Your Caledonian Travel Calendar for 2026

Most of us don’t plan a whole year of holidays in one go. But what we do like is knowing there are a few decent breaks dotted through the months, and things to look forward to. Dates that stand out, and plenty of places we wouldn’t mind heading to for a few days.

That’s how 2026 can unfold. Not all at once, but steadily.

Here at Caledonian Travel HQ, we’ve sat down and had a look at the largest number of breaks and holidays we’ve ever offered in a single year, and pulled out some highlights for the 2026 calendar. How do some of these take your fancy?

January to March

The start of the year is about getting back into your normal routine (and it doesn’t take long, does it!). But those early breaks usually have a clear reason behind them…

London theatre trips are a brilliant option for your first trip of the year. A show like ABBA Voyage, Paddington or Les Misérables means your 2026 is set on the stage, with time around it for food, wandering the city, and doing things at a calmer pace than you would on a rushed weekend.

Starlight Express, anyone?

We’ve also got a huge range of hotel breaks where evenings take the lead. Tribute shows featuring Elvis, Tom Jones or Adele bring people together after dinner, with plenty of chat before and after the performance. By the second night, faces become familiar and conversations carry on at breakfast. People settle into the break quickly, and can stay toasty indoors while the temperatures are still warming up.

April to May

As we move into spring and the brighter days arrive, holidays start to feel a bit broader. Some people want to get outside more, others are happy just being somewhere that feels lighter and less wintry.

Our Magic of Steam Train trips, including journeys on the Embsay Railway, are a really popular choice around this time of year. The train isn’t just transport, it’s part of a day that moves through countryside beginning to change.

With afternoon tea or Sunday lunch sometimes included, and plenty of scenery to look at and take it all in, it’s a lovely way to spend time away with people who matter to you.

Coastal towns like Llandudno and Torquay come back into focus too. Seafront walks, benches facing the water, cafés that are busy without being hectic. Days tend to unfold without much planning. Just going with the flow.

Spring also brings some major events our way. The Chelsea Flower Show draws people who enjoy seeing how gardens are put together, from large statement designs to smaller plots you could imagine at home. Moving between gardens, talking to growers, and picking up ideas that stick long after the visit is all part of the experience.

June

By June, plans are usually tied to dates rather than ideas. We do a lot of specialised music concert trips, but live music breaks in Scarborough at its Open Air Theatre sit firmly in the June to July calendar, with artists like Rick Astley and Billy Ocean giving people a reason to go.

Days are spent around the hotel, the town or the seafront, with the evening pulling everyone back in for the music. The concert might be the focal point, but the town gives the break even more.

June also sees people heading north to places like Arrochar, near Loch Lomond. Lochs, hills and open space set the pace here. Walks don’t need to be long. Views do most of the work, and time stretches out in a different way.

July and August

Things start hotting up in summer, when longer breaks come into play. Seaside towns are a huge favourite, each with their own bit of individuality that makes the place unique.

Blackpool is busy, bright and full of movement. Shows, lights and the constant sense of something going on make this one of our most exciting and popular destinations for Caledonian Travel customers. Evenings tend to be lively, with plenty of people around and plenty to talk about afterwards.

Scarborough offers a slightly different rhythm. More space, longer walks, and days that can be as full or as quiet as you want them to be. There’s a brilliant North and South Bay, as well as must-visit spots like Peasholm Park.

August brings football back onto the calendar. Breaks built around Manchester City matches or England Lionesses games have the fixture at their centre, with everything else arranged around it, including time in nearby cities or spare time in the town the match is played in.

The fun starts early on the coach and carries on long after the final whistle.

There are also big sporting weekends like Rugby League events, where matchday sits in the middle of the trip and the rest of the time fills in around it.

September to October

Once summer begins to fade, breaks slow down again. Coastal towns ease off, and scenic areas come into their own.

Llandudno, Torquay and Arrochar are all places people love to return to during these months. Days are unhurried. Walks are easier. There’s more time to sit, talk and enjoy being away without feeling pulled in different directions.

Many familiar faces travel again during this part of the year, and there’s a sense of picking up where the last break left off.

And let’s not forget the autumn colours you’ll see in places like the Lake District and across the Yorkshire Dales.

November to December

As the year draws to a close, atmosphere matters more than activity. Christmas market trips in cities like Liverpool and Birmingham bring lights, food stalls and busy streets, balanced by relaxed evenings back at the hotel.

Days are spent wandering the markets together, evenings spent eating, talking and enjoying the build-up to the festive season. It’s a comfortable way to end the year, without everything hinging on Christmas Day itself.

Sticking with the seasonal theme, The Polar Express is a lovely way to wind down the year with family or friends, a cup of hot chocolate in hand, and that sense of excitement as Christmas approaches.

Looked at this way, the year doesn’t feel daunting. Just a run of breaks that fall naturally into the months, giving you something to look forward to as the year goes on.

And with us, once your break is chosen, the rest is taken care of. Your holiday begins when you board the coach and say hello to the driver, with local departure points, reserved seating and everything organised in one booking.

You settle in, get chatting, and let your holiday take its course.

That’s how a good holiday year comes together. With Breaks to Make You Smile.