The Best Destinations to Visit in September

Aug 6, 2019

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While your mind may be on the impending arrival of back-to-school shopping and pumpkin spice lattes this September, it’s not too late to squeeze in a late summer vacation. Or, perhaps, you’re ready to embrace the changing season with open arms and admire the leaves as they begin to turn a little closer to home.

Either way, September is a great month to hit the road and travel.

That’s because September marks the beginning of shoulder season in many destinations, which means fewer crowds and better deals on everything from airfare to hotel rates. From far-flung countries like Kenya and Sri Lanka to domestic destinations like Vermont, here are six places you should visit in September if you’re itching for an early fall getaway.

Ready to plan the rest of your 2019 travels? Check out our guide to the 12 best places to visit every month of 2019.


Thanks to the relatively new nonstop daily flight from New York-JFK to Nairobi (NBO) on Kenya Airways, you can now get to the east African nation from the East Coast just a little bit faster — and much easier than before. Best of all, you can book your flight with Delta SkyMiles, because Kenya Airways is a member of the SkyTeam Alliance, and the two airlines have been developing a close partnership.

The Masai Mara, Kenya. (Photo by brittak / Getty Images)
The Masai Mara, Kenya. (Photo by brittak / Getty Images)

Obviously, Kenya-bound travelers probably have one thing on their minds: a safari. Since Kenya’s dry season runs through October, weather is at its best in September and you might even catch the Great Migration in the Masai Mara. Seeing millions of wildebeest, zebras and other game trek across Kenya’s savannah in large herds is truly an experience worth the 14-hour flight, even if you’re stuck back in economy.

But you don’t have to go all the way to Masai Mara to see game. One of the world’s most unique national parks is located right on the edge of the country’s capital: Nairobi National Park, where you can capture skyscrapers and lions, giraffes or rhinos all in the same shot.

For even more wildlife excitement, stay at the Giraffe Manor, where you’ll wake up to giraffes poking their noses through your bedroom window. Or, test out the recently renovated Beyond Bateleur Camp in the Mara plains, which reopened in 2018 after an extensive refresh.

For travelers with a Platinum or Centurion-branded card in their wallet, including The Platinum Card® from American Express and The Business Platinum Card® from American Express, the Fairmont Mount Kenya Safari Club can be booked through the American Express Fine Hotels & Resorts (FHR) program in September for 5x (on prepaid online bookings) Membership Rewards points and benefits like daily breakfast for two; a $100 spa credit; a room upgrade on arrival, when available; and complimentary late check-out. You can also use Membership Rewards Pay With Points for prepaid FHR bookings if you simply want to cut down on the total cost of your trip to Kenya.


Through Sept. 28, Windy City residents can still fly nonstop on the new seasonal route between Chicago O’Hare (ORD) and Athens International (ATH) on American with the airline’s reconfigured 787-8. The AA route from Philadelphia (PHL) to Athens (ATH) also operates its last flight of seasonal service on the same date.

Chania, Crete. (Photo by Aleh Varanishcha / Getty Images)
Chania, Crete. (Photo by Aleh Varanishcha / Getty Images)

Plus, the recently opened Four Seasons Athens definitely lives up to the hype. The hotel, located slightly outside the city center, is on the Athens Riviera (yes, that’s a thing) and has three private beaches as well as a pine forest on its 75-acre property.

Although the islands are still gloriously sunny, the hot summer heat dissipates along with the crowds as the month goes on, making things like taking ferries and braving the winding Greek roads in a tiny stick-shift Fiat rental just a little less intense.

And while visiting the more popular islands of Santorini and Mykonos is never a bad idea, smaller, lesser-known hotspots to consider for the 2019 season include islands such as Milos, Paxos and Sifnos. Travelers can also find a reprieve from end-of-summer crowds on Crete. The island is far from unknown, but offers the perfect mix of sandy beaches (one even made our list of the best beaches in Europe this year), rich history and Mediterranean cuisine.

There are even a few seriously stunning points hotels on Crete, like Marriott’s Domes of Elounda, an Autograph Collection property available from 85,000 points per night (or $314) and the recently-renovated Wyndham Grand Crete Mirabello Bay from 30,000 points per night (or $137).

Sri Lanka

This country was set to be one of the hottest destinations of the year. Then, devastating terrorist attacks occurred back in April.

Sri Lanka
Sri Lanka’s tea plantations. (Photo by Xsandra / Getty Images)

Tourist arrivals in Sri Lanka dropped 80% after the attacks. Understandably, travelers were — and still may be — nervous to visit.

But months have passed, and the situation has changed. The US State Department has lowered its Sri Lanka travel advisory down from a Level 3 warning to a Level 2. That’s the same level in place for countries such as the Bahamas, France, Spain, Denmark, the Maldives, the UK and Turks and Caicos.

In an effort to boost tourism, you can still expect to see a commensurate dip in airfare prices. The Sri Lankan government has just mandated a reduction in airline fees as well as encouraging airlines to increase the number of flights and drop prices. And, starting in August, the island nation has begun offering free visas on arrival to travelers from 50 nations, including the US, the UK, the EU, Canada and Australia.

