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What to Do in September

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Great-Value Flights in September

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Best Places to Visit in September: Where to Travel in Late Summer

Summer is coming to an end, the days are getting shorter, and the leaves are changing color and slowly falling from the trees. It's getting colder, maybe greyer, depending on what part of the US you live in, but you don't want to let summer go just yet. Understandable, who wants that?! So why not just pack your things and go on a vacation? If you're looking for some incredible travel deals for the month of September, you've come to the right place. Whether you're trying to find cheap flights to domestic destinations or an international vacation package in September, this is the page for you.

Looking to travel during another month of the year? Or during a public holiday?

Beach Vacation in September

It doesn't matter whether it's Florida, Central America, or Asia, in September you can always find a chic spot on the beach to relax. The time of main tourism in the summer vacation is slowly ebbing away and the crowds are making room for who? Exactly, for you! Our TOP 5 travel destinations for beach vacations in September are Miami Beach, Punta Cana, Greece, Indonesia, and Portugal. Are you ready?

1. Beach Vacations in Rhodes, Greece

"Greek wine, pour it again." Udo Jürgens once sang about the wonderful culinary highlights that are offered to you on a vacation in Greece. But in Greece, you can expect not only delicious food in the form of tzatziki, olives & Co., and wine in bulk. No, especially on a trip to Rhodes you will see ancient buildings, historical sites, lots of great vantage points, pure nature, and - of course - incredibly great bays that are waiting for you to swim and cool off.

2. Beach vacation in Bali

Turquoise blue water, fascinating temples, lush green rainforest, and an exciting animal world, all will bring you vacation in Bali. Not only can you relax and work on your tan in the most beautiful hotels on the beach, but you can also discover Balinese culture and indulge your taste buds with delicious Asian food. Bali is an island that will grow on you. Simply a true paradise on earth, which is ideal in September to simply leave everyday life behind.

3. Explore the Turquoise Beaches in the Dominican Republic

Palm-fringed, dreamy beaches boasting white sand and turquoise blue waters—that's probably the first thing that comes to mind when you think of a vacation in the Dominican Republic. And rightly so, as the DR has hundreds of picturesque beaches. But with so many to choose from, how do you know which beach to visit? 80 percent of all tourists end up in Punta Cana at the easternmost tip of the island. This is not surprising given the high number of dreamy beaches and luxurious hotels.

4. Beach Vacation in the Algarve

Portugal is a year-round paradise for sun-seekers, but September, in particular, is perfect for vacations in the Algarve. Wide, sandy beaches meet hidden bays and dreamy villages. In addition, the Algarve is a true surfer's paradise. It doesn't matter whether you hang out in Lagos, a great port city and a great surfing spot, or let the sun shine on you in Faro, there is something for everyone on a beach vacation in the Algarve.

5. Miami Beach: Cruise Down Ocean Drive

The main attractions of Miami are of course the numerous breathtaking beaches in the vicinity: the Lummus Park Beach on Ocean Drive, the nudist beach Haulover, or Pelican Island.

City Trips in September

City trips in summer can be exhausting. It's hot, you're sweating to death and you actually want to discover the city, but actually just sit in the café and sip one cool drink after the other. And city breaks in winter? It can rain, snow, storm - wherever you are. But late summer in September is perfect for a city trip. Not too warm, not too cold and the summer tourists retire too. We have selected the TOP 5 city trips for September for you.

1. City Break Marrakesh in September

What can you expect from a holiday in Morocco? Of course, a dream from 1001 Nights and Marrakesh embodies this perfectly. Get lost in the labyrinthine streets of the city and discover something new around every corner. Or visit a typical souk, a typical Arabic market, and stock up on great souvenirs. In addition, the smell of Moroccan spices fills your nostrils and the scent of freshly brewed tea is in the air. Marrakesh is a true paradise for a city break in September.

2. City Trip to Madrid in September

A city trip to Madrid means traveling to the heart of Spain and September is the perfect time to discover Madrid. Locals are returning to the city from their summer retreats and Madrid is reviving after the severe summer heat. The shops are opening again and yet the tourists are fewer and you can relax and enjoy a few churros or discover the architectural art treasures on the Gran Vía. So let's go and discover the rhythm of Madrid.

