Are Private Tour Guides
Worth It in Bermuda?
(An Honest Answer)

People ask me this all the time before they book, and I understand why. A private tour costs more than hopping on the public bus, and most people assume it costs more than a group excursion through the cruise line too. So before you spend the money, you want to know it's worth it.

Here's my honest answer: for most people, yes — but not for everyone. Let me explain who it's right for, who it isn't, and what you actually get, so you can decide for yourself.

I'm Greg Wales. I was born and raised here in Bermuda, I spent years as a police officer on the island before this, and I've been guiding visitors around for fifteen years. So when I tell you what a private tour can and can't do for your day, it's coming from someone who has done this a few times.

The Short Version
For People Short On Time

If that short answer is all you needed, the rest of this is the detail behind it.

What You Actually Get
With a Private Tour

The honest difference isn't the car or the air conditioning. It's that the entire day bends around what you want.

When you book me, there's no fixed route and no other strangers to wait for. If your ten-year-old decides halfway through the day that he wants to try Mr. Chicken, we go to Mr. Chicken. If you want the best Bermuda fish sandwich on the island, I'll take you where the locals actually eat. If you want to skip a stop because you've seen enough churches for one day, we skip it. Your day, your pace, your wishlist.

The other thing you get is local knowledge you simply can't find on your own. There are places on this island that are nearly impossible to find unless you've lived here your whole life. I had a group recently where half the party wasn't sure about hiring me for four hours. By the end we'd been out for over seven hours, and somewhere in there they mentioned that one of them had an old friend on the island she hadn't seen in years. I knew of her. So I took them to her. Watching those two old friends reunite was the kind of moment no group bus tour on earth could have given them. When they got back to their ship, they said the day with me was almost all they talked about.

That's what private really means. Not a fancier vehicle. A day that can do things a schedule can't.

But Is It Actually
More Expensive?

This is the part everyone worries about, so let me address it head-on.

I don't post prices online, because every tour is different — different group size, different number of hours, different wishlist — and I'd rather build the right day for you than sell you a fixed package. But I'll let one of my guests answer the money question for me. She brought a group of eleven, seven adults and four children, off their cruise ship in May 2026. Here's what she wrote afterward:

Read that again. A fully customised private tour for eleven people — kids included, local restaurants, every stop tailored to them — for less than what the cruise line wanted for the standard group excursion.

That won't be the case for every group size. But it surprises people how often a private tour, split across your own group, comes out comparable to or better than paying per head for a big bus you share with strangers. Don't assume private automatically means expensive. Just ask me, and I'll tell you honestly what makes sense for your group.

Who a Private Tour
Is Not Right For

I promised you an honest answer, so here it is.

I'd genuinely rather you have a good day in Bermuda than feel pushed into something that wasn't right for you. So if that's where you're at, no hard feelings, and I mean that.

The One Thing Guests
Wish They'd Done Differently

In fifteen years, I can't really tell you about people who regretted booking a private tour. The closest thing I hear — and I do hear it — is people wishing they'd booked more hours.

I had a lady who was tight on time because of her cruise schedule. She didn't feel rushed, and she said she wouldn't have changed a thing, but she simply couldn't fit everything in. That's the only real regret I come across. Remember that group who booked four hours and stayed for seven? That happens because once you're out here, you don't want the day to end.

What It Really
Comes Down To

People who travel the world and take tours everywhere they go tell me they've never had an experience quite like a day in Bermuda. I think that's because for my family, it was never really about transportation.

My wife's family has been driving visitors around this island for four generations. Her grandfather in particular had a real passion for it. He made friends from all over the world simply by showing people around and sharing his home with them, and that's what got handed down.

Tour 1660 is my chapter of that story. The brand is new, but the roots aren't, and the same passion that started it all is what you'll feel in the car with me. I'm not running you through a checklist. I'm showing you my island home, and I'm genuinely glad you came. One day my son Kace will carry it on.

Whether you've got grandparents in their nineties or kids who can't sit still, my job is to make every single person feel at home and actually enjoy their vacation. I've also got a few jokes I save for the road, but you'll have to book to hear those.

So — are private tour guides worth it in Bermuda? If you want a day that's truly yours, with someone who treats your family like his own, I think you already know the answer.