Every travel enthusiast knows that choosing the right time to visit a destination can make all the difference.
As summer wanes and fall approaches, September is an ideal travel month for so many reasons. With mild weather, fewer crowds and a plethora of cultural, culinary and festive events on offer, cities, towns and islands — from Louisville, Kentucky to the Maldives — present their unique allure.
Here are TPG’s top 10 places to visit in September.
Louisville, Kentucky
September is a month of celebration in Louisville with the 8th annual Bourbon & Beyond festival (Sept. 14-17) and the concurrent Kentucky Bourbon Festival. It offers an extensive range of bourbon and live music from acclaimed artists, so it’s a bourbon lover’s paradise.
Related: Baseball, bourbon and Barbaro: Why Louisville is the perfect destination for a father/daughter trip
Music enthusiasts should not miss the Louder Than Life Festival, a four-day music event attracting over 120,000 fans yearly (Sept. 21-24).
Plus, Bourbon fanatics can also enjoy a visit to Rabbit Hole Distillery right next door to Hotel Genevieve before spending the night in Louisville’s newest chic boutique hotel (and the first boutique hotel for the hip East Market district — an emerging area near downtown dotted with bourbon distilleries, craft breweries, stylish bars, elevated restaurants and vintage stores).
TPG tip: Book a stay at the Moxy Louisville Downtown from 31,000 Marriott Bonvoy points or $129 per night.
Vienna, Austria
Vienna shines in September, offering a delightful blend of summer’s warmth and outdoor fun without the usual crowds.
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As temperatures remain pleasant, the city becomes a haven for visitors seeking enjoyable outdoor activities. Join the Viennese locals in celebrating the start of the opera season, a grand event from September through June. Don’t miss the annual WienerBierfest, a lively beer festival that adds cheer to the city.
Moreover, September marks the beginning of the harvest season for Vienna’s vast urban vineyards, spanning more than 1,700 acres. With its rich cultural heritage, stunning landmarks and vibrant atmosphere, Vienna in September is a true delight for any traveler.
Related: How to spend 48 hours in Vienna
TPG tip: Stay local with the Austrian-owned Almanac Palais Vienna, which just debuted in March. It is a boutique property set inside a pair of former Palais dating to 1871 and owned by the Austrian Haselbacher family. Rates start from $268 per night. Or splurge on the exquisite Rosewood Vienna, with a fabulous location, sumptuous rooms and impressive amenities, including a spa and rooftop bar. Rates start at $800 per night.
Maldives
September in the Maldives is a surfer’s dream. With consistent waves, steady trade winds and tropical water temperatures, it’s the perfect time for surfing. Gili Lankanfushi offers the opportunity to ride waves where surfing in the Maldives was born. Guests can enjoy renowned surf breaks, including the legendary Jailbreak spot just a short boat ride away. Partnered with Tropicsurf, the resort provides surf instruction for all ages and levels. State-of-the-art equipment is available for rent at Gili’s surf shack.
Related: Dreaming of the Maldives? These new and updated points resorts are waiting for you
TPG tip: The Conrad Maldives Rangali Island is a gem and available from $690 or 120,000 Hilton Honors points per night.
Napa Valley, California
In September, Napa Valley becomes a captivating destination that showcases its picturesque charm. The pleasant weather with ideal daytime temperatures sets the stage for an unforgettable visit.
As the leaves transition into vibrant yellow, orange and burgundy hues, the entire valley transforms into a breathtaking autumnal landscape. The air is filled with delightful harvest aromas during the bustling “crush” season. September also offers a host of seasonal events, from grape smashing to wine blending, festivals and harvest dinners.
Furthermore, Napa Valley’s culinary scene continues to evolve with exciting additions like Scala Osteria & Bar, offering delectable Italian cuisine, and Morimoto Asia, a pan-Asian concept by renowned chef Masaharu Morimoto.
TPG tip: At Meadowood Napa Valley, American Express Platinum Card members receive early and late checkout, daily breakfast for two, $100 toward spa services, and you can use 50,000 points (worth $500) towards your stay when booking through the American Express Travel Portal.
Trancoso, Brazil
Trancoso’s boutique UXUA Casa Hotel & Spa, located on the historic main square (rates from $578), gears up for the area’s annual Organic Festival, promoting sustainability and community outreach. From Sept. 27 to Oct. 1, this event raises awareness about organic food’s positive impact on the environment and locals. After a hiatus due to Covid, the festival returns, featuring renowned Brazilian chefs who offer their culinary delights at affordable prices.
In addition, this year’s focus expands to encompass the region’s rich food history, tracing its origins from indigenous cultures to its hippy haven past. September provides the final chance to explore Brazil before visa requirements come back into effect for U.S. travelers starting Oct. 1.