It’s not just flying there that’s affordable. Hotels all over the country have also lowered their prices. We found rooms in boutique properties and vacation rentals from $15, where popular hotel local chains including JetwingCinnamon and Blue Water have been offering discounts of 30% or more for 2019 reservations.

Once you’re there and settled in, you’ll find September is the perfect time to explore the beaches of the east coast, like surfer paradise Arugam Bay or the sand-swept Trincomalee. Or, perhaps, the hilly tea plantations of Ella are calling your name, or Sigiriya, where you can spot wild elephants.

No matter what, don’t miss out on your chance to experience one of the most scenic train rides in the world, from Kandy to Ella.


Malta is another European island destination that’s often packed during the peak summer months of July and August, but is much less crowded in the still-sunny, still-warm month of September. Although the water can be a little chilly toward the end of the month, you can still enjoy dipping into swimming holes like St Peter’s pool — a unique beach formed from stone that will make you feel as if you’re sunbathing on the moon.

The skyline of Valetta, Malta. (Photo by joe daniel price / Getty Images)
The skyline of Valetta, Malta. (Photo by joe daniel price / Getty Images)

While you can’t fly nonstop to the island from the US, you can connect through many European hubs including London, Paris and Madrid. Or, you can also take the ferry over from Sicily.

For a bonus, visit the two smaller islands off the coast of Malta, Gozo and Comino. Both are known as budding dive destinations — you can spot the famous P31 shipwreck just off the coast of Comino or swim through the Blue Hole in Gozo.

You’ll have to wait until 2021 to stay at the Hard Rock Malta hotel, but in the meantime, consider a suite at the Cugo Gran Macina Hotel (opened in 2018), each crafted with local design elements. Although you can’t use points at the property, September rates are more reasonable than you’d find earlier in the season. For those with points, the Category 5 Westin Dragonara (from 35,000 points per night) and the Hilton Malta (from 60,000 points per night) are both relatively close the UNESCO World Heritage site of Valletta.


While the sun and heat continue to beat down on many parts of Europe, the northeastern US is celebrating the early signs of fall. If you want to spend your September vacation viewing the changing shades of leaves, sipping tea and cozying up around a fire during cool nights, Vermont is the place to be.

A small rural town near the Waits River in Vermont. (Photo by DenisTangneyJr / Getty Images)
A small rural town near the Waits River in Vermont. (Photo by DenisTangneyJr / Getty Images)

The foliage change normally starts mid-September and extends through mid-October. The change is determined by many different factors, some of which include temperature, light and soil conditions, but usually begins in the northern regions and at higher elevations, so plan accordingly.

Travelers based in Florida can now get a taste of fall, too. This year, Frontier has launched nonstop service between Orlando International (MCO) and Burlington International (BTV), in addition to already-existing routes between the Vermont hub and Denver, New York City, Philadelphia, Atlanta, Chicago and Washington, DC, among others.

In order to ensure you get to witness some of the color change, consider embarking on a road trip through some of the Vermont’s smaller villages such as Manchester, Dorset and Somerset. You’ll get to witness the varying hues of the leaves, and also soak in the New England charm that is generally most prominent in smaller towns and hamlets.

Plan to stop along the way to enjoy other autumnal activities like apple picking and visits to pumpkin patches. And if you’ve got the family in tow, a stop at Vermont’s Teddy Bear factory will definitely be a crowd-pleaser. Spend the night at Marriott’s Equinox Golf Resort & Spa, a Category 6 Luxury Collection property where some US presidents have stayed. Rates start at 50,000 points per night or $176 when booking a package to celebrate the resort’s 250th anniversary.


Experience solid weather and lower prices when you visit Colombia in September. This South American county broke several tourism records in 2018, and numbers just keep rising. Plan to go soon before tourists completely saturate some of the most popular destinations such as Cartagena, Bogotá and Medellín.

Near the town of Leticia, Colombia from the Amazon River. (Photo by Kim Schandorff / Getty Images)
Near the town of Leticia, Colombia from the Amazon River. (Photo by Kim Schandorff / Getty Images)

Medellín, an urban destination known for its mild weather year-round, is often called the City of Eternal Spring. With noticeable improvements to public spaces, such as the planting of trees and other flora, and the city’s Metrocable, which opened in the early 2000s, accessibility and culture are thriving in Colombia’s second most-populated metropolitan hub. It’s no surprise that The Points Guy himself, Brian Kelly, chose the spot as the first city to film his new travel vlog, Being The Points Guy.

September is also an ideal month to view wildlife. Spot turtles laying their eggs on beaches along the Pacific coast, and watch for humpback whales migrating south. The month is also ideal for visits to the Amazon area, where you’ll view a variety of mammals, reptiles and birds active in their natural habitats.

With nonstop flights on airlines including American, Avianca, Delta, United and JetBlue from various US cities to Cartagena, Bogotá, Medellín and Cali, it’s easier than ever to get to Colombia. Travelers on a budget (or without points) should consider a low-cost carrier such as Viva Air or Spirit, where September rates drop as low s $100 each way.

Featured photo of Sri Lanka by egle sidaraviciute / Unsplash.

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