan.
Encourages honesty about behavioural or medical concerns.Suggests behavioural issues aren’t important.
Treats your dog calmly and allows them to approach at their own pace.Forces interaction or ignores signs that your dog is uncomfortable.
Is open about insurance, experience and policies.Avoids discussing insurance or terms of service.
Explains how they will keep you updated while you’re away.Doesn’t explain how you’ll receive updates or communicate during the booking.

The most important thing is that both you and your dog feel comfortable with the arrangement. A good pet sitter should welcome your questions and take the time to understand your dog’s individual needs.

Frequently Asked Questions

Will my dog miss me?

Many dogs notice when their owners are away, but familiar routines, familiar surroundings and calm, consistent care can help them settle.

Every dog is different. Some adjust quickly, while others take a little longer.

Should I say a long goodbye?

Most behaviour professionals recommend keeping departures calm and low-key.

A long, emotional goodbye may unintentionally make the situation feel more significant for some dogs.

Instead, stick to your usual routine and allow your pet sitter to take over naturally.

Is it normal to feel guilty?

Yes.

Many owners worry about leaving their dog, especially for the first time.

Planning ahead, arranging a meet-and-greet, and choosing someone you trust can help you feel much more confident.

Can my pet sitter send updates?

Many professional pet sitters are happy to provide updates during longer bookings.

Before your holiday, discuss:

  • How often you’d like updates.
  • Whether you’d like photographs.
  • The best way to communicate.
  • Any times when you may not have phone or internet access.

Agreeing expectations beforehand helps avoid misunderstandings.

What if my dog won’t eat?

Some dogs eat less than usual when their owners are away.

Keeping feeding times, bowls and food the same often helps.

If your dog refuses several meals or appears unwell, your pet sitter should contact you and, if necessary, seek veterinary advice.

Should I leave treats?

Yes, if your dog normally has them.

Let your pet sitter know:

  • Which treats are suitable.
  • How many they can have.
  • Whether any foods should be avoided.

If your dog has allergies or a prescribed diet, make this especially clear.

What if my plans change?

Travel plans sometimes change unexpectedly.

Before your booking, discuss:

  • Extensions.
  • Early returns.
  • Flight delays.
  • Emergency contacts.
  • How changes to the booking will be managed.

Clear communication helps everyone plan accordingly.

Helping Your Dog Settle While You’re Away

You don’t need to entertain your dog every minute of the day.

For many dogs, the most reassuring things are familiar routines, calm interactions and opportunities to rest.

Simple enrichment activities may also help some dogs enjoy their day.

Examples include:

  • A snuffle mat using part of their normal meal.
  • A stuffed food toy if they’re already familiar with it.
  • A simple scent-search game.
  • A favourite chew suitable for their age and health.
  • Quiet time in their usual resting place.

If you’re looking for ideas, read my guide, Canine Enrichment Ideas for Everyday Life, or my guide, Indoor Brain Games for Dogs.

A Holiday Information Folder

One of the easiest ways to prepare for any future pet sitting booking is to keep all your dog’s important information together.

Consider creating a simple folder containing:

IncludeWhy It Helps
Veterinary detailsEasy to find if needed.
Emergency contactsSaves valuable time.
Medication instructionsHelps ensure correct administration.
Feeding routineKeeps meals consistent.
Walking preferencesMaintains familiar routines.
Behaviour notesHelps avoid unnecessary stress.
Home informationMakes visits run smoothly.
Spare key arrangementsUseful in unexpected situations.


Updating this information once or twice a year can make future bookings much easier.

Looking Ahead

Many owners find that the first booking is the hardest.

Once you’ve found a pet sitter you trust and your dog has settled into a routine, future bookings often become much easier.

Building a long-term relationship also means your pet sitter becomes increasingly familiar with your dog’s personality, preferences and routine.

Related Guides

Continue exploring my Choosing Care guides:

You may also find advice from the RSPCA, and The Kennel Club helpful when planning your dog’s care.

Final Thoughts

Leaving your dog with a pet sitter for the first time can feel like a big step, but careful preparation makes a real difference.

By arranging a meet-and-greet, sharing clear information, and keeping your dog’s routine as familiar as possible, you’re helping both your dog and your pet sitter start off on the right foot.

Remember, there isn’t a perfect solution that suits every dog. The right choice is the one that reflects your dog’s personality, health, routine and individual needs.

If you’re looking for calm, one-to-one pet care in Finchley and the surrounding areas, I’d be happy to answer any questions and arrange an informal meet-and-greet before any booking, so please get in touch

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