Best Holiday Destinations in May for Your Next

In my 15 years leading teams and managing business cycles, one thing I’ve learned is that good timing changes everything – in business and in travel.

May offers that perfect intersection: lower crowds, moderate prices, and sunny optimism before the high-season rush.

From European escapes to UK staycations, the best holiday destinations in May can renew your outlook and creativity for the months ahead.

Santorini, Greece

Back in 2018, everyone was talking about summer getaways to Mykonos, but Santorini quietly held its charm for those who arrived early in May. The weather hovers comfortably around 23°C, and the island’s iconic white villas bask in gentle sunlight.

I once worked with a client who planned an off-season retreat here, and the clarity they found—both in thought and in the air—was unmatched. The pace slows, service quality rises, and local hospitality feels more authentic than during the crowded months.

Amalfi Coast, Italy

We tried doing business retreats in August once, and it backfired because the Amalfi Coast is packed and expensive that time of year. In contrast, May provides that sweet spot: lush lemon groves, mild seas, and space to breathe.

Positano and Ravello sparkle under the spring sun while you enjoy that unmistakable Italian rhythm. The reality is, when travel feels effortless, ideas flow. For creative professionals or leaders seeking perspective, Amalfi in May offers restorative calm with professional-grade inspiration.

Scottish Highlands, UK

Sometimes, the best holiday destinations in May aren’t abroad at all. The Scottish Highlands transform in spring, and the landscapes rival any postcard-perfect European scene. During the last downturn, when international travel felt uncertain, I chose a Highlands retreat instead.

We held strategy sessions overlooking Loch Lomond, mixing mindfulness with productivity. The payoff? Sharper thinking and genuine connection among our team. May’s long daylight hours and crisp air provide the focus you didn’t know you needed.

Algarve, Portugal

Here’s what nobody talks about: business leaders need downtime that truly disconnects them. The Algarve in May delivers that balance—sun-drenched beaches, affordable stays, and genuinely slower living. I’ve seen this play out when teams return from Portugal more creative and laser-focused. The water’s warm enough for morning swims, yet the beaches remain uncrowded. From a practical standpoint, it’s one of the best-value luxury destinations near the UK. May’s moderate warmth sits perfectly between spring chill and summer heat.

Cornwall, England

Cornwall used to be the underrated gem of domestic breaks, but now it’s reclaiming its prestige. Locals prepare for peak season, yet May still feels personal—you can chat with artisans, sample coastal kitchens, and watch surfers at sunset without the overwhelm.

I once advised a client who chose Cornwall for a team retreat, and their post-trip ROI was intangible but evident: refreshed minds, better ideas, happier people. The bottom line is, you don’t always need to fly to feel worlds away.

Conclusion

The best holiday destinations in May let you reconnect with purpose, creativity, and life beyond work pressures. Whether you’re walking through Santorini’s alleys or hiking Glen Coe, these early-summer getaways mirror what business leaders crave—clarity, perspective, and renewal. The data tells us time off improves performance; but personal experience confirms May is when that magic truly happens.

What makes May ideal for travel?

May offers great weather, fewer tourists, and better deals before the summer rush. For UK travellers, it’s the perfect mix of comfort and calm.

Is Europe affordable in May?

Yes, many destinations in Europe see lower accommodation and flight prices in May, giving you premium experiences at mid-range rates.

Which UK spots shine in May?

Cornwall, the Lake District, and the Scottish Highlands are fantastic in May—lush scenery, long daylight, and comfortable temperatures.

What are the best beach destinations in May?

Portugal’s Algarve and Greece’s islands top the list. Waters warm up, yet beaches stay pleasantly uncrowded before high season hits.

Is May good for family holidays?

Absolutely. Schools in the UK still operate, which means quieter resorts and family-friendly packages that stretch your budget further.

Should professionals plan breaks in May?

From experience, yes. Travel in May recharges energy before mid-year targets intensify, helping leaders return with clarity and focus.

How is the weather in Europe in May?

Expect temperatures between 20–25°C across southern Europe, ideal for exploration without the exhaustion of full summer heat.

What’s the best short-haul trip from the UK?

Spain and Portugal offer quick connections, affordable flights, and just the right blend of sunshine and cultural richness.

How do May holidays affect productivity?

Leaders returning from May breaks often report better focus and creativity. It’s an investment in well-being that drives performance.

Are UK staycations worth it in May?

Yes, May’s mild weather and blooming landscapes make UK destinations both cost-effective and rejuvenating without travel hassle.