TPG tip: You can get a roundtrip economy ticket to Porto Seguro with one stopover for as little as $761 during the month of September on LATAM Airlines, which is a Marriott Bonvoy transfer partner.
London, England
London is a captivating destination to explore in September, and it’s no surprise that it tops the travel charts for Americans.
With a vibrant array of events, the city offers something for everyone. From July 19 to Sept. 9, the renowned BBC Proms features female conductors opening and closing the event for the first time in history. Fashion Week (Sept. 15-19) showcases the latest trends, while the Victoria and Albert Museum hosts a fascinating exhibition dedicated to Coco Chanel, debuting on Sept. 16.
TPG tip: Stay at St. Pancras Renaissance Hotel where the Spice Girls filmed their famous “Wannabe” music video. Rates start from 61,000 Marriott Bonvoy points or $378 per night.
Related: The top Renaissance hotels you can book and earn Marriott Bonvoy points
Cancun, Mexico
Cancun, Mexico is a fantastic destination to visit during the “shoulder season,” offering an excellent opportunity to enjoy the country’s beaches, historical sites and cultural events away from the bustling crowds. It’s ideal for travelers seeking immersive cultural experiences, particularly during Mexico’s Independence Day celebrations on Sept. 16. The streets come alive with vibrant festivals featuring mariachis, mesmerizing garage tapatío performances (the national dance of Mexico), mouthwatering Mexican street food and much more. This is the perfect time to soak up Mexico’s rich traditions and flavors while enjoying the beauty of Cancun’s stunning coastline.
TPG tip: Book a room at InterContinental Presidente Cancun Resort from $200 or 32,000 IHG One Rewards per night.
Related: 14 of TPG’s favorite points hotels on the beach in Mexico
Grapevine, Texas
Grapevine, a hidden gem within the Dallas-Fort Worth Metroplex in Texas, offers a delightful retreat for travelers seeking a quaint and charming destination.
Strolling down Main Street, visitors will discover an array of wine-tasting rooms, local artists and unique shops, set against the backdrop of a storybook-esque clock tower that graces the downtown area.
The highlight of September in Grapevine is the largest wine festival in the southwest, taking place this year from Sept. 14-17. This four-day extravaganza offers annual events, special wine tastings and family-friendly activities. With Main Street closed to traffic, visitors can sip on Champagnes and sparkling wines under the shaded oaks at Champagne Terrace, embark on a unique tasting experience at Liberty Park Plaza, and participate in entertaining events like the Champagne Cork Shoot-Off and Grape Stomp. Grapevine promises a memorable and fun-filled experience for wine enthusiasts and travelers alike.
TPG tip: For easy access to all the major attractions in the area, book a room at Hilton Garden Inn Grapevine at Silverlake Crossings from 34,000 Hilton Honors points or $109 per night.
New York City, New York
NYC celebrates the arrival of fall with an irresistible blend of sports and fashion. Sports enthusiasts can witness the excitement of the US Open, taking place from August 28 to Sept. 10, where the world’s top tennis players compete for glory.
Simultaneously, the city transforms into a fashion hub as Fashion Week unfolds from Sept. 7-13, showcasing the latest trends and designs. Additionally, September marks the transition into the enchanting fall season, where the city’s parks and streets are adorned with the vibrant colors of changing leaves. New York City in September becomes a dynamic and captivating destination that seamlessly blends sports, fashion and the magic of autumn.
TPG tip: There’s no shortage of great places to stay in NYC. For easy access to September’s top attractions, the Pendry Manhattan West is available from $761 or 59,000 Chase Ultimate Rewards points per night.
Orléans, France
Orléans, located on the banks of the majestic Loire River, becomes an enchanting destination during the eleventh edition of the Loire Festival, Europe’s largest gathering of the river navy, from Sept. 20-24, 2023.
This biennial event attracts hundreds of thousands of visitors who come together to celebrate the rich historic naval traditions. With more than 200 boats, 700 sailors and 500 artists participating, the festival showcases nautical demonstrations, regattas, jousts and rowing races.
Visitors can immerse themselves in the festive atmosphere while savoring local specialties and enjoying drinks by the water at charming taverns known as “guinguettes.” As night falls, the city comes alive with breathtaking fireworks and illuminations. Orléans, one of France’s oldest cities and the gateway to the historic Loire Valley region, exudes a palpable sense of history with its ties to Joan of Arc and a fascinating medieval past.
TPG tip: Mercure Orléans Centre is available from $144 or 9,646 Chase Ultimate Rewards points per night.
