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Free spirit or meticulous planner? Meet three holiday personality types – and read their top tips | Are You Travel-Ready, Chief Holiday Officer?

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The type of holidaymaker you (and your travel companions) are can have a big impact on the kind of getaways you’ll enjoy. If you’re the type to pore over endless reviews, book everything in advance and use a spreadsheet to tick off every detail, you’ll have a very different experience to the fly-by-the-seat-of-your-pants type of traveller, who prefers to just grab their passport and see where it takes them, carry-on in hand.

Or perhaps you’re more the flexible type, who likes to plan a few things in advance, but leaves space for spontaneous fun? Or maybe you’re the one who breathes a sigh of relief as your super organised friend hands out colour-coded itineraries at the airport?

We gathered together some of the holiday heroes that bring getaways to life to find out how they do it – and to discover some of the clever ways Barclays can help your holiday go even further, whichever group you belong to.

The chief holiday officer

‘I create a visual itinerary for every trip,’ says Sian Downes, 36

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Over the years, I’ve organised girls’ trips, multigenerational family holidays and surprise getaways. As the founder of an events company, I’m a natural organiser. I enjoy finding bargains, and I don’t mind taking on the planning. In fact, I love it.

I wasn’t always like this, but after a few holidays where nothing was planned and we had a terrible time, I realised it’s better to know exactly what you’ll be doing in advance. There’s nothing worse than traipsing around looking for a restaurant when you’re hungry, and when you’re busy with work and family, you want to maximise your holiday time. Being organised is the best way to do that.

My holiday organisation can get a bit extreme, but it’s always worth it – I love looking things up on maps and working out the most affordable way to get around. I generally pay for as much as possible in advance, from accommodation to drinks packages, and put everything on my Barclaycard Rewards card* so I can take advantage of rewards such as cashback, then ask people to pay me back.

I’ll also draw up an illustrated itinerary, so everyone can see our plans at a glance. The first time I presented my husband with one, he didn’t know what to make of it. He’d never seen a holiday itinerary before, but I think it makes a trip special, and it’s a great souvenir, too. I certainly won’t be hanging up my chief holiday officer mantle any time soon!

*Representative 28.9% APR variable. The approval of your application depends on your financial circumstances and borrowing history, so do the terms you may be offered. The interest rates may differ from those shown. T&Cs apply.

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The holiday free spirit

‘I use word of mouth to guide our getaways,’ says Jessica Shaw, 49

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When I was growing up, my mum liked to choose a country, book a place to stay, then see where it would take us. We once went on a package holiday to Egypt, but she still chose to take public transport to the pyramids!

That approach has definitely rubbed off on me. When I go on holiday, I like to let things unfold naturally – I don’t pre-book excursions or restaurants. Luckily, my partner is incredibly laid-back, and all the friends I’ve travelled with have the same spontaneous outlook. Perhaps that’s because my travel style reflects my approach to life in general – my creative training business is all about embracing the power of play, and that naturally seeps into other areas of my life.

It’s certainly led to some memorable moments. During a recent holiday to Greece, we were asked if we wanted to join a snorkelling trip. If we’d had plans, we would have had to say no – but instead, we had the most incredible day swimming in clear blue waters.

The secret to keeping holidays adventurous is to be prepared for any eventuality. I have annual multi-trip insurance, and make sure I take enough money to cover any emergencies. You should also be ready to chat to locals and fellow travellers and ask for their recommendations. I’ve discovered some beautiful places that way, from hidden waterfalls to beaches surrounded by snow-capped mountains. When you exchange stories of your adventures, you never know what you might discover.

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The holiday harmoniser

‘I take a 50-50 approach to holiday planning,’ says Furrah Syed, 57

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I love travelling – with my friends, my husband, or alone – but as time is limited during each trip, I want the best of both worlds, planning some things but also embracing unexpected adventures. I’ll do my research beforehand, and will book tickets in advance if an attraction is very popular. I learned that the hard way, after a visit to Rome – as an artist and educator with a focus on colour, I was desperate to see the Sistine Chapel, but it was impossible as I hadn’t booked.

