9 Surprisingly Powerful Ways to Slay Your Vacay with Off-Season Travel
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When you first set out to plan the perfect vacation, the mere idea of it might keep you up at night. You scroll on Instagram, see folks sipping champagne in Santorini or posting beach pics from Tulum, and suddenly you’re in a spiral.
Why aren’t you there yet? Are you missing some magic secret ingredient to travel success?
Sis, let me stop you right there.
Chances are, there’s no secret. What those people really did was book smart, and one of the smartest ways to travel is hitting up destinations during the off-season. No crazy crowds, no wild prices, just you living your best life with more peace and more coin left in your pocket.
So in this post, I’m going to help you shake off that comparison game and start feeling confident that your next vacation can be just as fly (and affordable) as the ones you see online.
I’m breaking down 9 surprisingly powerful ways to crush your off-season travels without stress, confusion, or overwhelm.
Make sure you read to the end, because I’ve got a bonus freebie you can download that’ll make planning your next trip even easier!
#1. Forget about “You Have to Travel During Peak Season”
If you want to really experience a destination, the exact opposite is true. You’ve got to slide in when everybody else ain’t there.
Here’s why this is #1: off-season travel means lower prices on flights, hotels, and excursions. We’re talking 30–50% cheaper sometimes. That’s a whole new outfit or spa day right there!
The pitfall? Some people think “off-season” means bad weather or nothing to do. Nah, don’t fall for that. A little drizzle in Paris or a chillier beach in Greece doesn’t cancel the vibes.
Instead, lean into what makes the off-season unique. Think cozy cafés instead of sweaty lines, local festivals instead of tourist traps, and time to actually breathe and soak it all in.
For example: when we hit up Rome in February, we got to walk through St. Peter’s Basilica without shoulder-to-shoulder crowds. I could actually see the Pantheon without somebody’s selfie stick in my way. And the gelato still slapped—even in the cold.
#2. Hold Off on Booking the “Instagram Famous” Spots First
Listen, I know Bali and Santorini look bomb in the feed. But when you rush to book the same destinations as everybody else, even off-season, you risk overspending and underwhelming yourself.
Instead, look into emerging off-season gems. Places like Cartagena, Colombia; Porto, Portugal; or Belize in late spring. They’ve got all the beauty, culture, and fun—without the oversaturation.
The benefit? You’ll spend less, discover more, and come back with stories people actually haven’t heard 1,000 times.
✨ Quick recap: Cartagena for Afro-Latin culture + beaches, Porto for wine + cobblestones, Belize for chill vibes + adventure.
#3. Supercharge Your Trip Planning with a Seasonal Calendar
Before you start chasing flight deals, you need to know when each destination is considered “off-season.”
This one simple step will keep you from booking blindly. For example:
Paris off-season = November–March
Caribbean off-season = late April–early June, September–early December
Japan off-season = mid-January–March, excluding cherry blossom season
If you’re serious about getting the best deals, write it down. Create a travel calendar where you mark off-season months by region. This helps you stay organized and spot patterns—like when flight prices usually dip.
That way, you’re not just scrolling aimlessly, you’re hunting strategically.
#4. Always Check Local Festivals & Events
Regardless of where you’re going, checking the local calendar is smart. Off-season doesn’t mean boring—it often means different.
For example, Spain in November? Hello, Flamenco festivals. Mexico in October? Día de los Muertos magic. Jamaica in September? Food and rum fests, less crowded beaches, and hotels running promos.
Pro tip: don’t just rely on Google. Hit up local tourism boards or even Instagram hashtags (#ParisEvents, #TokyoLife) to see what’s popping when you plan to go.
When you catch an off-season event, you get the culture and the savings.
#5. Get Guidance When You Need It
It’s easy to feel stuck. Maybe you’re putting the time in but still overwhelmed by choices. Should you do Costa Rica in May or wait for Thailand in June? Should you risk hurricane season in the Caribbean or switch to Europe?
Sis, you don’t have to figure it all out solo. That’s literally what travel advisors like me are here for.
When I hit a wall planning my first multi-country trip years back, I tapped a mentor who’d been there/done that. Saved me hours, dollars, and stress.
Sometimes you just need somebody to:
Get clear on the best times to travel
Keep you accountable (aka remind you to actually book and not just dream)
Help with the nitty gritty like flights + tours
👉 If you’re ready for clarity and ease, schedule a call with me here.
#6. Level Up with Skyscanner’s “Everywhere” Tool
Have you seen Skyscanner’s “Everywhere” tool? It’s a game-changer.
Here’s how it works: instead of putting in a destination, you just put your home airport + travel month. The tool shows you the cheapest destinations you can fly to.
How I use it:
When I want a quick getaway but don’t care where, I’ll search “Atlanta to Everywhere, November.” Boom—Portugal for $350 roundtrip popped up one year.
After I book flights, I run the tool again to see what nearby countries are cheap add-ons.
I also track how flight prices dip month-to-month so I know the sweet spot.
There are other tools like Google Flights, but I love Skyscanner because it keeps it super simple and shows hidden gems.
#7. Use My “Double Dip Travel Strategy”
Here’s my signature move: Double Dip Travel.
Most people think you pick one destination and call it a day. But if you’re already overseas during off-season, flights between countries can be dirt cheap.
For example: I once booked a trip to Barcelona in February. Then I “double dipped” and snagged a $40 flight to Morocco while I was there. Two vacations in one for less than what folks spend on one flight to Miami.
That’s the beauty of off-season—airlines and hotels are just trying to fill seats and beds. You can scoop up deals that feel unreal.
We also do this on cruises with long times in port or an overnight. This is how we saw so many sights in Europe on our Mediterranean cruise. Overnight in Cannes turned into a day trip to Monaco and Nice. All for the cost of a train ticket of like 8 euros.
So when you’re planning, always ask: what nearby spot could I tack on for cheap?
#8. Put It Down on Paper
Off-season travel feels like magic, but it only works if you plan it out. Write down:
Your travel calendar by region
Your budget + price alerts
Local festivals/events you want to hit
Backup plans (like indoor activities if the weather flips)
Checking in every 3–6 months keeps you on track. Maybe you realize Europe is pricier than expected, so you pivot to South America. Or maybe you see flights drop to the Caribbean right before hurricane season—worth the gamble if you’re flexible.
Having it in writing makes your dream tangible.
#9: Bonus! Download the Off-Season Travel Cheat Sheet
Whew—you made it to the end! 🙌🏾 You deserve a cookie and my Off-Season Travel Cheat Sheet.
This free printable PDF breaks down:
The best months to visit top destinations
My favorite booking tools
A checklist to make sure you don’t miss a deal
👉 Click here to download it now
Keep it in your bag, and planning your next trip will feel like a breeze.
I hope this post showed you that every step you take towards off-season travel is a major win.
From forgetting the peak-season hype to using my Double Dip Travel Strategy, these moves will save you money, stress, and time—while giving you unforgettable experiences.
So raise your hand, pat yourself on the back, and get ready for your next getaway.
Now I want to hear from you:
Which of these strategies will you try first? Are you checking out Skyscanner’s Everywhere tool, or pulling the trigger on Double Dip Travel?
Drop your thoughts in the comments—I’d love to hear your plans!
