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Where’s Jessie B.

Where’s Jessie B… Going Next?

Two off-the-beaten path travel ideas every other Monday.

Happy Monday, Subscriber First Name! It’s Jessie B, bringing you two off-the-beaten-path travel ideas for the week: one for a last-minute getaway, and one to plan for later in the year. Let’s get to it!

WHERE TO TRAVEL NOW

Healdsburg, California

August 7th or September 4th

Sometimes β€œoff the beaten path” is less about where you go than when. In this case: a mid-week escape to Sonoma wine country. I love doing this when I have flexibility because it means cheaper hotel rates, more restaurant and tasting room availability, live music at Little Saint, andβ€”for 2 more nights this summerβ€”Wednesday outdoor movie nights at The Madrona ($65 per person for a ticket; includes wine and snacks).

βž› Things to do: Wine tasting, naturally. I love the indoor/outdoor spaces at Flowers, Bella Vineyards, and Aperture. In town, go to the beautiful tasting room for Marine Layer. For an active activity, rent a bike or kayak with Russian River Adventures (they also have guided tours).

βž› Eat, eat, eat: Start your day at Black Oak Coffee or Quail & Condor. For lunch, grab a sandwich in between wine tastings at Dry Creek General Store or stock up on picnic goods at Ciao Bruto. For dinner, try Troubadour for French bistro fare, Molti Amici for Italian, or have any meal at SingleThread’s vegan restaurant and cafe, Little Saint.

βž› Where to stay: The Madrona is a gorgeous, maximalist boutique hotel in a refurbished mansion, complete with a pool, cocktail lounge, and destination-worthy restaurant. It’s a splurge, though they give discounts to California residents on stays Sunday-Thursday. Otherwise, H2Hotel or Harmon Guest House (sister hotels next door to each other) are my picks for a more mid-range option, and Hotel Trio (by Marriott) is a solid, affordable option.

Want to take this trip?

I’ll plan and book it for you. Respond to this email to make a request, and I’ll take care of the rest 😎 β€” I’ll even score you exclusive advisor discounts and perks at select hotels (20% discount, $50 restaurant credit, and a free wine tasting at H2Hotel, anyone?), when available.

WHERE TO TRAVEL LATER

Todos Santos, Mexico

November / December

On your next trip to Baja California, skip Cabo and go to Todos Santos, a charming, historic town just an hour northwest of the airport. Tourist season starts to ramp up in November, but it’s still a relatively chill time to visit. Bonus: the laidback, boho surf town, Pescadero, is just a 10-15 minute drive away.

βž› 3 things to do: Surf at El Cerritos beach, hike Punta Lobos, and release baby turtles into the ocean at sunset at Tortugueros Las Playitas A.C. (winter only).

βž› Eat, eat, eat: Go-to coffee and pastry spots are DoceCuarenta and CabaΓ±as Las Tunas. At lunch, you can’t beat ceviche at El Compa Chava or tacos at Barracuda Cantina. For dinner, try chocolate clams at the new, trendy Oystera or seasonal seafood at El Coyote, a romantic restaurant hidden in the desert. One place you shouldn’t miss: sunset drinks and/or dinner at The Green Room.

βž› Where to stay: The best budget-friendly hotel is Perro Surfero, a welcoming, digital nomad hub in town. I also loved Tribu Todos Santos / Tribu Pescadero, a mid-range boho retreat with two, beachy locations in the area (the adobe teepee rooms are very cool). For a real treat, splurge on Hotel El Perdido, a small, boutique luxury hotel in Pescadero, or hipster, beach hotel San Cristobal.

βž› Getting there: Fly to SJD (Cabo) and rent a car from Cactus Car Rentals. It’s about 1-1 hour 20 mins from the airport.

βž› Packing list: I’ve got you, girl πŸ’β€β™€οΈ

Want to take this trip?

I’ll plan and book it for you. Respond to this email to make a request, and I’ll take care of the rest. 😎

Prefer to DIY? Buy my Google Map list ($7.99) to save all my favorite Todos Santos spots in your app (including a few lesser-known beaches and tips on how to get there πŸ˜‰).

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