September is one of the best months to travel, with ideal weather, fewer crowds, and that sweet spot between the summer rush and holiday madness. If you’re looking for the best places to visit in September, now is the perfect time to start planning!

If you’re wondering, “Is it really time to start planning for next fall?” — I get it! But as a trusted travel advisor, I can tell you that the best trips come together when you plan ahead. Here’s why:

The Perks of Booking Your September Trip Now

• More Choices, Less Settling: The best hotels, villas, and experiences book up fast, especially in dreamy destinations like Greece and the Caribbean. Early planning = first dibs.
• Smarter Spending: Booking now means better rates on flights and accommodations (plus, more time to budget for those once-in-a-lifetime experiences).
• Less Stress, More Excitement: Imagine having your fall getaway locked in while everyone else scrambles for last-minute plans. Future you will thank you.

So, where should you go? Here are four destinations that we think are the best places to visit in September — whether you’re craving coastal charm, mountain air, or a far-flung adventure.

Cyclades, Greece

You know those Instagram photos of impossibly blue water, whitewashed buildings, and dreamy sunsets? Yeah, that’s the Cyclades. And September is the time to visit — mild temperatures, fewer tourists, and that golden Mediterranean light that makes everything look like a postcard.

Must-Do Experiences in the Cyclades

• Explore ancient ruins without the crowds. Wander the sacred island of Delos or explore Akrotiri, Santorini’s version of Pompeii.
• Dine by the sea. Head to Dimitris Ammoudi Tavern and enjoy a meal right at the water’s edge in Ammoudi Bay. Fresh seafood, stunning views, and you can even dip your toes in the water.
  • Bonus Hidden Gem experience – Take a post-dinner dip in the hidden swimming spot just beyond the bay!
• Sail between islands at your own pace. Hop from Mykonos to Naxos to Milos, discovering hidden beaches and charming whitewashed villages along the way.
• Stay at Canaves Oia Suites, a stunning cliffside retreat with private plunge pools, incredible caldera views, and exclusive perks when booked with a Virtuoso travel advisor (that’s me!).

Curaçao

Nestled in the southern Caribbean, Curaçao is where crystal-clear waters meet a vibrant Dutch-Caribbean culture. September is prime time for sun-soaked adventures without the summer crowds (and without the threat of hurricanes).

Must-Do Experiences in Curaçao

• Snorkel or dive in an underwater paradise. Check out Tugboat Beach, where a sunken tugboat is now home to colorful marine life.
• Wander the pastel-hued streets of Willemstad. This UNESCO-listed city bursts with color, street art, and a lively café scene right along the waterfront.
• Find your own secret beach. With over 35 hidden coves, you can beach-hop all day and still find new favorites.
• PRO TIP: Skip the big resorts and book a boutique stay at Baoase Luxury Resort. With just 23 rooms and villas, think secluded beachside villas, personal butlers, and pure island bliss.

Switzerland

Alpine scenery? ✅ Charming villages? ✅ Fondue that will change your life? ✅ Switzerland in September is an absolute dream, with crisp mountain air, breathtaking landscapes, and way fewer tourists than peak summer.

Must-Do Experiences in Switzerland

• Ride the Glacier Express. This world-famous train winds through snow-capped peaks and postcard-perfect valleys from Zermatt to St. Moritz.
• Enjoy an authentic Swiss fondue experience. Nothing beats dipping warm, gooey cheese while looking out at a snow-capped mountain.
• Hidden Gem: Visit Lauterbrunnen Valley for fairytale waterfalls and dramatic cliffs. This place feels straight out of a fantasy novel (and inspired Tolkien’s Rivendell!).
• Stay at Badrutt’s Palace, St. Moritz, a legendary luxury hotel with breathtaking lake views, an award-winning spa, top-tier service, not to mention additional exclusive Virtuoso benefits you’ll receive.

Germany

September in Germany? Two words: Oktoberfest season! 🍻 But beyond the beer halls, this is also the perfect time to explore charming villages, medieval castles, and beautiful fall foliage.

Must-Do Experiences in Germany

• Drive the Romantic Road. This scenic route takes you past medieval towns, rolling vineyards, and the fairy-tale Neuschwanstein Castle (aka the inspiration for Disney’s Cinderella Castle).
• Celebrate Oktoberfest in style. Munich’s famous festival kicks off in late September, but I can help you secure VIP seating so you’re not stuck in the back of the beer tent.
• Sip wine in the Moselle Valley. If Oktoberfest beers aren’t your thing, swap pints for some of Germany’s best Rieslings in this stunning wine region.
• PRO TIP: Want a castle stay fit for royalty? Book a night at Schlosshotel Kronberg, a luxury castle hotel that once belonged to German royalty.

Whether you’re dreaming of a Greek island escape, a Caribbean getaway, or an adventure in the Alps, these are best places to visit in September! Plan ahead and book early. Not only does it give you first dibs on the best hotels and experiences, but it also allows you to enjoy the excitement of looking forward to your getaway. So why wait? Contact me and let’s make your fall vacation a reality today!