May always sneaks up,  First name / friend? One minute you’re debating whether to pack away the winter coats, and the next you’re knee-deep in Mother’s Day brunch reservations, graduation ceremonies, and the sudden realization that summer is basically here️. Guess what, it is. 

 

That’s why May can be a tricky month for travel: it sits right on the edge of busy season. Flights fill, hotels sell out, and the “we’ll figure it out later” approach usually ends with sky-high prices and slim pickings.  I have been booking May for the past 2 months, you are close to being late. 

 

The travelers who think ahead? They get the good stuff: the villa with the sea view, the best safari lodge, the hot spot before it triples in cost come July.

 

 

 Sicily: Snag boutique stays before summer crowds take over

 Maui: Lock in flights and resorts ahead of the summer surge
 Zambia: Secure prime safari camps as dry season demand builds
 

The start of busy season doesn’t have to mean stress—it just means it’s time to get moving! 

 

So, where am I sending you in May? ✈︎

Sicily in May is the Italy you dream about — sunny piazzas, seaside towns, and long lunches without the midsummer chaos. The island balances history, culture, and  beauty, and May is warm but not scorching.

 

 Perfect for: Couples chasing romance with a side of history, or foodies who want to ruin “regular” pasta forever.

 

️ How long to stay: 7–10 days so you can both sides of the island. You will want to see it all.

 

Can’t miss: Exploring Mount Etna — trek the lava fields, take in the panoramas, and sip the wines grown in the mountain’s volcanic soil.

Maui in May is  magic — lush waterfalls, golden beaches, and that sweet spot between spring and summer when the island feels wide open. It’s equal parts adventure and pure relaxation.

 

 Perfect for: Beach lovers who also want epic hikes, road trips, and spa days with mai tais at sunset.

️ How long to stay: 6–8 days so you can conquer the Road to Hana and still leave time for poolside lounging in Wailea.

 Can’t miss: Sunrise at Haleakalā followed by a downhill bike ride through the clouds. Yes, it’s as epic as it sounds.

Zambia in May is shoulder season safari at its finest — wildlife everywhere, fewer tourists, and the thrill of adventure that feels a little off the beaten path. With the dry season beginning, game drives and walking safaris are at their absolute best.

 

 Perfect for: Adventurers, wildlife junkies, and anyone who wants bragging rights for skipping the Serengeti.

️ How long to stay: 9-11 days, split between South Luangwa for the walking safaris and the Zambezi River for those golden-hour boat rides.

 Can’t miss: A bush walk with an expert guide (Zambia invented the experience) and a helicopter ride over Victoria Falls

May travel could look like twirling pasta in Sicily, spotting elephants in Zambia,  or chasing sunrises in Maui.

 

The only decision you have to make? Which trip has your name on it. 

 

P.S. Can’t decide? That’s the perk of having me!  I’ll help you match your vibe to the right destination.