One of the things I always book is a walking tour. Getting a local’s perspective uncovers places you won’t find online. It also helps you to spot the restaurants filled with locals, which is always a good sign. Another tip is to travel by road wherever possible, as it takes you through so many different landscapes and allows you to see people’s day-to-day lives. You don’t get that on a plane.

When I’m budgeting for my holiday, I always keep some money aside for spontaneous adventures – the last thing I want is to come home regretting not being able to do something unexpected. I’d say my approach overall is 50% planned and 50% go-with-the-flow, and that works really well for me.

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17 Best Airbnbs for Enjoying Fall Foliage, From Vermont to Colorado

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Bed & bath: 4 bedrooms, 2 bathrooms
Top amenities: Hotel-grade Endy mattresses, sauna, wraparound deck and patio with a grill, parking for six-plus cars

Raw forest surrounds this super-size (sleeping 10 people) waterfront cabin in Ontario. Located 30 feet from the shore of Thirty Island Lake, fall guests get spectacular views of not only the dazzling canopy of gold, orange, and red leaves—but also their blurred, kaleidoscopic reflection on the water’s surface. And if you want even more of the beauty, you can take in these sights from the center of the lake itself—just hop in one of the watercrafts—a kayak, canoe, or stand-up paddleboard—from the private dock. Walk into the house, and you’ll quickly realize that despite the rustic setting, you won’t be roughing it. Hotel-worthy amenities abound: a completely stocked kitchen with an array of spices, a sauna, and Pendleton blankets in the bedrooms are just a few of them. (Take a look at our list of the best Airbnbs in Ontario within driving distance of Toronto for more options.)



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The Best Time to Cruise Alaska 2024: A Month-by-Month Guide

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Celebrity Cruises’ Celebrity Edge sets sail for its second season in Alaska this year.

Michel Verdure/Courtesy Celebrity Cruises

April and May

If your schedule allows, not only does sailing Alaska in April and May afford the possibilities of glimpsing the Northern Lights and seeing wildlife emerge from their winter hibernation, it’s a more affordable and less crowded time to cruise, too. April and May are also the driest months in Alaska, so the chances of rain are slim.

Smaller ships like those that comprise Alaska Dream Cruises’ and UnCruise Adventures’ fleets can maneuver closer to the coastline for better views of bears rambling along the beaches and on-land excursions without another soul around. Alaska Dream Cruises added two new eight-day itineraries this season, both of which focus on remote wilderness, hiking, kayaking and wildlife viewing. UnCruise also has a new itinerary this year, a 10-night Aleutian Islands Adventure with Dutch Harbor and Kodiak itinerary.

June to August

Warmer temperatures, an average of 17 hours of daylight, and school vacations all make Alaska a popular destination for cruising in June, July, and August. Expect crowded ports and more ships out on the water, but that’s not to say it’s not a good time to set sail: bears are still active, as are whales and native bird life.

Oceania Cruises’ 1,250-guest Riviera sets sail to Alaska for the first time this season with itineraries ranging from 7 to 12 days through September, including a 10-day voyage roundtrip from Seattle. American Cruise Lines doubles its Alaskan offerings this year with five itineraries, including two new 16- and 19-day Alaska National Parks cruises. For a shorter option, check out the 9-Day Southeast Alaska Cruise, roundtrip from Juneau.

September

Not only is school back in session in September, which means fewer crowds at ports, but the chances of seeing the Northern Lights return, especially if combining your cruise with a land tour that takes you further north into Alaska. Fall is also mating season for wildlife, so expect to see some friskiness.

In partnership with Lindblad Expeditions, National Geographic Expeditions’ new 11-day Voyage to the Great Bear Rainforest travels from Ketchikan to Seattle with plenty of adventure in between, including seeking out the spirit bear (a subspecies of American black bear also known as a Kermode bear). Celebrity Cruises’ Celebrity Edge is sailing her second season in Alaska, offering seven-night Alaska Dawes Glacier itineraries in September, either roundtrip from Seattle, or one-way from Seattle to Vancouver, British Columbia. For a longer cruise-tour option, take a look at one of Princess Cruise Line’s new offerings highlighting the National Parks, like the National Parks Expedition that visits five parks over the course of 15 days.

