What To Plan Now: Looking Ahead to May 2026
May always sneaks up, doesn’t it? 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, Memorial Day BBQ planning, and the sudden realization that summer is basically here ☀️
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.
The travelers who think ahead? They get the good stuff: the villa with the sea view, the safari lodge with the best guide, the island inn before it triples in cost come July.
Here’s what’s waiting if you plan now for May 2026:
🍝 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
🚲 Nantucket: Book ferries and inns before Memorial Day peak pricing sets in
The start of thebusy season doesn’t have to mean stress—it just means it’s time to get serious about planning.
So, where are we sending you in May? ✈︎
Sicily, Italy
THE EUROPE PICK
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 coastal 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’re not choosing between seaside villages, vineyards, or the bustling energy of Palermo — you’ll want them all.
✨ Can’t miss: Exploring Mount Etna — trek the lava fields, take in smoky panoramas, and sip wines grown in the mountain’s rich volcanic soil.
Maui, Hawaii
THE SUN & SAND PICK
Maui in May is pure 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
THE FAR FLUNG PICK
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: 7–9 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 when it’s at its most powerful.
Nantucket, Massachusetts
THE CLOSE TO HOME PICK
Nantucket in May feels like you’ve beat the system — all the cobblestones, lobster rolls, and sea breezes, none (okay, almost none) of the summer chaos. It’s chic coastal living before Memorial Day ruins the secret.
🫶 Perfect for: Couples, weekenders, and anyone who loves New England charm (bonus points if you pack a striped sweater).
🗓️ How long to stay: 3–4 nights — enough to bike to Sconset, browse the boutiques, and claim bragging rights for “beating the crowds.”
✨ Can’t miss: A dockside lobster roll with no wait. Come June, that line will test your patience.
Book With An Advisor
May travel could look like twirling pasta in Sicily, spotting elephants in Zambia, biking the cobblestones of Nantucket, or chasing sunrises in Maui.
The only decision you have to make? Which adventure has your name on it. Comment and tell me your pick for May 2026 ✈️
🤔 P.S. Can’t decide? That’s the perk of having a travel advisor in your corner. I’ll help you match your vibe to the right destination — no second guessing required.
