BEST SEPTEMBER TRAVEL DESTINATIONS Positano Italy Travel Like a Chieff Luxury Travel Blog

Best September Travel Destinations Around The World

Those with children in school may not consider September the best month to travel, for obvious reasons. For everyone else, this is a great month to visit various destinations all around the world. Most destinations are a lot less crowded, the weather is still relatively mild in most countries and you get way more bang for your buck. The following are some of the best September travel destinations chosen by travel writers, including me. Whether you are looking for a city break, an adventure packed getaway or sipping champagne on a yacht, there is a destination for each activity!

Amalfi Coast From Yacht Best September Travel Destinations Luxury Travel

Amalfi Coast By Pamela Chieffallo From Travel Like A Chieff

The Amalfi coast is one of the best September Travel destinations for so many reasons! The weather is perfect during this time of year, the tourists are gone and the locals are enjoying the calm after the Ferragosto holidays. September is the last month before most hotels, cafes, and restaurants close up shop for the winter.

There is no shortage of beautiful beaches, villages, grottos, and islands to visit near the Amalfi coast. The best way to tour the coast is by boat, even better, a yacht. We did just that during our visit last year and absolutely loved it! You can head to the Saracen beach, the marine village of Conca dei Marini, the Emerald Grotto, the Li Galli Islands, Positano, Capri and/or Nerano.

Fancy a lunch at a cliffside restaurant with stunning views? There are plenty to choose from but we opted for Il Riccio in Anacapri and the food was fantastic. Amalfi Charters, the company we hired, offers a variety of tours depending on your interests. If a fishing trip is what you are looking for then head out with the “lampare” which are local fishing boats with lights. A more romantic option would be to take a boat ride under the moonlight, nothing beats the reflection of the moon on the sea while you sip on champagne with the one you love. Finally, for those seeking adventure, there is nautical skiing along the coast. Read More…

Stockholm Sweden Best September Travel Destinations Luxury Travel

Stockholm is one of the coolest places to visit in Europe - it is stylish, fun and hip.

The public transportation system is excellent so it is easy to get around, it is safe and clean - so there are plenty of reasons to visit one of the most beautiful cities in Europe.

You can visit any time of the year and every season has its charm, but it is one of the best September travel destinations. The extreme heat is over which means you can still stroll the city and discover all the beautiful sights and places without feeling too warm.

It does not get dark until 6 pm, so you still have a lot of time to visit places like Gamla Stan, the old town, where sights like the Royal Place or Nobel Museum are located. You can also take a stroll by the beautiful waterfront, do a boat tour, head to Drottningholm Palace, shop in the city center or hit one of the cool bars.

Even if you are not a fan of museums (talking about myself) Stockholm has some pretty cool museums to visit. So when you visit the Swedish capital in September, make sure to also add the Vasa Museum, or the Abba Museum before ending your day with a warm drink in Gamla Stan or Södermalm. Read More…


Chicago Best September Travel Destinations Luxury Travel

Chicago is one of the best September travel destinations, although I think Chicago is a great city to visit year round, if I had to pick one month, it would be September. September has the perfect combination of plenty of things to do, great weather and fewer crowds. Chicago can be brutally cold, windy and snowy in the winter and hot and humid in the summer. Fall and spring are very unpredictable in terms of weather, the temperatures can be more moderate and pleasant or they can be a continuation of winter or summer. September usually has the best weather, it is one of driest months and the temperature is usually almost as warm as it is in the summer.

Visitors to Chicago in September can still enjoy many of the same fun outdoor activities and attractions that are available in the summer with fewer crowds. This includes architecture river cruises, boat cruises, outdoor festivals, dining or drinking at outdoor patios and rooftops or just hanging out, walking or jogging along the lakefront or river.  Although many tourists still visit Chicago in September, because school has started all the attractions are less crowded than they are in the summer or during spring or winter break. Read More…


Nicaragua Best September Travel Destinations Luxury Travel

September is wet season in Nicaragua but I highly recommend a visit during that time! It rains, but not much, a drizzle or two during the afternoon and heavier rain during the evenings. And since it is so hot there, the rain is very much welcome!

We had the whole month there and visited 3 cities, Leon, Granada, and Managua, and the rain did not stop us from doing anything.

It's also the low season, so it is less expensive, less crowded, and it is just as beautiful as in any other season! Some evenings there is lightning, and it is quite a show, it is so stunning and impressive!

It's also the beginning of the sea turtle nesting and hatching season, so you can witness one of the most amazing moments of nature. Just make sure you don't disturb them - remember they are endangered species. If you wish to help release baby turtles into the sea, it is best to plan your trip towards the end of September. We were in the turtle region early on and missed it. Nicaragua is great in September and we couldn't recommend it enough!


Sofia Bulgaria Best September Travel Destinations Luxury Travel

Bulgaria’s beautiful capital city, Sofia, is one of the best September travel destinations. For one, the summer heat has cooled off a bit from its peaks in July and August, but it is still warm. This is a great time to do hikes in the surrounding mountains of Sofia, such as Vitosha, which is just a 30-minute bus ride from Sofia center, or the 7 Rila Lakes hike which is also a great Sofia day trip.

If hiking isn’t your thing, there are still plenty of things to do in Sofia in September. You can enjoy the cool summer nights in the many parks and green spaces, check out the many interesting museums or photograph the beautiful architecture in the city center. September also marks the Kvartal festival, a three day long festival in Sofia that celebrates culture, art, and music. There are live shows, concerts, art exhibits, poetry and literature readings, and many other cultural celebrations. And as the month of September comes to a close, the leaves in Sofia start to change to brilliant autumn colors of red and orange making September one of the best months to visit this Balkan capital.


I hope you enjoyed this list of the best September travel destinations chosen by experienced travelers. There is something for everyone all around the world so why wait? Go ahead, start planning your next September getaway!

What is the best September travel destination you've been to?

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Stockholm Sweden Best September Travel Destinations Luxury Travel
Positano Amalfi Coast From Yacht Best September Travel Destinations Luxury Travel
Chicago Best September Travel Destinations Luxury Travel

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