October

The Alaska cruise season winds down in October, with only a few ships setting sail. Just as in April and May, you’ll likely have the water to yourself, and even fewer people in the ports you call upon. Along with cooler weather, you’ll also find lower fares that will please your bank account. Holland America Line, Princess Cruises, and Royal Caribbean International all sail in Alaska into the fall, but Norwegian Cruise Line is the last to set sail in the state with seven-day itineraries roundtrip from Seattle.

2026 and beyond

Though we’re in the midst of the 2025 sailing season, if you’re looking to plan ahead for 2026 and even 2027, there’s even more from which to choose. For example, in May 2026 Princess Cruises’ newest ship, Star Princess, will sail roundtrip from Seattle to the Inside Passage. And for the first time, family favorite Disney Cruise Line will have two ships in Alaska in 2026 when Disney Magic joins Disney Wonder to offers 35 seven-night itineraries over the summer. Holland America Line, which has sailed in Alaska for more than 75 years, is debuting its new 14-day Great Alaska Explorer in 2026. Itinerary highlights include Anchorage, Juneau, Ketchikan, Kodiak, Valdez, and Prince Rupert, not to mention Glacier Bay scenic cruising.

A handful of cruise lines are sailing to Alaska for the first time in 2026, with another making a return to the Far North. MSC Cruises embarks upon its inaugural Alaska cruise season in May 2026 when MSC Poesia sets sail on seven-night itineraries roundtrip from Seattle. Another newcomer is The Ritz-Carlton Yacht Collection with Luminara setting sail on seven- to 11-night itineraries, including the seven-night roundtrip voyage from Vancouver. And Virgin Voyages will embark upon seven- to 12-night itineraries aboard Brilliant Lady, like the Alaskan Glacier Blues & Coastal Views sailing. Azamara Cruises returns to Alaska when Azamara Pursuit sets out on its 10- and 11-night itineraries with new immersive cruise-tours for those who can linger longer.

Looking further ahead to 2027, Explora Journeys embarks on its first cruises in Alaska from Vancouver, Canada, on board Explora III. Her inaugural voyage will be an 11-night “Journey Through Untamed Landscapes & Coastal Treasures” in May.



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In the Faroe Islands, Nature Rewards Patience

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As the Faroes become increasingly popular with international travelers—a trickle of visitors has turned into more of a cascade in recent years, particularly since 2023—there is a greater need for creatively expanding infrastructure, while prioritizing the needs and lifestyle of locals. The Faroese are essentially asking themselves: How can we invite visitors into the home we love, without losing what we love about it?

I hoped to find out. In April, my husband and I flew into the airport on Vágar, the third-largest island, with a plan to drive to the Northern Isles before slowly making our way back through Eysturoy and Streymoy. It was a route that would allow us to also travel through those undersea tunnels, while also being conscious of the number of pricey tolls we’d rack up from using them. We hoped to also tap into the Faroese rhythm of daily life. What would it mean to take cues from the people who know these wild landscapes best?

On our first day, we beelined for the Visit North tourism office in Klaksvík, a small city of brightly colored houses on a spit of land between the open ocean and a sheltered bay of fishing boats. Reni Heimustovu, who staffs the front desk, smiled when we asked about hiking that day. “Last time someone wanted to go hiking in weather like this, we told them, ‘Choose life!’” she laughed knowingly. Outside, the long grass was blown flat on the surrounding mountains.

And so we learned our first lessons of traveling in the Faroes: One must always be adaptable.

We climbed back into the car, and ditched the hike, instead driving along a muddy road toward Klakkur Viewpoint, below which the sea yawned expansively. In scenic, rural parts of the islands, which describes just about everywhere in the Faroes, a source of tension with rising tourist numbers has come from the fact that visitors aren’t always prepared for sheep on the road. There are so many of the animals here, that in 2016, locals used their ovine population to map areas not yet canvassed by Google Maps’ cars; famously, the Faroes have more sheep than people, and their wavy wool provides a living for many locals. New signage on roads like these gently reminds visitors which grazing lands are off limits to hiking and sightseeing: the sheep have the right of way.

Sheep, whose wooly coats provide a living for many locals, outnumber people on the Faroes—and road trippers are reminded that the animals retain the right of way.

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