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Best Places to Visit in October: Where to Travel This Fall

The summer has just come to an end, and fall weather is on it's way as we enter October. The leaves are starting to turn, the air is getting crisp and cool, and the days are growing chillier as we inch our way towards winter. Overall, October is a great month to travel, especially if you're trying to avoid crowds. The peak summer season has ended, school is back in session, and many people are saving up their remaining vacation days to visit friends and family over the upcoming holidays. Whether you want to embrace the fall weather on a hiking trip on colorful trails, or escape the incoming cold with a beach vacation, we've got plenty of choices for an ideal October trip. 

Check out our best October travel deals:

Where are we traveling in October?

At TravelPirates, we're always on the move and we love nothing more than exploring new destinations. We sat down with one of our editors, David Greer, to find out where he's traveling this October. Read on for his top tips on how to make the most of your trip, travel hacks, and where he's headed this fall.

How To Travel Like a Pirate! An Interview with David Greer

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David riding the Circumetnea railroad in Sicily (Photo by Rasa Puzinaite)


David Greer

Job Title

I’m an editor/travel deal hunter, which means that I search the internet for the best travel deals and write them up for you.


I spent a few years working as professional musician at night and in a coffee shop during the day, spent a few years teaching Spanish and English, and traveled whenever I could. I was born in Atlanta, raised in the Washington, D.C. area, lived for three years in New York City, two years in Richmond, Virginia, one year in Madrid, and another six months or so between Buenos Aires and Lima. I decided to make the permanent move to Berlin about a year ago and have never felt more at home.

How many countries have you visited?

Between 30 and 40.

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

Truthfully I’ve had life-changing experiences in more than one place while traveling, but the San Telmo neighborhood of Buenos Aires might be the single place that brought me the most fond memories to look back on. I also really loved Cabo Polonio in Uruguay. Guess it’s a tie.

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David in Rouen, France, right before arriving in Berlin (Photo by Rasa Puzinaite)

Where are you traveling in October?

I try to go somewhere every month and October, 2018 is no exception! I usually travel with my partner and we’ll be headed to Leipzig and then Prague—we leave on a Friday evening and come back to Berlin the following Tuesday. My plans for the trip started when I was at work and came across a $1 night’s stay at a 4-star hotel in Prague. We rarely bother with luxury travel, but for $1 who could say no!? I’m most excited for a nice walk around Prague, visiting some family friends in Leipzig, a nice frothy mug of unpasteurized Czech beer, and the famous breakfast at the Leipzig zoo. I’m also looking forward to taking the train back from Prague to Berlin, as I haven’t taken that route yet.

What are 3 tips you have for someone looking to plan a vacation on a budget?

1. Do your research and have patience—if you want to save money, you’ll usually need to put more time into planning.

2. Be flexible in some way. If your job is flexible with vacation time, then go for the cheapest dates you can find. If not, perhaps settle for cheaper flights with a long layover and go out and explore the layover city.

3. Stop checking baggage. Some airlines may still let you check baggage without a fee, but unless you’re bringing a musical instrument or sports equipment, you don’t need to be weighed down by more than a large backpack/smaller suitcase for a trip of less than a month. Wear your heavy jacket onto the plane!

What’s the most underrated travel destination?

With North American travelers in mind I’d probably say the Canary Islands, specifically Tenerife. It can be super cheap to get to, and once there it’s also super cheap and really has something for everyone.

What song/album/artist gets you in the mood to travel?

As a musician and music lover, I don’t have any single answer for this question. I associate different music with different places, ideas, or experiences. I heard John Coltrane’s album “My Favorite Things” this morning and instantly found myself in the mood to get on one of the cheap American flights to New York City to go hang out in upper Manhattan. Luckily the moment ended and I was able to finish up the deal I was working on!

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David in Tenerife during the winter (Photo by Rasa Puzinaite)

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 love the feeling of spontaneity, but as a border-line control freak, I tend towards more detailed planning. A part of me always hopes that something doesn’t go quite as planned, though—it’s just more interesting that way!

You’ve been gifted an all-expenses-paid trip anywhere in the world–where do you go?

That depends a lot on the time frame, but I’d settle for a few weeks somewhere coastal towards the Southern part of Argentine Patagonia in November or December.

What was your most memorable/unique travel experience?

Again, it’s hard to choose just one, but the 36-hour train ride that I took from Buenos Aires to Córdoba is memorable to me and definitely unique in the sense that most visitors to Argentina don’t even know the train exists. Somewhere between the haziness that comes with exhaustion, the constance mosquito ambushes from the open train windows, and the philosophical conversations that I found myself in with fellow train riders I felt a sense of freedom that I hadn’t felt before.

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

For the destination, it depends on that person’s interests, but I would recommend a place where the traveler already has a connection to—things like interest or ability in a language, historical knowledge of the place, friends with connections to the place, interest in the local cuisine, or anything like that. As for the kind of trip, I would highly recommend straying away from only staying at all-inclusive resorts or taking full tours, not that I’m against that kind of thing. It’s just that, to me, the investment in planning and exploring gives you the chance to develop yourself and really enjoy life in a way that more luxury travel simply could never provide. This is especially true for someone traveling out of the US for the first time!

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David at Stonehenge (Photo by Rasa Puzinaite)

Fill in the blank: When I travel to a new city, the first thing I like to do is ___________________

Take a (long) walk and stop somewhere for a coffee, a beer, or a meal.

Fill in the blank: When I discovered ________________ it made travel so much better

Completely sealable coffee mugs

Fill in the blank: I know a lot of people love ______________ when traveling, but I hate it.

Getting to the airport early

What was your longest trip?

Outside of living in countries other than the US, I spent about six months slowly traveling from Uruguay to Peru.

What was your shortest trip?

I’ve taken lots of day trips, so ruling those and stopovers out, my shortest trip must have been a little under 24 hours in Dublin.

Tell us about a time when you felt like a pirate on your travels

Well I always feel like a pirate while booking transportation for my trips. While traveling in Morocco, I’d say I felt pretty pirate-like. I traveled around using the train system and found rooftops to stay on when I got to each new city—it barely cost me anything at all and I saw a lot!

Looking for more travel inspiration? Browse more of our latest October travel deals: