When I’d Go - Timing Your Dream Trip the Smart Way
🌍 Because the best time to travel isn’t just about weather — it’s about how you want to travel.
After years of helping families, couples, and first-time explorers plan their dream trips, I’ve realized something:
The “best” time to go isn’t a single answer.
It’s a balance of weather, crowds, energy, and those once-a-year natural moments that make a place unforgettable.
So, instead of giving you textbook answers, here’s when I’d personally go — and why.
🌺 Hawaii — December to March
When the mainland is buried in snow, Hawaii feels like pure sunshine therapy.
This is whale season — and seeing mamas and calves breaching off the coast of Maui never gets old. It’s warm, peaceful, and the perfect mid-winter reset.
Pro tip: book early if you’re eyeing February. It’s a local favorite, too.
🐒 Costa Rica — January or February
If you’re craving a quick, easy flight from the U.S. (and a full dose of vitamin D), this is your sweet spot.
Rainy season’s over, which means beach days in Guanacaste and lush rainforest mornings in La Fortuna.
Pack both a rain jacket and a swimsuit — you’ll use them on the same day, and that’s the beauty of Costa Rica.
🍋 Amalfi Coast — End of May or September
I’ll pass on the July crowds, thanks.
Late spring and early fall are where the magic happens: sunny skies, warm water, and a calmer rhythm.
Everything’s open, but you can actually hear the church bells echo through the hills.
I always plan a midweek stay — because weekends belong to the locals (and the brave).
🦁 South Africa — February or March
Think warm days, crisp evenings, and golden light that makes every safari photo glow.
It’s also harvest season in wine country, which means vineyard picnics, tasting rooms, and the perfect excuse to end your trip in Cape Town with a chilled Chenin Blanc.
Bonus: the pools are perfect this time of year, so yes — pack the swimsuit.
✈️ Before You Pick a Date, Think About…
☀ What’s the weather really like?
👥 Do you want to avoid crowds or lean into the buzz?
🏝 Does the region “close” down off-season?
📅 When are you actually free to travel?
✨ And are there any seasonal moments worth chasing — whales, Northern Lights, harvest festivals, or something that happens only once a year?
Because there’s no single best time — only the right time for you.
And that’s exactly what I help my travelers figure out. 💛
Adventure Smarter — because your timing should be as thoughtful as your destination.