3. Singapore in September

Singapore - a metropolis, a city of superlatives, Asia's "melting pot" of cultures and inventions. Vacations in Singapore will surprise you every time and the city is perfect for a city trip. Foodies, explorers, collectors, action lovers, culture lovers, and socializers from all over the world meet in the lively island state —and create new, exciting things together every day. Singapore is more than just a travel destination. It is the place where passion can become reality.

4. September in Venice

A city trip to Venice - there is hardly anyone who has not yet landed the city in north-eastern Italy on their bucket list. With the curved canals that meander through Venice and can be explored with a gondola, the almost 3000 narrow and typically Italian streets, and the historic buildings, Venice is a dream destination, not only for the romantics among you. The foodies will of course be rewarded with delicious pizza and pasta. Here too, in September, the masses of tourists are slowly retreating and the city is becoming quieter. On to your next vacation in Venice, we would say.

5. Trip to Malta in September

Alta Falta, we want to go to Malta. The island, which combines influences from English, Roman, and French culture, can be found in the Mediterranean Sea between Sicily and North Africa. Vacations in Malta also mean planning a city trip to the capital - Valletta. Valletta was declared a World Heritage Site by UNESCO and looks extremely romantic, especially with the golden autumn light. The city was built by the Knights of St. John, on a peninsula less than a mile long. You will also find numerous architectural highlights, and art, as well as numerous bays and grottos in Valetta, and the city was voted European Capital of Culture in 2018.

Where Are We Traveling in September?

You know us, we're the TravelPirates, and we're always on the move. September is no exception. We set down with one of our content marketing manager, Eduardo Vega Augusto, to chat about where he's headed this September, along with tips to help you make the best of your next trip

Travel Like a Pirate! An Interview with Eduardo Vega Augusto

Job Title

Content Marketing Manager


Over 10 years of Marketing experience, focusing on branding, and working with international brands.

How many countries have you visited?

Around 17 give or take

What is your favorite place you’ve traveled so far and why?

Guatemala! People are so welcoming, the food is amazing, and it’s very easy to travel to and move around.

Where are you traveling this September?

I’ll be in Tuscany for a friend’s wedding, and will take a few days after to visit Mykonos.

Wow, how do you feel about traveling for a wedding? Have you ever traveled for a wedding before?

My first time traveling to Spain was actually to go to a friend’s wedding, I’ve been a big fan of destination weddings ever since. I also recently spent a couple days in New York for a close friend’s wedding.

Where is the best lgbtq+-friendly destination you’ve been to? Why?

New York and Amsterdam have a special place in my heart, maybe I’m a little bias, but have always felt very welcomed in both places. Amsterdam Pride parade is one of the best things I’ve experienced.

What are other destinations would recommend to folks looking for lgbtq+-friendly fun?

Spain, especially Barcelona, is very liberal. Sitges, just a few minutes outside of Barcelona is one of the best LGBTQ+ destinations in Europe.

Some people like to plan everything down to the tiniest detail when they travel, and some prefer to be completely spontaneous. Where do you fall on the spectrum?

I like to have a list of things I would like to do, but then see where day takes me. I usually like to walk to most places when I’m traveling and explore the cities, I’ve found some of the best restaurants this way.

What is your biggest piece of advice for someone looking to plan a comfortable, budget vacation?

Plan ahead! Tickets and reservations for popular places can get quite pricey the closer you get to the dates.

What kind of trip/destination would you recommend for someone who has never traveled outside the US?

Travel with friends, maybe someone who has gone to that destination before. Places you can move around walking, or where they speak English.

What’s the longest trip you’ve ever taken?

Around 2 weeks to Guatemala and Curacao for work, it was incredible, but not the best for sightseeing.

The shortest?

I went to Rome for only 8 hours, managed to do most of the touristy things, and had a blast

What’s the first thing that goes in your suitcase when you start packing?

My headphones, there’s nothing worse than a long flight with nothing to watch or listen to.

Which single discovery impacted how you travel the most?

Learning a few words in the native language will make people more willing to help.

What’s a popular travel trend that you despise?

Traveling to NYC for New Year’s, or really anything around Times Square, is a tourist trap.

Tell us about a moment during your travels when you felt like a pirate.

I would extend my work trips to be able to experience more of the cities, my company paid for flights, so all I needed to do was pay for a hotel for any extra days.

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