Curtain Bluff resort in Antigua is a favourite with James Max © dbimages/Alamy

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Every holiday or staycation I’ve planned since March has been a casualty of Covid. I know. Diddums.

My usual trips to my pad in the French Alps, cancelled. A road trip to the west coast of France, scuppered. My annual pilgrimage to the temple of luxury, Hotel Cipriani in Venice, ditched. A cheeky long weekend to Norfolk, abandoned. And a walking trip to the Lakes, postponed.

What a total ’mare. I am now left wondering whether I should even bother building up my hopes to go away or simply resign myself to the fact that travel before the vaccine rollout is a risky business.

I’m well aware that the pandemic has seriously impacted economies and people around the globe. With many deaths, prolonged illness, disruption to daily lives and businesses wrecked, my demands for a holiday may seem trivial.

Perhaps, but I have worked every day since mid-February. Although I am energised and fortunate to be busy, everyone needs to rest sometimes. My batteries need a recharge. This is the longest stretch that I’ve not been abroad since the 1970s. I’m hankering for a sunshine lunch that starts at 12pm and finishes at 2. That’s 2am, the next morning. Washed down with lashings of fizz and rosé.

The first lockdown taught us many things. Gardening is great fun. Owning dogs is essential. A house at the seaside is epic. Working from home can be a joy. English fizz is delicious. And home-made produce is fun to create and great to consume.

It’s not been as much fun the second time around. Partly because the weather has been awful, outside activities and drinks over the fence with the neighbours have been curtailed. It’s also more difficult to play catch the popping cork in the dark. But also, on day three of Lockdown 2.0, my NHS app pinged me. I’d been in contact with someone who tested positive for coronavirus and had symptoms. Cue 10 days in self-isolation.

I can broadcast and write from home. While I miss my shopping experiences to buy “essentials” it’s hardly the end of the world. Using supplies, thankfully panic-purchased last time around, I’ve enjoyed different kinds of baking and made a challah (Jewish plaited bread) for the first time. I picked apples from my trees and baked apple turnovers. Not a soggy bottom in sight. And I harvested the last crop of the season from my vegetable patch — Jerusalem artichokes.

If you have ever eaten one, you will know the ferocity of the impact on one’s digestive system. Perhaps they’re the ideal food for lockdown? Under usual circumstances, you’d not trust yourself to leave the house. A trump of Jerusalem artichokes, one could say.

Despite all this horticultural and culinary activity, I’m feeling restless. We’re living with unprecedented uncertainty. There are so many things to worry about in a post-pandemic world. Taxes will rise, but which ones? Which investments should I keep? Will I have enough money to do all the works to my house that working from home has made me realise I need to do? Should I be cautious with money, even if it is burning a hole in my pocket?

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That’s not the only “post” thing to be thinking about. What about post 9-to-5, five days a week in the office? Will working from home still be a “thing”? Will I still be able to do Zoom meetings in my shorts? Or socks? Will I be able to go out for lunch or dinner with friends? Will there be any pubs left after all of this? So many questions. Which brings me back to the biggest question of all: should I book a holiday?

If any mail happens to drop through your letter box, the chances are it will be choc full of travel deals. If I were allowed to go to France, I could get a return flight to Lyon for £50 at pretty much any time I chose. Even BA is £100 (scheduled, return and including tax). It’s usually double.

The problems of Covid-19 and quarantine aside (and whether the ski resorts will even open), my flat in the mountains is still not ready to welcome me back after being flooded. My builder has been unable to work, source materials or make any meaningful progress. So much for the convenience of owning one’s own place. It would be even worse if I were relying on rentals to cover a mortgage or costs. So, I have been looking further afield.

For many years I’ve been a fan of Antigua. It’s laid back and unstuffy. There are some lovely restaurants, amazing beaches and it makes for an epic holiday destination that’s within a travel corridor. In fact, it was the last trip I made before lockdown. So, I am thinking of booking again.

I could go all out and splash the cash. There’s something rather nice about travelling upper class and staying in a ritzy hotel. And yes, I could do a week and rinse the account staying at Curtain Bluff or Carlyle Bay, drop £10,000 for a trip that usually costs £15,000 to £20,000 and be done with it.

But I want to go for longer, explore the island, and throw some cash at some memorable excursions. I’m neither a footballer nor a pop star, so the sums required to live the high life for a longer break can’t be justified. With the deals that are out there, I regard it as a challenge. A two and a half week trip for weekend skiing money. Can it be done?

Don’t tell anyone, but I don’t really mind sitting in steerage for a daytime flight. You may balk at turning right, but the deals are currently so good, it might be worth the sacrifice. Last year, an economy class ticket to the Caribbean would have set you back £900 including tax. This year? The cheapest I’ve found is £344 return. And with hotels desperate to grab your business, I think I’d rather slum it in the cheap seats.

I'll book a 16-night epic for £1,500 and spend the money I've saved on home renovations including some swish Bert & May tiles and fetching furniture pieces from Timothy Oulton. Those five star interior additions will last longer than a holiday. Maybe I'll have enough left over to splash some cash and book a table for lunch at a glitzy Caribbean palace. Anyway, I'll only want the table until two.

James Max is a property expert and radio presenter. The views expressed are personal. Twitter: @thejamesmax. If you have a problem for James, contact him at richpeoplesproblems@ft.com

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