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James O’Leary - Travel Counsellors Travel. Tailored by a human. I plan travel full-time, so you don’t have to.

The Caribbean island I’d choose for something quieterI’d choose Grenada.It doesn’t have the same big-resort feel as some...
05/10/2026

The Caribbean island I’d choose for something quieter

I’d choose Grenada.

It doesn’t have the same big-resort feel as some of the better-known Caribbean islands, and that’s exactly why I like it.

You still have beautiful beaches and some excellent hotels, but there’s much more of a sense of being on an island rather than simply staying in a Caribbean resort.

I’d spend time around Grand Anse, but I’d also get out and explore.

Rainforest.

Waterfalls.

Spice plantations.

Small towns and fishing villages.

And plenty of places where you can stop for lunch without everything feeling particularly polished or manufactured for tourists.

It’s not the Caribbean island I’d choose if I wanted endless nightlife or a huge choice of resorts.

But if someone said to me, “I want somewhere beautiful, but I’d really like it to feel peaceful…”

Grenada would be one of the first places I’d look.

⸻

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Call / WhatsApp: +44 207 112 8135

Why I’d spend two nights in the W**elands instead of doing a day tripYou can visit the Cape W**elands from Cape Town for...
04/10/2026

Why I’d spend two nights in the W**elands instead of doing a day trip

You can visit the Cape W**elands from Cape Town for the day.

But I wouldn’t.

I’d stay for at least two nights.

Because places like Franschhoek and Stellenbosch aren’t somewhere I’d want to race around ticking off vineyards before driving back to the city.

I’d want a long lunch at a w**e estate.

A tasting without watching the clock.

Time to wander around Franschhoek.

Dinner somewhere brilliant that evening.

Then wake up surrounded by mountains and vineyards rather than heading straight back into sightseeing mode.

Two nights also gives you the freedom to choose a beautiful W**elands hotel and actually enjoy it.

And if you’re in Franschhoek, you’ve got the W**e Tram as another way to explore without worrying about who’s driving.

Cape Town and the W**elands are close enough to combine easily.

But they’re different enough that I think they deserve to be treated as two separate parts of the holiday.

For me, that’s much better than squeezing the W**elands into a day trip.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

**elands

03/10/2026

Wow. 50 today! To all those that have dressed me over the years, a big thank you from me. Be that when I wasn’t allowed to have my own sense of fashion, and to my partner in crime of the past 18.5 years who has countless times had to dress and undress when I was too drunk to care. Thank you, one and all ❤️ #50

The hotel room location I’d ask for – and the one I’d avoidTwo rooms can be exactly the same category and still give you...
03/10/2026

The hotel room location I’d ask for – and the one I’d avoid

Two rooms can be exactly the same category and still give you a very different stay.

If I had the choice, I’d usually ask for a room away from the lifts and main thoroughfares.

Ideally, somewhere quieter with less foot traffic outside the door.

And the location I’d be particularly wary of?

A room directly underneath a rooftop bar, restaurant or entertainment area.

The hotel might look wonderfully peaceful in the photographs, but chairs being moved around above you at midnight can quickly change that.

I’d also check what’s outside the room.

A “garden view” beside the evening entertainment isn’t necessarily peaceful.

A ground-floor room next to the main pool might be incredibly convenient for a family, but completely wrong for a couple wanting quiet.

That’s why I don’t just look at the room category when I’m comparing hotels.

Sometimes where the room is within the hotel matters just as much as what’s inside it.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

Destination Comparison: Marrakech or Dubai?Both work brilliantly when you want warmth without travelling too far, but th...
02/10/2026

Destination Comparison: Marrakech or Dubai?

Both work brilliantly when you want warmth without travelling too far, but they’re very different holidays.

Marrakech is the one I’d choose for atmosphere.

Riads hidden behind unassuming doors, rooftop restaurants, souks, gardens and the Atlas Mountains within easy reach.

It can feel busy and chaotic at times, but that’s part of its character.

Dubai is the easier option.

Exceptional hotels, brilliant restaurants, beaches, shopping and almost endless choice when it comes to how you spend your days.

It’s polished, convenient and particularly good if the hotel itself is an important part of the holiday.

If I wanted culture, character and somewhere that felt completely different from home?

Marrakech.

If I wanted sunshine, a fantastic hotel and everything to feel incredibly easy?

Dubai.

Neither is the better destination.

They’re just right for very different trips.

Which sounds more like yours?

🇲🇦 Marrakech

🇦🇪 Dubai

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

The destination I’d choose for autumn sunshine without a long-haul flightI’d choose Crete.By October, I’m not necessaril...
01/10/2026

The destination I’d choose for autumn sunshine without a long-haul flight

I’d choose Crete.

