In my dreamiest dreams, I am a travel agent, Airbnb connoisseur, and Curator of Good Vibes all rolled into one. If anyone knows how I can actually turn this into a legitimate career, please let me know. Until then, I’ll be dropping all of my hard-won research on Substack in a new (sporadic) series called Steal This Trip.
One week after my 39th birthday, I informed my husband that I was opening a temporary savings account for my 40th birthday. For the past year, I’ve been squirreling money away—a little here, a little there—every time I’ve taken on an extra work commitment (speaking gigs, workshops, cohorts, photo shoots, etc). The end goal: I wanted to celebrate this momentous birthday with my ride or die friends … and I wanted to do it right.
Cut to me texting my three closest friends in Spokane, North Carolina, and Virginia: “If you fly to California for my birthday, I will handle the rest.”
Once we landed on the general location, I gave my life to Reddit.1 Best food. Best drinks. Best winery. Best shopping. Best hike. Best everything. What I wanted, generally-speaking: 80-degree weather, a fabulous pool to lounge by, good ambiance (always), and zero cooking.
I’m happy to report that all of my birthday wishes came true. We ate, we drank, we laughed, we cried, we ate sandwiches and ice cream cones the size of our heads. Naturally, I brought my favorite 40th birthday gifts: the vibration plate and red light mask. We spent far more time in sweatpants and bathing suits than anything else. So many inside jokes (”But where is Jesus?” “In this economy?!” “That’s L-E V-I-B-E”) It was, in a word, perfect.
Whether you’re celebrating a milestone birthday, planning a low-key bachelorette party, or just need to get away for some serious R&R with your people, feel free to steal this trip!
The Airbnb of my DREAMS. I have stayed at 30+ Airbnbs over the years, and this was, by far, my favorite one to date. Stunning views, aesthetics on point, comfy beds, well-equipped kitchen, absolutely no notes. The house is roughly 15 minutes from Healdsburg, 30 minutes from Calistoga, and 50 minutes from Sonoma. Best airport to fly into is The Charles M. Schulz – Sonoma County Airport (literally a 15-minute drive to the Airbnb). Or, fly into Oakland/San Francisco/Sacramento, and make the 1.5-2 hour drive.
Note: like most Airbnbs, pricing changes with the seasons — it’s far more expensive to visit in the summer. We were here mid-May, which is considered off-season (this was still a splurge, but I can confidently say it was worth every penny). The weather was perfect, nice and cool in the mornings/evenings, and mid-70’s/low 80’s during the day.
Day one: Soak up the house, the sun, the views. Pass out custom swag bags (protein snacks, shower steamers, mints, eye patches). Charcuterie for dinner. Chocolate for dessert. Followed by hot tub, sweatpants, and face masks.
Day two: Spend the morning by the pool, then grab a resort pass2 to Dr. Wilkinson’s Backyard Resort & Mineral Springs for the second half of the day. Order tacos and palomas and french fries and anything else that sounds good. Lounge, talk, read, swim, repeat. On the way out, grab ice cream at Calistoga Creamery. The handmade waffle cones are not to be missed.
Day three: Kick off the morning with a private yoga session3 at the house, then head to downtown Healdsburg for Michelin-star sandwiches at Troubadour. After lunch, choose your own adventure: shopping or wine tasting. Sarah and Sonya ventured to MacRostie Winery while I wandered around Copperfield books and treated myself to a new pair of barrel jeans at Gathered. Pop back to the Airbnb for a little rest before taking an Uber to dinner at Roof106. Do not sleep on the burrata and sourdough flatbread! Linger until you are the last guests at the restaurant.
Day four: Spend the morning by the pool, (sadly) check-out of the Airbnb, and then hop over to Armstrong Redwoods State Natural Reserve so your friends who have never seen the redwoods can (literally) hug a tree. Hike, listen to the birds, feel very very very small in the best possible way. Inhale wonder. Exhale gratitude. Make a quick pit stop at Coffee Bazaar on the way out to re-fuel before heading to Salt & Stone for a late lunch on your way home to Sacramento. DO NOT SLEEP ON THE TRUFFLE FRIES. I repeat: do not sleep on the truffle fries!!! Soak up every last minute of this food and this place and these friends. Order a blackberry mimosa because why not. Clink your glasses one final time. Cheers.
TL; DR — we all came home with full bellies and full hearts. Probably won’t be celebrating a birthday this extravagantly anytime soon. Where should I spend my 50th?!
P.s. A wild thought … the light in this Airbnb was INSANE and I’d love to photograph a family in this house for my portfolio. I’d actually love to shoot a maternity session here. If you live in/around Santa Rosa or Healdsburg and are pregnant or hope to be soon, reply to this email or slide into my DMs! ❤️
Other posts you might love: Friendship in Three Acts | Taste & See | This Is How We Do: Traveling with Friends | Moms Have Birthdays, Too
Fun fact: I trust Reddit 4,000x more than I trust AI. 😜
Note: this link will get you $20 off your first booking of $100+
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