Hey First name / friend!

 

I should practice what I preach.  

 

Right now Sam and I are in Anguilla, a VERY last minute trip.  We are staying at the fantastic Frangipani that belongs to one of my colleagues.  Click the link below for more info on incredible Anguilla. 

 

So what is wrong with a last minute trip?  EVERYTHING.  You just can not wing it anymore.  Spontaneity was a casualty of Covid.   

 

I struggled to find a room in Saint Martin that was not  $1500 a night.

 

And I KNOW people. 

 

$1500 seems pretty steep to me ( and my Amex card)  for an 18 hour stay. 

 

We got the last room available at this adorable place right on the beach. 

What was wrong with it? The night club right next door. Our room was literally pulsing with music for half the night.   The beach bar was located UNDER our room, so we got to listen to that music too.  THATS why that last room was available.   

 

Flights.  Airfare is going no where but up. So we had sky high fares, and terrible seats.   We are both very fussy about seats.      

 

We would love to stay in Anguilla a few more days…this hotel is amazing…but  guess what?  Zero availability.       

 

Restaurant reservations, well, this works in our favor since we eat embarrassingly early.   You want between 7:00-9:00?  Forget it.    

 

I needed a reservation for BREAKFAST this morning.

 

Spa appointments?  Wait list. 

 

I know planning for next September might feel like a future you problem, but don't be like me.  Anyhoo, anything less than 90 days out and I consider it a rush assignment.  

 

So let's talk fall! September can be a great month to travel.  Nice weather, fewer crowds, and a sweet spot between summer rush and holiday madness.  

 

If you're thinking, “Is it really time to start planning for next fall?”

 

Here’s a recap:

 

1️⃣ More Choices, Less Settling: The most sought-after hotels, villas, and experiences book up fast, especially in destinations like France and Greece.   Planning = first dibs.

 

2️⃣ Smarter Spending: Booking now means better rates on flights and accommodations (plus, more time to spread out payments and budget for those once-in-a-lifetime experiences).

 

3️⃣ Less Stress, More Excitement: Imagine having your fall getaway locked in. Future you will thank you.

 

So, where should you go? Here are four  destinations that are perfect for September 2025—whether you're craving wine, island vibes, or a far-flung adventure. 

A picture-perfect collection of islands in the Aegean Sea, the Cyclades are known for their whitewashed villages, dramatic cliffs, and endless shades of blue. September is one of the best times to visit—mild temperatures and fewer tourists make these islands even more magical.

 

 

 Explore ancient ruins with fewer crowds. Visit Delos, the mythical birthplace of Apollo, or wander through the ruins on Naxos. 

 

 Dine on the freshest seafood by the water. Whether it’s a seaside taverna in Folegandros or a clifftop meal in Oia, Greek island dining is an experience in itself.

 

Sail between islands at your own pace. Hop from Mykonos to Paros to Milos, discovering hidden beaches, crystal-clear coves, and charming whitewashed villages along the way.  Isn't everything better by boat? 

City culture, and epic adventures await in Sydney and Tropical North Queensland, Australia. September is the perfect time to visit— clear skies, dry season, and incredible wildlife sightings.   The summer crowds have left, and the weather is pleasant. 

 

 

Take a Seaplane up the coast from Sydney for lunch.  One of the highlights of my last visit to Sydney was flying a seaplane up the coast for lunch.  The views were amazing.  And a surprisingly affordable day! 

 

Hike the Daintree Rainforest  After a few days in Sydney, hop a short flight to Cairns.  The oldest rainforest in the world, Daintree is a popular day trip from Cairns and Port Douglas. Saltwater crocodiles, vibrant birdlife, and other tropical creatures inhabit the country's  largest rainforest. .

 

Snorkel or Dive the Great Barrier Reef.  an hour off the coast by boat, the worlds largest coral reef system awaits.  Don't want to get into the water? Enjoy the endless gorgeous coastline and many fabulous resort accommodations.  

Nestled in the southern Caribbean, Curaçao offers crystal-clear waters, vibrant Dutch-Caribbean culture, and colorful streets begging to be explored. September is prime time for sun-soaked adventures without the summer crowds (and without the threat of hurricanes).

 

 

Snorkel or dive in an underwater paradise. Discover world-class dive sites, from sunken ships to coral-covered walls, all teeming with marine life.

 

Wander the pastel-hued streets of Willemstad. This UNESCO-listed city bursts with color, culture, and a lively café scene right along the waterfront.

 

 Find your own secret beach. With over 35 hidden coves and sandy stretches, you can spend your days hopping between idyllic spots like Playa Kenepa and Cas Abao.

Cool air, rolling hills, and scenic drives make the west coast wine country an ideal early fall escape. Enjoy golden-hued landscapes, the crush, charming towns, and lots of wine! 

 

 Take a drive on Pacific Coast . This winding scenic highway offers breathtaking ocean overlooks, whale sightings and easy access to hiking trails..

 

 Sip your way through the Crush. Explore charming vineyards and sample award-winning wines during harvest season. 

 

The food!!!! Eat your way through some of the top restaurants in the country.  It is really had to find a bad meal.  

P.S. Which of these destinations is calling your name for a September escape? Hit reply and let me know—I’d love to help you start planning!

 

Not looking to travel next fall? Feel free to forward this newsletter to someone who might be dreaming of their next getaway 😊