The Newly Wed: The Best Vacation of Your Life

Diana details how she and Ben planned their romantic honeymoon.

Ben and Diana in Rome.

A honeymoon is an opportunity to have the most romantic vacation of your life. Unlike the wedding, this is all about the two of you. When you’ve just planned the most important celebration of your life, you definitely deserve the best vacation of your life. (Believe me, you’ll need it!)

Ben and I planned our honeymoon six months in advance, which worked perfectly because we were able to finalize our plans before travelers snatched up all the deals. When you’re planning a wedding, it’s easy to put the honeymoon on the back burner. The problem is that by the time “later” rolls around, everything is booked. It’s your honeymoon, and you want to have your choice of locations and hotels—not the leftovers.

The first thing we did was figure out timing. Our wedding was August 15, and we decided to wait two weeks until we took our honeymoon. Tourist season would die down a bit when the schools reopened, and we wanted to have some time to rest after the wedding and settle things at work before we left.

It worked out, because Ben and I got sick after the wedding. But if I were to do it again, I’d plan the honeymoon for one week after the wedding instead of two. The second week left us feeling in wedding limbo. We were married but hadn’t been able to enjoy it yet because we were so busy at work. By the time we left, we were back into the swing of things and felt bad leaving work again.

When you’re planning your honeymoon, think about each of your priorities and use those to choose your location. Do you want a completely relaxing trip where you don’t have to lift a finger? Culture and sightseeing? Something low-key? Adventurous activities? We wanted somewhere we could relax, experience a different culture and sightsee, and eat amazing food. After some research, we decided on Crete and Italy.

If you want to find memorable restaurants, make sure to do your research and ask locals where to get the best grub. Your best bet is to stay away from anything touristy (think menus in five languages and people standing at the door harassing you to go inside with offers of free wine and appetizers). We used Lonely Planet,, Travel & Leisure, and Condé Nast Traveler.

To find off-the-beaten-track places, we rented a car in Crete and drove to a pink-sand beach, Elefonisi, and stopped in a little agricultural mountain town called Milia along the way. The one tavern had a daily menu, and everything—including the cheese and wine—was prepared from the local farm.

While our honeymoon was fantastic, we did have some travel snafus. After writing copious notes about every phase of our travel plans, I misread our flight time from Crete to Italy and we missed our plane. This started a sequence of events that included missing another flight, a train, and getting on the wrong train. We ended up somehow communicating with a guy who spoke little English and getting on a midnight train to a small town about two hours from our intended destination. We paid a guy to pick us up at the train station and drive us to our hotel at 2 AM.

One thing everyone wants to know when booking a trip is how to get honeymoon freebies. It turns out they’re hard to come by. The starry-eyed “We’re on our honeymoon!” line doesn’t really work at ticket counters. Here’s a couple of tricks I picked up along the way:

• Travel agents can get you room upgrades and freebies, but it’s cheaper to book travel online.
• If you want cheaper first-class tickets, buy a full-fare coach ticket, then either pay for an upgrade or sweet-talk the ticket-counter representative.
• If you want to be considered for an upgrade, dress the part: If you look like a schlub, they probably won’t put you in with the movers and shakers.
• Mention you’re on your honeymoon when you book your hotel. Mention you’re on your honeymoon to the waiter. Mention you’re on your honeymoon to your tour guide. You get the point. Slip it into conversation without being obvious or obnoxious, and at the very least you might find yourself with a free bottle of wine.
• The best time to get upgrades is during the off-season. If premium rooms are empty, hotels don’t lose anything by giving you one at no additional cost.
• Remember the magic words: please and thank you. Just being genuinely friendly and appreciative without expecting anything in return goes a long way. Even without freebies, your honeymoon will be spectacular because you’re spending it with the love of your life.

Our honeymoon was everything we could have hoped for. We had delicious food, beautiful scenery, exotic culture, and best of all, lots of time for just the two of us. It’s crazy to watch our first home videos and look at our pictures and think how many more we’re going to accumulate over the years. Even though we’re back home, it’s hard not to get excited. The honeymoon might be over, but the adventure has just begun!

To read last week's column, click here. For the latest Bridal Party blog posts, click here.