The Best Places to Travel in the World in October (When You Can Actually Leave Whenever the Work Allows)

You can leave whenever you want, in theory. That is the whole reason you built this thing. And yet October rolls around, the crowds have thinned, the flights have dropped, and you are still sitting where you were in July - telling yourself you will go once the business is "further along."

Let me give you the practical version of the best places to travel in the world in October, because the season is on your side and you are the person who can use it. October and November are shoulder season across a lot of the planet. That means fewer people, lower prices, and mild weather in places that were unbearable or unbookable a month earlier. If your income is not where you want it yet, this is the window that stretches your money the furthest.

Why October and November are the smartest months to move

Shoulder season is the stretch between a destination's peak and its off-peak - roughly October and November for a big chunk of the northern hemisphere. Prices soften, queues shrink, and you get the good weather without the July circus.

I have been location-independent since January 2016. Sixty-plus countries, more than 80 house sits, over $250,000 saved on accommodation. The single biggest lever on that number was not some clever hack. It was when I went.

Move in shoulder season and the same apartment that costs a fortune in August is suddenly affordable. My $250-a-month place in Fethiye, Turkey, was not a fluke - it was timing. When you can travel on your own calendar instead of the school-holiday calendar, you are playing a completely different game to most people. That is the actual advantage of the business you built, and most women who run one never fully use it.

So the question is not really "where." It is "why haven't you gone yet." Hold that thought - we will come back to it.

What are the best places to travel in the world in October?

Here is my practical October list - built around cost, comfort and the reality that you need decent wifi to keep the work ticking over.

Turkey (the coast, before it empties)

The Turkish coast in October is my quiet favourite. The summer heat breaks, the sea is still warm enough to swim, and the peak-season prices vanish. Fethiye, Kaş, Antalya - long, slow, cheap. I lived in Fethiye and would go back in a heartbeat for an autumn.

Portugal (Lisbon, Porto, the Algarve)

October in Portugal is warm days, cool evenings and a fraction of the summer crowds. The wifi is solid, the coffee is good, and the cost of living is one of the gentlest in western Europe. It is a soft landing if you have not done a long stint away before.

Mexico (before the high season kicks in)

We are moving to Mexico, so I am biased, but October sits just before the winter high season really lands. Oaxaca in late October gives you Día de los Muertos without the December price tags. Good value, good food, and a big enough remote-work community that you are not doing it alone.

Japan (autumn colour, no summer humidity)

Japan in October is one of the great travel windows. The brutal summer humidity is gone, the autumn leaves start turning, and you dodge the spring cherry-blossom price surge. It is not the cheapest option on this list, but for value against experience it earns its place.

What about the best places to travel in November in the world?

November keeps the shoulder-season logic going and adds a few options that October does not.

Southeast Asia (the dry season begins)

Northern Thailand, Vietnam and Cambodia move into the dry season in November. Chiang Mai in particular is one of the most established remote-work bases on earth - cheap, fast wifi, and a community that has been doing this for years. If your money needs to go a long way, this region does it.

The Canary Islands

When mainland Europe turns cold, the Canaries stay mild. Spanish, sunny, well-connected and far cheaper than the summer scramble. A good spot to keep the year warm without a long-haul flight.

Southern hemisphere spring

November is spring heading into summer in places like Argentina, Chile and South Africa. If you want the season flipped - warm and lengthening days while the north shuts down - this is your move. Cape Town in November, before the December peak, is hard to beat.

I could keep listing places. But a longer list is not what is keeping you home, and we both know it.

Beauty is not the thing that is stopping you

Here is the part nobody puts in these articles. You do not have a destination problem. You have a business problem dressed up as a "someday I will travel" problem.

I know because I lived the trapped version. My cake business, Cakes by Karen, did multiple six figures and I loved it - until it became a prison. Seventy and eighty-hour weeks. Copycats undercutting me until I was nearly working for free. I could not have left in October or any other month, because the business could not run without me standing in the kitchen.

The turning point was my three-year-old's Mother's Day painting. "My mum's favourite thing to do on the weekend is sleep." That was the smack in the face. I had built the freedom on paper and none of it in real life.

If you feel that - the flights are cheap, the season is right, and you still cannot go - the honest read is that your stuck business is the problem, not the laptop lifestyle. And that is fixable. It is also the whole reason I write the grown-up guide to travelling the world without blowing up the business you built: the goal is a business that funds the trip and survives you being on a different continent.

How to actually leave in shoulder season

Wanting to go is not a plan. Here is the practical order I would put it in.

• Pick a real date, not a "someday." Book something small and non-refundable first. The commitment forces the business decisions you have been avoiding.
• Find the one task the business cannot run without you doing. That is the bottleneck. Every trapped business has one, and it is almost always the founder trying to do everything.
• Choose a slower first destination. Portugal over a remote village. You want easy wifi and a soft landing while you prove to yourself the work still gets done.
• Match the trip length to the season, not your nerves. A month somewhere cheap in shoulder season costs less than a fortnight at home. Longer is often the frugal choice.

According to the UN Tourism Barometer, international tourism has fully rebounded to pre-pandemic levels, with over a billion arrivals recorded in a single recent period (UN Tourism). Translation: the crowds are back, which makes the quiet shoulder-season months worth more, not less.

The reason most women stay put is not money. It is that the business has become a job that happens to have their name on it. If that is you, the fix is not another destination list - it is deciding what one thing to actually focus on so the business can run while you are gone.

The version of you who can go

I grew up in an Air Force family - 30 houses by the age of 21. Newness is in my bones. When I read The 4-Hour Work Week flying out of Bolivia and hit the question "if money were no object, what would you do?", I could only write two words: travel, help people. I had lost myself inside a business I built.

Getting it back was not about finding the perfect country. It was about building something that let me go anywhere. Once I finally focused, the freedom came - and the shoulder-season calendar became mine to use however I liked. If you are already years in and still stuck, how to make money travelling when you are already years into this is the honest next read.

Frequently Asked Questions

What are the best places to travel in the world in October?

My practical picks are the Turkish coast, Portugal, Mexico (especially Oaxaca) and Japan. All four give you good weather, thinner crowds and lower shoulder-season prices while keeping the wifi solid enough to work.

What is the best place in the world to travel in November?

Southeast Asia comes into its own as the dry season starts - Chiang Mai in particular for cheap living and fast wifi. The Canary Islands and southern-hemisphere spots like Cape Town are strong alternatives for warmth.

Is October a cheap time to travel?

Often yes. October falls in shoulder season across much of the northern hemisphere, so flights and accommodation drop below peak-summer prices while the weather stays pleasant.

Can I travel in October if I run my own business?

You can, if the business runs without you doing every task yourself. If it cannot, the real fix is removing yourself as the bottleneck first - not waiting for a better month.

The best places to travel in the world in October are not the point. The point is that you built a business so you could go, and the calendar is currently in your favour. If cheap flights and quiet seasons still are not enough to get you out the door, the problem is upstream in the business - and that is exactly what The Reality Check is built to help you diagnose. Book the small thing. Then fix the one task keeping you home.