Ten weeks. Ten destinations. One very big birthday for America.

It has been so fun taking you along for this summer series, and I hope at least one of these emails planted a seed for a trip worth making happen. From the cobblestone streets of Charleston to San Diego sunsets from a sailboat on the bay… America showed up this summer.

But here’s the thing about August…. It has a way of sneaking up on you.

School is starting back soon. The calendar is about to get very full, very fast. And before you know it, it’s October! 

So before the back-to-school chaos fully sets in, let’s talk about what comes next. Because the school year is full of travel windows if you know where to look. 

Consider this email your syllabus for the first half of the school year and the break you absolutely deserve!

🍂 “WE ONLY HAVE A LONG WEEKEND.”

Don’t spend half your vacation getting there! When you only have three or four days, think closer to home. A quick road trip or nearby city getaway can provide the reset you’re craving without turning travel days into a marathon.

• Ideas to Explore: A boutique wine country escape in Texas Hill Country or a long weekend in New Orleans

🎃 “WE’RE TAKING ADVANTAGE OF FALL BREAK.”

Fall might just be one of the best-kept secrets in travel (don’t tell the others). Summer crowds have thinned out, many destinations still have beautiful weather, and you’ve got options.

• Ideas to Explore: New England foliage from a luxury inn in Vermont

🦃 “NOBODY WANTS TO COOK THANKSGIVING DINNER.”

Imagine Thanksgiving where the food is still delicious, but someone else does the grocery shopping, cooking, serving, and dishes. Thanksgiving travel lets you keep the family traditions while skipping the kitchen chaos.

• Ideas to Explore: A private villa in Turks & Caicos or a luxury resort in Los Cabos

🎄 “WE WANT MAXIMUM HOLIDAY MAGIC.”

A magical holiday season doesn’t have to include last-minute shopping or tackling a mountain of dishes. Instead, trade holiday stress for twinkling lights, festive traditions, and memories your family will talk about long after the

decorations come down.

• Ideas to Explore: European Christmas markets paired with a five-star city hotel in Vienna or Zurich, or a ski week in Aspen or Park City

‍‍‍‍‍‍‍ ✈️  “THE WHOLE FAMILY IS COMING.”

Multi-generational trips can create incredible memories… when they’re planned well. Look for destinations with plenty of space to spread out, activities for different ages, and enough flexibility for adults to relax while the kids burn off energy.

• Ideas to Explore: A luxury resort in Hawaii, or a private villa in the Caribbean

Whether you’re hoping to sneak away once or make the most of every school break, you know where to find me! 

P.S. Before the back-to-school chaos fully sets in, take a look at your family’s calendar and start thinking about those fall and holiday breaks! The earlier we start planning, the more options you’ll have before the busiest travel dates begin to fill.