One of today's most popular ways to get engaged: a destination proposal. There's something so romantic about being away together, and alone, in your little corner of the world, whether it's in a cabin two hours away or on an island in another hemisphere. Plus, the very nature of being on vacation makes even the simplest proposal spectacular.
There are two types of destination proposals: The first is that she knows you're going on a trip; she might've even helped plan it, but she doesn't know that you're packing a ring. The other is a complete surprise: You book a night in New York/weekend in Napa/week in Europe, and she's completely in the dark. More difficult? Yes. More wow? Definitely. Here's how to pull the proposal off.
If She Knows About the Trip...
Prep before you depart. Don't wait 'til you get there to plan the specifics of your proposal. Do advance research to find the perfect locale. Call the hotel's concierge to help make dinner reservations at the most romantic restaurant around, choose the best stretch of sand for a seaside-at-sunset proposal, and order her favorite flowers for your room. Some high-end resorts actually have romance coordinators on staff (seriously) who will assist with the perfect proposal plan, rose petals included.
Pack the ring properly. If you're not flying, keep the ring secured in an inside coat pocket or locked in the glove compartment of your car. If you'll be boarding a plane, pack the ring in your carry-on luggage to prevent the TSA from spoiling the surprise—don't carry it on your body, since you may then have to remove it when you walk through security, and obviously don't put it in your checked luggage. Your carry-on should be loosely filled with nonsuspicious items. Think sweaters and a paperback book; not toiletries, pocket knives, or electronics that might trigger the screeners. And don't put the ring in a ring box -- if you do get called for a closer check and the security guard starts tossing your stuff, you're better off having the ring in a nondescript medium-sized box.
Let the suspense build (just a little). After all this planning, you'll be understandably eager to blurt out your big question and let the celebrating begin—but resist the temptation to propose in the car on the way to the airport or the second you've tossed your bags onto the hotel room floor. Your girlfriend most likely hopes and suspects that a proposal is part of the travel plan, but let her savor the suspense for a day or two (or at least an evening) before you break out the engagement ring. That said, don't wait until the last day of a week's vacation to do it. She'll overanalyze every moment of the trip because she's anticipating a proposal, and all that waiting could make her more than a little grumpy.
If She Doesn't Know About the Trip...
Pick the perfect destination. Think about travel times. You want to devise a plan that's simple and not too stressful (like one that doesn't require passing through two airports, a train station, and a grubby ferry terminal). Even one night at a luxe hotel in a different city will capture the same excitement. Also, it's important to take your girlfriend's personality into account. If she's an outdoorsy type, a ski lift might be the perfect place. For a traditional romantic, a classic setting like a Caribbean beach or a hotel balcony in Paris is probably more her style.
Clear her schedule. Even if it's just for a weekend, ask her boss if there are any Monday deadlines that she'll have to prep for. If you're planning to be away for more than a weekend, check to make sure she won't be missing any crucial meetings on those days off. Then, check her Outlook calendar for can't-be-missed social obligations. There's no need to ask her mom/dad/best friend/coworker about all upcoming plans. Enlist one ally. The more people you tell and the more notice you give them, the more likely word will spread. If you'll be stealing her away from brunch with her college roommate or her cousin's birthday party, they'll forgive her when they find out why she was a no-show.
Pack her bags. There are two ways this can go: 1) Tell her she's leaving in 30 minutes for a surprise trip and to pack for, say, three days in a tropical climate. 2) You go for the ultimate shocker and pack her bags yourself. Be warned: This will require outside help (which means revealing your intentions to others). Even if you live with her and are unusually confident in your command of women's fashion, it pays to ask her sister or close friend to advise you on which outfits, shoes, and toiletries to tote for her on your getaway. And, if you don't live with her, you'll have to sneak into her place and escape with a packed suitcase, something that probably should be done with the help of one of her friends. If you're heading out of the country, don't forget to grab her passport. No idea where it is? Build enough time into your plans for her to go home and retrieve it before you head to the airport.
See More: Popping the Question