Is It Worth Paying More For Your Next Vacation?

Most of the time, when I'm planning a trip with someone, the conversation starts with price. What's the flight? What's the hotel? Is there something cheaper? That's normal, and it should matter because nobody wants to overspend just because. So let's have an honest conversation about spending more on your vacation… and why I'm not automatically going to tell you to do it.

Because here's what I actually care about more: what are you getting for that extra money? Spending more for the sake of spending more isn't a strategy, it's just, spending more. My job isn't to upsell you into the priciest version of everything. It's to help you figure out where the extra cost actually buys you something.

So when does spending more actually make sense?

When you're buying back your time. You've only got so many vacation days a year and at some point, time is the more expensive thing to waste. Take airfare - a flight that's $400 cheaper but adds an eight-hour layover isn't really cheaper once you factor in the day you just lost. Or a cheaper hotel with a nicer room, that is 40 minutes from everything you came to London to do. Paying more to stay close to what you want to see can save you money on cabs, save you hours of commuting, and honestly just let you experience more of the place instead of spending all of your time getting to places.

When convenience is worth paying for. Breakfast included. Experiences booked ahead. An itinerary with fewer hotel switches. Someone (me) narrowing down the options so you're not doing it yourself at 11 pm, scrolling through endless TikToks. Some of the best money you can spend on a vacation is to decrease the mental load while you travel.

After a long flight, that private transfer means someone's there, you get in the car, and you go straight to the hotel. No figuring things out, no extra stops, no standing around with your luggage. You're not paying for a nicer car, you're paying to skip the most exhausting part of arrival.

When it really is just about the experience. The polar plunge in Antarctica. Being in Port Hercule during the Monaco Grand Prix. The dinner you've been thinking about since you booked the trip. If there's something you'll still be talking about five years from now, that's where I'd rather see your money go.

Here's the thing about your vacation budget: it's not just dollars. It's your time, energy, patience, everything that doesn’t show up on a receipt but absolutely shows up on your trip. The trick is knowing when it adds value and when the cheaper option is the better option. And it comes down to you and your travel priorities.

What matters to you might mean nothing to the next traveler, and that's exactly why there's no universal checklist of what's "worth it." So instead of asking "what's the cheapest option," ask "what actually gives me the most value here." That's the question I want to help you answer, not to talk you into spending more, but to make sure whatever you spend is going toward the trip you actually want. If you're not sure where that line is for you, let's figure it out together.