Hey First name / friend!

 

I know, I know… you haven’t even wrapped up your summer travel plans and here I am talking about fall. But if you’ve been with me for a while, you know there’s power in planning ahead—especially in bulk. So wherever you are in your process, let’s dig into my favorite travel month.

 

There’s something about October travel—it hits that sweet spot between the summer crowds and the holiday rush, in a window the world hasn’t fully caught onto (yet) 🤫

 

One of my favorite trips ever was in October. I was overworked, uninspired, and all I wanted was to read a book cover to cover without being interrupted. So I went to the Finger Lakes in upstate New York, sat on a porch overlooking the water, and read for four days straight—rotating between a teacup and a wine glass from morning till night. It was heaven.

 

Here’s why October is such an underrated time to get away:

 

1️⃣ Perfect Weather – From crisp mountain air to sun-drenched beach days, October hits the seasonal sweet spot in many places.

 

2️⃣ Lighter Crowds – Skip the chaos. Enjoy destinations with more space, more calm, and more “you time.”

 

3️⃣ Beautiful Scenery – Whether it’s fall foliage or spring blooms (hello, southern hemisphere), the views are hard to beat.

 

4️⃣ Better Value – Shoulder season = better rates, more availability, and upgrades you might not expect.

 

5️⃣ Time to Recharge – Shake off the summer sprint and take a breather before the holiday madness kicks in.

 

Whether you’re craving cool air, warm water, or something a little further afield, I’ve rounded up three destinations for October and the stays that make them shine.

 

Scroll down to find your perfect fall fit 🍁

Can you see yourself here? Trade in fall layers for salty hair, sea breezes, and slow days on island time.

 

October brings a quieter side of St. Barth—warm, breezy weather and room to enjoy its beaches, boutiques, and bistros without the winter-season buzz. It’s an ideal time for swimming, sailing, and savoring the good life, French-Caribbean style.

 

✨ Perfect Fit For: Design lovers, relaxed romantics, solo sunseekers, and anyone who prefers their tropical escape with a side of rosé.

 

📌 Good to Know: St. Barth is compact and in demand and it shines with boutique hotels—early bookings are recommended to get the good spots.

 

Stay at Gyp Sea St. Barth: Set above the bay or right on the beach in St. Jean, Gyp Sea offers barefoot style with a touch of boho chic. Choose a hillside bungalow with a plunge pool or a multiple bedroom beach house steps from the sand—both come with access to the island’s most laid-back beach club.

Your fall plans? A true adventure, complete with snow-capped peaks, sacred temples, and crisp mountain air.

 

October is one of the most beautiful times to visit Bhutan, with clear skies and colorful festivals like Thimphu Tshechu bringing the country’s spiritual and cultural traditions to life. Hike to cliffside monasteries, explore peaceful valleys, and experience the rhythm of life in the Himalayas.

 

✨ Perfect Fit For: Inquisitive travelers, culture seekers, wellness goers, and those craving that once-in-a-lifetime type trip.

📌 Good to Know: Bhutan limits tourist numbers through a daily visa fee—your trip must be booked through a licensed tour operator (we’ll take care of the details).

 

Stay at Gangtey Lodge Bhutan: Gangtey Lodge sits in Bhutan’s Phobjikha Valley, where black-necked cranes glide in each fall and everything feels grounded in nature. With timber beams, deep soaking tubs, and views that stretch over farmland and forests, it’s the kind of remote you don’t reach by accident—and that’s exactly the point.

Cozy fall bursting with color? Say no more. Kennebunkport boasts fiery foliage, charming inns, and coastal charm just 90 minutes north of Boston.

 

October in Maine is pure autumn magic. Whether you’re leaf-peeping along scenic byways, sipping cider at a roadside farm stand, or simply cozying up by a fireplace overlooking the sea, this is the kind of getaway that feels both nostalgic and refreshing.

 

✨ Perfect Fit For: Fall fanatics, couples, laid-back resets, bibliophiles, and anyone who lives for sweater weather and scenic drives.

📌 Good to Know: Foliage typically peaks between mid to late October in southern, coastal Maine

 

Stay at White Barn Inn: A longtime New England classic (150 years classic!) with a fresh touch. Think fireplaces, fresh oysters, and pine-scented air—fall here feels serene, golden, and just a little bit cinematic.

P.S. So, what’s calling you? A crackling fire in Maine or sunbathing in St. Barth? I’d love to hear which October escape speaks to you most—hit reply and let’s dream it up together.

 

And for anyone traveling within the U.S., a quick reminder: the REAL ID deadline is coming. Starting May 7th, even domestic flights will require updated identification. Now’s a good time to make sure you’re set.