Best Four Cities for Family Travel in May

3
Minute Read
April 24, 2025
Travel Tips

May is the sweet spot for family vacations—just before the summer crowds hit, but warm enough to explore without jackets in tow. Whether you're planning a surprise vacation, looking for cheap flights this weekend, or simply want to create an itinerary the whole family will enjoy, we’ve got you covered. Using a travel itinerary planner like iMean can make your trip smoother, more fun, and even more budget-friendly. Here are four of the best cities for family travel in May—plus how to organize a trip that ticks every box.

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1.Barcelona, Spain

Why it’s great for families: Parks, beaches, history, and churros!

Best for: Multi-generational fun

Barcelona offers a vibrant mix of culture and relaxation that appeals to all ages. Stroll through Park Güell, explore the narrow alleys of the Gothic Quarter, or hit the beach for a sandy afternoon. The weather in May is perfect for outdoor activities—sunny, but not scorching.

How to plan a trip to Europe with iMean:

With iMean’s itinerary  website, you can easily create an itinerary that balances sightseeing with downtime. The itinerary builder lets you plug in multiple destinations, so if you want to squeeze in a quick trip to nearby Sitges or Tarragona, you can do that without breaking a sweat. Looking for cheap flights to no destination? Let iMean suggest affordable entry points to Europe and build from there.

2.Kyoto, Japan

Why it’s great for families: Culture meets calm

Best for: Families who love nature and tradition

In May, Kyoto’s gardens and temples are in full bloom, minus the cherry blossom crowds. Kids will love feeding monkeys in Iwatayama Monkey Park, while adults can enjoy the serenity of Zen gardens and historic tea houses.

How iMean helps: Finding multi-city flights to include Tokyo and Osaka? No problem. iMean’s travel planner simplifies flight searches so you can choose the best flight time based on your family’s routine (nap schedules included). From luxury ryokans to family-friendly hotels with onsen baths, iMean's hotel search engine filters by real geographic locations and amenities that actually matter—like bathtubs and extra beds.

3.Vancouver, Canada

Why it’s great for families: Nature in the city

Best for: Outdoor-loving families

Vancouver is the perfect mix of city and wilderness. From biking the seawall to whale watching, there's no shortage of adventures. May brings mild weather and blooming cherry trees—plus it’s still early enough to find cheap flights this weekend if you’re booking last-minute.

How to organize a trip with iMean:

iMean’s AI allows you to plan your trip flexibly. So if the kids want to stay longer at the Vancouver Aquarium or your partner wants to sneak in a brewery visit – it’s easy! You can adjust your vacation plans at any time.

4.Lisbon, Portugal

Why it’s great for families: Charm, history, and cable cars!

Best for: Budget-conscious travelers

Lisbon’s colorful trams, tiled buildings, and easy pace make it a delight for families. Enjoy egg tarts in Alfama, ride a tuk-tuk to São Jorge Castle, or take a day trip to fairy-tale Sintra. May temperatures are perfect for exploring without overheating.

Plan your vacation with iMean: With iMean, you can quickly book flights, find cheap flights to anywhere this weekend, and secure accommodations in neighborhoods with family-friendly cafés and walkable streets. Whether you're after business class flights or budget options, iMean tailors options to your needs without overwhelming you with irrelevant choices.

Final Tip: Keep It Flexible

Planning a family trip doesn't have to be stressful. iMean works like your personal holiday travel planner, helping you make confident decisions—from finding cheap flight features to selecting the best travel app for your needs. Whether you’re heading to Europe or staying closer to home, use the itinerary planning template to organize your days while still leaving room for surprise gelato stops and impromptu beach detours.

So go ahead—book flights, pack the snacks, and let iMean take care of the rest.

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