By October, I’m not necessarily looking for the intense heat of midsummer.

I want warm days, somewhere I can still sit outside for lunch, a good chance of some beach weather and plenty to do if the temperature does dip.

Crete gives you that.

But what really makes it work for me is everything beyond the beach.

You can wander around Chania’s Venetian harbour, drive into the mountains, find tiny villages for lunch, visit olive groves and spend an afternoon on a beautiful stretch of coast.

And because it’s such a large island, I’d think carefully about where I stayed rather than simply choosing a hotel anywhere in Crete.

For me, that’s the appeal of an autumn escape.

I’m not chasing 35°C heat.

I’m looking for somewhere that still feels warm and bright when things are becoming distinctly more autumnal at home.

And Crete would be very high on my list.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

Where I’d travel in November – and whyI’d choose Oman.November is when it really starts to come into its own.The tempera...
30/09/2026

Where I’d travel in November – and why

I’d choose Oman.

November is when it really starts to come into its own.

The temperatures are far more comfortable than the height of summer, which means you can actually get out and enjoy it rather than moving between air-conditioned spaces.

And Oman gives you a really good mix.

You can spend time in Muscat, head into the mountains around Jabal Akhdar, stay in the desert, explore wadis and finish with a few nights by the coast.

That’s what appeals to me about it.

It feels warm enough for winter sun, but it isn’t just a beach holiday.

You can do something with the day, see a completely different landscape and then still come back to a beautiful hotel at the end of it.

For a November escape, that balance is hard to beat.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

New York or Singapore?If I had to choose one…I’d go for Singapore.New York is one of those cities everyone should experi...
29/09/2026

New York or Singapore?

If I had to choose one…

I’d go for Singapore.

New York is one of those cities everyone should experience at least once.

The skyline, the neighbourhoods, Broadway, Central Park, the restaurants — there’s nowhere quite like it.

But Singapore gives me a bit more contrast.

You can have incredible food in a hawker centre, rooftop drinks with the city lit up below you, beautiful gardens, neighbourhoods like Chinatown and Little India, and then use it as the starting point for a wider trip through Asia.

It also feels incredibly easy to navigate, which makes a big difference on a short city stay.

New York is the one I’d choose for energy.

Singapore is the one I’d choose for variety.

So, which would you pick?

🗽 New York

🌆 Singapore

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

Three things I’d spend more on – and three I wouldn’tI don’t think every part of a holiday needs upgrading.There are som...
28/09/2026

Three things I’d spend more on – and three I wouldn’t

I don’t think every part of a holiday needs upgrading.

There are some things I’d happily spend more on because I know they’ll genuinely improve the trip.

I’d spend more on:

1. The right location.
I’d rather pay more to stay exactly where I want to be than save on the hotel and spend the week getting taxis backwards and forwards.

2. A room with a genuinely exceptional view.
Not just “sea view” because you can see a sliver of blue between two buildings. I’m talking about the caldera in Santorini, Table Mountain or a safari lodge overlooking a waterhole.

3. A private guide for the right experience.
Some places are transformed by having someone brilliant showing you around. I’d much rather have an exceptional private guide for one day than add another generic excursion.

And the three things I wouldn’t automatically spend more on?

1. The highest room category.
A bigger room isn’t necessarily a better room. I’d look at what you’re actually getting for the difference.

2. Club lounge access.
Lovely if you’ll use it. A waste if you’re going to spend every evening eating and drinking elsewhere.

3. Business class on a short daytime flight.
Give me a good seat, a sensible flight time and put the difference towards something I’ll enjoy for more than a couple of hours.

That’s generally how I look at upgrades.

Not “What’s the best option?”

But “Which option will actually make this particular holiday better?”

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

The destination I’d recommend if you’ve “done” ItalyI’d look at Slovenia.Especially if what you love about Italy isn’t j...
27/09/2026

The destination I’d recommend if you’ve “done” Italy

I’d look at Slovenia.

Especially if what you love about Italy isn’t just the famous cities.

Beautiful food.

W**e.

Mountains.

Lakes.

Small towns.

Long lunches somewhere with a ridiculous view.

Slovenia gives you plenty of that, but in a country that still feels quite different.

I’d start in Ljubljana, then head towards Lake Bled and the Julian Alps before spending some time in the w**e regions or continuing towards the Adriatic coast.

And because the country is relatively compact, you can see a surprising amount without spending half the holiday travelling between places.

Is it a replacement for Italy?

Not at all.

But if you’ve already done Rome, Florence, Venice, Tuscany and the Lakes and you’re wondering where to go next, Slovenia would be very high on my list.

Sometimes the answer isn’t finding another corner of the country you already love.

It’s finding somewhere that gives you some of the same reasons you loved it in the first place.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

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