Where to Travel in May: Sicily, Northern Thailand & Maui
🌍 Why May Is the Smartest Month to Travel (And Where to Go Next)
If you’ve ever dreamed of having Europe’s coastlines, tropical islands, or jungle hideaways almost to yourself, May is your month.
It’s that sweet spot between spring and summer — the shoulder season — when the crowds haven’t arrived yet, the weather is perfect, and your favorite hotels are still smiling about availability (and better pricing).
Whether you’re craving Mediterranean charm, soul-soothing jungles, or barefoot island luxury, these three destinations hit their stride in May: Sicily, Northern Thailand, and Maui.
🇮🇹 Sicily: For the Dolce Vita Dreamers
Perfect for: Food lovers, culture seekers, and anyone who wants all the Italian flair without the summer chaos.
May in Sicily feels like the world’s best secret. Wildflowers blanket the hills, café tables spill into the streets, and the sea is warm enough for your first swim of the season. You’ll find the locals out enjoying the sunshine — and far fewer tourists at the island’s biggest sights.
Ideal Trip Length: 8–10 nights
Can’t-Miss Experiences:
Wandering the cobblestoned lanes of Taormina with Mt. Etna in the background
Wine tasting on Etna’s volcanic slopes
Visiting the baroque jewels of Noto and Ragusa
Taking a private boat day to the Aeolian Islands
Stay here:
Belmond Grand Hotel Timeo, Taormina — old-school glamour with cinematic views
Monaci delle Terre Nere, Etna — a sustainable hideaway among vineyards
Villa Sant’Andrea, Taormina Mare — toes-in-the-sand luxury on a private beach
🌿 Northern Thailand: For the Culture-Curious and Nature Lovers
Perfect for: Adventurous couples, wellness travelers, and anyone craving something authentic but refined.
While much of Thailand heats up in May, the north is lush, green, and blissfully uncrowded. It’s a perfect time to slow down, sip coffee in Chiang Mai’s creative cafés, and let the sound of cicadas replace the city buzz.
Ideal Trip Length: 10–12 nights
Can’t-Miss Experiences:
Temple-hopping and street food tastings in Chiang Mai
Visiting the surreal White Temple (Wat Rong Khun) in Chiang Rai
An ethical elephant encounter at a conservation-focused camp
Massage rituals and jungle views at a secluded mountain spa
Stay here:
Four Seasons Resort Chiang Mai — rice paddies, open-air pavilions, and serenity
Anantara Golden Triangle Elephant Camp — five-star luxury meets wildlife rescue
137 Pillars House, Chiang Mai — historic boutique hotel perfection
🌺 Maui: For the Sun Seekers and Soft Adventurers
Perfect for: Honeymooners, wellness travelers, and families wanting Hawaii’s magic before summer crowds hit.
May in Maui feels calm and golden — trade winds are soft, the ocean is clear for snorkeling, and resorts still have room to breathe. Think morning hikes, lazy beach afternoons, and cocktails at sunset.
Ideal Trip Length: 7–9 nights
Can’t-Miss Experiences:
Road to Hana drive for waterfalls, rainforests, and roadside banana bread
Sunrise (or sunset) at Haleakalā volcano
Snorkeling or sailing along Kāʻanapali Beach
A farm-to-table dinner in Upcountry Maui
Stay here:
Four Seasons Maui at Wailea — polished, peaceful, and effortlessly romantic
Hana-Maui Resort — wild beauty at the end of the Road to Hana
Wailea Beach Resort by Marriott — oceanfront, modern, and great value
✨ Why You’ll Love Traveling in May
🌤️ Perfect weather: Warm, sunny, but not sweltering.
💰 Better pricing: Shoulder-season perks = more luxury for less.
🚫 Fewer crowds: Sightsee without the selfie sticks.
💬 More connection: Locals have time to chat, guides aren’t rushed, and you can actually hear the waves.
Ready to start planning your May getaway?
Whether you’re sipping Nero d’Avola in Sicily, watching elephants roam at sunrise, or chasing waterfalls in Maui — May is the secret season for travelers who know.
Let’s start designing your next escape before the world catches on. 🌸