The Americas
From Canada’s prairies and the Pacific Northwest to New England, California, Mexico, Costa Rica and the Chilean Lake District.
★★★★★ Rated 4.5 out of 5
The same place can be perfect in May and miserable in August. Choosing where to go around when you can travel is what stops a trip that looks brilliant on paper from falling flat.
By this point in planning, your options should already be narrowing. You know who you’re travelling with, what type of holiday you want and when you can realistically go. The next step is to match those choices to places that are actually at their best during your travel window.
This is Stage 4 of our Platinum Travel Planning Roadmap, and it’s where the question stops being “where do I want to go?” and becomes “where makes the most sense right now?”. That small change makes a big difference to how the trip turns out.
Quick answer: Where to go when means choosing a destination for the time you can travel, rather than the other way round. Decide who’s going, what kind of trip you want and when you can go, then look for places at their best in that window. Europe’s cities shine in spring and autumn, the Mediterranean in summer, and the Middle East, the Caribbean and the southern hemisphere in the UK winter.
The where to go when idea is simple. You choose destinations based on the best time of year to visit them, whether that’s for good weather, fewer crowds or something special happening locally. It helps you avoid being washed out by rain, or travelling when it’s too hot, too busy or too expensive for you.
Take a winter holiday where you’re hoping for some sun and a few activities, with teenagers in tow. From the UK, the Canary Islands give you warmer days, fewer crowds and short flights, which is ideal when annual leave is limited. Mexico or Florida offer reliable winter sun, with longer flights and a real trade-off in time on the ground. Australia and South Africa are options too, but it’ll be their peak summer, which means hotter days, higher prices and busier places.
Same trip, four very different experiences, depending on where you go. Thinking about where to go when, rather than just where to go, is what stops you booking a holiday that underdelivers.
It surprises people that destination isn’t the first thing we decide. ABTA’s Holiday Habits report for 2025 to 2026 found that destination is the biggest single factor in UK holiday booking decisions, with 45% of people ranking it first, ahead of cost (33%) and dates (12%). We agree it’s the heart of the planning. We just don’t think it should come first.
Pick a destination before anything else and you can spend the rest of the planning process fighting it. The flights don’t suit the school holidays, the weather is wrong for the kind of trip your group wants, or one person’s needs make it hard work. Over the years, with a family of five, a severe nut allergy and a changing mix of who’s actually coming, we’ve found that the order of the decisions matters more than the decisions themselves.
So by the time we get to the where, we already know the who, the what and the when. The list of places that fit is much shorter, and much easier to choose from.
Choosing a destination doesn’t have to be a chore. These are the steps we follow before we book anything.
Sometimes it works the other way round. You might have one place in mind, such as seeing the tulips in bloom in the Netherlands, and build the whole trip around it. That’s fine too. At least the goal is clear, and you can work backwards from it, fixing the dates first and fitting everything else around them.
If you’re still looking for ideas, our travel inspiration pages are a good place to start.
The best time to visit anywhere depends on what you’re looking for. These are the places we’d look at in each season from the UK. Big regions vary a lot inside themselves, so treat this as a starting point and check each country’s climate on its own.
Spring is a lovely time for European cities, before the summer crowds arrive. Amsterdam, Berlin and Hamburg are all good choices, and spring is when the tulips flower in the Netherlands. Further afield, California’s clear skies around Easter are perfect for a drive like our Pacific Coast Highway road trip, and spring is a good time for Costa Rica, though it’s rewarding at other times of year too. In Australia, Perth and the south west of Western Australia are at their best around Easter, a good time to find out whether Perth is worth visiting.
In Europe, summer is the time for the Mediterranean beaches and islands, such as a week in Ibiza or island hopping in Greece. Canada is at its best in July and August, when you can make the most of the outdoor activities and wildlife spotting. Our Pacific Northwest road trip crosses into British Columbia if you want ideas. In Australia, the northern coast from Perth up to Broome and the Kimberley, and Uluru in the centre, are better over the UK summer months. Closer to home, August is festival month in Edinburgh, and our Edinburgh Festival planning guide helps you plan for it.
Autumn brings the European city break season round again, with cooler days and quieter streets. It’s also the season for autumn colour in North America, from Virginia to New England, where our New England fall road trip follows the leaves, and October is a fun time to take a day trip to Salem from Boston.
Winter is the time for cosy Christmas markets, in York or Vienna, or skiing in the Alps. It’s also when the far north comes into its own, and our Tromso winter city break guide covers the northern lights season. For winter sun, the Middle East, such as Oman and Dubai, is best visited roughly between November and March, when it isn’t too hot. Florida, the Caribbean and Mexico’s Riviera Maya are reliable winter sun choices too.
Oceania’s reversed seasons make it a top choice for a warm getaway in the UK’s colder months, but it isn’t a simple swap. Tasmania and New Zealand are further south, so they’re better visited earlier in the year if you can.
Every place we’ve written about sits under one of five continent pages, with the countries and our guides beneath them. We’re adding to them all the time, so it’s worth checking back.
From Canada’s prairies and the Pacific Northwest to New England, California, Mexico, Costa Rica and the Chilean Lake District.
City breaks, villas and road trips, from Venice and Rome to Seville, Berlin, Vienna, Croatia and the Arctic north of Norway, much of it easy to reach by train.
Desert road trips in Oman, old and new Dubai, Georgia’s mountains and wine, and Hong Kong and Macau.
Western Australia, Adelaide, the Limestone Coast and the Great Ocean Road, with Rapa Nui for the most remote trip of all.
England, Scotland and Northern Ireland, from Yorkshire’s walks and wonders to the Hebrides, Cornwall and the Causeway coast.
It means choosing a destination based on the time of year you can travel, so you arrive when the place is at its best. Good weather is part of it, but so are crowds, prices and local events. It’s the opposite of choosing a place first and then hoping the timing works.
The Canary Islands are the closest reliable winter sun, with short flights. The Middle East, including Oman and the UAE, is warm and settled from roughly November to March. Further away, Florida, the Caribbean and Mexico are good choices, and Australia and South Africa are in their summer, though that means peak prices there.
For cities, spring and autumn are usually best, with comfortable temperatures and fewer crowds. Summer suits the Mediterranean beaches and islands. Winter is the season for Christmas markets, skiing and the northern lights in the far north.
Start with who’s going and what kind of holiday you all want, then fix the dates you can travel. Make a short list of places that are at their best in that window, check them against anyone’s specific needs, such as a food allergy, and compare the cost of getting there before you decide.
If your dates are fixed, for example by school holidays, choose the dates first and find a destination that suits them. If there’s one place you’ve always wanted to see at a particular time, such as the tulips in spring, start with the place and plan the dates around it.
Some of our best trips came from asking where makes sense right now, rather than where we'd always wanted to go. Winter sun on the Riviera Maya, Vienna in winter, the Arctic dark in Tromso. The timing made those trips as much as the places did.
Once you have a short list of places that suit your window, it's time to work out what the trip will cost and how to make it happen. That's Stage 5 of the Roadmap, budget and ways to save.
Happy exploring, whenever you can go.