How to Book Your Trip of a Lifetime Like a Pro

Here are the tips you need to book your perfect honeymoon.

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Confession: I’m the absolute worst travel planner. OK, that’s a bit dramatic — after all, I am a bona-fide expert. And when I look at the globe, I know the next destination I want to explore and have a solid idea of what kinds of excursions I’d like to experience and where I’m most jazzed to stay. But the ins and outs of booking airfare, cars, and figuring out if I need insurance admittedly can give me hives. Since it is my job to make your vacation planning smooth sailing, I'm sharing some lessons I’ve learned over the years so you can have your best honeymoon.

Make a List

Sure, it pays to shop smart, but choosing your honeymoon destination based purely on the bottom line doesn’t really scream “trip of a lifetime.” And believe it when I say this — not all beaches, all-inclusive resorts, and historic cities are created equally. The best way to whittle down your destination options is to make a list of your top three desires — which might be stellar cuisine, over-the-top pampering, and awesome natural scenery. Have your guy make a list of his own, then compare notes and explore options to zero in on the right destination for you. Of course, it also helps to read the travel coverage in Bridal Guide and on It’s a good idea to hammer out your resort choices now, too.

Go Online

Now that you’ve decided on Jamaica or Italy or Bali, you want to nail down your airfare. Start the process six to eight months before departure. Flights can be the most difficult — and expensive — to switch, which is why having dates and hotels mapped out is key. Booking online is by far the most economical way to go. For carrier comparisons and real-time price fluctuations, go to Google Flights. The relatively new online and mobile tool also gives various date and airport options based on price. Reservations are made directly with the airlines, so you can still use your miles and other rewards.

Get Packaged

Not only is it easier to do a single booking, it can also save some Benjamins, at least according to the folks at Travelocity. Consider the site’s vacation bundles and you can get air, accommodations and, depending on the offer, some excursions or car rentals. Orbitz has similar deals. Jetsetter, a personal top choice, offers flash sales for high-end hotels, sometimes months in advance, that often include meals and some activities. Similarly, resorts are constantly wooing romance travelers with just-for-them packages that often include champagne, breakfast in bed, and couples spa treatments. You can look online at promo offers or call the hotel for unlisted deals.

Call in the Experts

After all the wedding planning, you may feel like you simply can’t Google anything else that isn’t work related. It may be time to hire an expert. If you, like me, need help organizing tours and the transfers, use a specialty outfitter. On a recent trip to Latin America, I called Nicaragua Vacations, and they arranged all of my taxi rides and long-haul ground transportation in addition to a cool volcano excursion and colonial city tour. Personally, I prefer having drivers while traveling. Not only do they know the roads and local car culture, they also have the best tips on delicious — and cheap — food and untouristy sites. Also, nothing says “ah, yeah, vacation” like an air-conditioned chauffeured car complete with a chilled bottle of water. To have someone put together the whole shebang, contact a travel agent, also known as a travel specialist these days. In addition to booking it all from air to ground, an agent can also advise on the best fantasy location for you. Virtuoso is a consortium of luxury advisors with boots-on-the-ground experience.

Double Check

Trust me: It pays big to be like Santa and check everything twice. On more than one occasion, I’ve misread an itinerary to find that my return date was, in fact, a different day, month and — believe it or not — year. Catch those snafus upon receiving an email confirmation, and there’s no change fee. If you do spy something off, it is best to call and get it rectified immediately.