🌴 A Little Planning Now = A Year of Cheaper, Smoother Travel Later 🌴
Published: Mon, 12/22/25
Updated: Mon, 12/22/25
Most people wait too long to plan travel. Here’s why starting now gives you a huge advantage.
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A Little Planning Now = A Year of Cheaper, Smoother Travel Later
I'm almost fully recovered from my last trip, but I've mostly been at home editing videos.
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I have so much video content that I could stop traveling for a year and still have stuff to post. If you know video editing and are looking for side work or are interested in
learning how to video edit, reply and we'll talk.
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Now that the year is almost over, here are some questions you should ask yourself about where you want to travel in 2026.
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Here's why: Planning ahead will
give you peace of mind and help you save a lot of money!
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Your friends will not only start wondering if you hit the lottery because you're traveling so much, but they'll also wonder how you have the energy to do all this planning.
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I could go on and on… But here's what you need to know right
now…
Where do you want to travel?
Make a spreadsheet with different options. For example, in spring, I want to go to Madrid or Athens. The goal isn't to book everything now, but when deals show up, you can decide quickly where you want to go.
Don't forget: Be sure to travel during shoulder season, where you can have the best
prices and best experience. For those who like traveling to Europe, that's in the spring and fall.
What type of trips do you want to go on?
For example, do you want to do outdoor camping or explore a city? Figuring out this type of stuff will also help you assess whether you have the right equipment, and there are still end-of-year sales to be had.
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How many times do you want to travel?
Plan both the big trips and the light trips. The big trips are 5+ days and require extensive planning, while the lighter trips are more weekend-friendly and may involve domestic travel or a road trip.
Who do you want to travel with?
Seriously, who you travel with can make or break your trip. Think about who would bring you joy on the road, but it's more than
that. I like to use a mental trick: Who would bail you out of jail and make you laugh at the same time?Â
Or are you ready to try solo travel in 2026?
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When do you want to travel?
Which holidays do you want to combine with your time off to maximize your days away? I made a calendar last year showing the best times to take off, and I might make one for this year too.
Booking travel is like
Goldilocks—there's just the right time. You don't want to book too soon or too late, or you'll pay a lot more. For international flights, the sweet spot is 2 to 8 months before departure, and for domestic flights, it's 1 to 3 months.
How are you going to pay for it?
Figure out which credit cards you want to get this year to earn the most points. Also, check the
credit cards you already have to make sure you're using them in the best way possible.
I currently see tons of deals on Going.com, so start booking them now to capture your savings.
Did you take care of the boring stuff?
Check to make sure your passport is still valid. If your passport expires this year, renew it first because many countries won't let you visit if your passport is expiring in 6 months.
Find a travel insurance provider. If you don't already have one, start doing some research so when it's time to travel, everything is automatic.
As you know, I use
Safety
Wing
.
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One thing to note is to be flexible. Not leaving room for life will make you miserable, and you might miss some major life events, so don't plan things too much.
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In short, a little planning now will make traveling much easier for the rest of the year.
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Give it a try and let me know how it turns out.
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Keep traveling,
Andrew
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What's the number one place you would like to travel to in 2026?
Cocktail of the Week
The Zombie cocktail was invented in the United States, specifically by Donn Beach (also known as Don the Beachcomber) in the 1930s in California. It was originally created to help a hungover
customer get through a business meeting, but the drink was so strong that the customer later claimed it made him feel like a zombie. Â
Ingredients:
1 ½ oz light rum
1 ½ oz dark rum
1 oz lime juice
½ oz falernum (or simple
syrup)
1 oz passion fruit juice
½ oz grenadine
1 dash Angostura bitters
½ oz overproof rum (for float)
Crushed ice
Mint sprig and cherry (for garnish)
Preparation:
Fill a cocktail shaker with ice.
Add the light rum, dark rum, lime juice, falernum, passion fruit juice, grenadine, and bitters.
Shake well until chilled.
Strain into a tall glass filled with crushed ice.
Gently float
the overproof rum on top by pouring it over the back of a spoon.
Garnish with a mint sprig and a cherry.
Serve with a straw and enjoy!
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Random Travel Thought
The good thing about putting my life on social media is I don't have to bore my friends with my travel stories because everything is already out there.
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Follow me on Instagram.
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The Plug
Cheap flights:
Going.com: This might be the only discounted flights website you need. It’s a paid service that sends you notifications when deals become available, but they expire in a couple of days so Act Fast!!Â
Secret
Flying
🤫: This website emails you about free flight opportunities and even better… it doesn’t cost a thing!!
Skyscanner
:
An older, but still reliable website that’s also *FREE* so there’s no reason not to use it. Use the "Explore the World" feature and set your departure date to "Whole Month" to find the cheapest deals.
Insurance:
Safety
Wing
:
I use Safety Wing as my travel insurance because the plans are flexible. You can easily insure a 1-week trip for like $11 dollars which is less than the cost of a cocktail at the bar.
Travel Gear
Compression socks: Sitting for extended periods of time is not good for the body, so keep yourself healthy enough to go on more trips. Link
Apple AirTags: Consider getting Apple AirTags for the peace of mind of always knowing where your luggage is. Link
Smart Phone holder: It's a foldable sheet that can be used as a stand for your iPhone or iPad.Link
Packing cubes: Having a separate container works wonders for keeping
clothes wrinkle-free. It also makes packing/unpacking much easier.Link
Donut Power Strip: Power outlets are always in demand, but sometimes they're in weird spots. I use this bagel because it's lightweight, and I don't have to think about it. Link
Travel Case Organizer: Cable organizers can be a pain, but this is what I use to keep my cables organized. Link
Backup batteries: I like these backup batteries because they have three important components for me: 1. They have enough power to recharge my phone multiple times at once, 2. Are small enough to put in my pocket, and 3. Are sturdy enough to survive a fall. Link
Yoga Mat: I use this thin mat to get my stretching in even when I'm traveling. Link
Jump Rope: It's so easy to bring a jump rope with you for exercise because it
weighs almost nothing and takes up no space. Link
Liquid IV: Great for hydration to keep you from dying. When you're traveling, it's time to live it up! Link
*Above are Affiliate links at no additional cost to you.
