Planning a holiday is an irrevocably exciting pursuit, but one which quickly gives way to frustration, vexation, and the potential for popping a vein. Between corralling friends and family to agree on a departure date, canvassing accommodation options for the right combination of modern conveniences, and planning an itinerary that suits everyone, it’s easy to see why we default to the same old sun-and-sea destinations year on year.

But there’s a wider world to explore than the closed resorts of the Costa Del Sol. Planning your next holiday needn’t be the difficult affair it often promises to be; it can be exciting again, provided you sharpen up on the destinations you ought to be looking at. Here, we’ll be doing just that: introducing you to a variety of destinations known for being easy to organise a holiday around, making them ideal for travellers who want a smooth, stress-free experience from the start.

Why Some Destinations Are Easier to Plan Than Others

But what makes one destination an easier place to plan a holiday around than another? In a word: infrastructure. So many holiday trips take a lot of planning to organise due to the sheer volume of activities to complete in a short period of time. If one is not willing to compromise on the content of their holiday, they might then look to minimise travel time by looking for destinations that offer excellent transport links, or minimal distances between landmarks. Case in point: Orlando.

Orlando: A Well-Organised Holiday From Start to Finish

Orlando, Florida is the de facto Resort Town of America. Though a sprawling, populous city right in the epicentre of the state, Orlando is also a hugely dense experience, particularly for families. This is with thanks to the huge variety of family friendly attractions, from Universal Orlando Resort to Walt Disney World Resort to SeaWorld to Legoland – and beyond. 

Orlando holidays are jam-packed with opportunity, and supremely easy to plan out, whether or not you go for a package holiday. Everything’s on your doorstep, and nothing can be left to chance.

Amsterdam: Compact, Walkable and Well Connected

If you’re travelling yourself, or with friends, then you may not be in the mood for happy-go-lucky amusement-park vibes. For an altogether more cultural easy-to-plan holiday experience, there’s no better destination than Amsterdam.

Amsterdam is a compact urban centre, with landmarks, local culture and nightlife all encroaching on one another in the most intoxicatingly maximalist of ways. And yet there’s a calm to the city, lent by its museums, botanical gardens, endless cycle infrastructure and quietening stone architecture. This city is a delight to be in, and you’re only ever a 20-minute walk from the next thing.

Barcelona: Easy Transport and Flexible Accommodation

Finally, and if sun-and-sea holidaymaking is an absolute non-negotiable with you, there is Barcelona. The be-all and end-all of Spanish getaways. A coastal city with so much more going for it than its stunning beaches – from which you are only ever a short walk, or short hop on public transport. You could do all the major landmarks, from Parc Guell to La Sagrada Familia, in one day if you wanted to. You won’t, though.