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The holidays are coming!

Diamond Crystal

Peace Sistas,


WHAT? Less than 40 days until Thanksgiving?? If you're feeling the pull of the holidays, the shorter days, and that "where am I spending this season?" question, you are not alone. This is the time of year when housesitting quietly becomes one of the smartest moves in the book.


This edition is packed:

*Why holiday sits are worth a second look.

*The international travel tips I wish someone had told me.

*How to stretch every holiday and day off into maximum travel.

*The wellness habits that keep full-time sitters going.


Grab your favorite libation and let's GO!

Dynamic Duo

For Our New Members - WELCOME

My Go-To for Finding Sits: TrustedHousesitters

I get asked all the time how I find the sits that let me travel without ever booking a hotel — and TrustedHousesitters is still my answer. It's the platform behind most of my own housesitting wins, and it's where I'd point any new member getting started.

Check out TrustedHousesitters here

(Heads up: this is my affiliate link — using it supports this newsletter and community at no extra cost to you.)

Holiday Housesits

Why holiday sits are worth it.


Here's the secret nobody tells you: the most expensive time to travel is also the time pet parents need us most. That alone makes the math, MATH!

  • Dodge the holiday price spike. Flights, hotels, and restaurant bills all climb from late November through the New Year. A sit covers your lodging, so your budget goes to the experience instead.

  • Owners are looking for you. Many pet parents don't want to kennel their fur babies over the holidays, and family and friends are busy with their own plans. Holiday listings fill early, so now is the time to apply.

  • Cozy beats crowded. A real home, a pet on your lap, and a kitchen to cook in will always beat a hotel room with a view of the parking lot.

  • Keep your traditions. Some veteran sitters have their family celebration a few days early, then head off to sit through the actual holiday. You get the family time and the adventure OR...do like I do and score a family-friendly sit.

  • Build in buffer days. Remember what we said about sitter fatigue? Give yourself a day or two on either side of a holiday sit to rest and reset.

  • Lean on your community. As I've said before....get in community! The sistahood is alive and well on WhatsApp. Tap in!

REMINDERS: Update your profile, refresh your photos, and keep your dates flexible.


Back2theWater 2026

International travel tips for the season


Stretch every holiday into a trip!

This year's big holidays land on Fridays, which makes bridging easy. A few days of time off can turn into a week or more away.

  • Say yes to bridge sits. Owners use the same long weekends to get away, so short 3 to 5 day sits pop up around holidays. They're a great way to test a new area or a new pet without a big commitment.

  • Stack your sits back to back. A holiday sit followed by a short sit keeps your lodging free for the whole stretch.

  • Fly around the crowds. The day before a holiday and the Sunday after are usually the busiest. Travel on the holiday itself or midweek when you can.

  • Book open-jaw flights. Fly into one city and out of another, and sit in between. It stretches your route without adding a second ticket.

  • Still working or consulting? Ask hosts about their wifi speed before you accept a sit, so a work week abroad doesn't turn into a scramble.

Freedom

Wellness for the full-time sitter


Freedom is only freedom if your body and mind can keep up with it. These are the habits that keep me going from sit to sit.

  • Make movement automatic. Dog walks count. Treat every morning stroll as your daily dose of sunshine and steps, and add stretching at night.

  • Protect your sleep. A new bed every few weeks is hard on anybody. Pack a travel pillow and an eye mask, and keep the same wind-down routine in every home.

  • Stock the kitchen on day one. Your first grocery run sets the tone. Keep your staples, hydrate, and go easy on holiday treats so your energy stays steady.

  • Plan your medical care like a pro. Book annual checkups and screenings during a stretch at your home base, not in the middle of a sit. Ask your provider about traverel-length prescription supplies and keep a current medication list on you.

  • Check in on your mind, not just your body. Adjusting to new places and routines can be stressful, and the holidays can stir up feelings, especially when you're far from home. Schedule a weekly call with someone you trust, and reach out when you need support.

  • Care for your nervous system. Rest and healing belong in this lifestyle. That's why Dr. Lyn (sound healing) and Tayvi (mental health counselor) are part of the Back2theWater™ family.

  • Know your holiday pet hazards. Chocolate, rich leftovers, and some decorative plants can make pets sick. Keep the vet's number and the nearest emergency clinic saved in your phone.

Back2theWater 2026

Back2theWater™ 2027: San Andrés, Colombia


Here's where the housesitting life and the water meet. Back2theWater™ returns to San Andrés, Colombia in August 2027 and your spots are open.


This retreat is for BIPOC women who are ready to trade fear for freedom. Our women from the first two cohorts swam independently and jumped into open water, many for the first time in decades. This is water, sistahood, sound, and support; holding space for the mental and emotional side of the journey.


Here's the housesitting connection: you have ten months to get ready, and sitting is the smartest way to fund it. Stack a few sits this winter and spring, let the savings on lodging add up, and put that money toward your deposit. Then tack a sit onto either end of your trip and make a bigger adventure out of it.

If 2026 taught us anything, it's that this retreat fills up.


Reserve your spot with a deposit here, and visit our Back2theWater YouTube channel to hear from the courageous women who stepped into the water.


Plan 2027 now. If you need to request time off, put in for your August Back2theWater™ dates early. And if you want to use PTO to attend, check this video for HR tips!



Until next time, rest well, travel smart, and continued blessings.

Diamond

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The Gallivanting Grandma™

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