Well, Barry, it really depends on the scale of the proposal that you have in mind. If the plan is to trek up a hill and whip out the ring at sunset, then you can more than likely manage that on your own steam without too much trouble. If you’ve got trained monkeys, parachuting dancing girls and skywriting in mind, then one suspects you’ll need to call in for reinforcements.
Choosing a familiar destination will certainly be handy in that you already have the lay of the land and know what to expect—bonus points if it's also a place the two of you have shared special times together in the past. Having said that, there’s nothing to say you can’t pop the question in some new and exotic locale, why not?
Whichever you choose, the overriding consideration should be on preparing as much as possible in advance of your arrival. When you’re on a romantic overseas getaway, it’s a little tricky to steal away from your other half without causing alarm or offence. Popping down to the markets and sneaking off into the crowd and leaving a woman to fend for herself isn’t particularly chivalrous. By the time she’s negotiated the beggars and touts to hitchhike back to the hotel, you’ll be lucky if she’ll even look you in the eye let alone faint with joy when you drop to one knee.
Booking her in for a massage, pedicure and facial will buy you a couple of hours to put the finishing touches on any special plans, but don’t turn up at the airport with nothing but grandiose plans and crossed fingers. A local perspective is always useful to help fill in any blanks—if you don’t have friends of friends you can call upon, your hotel or resort should be pleased to offer up ideas and answer questions. If their service is half decent, they’ll be only too happy to lend a hand and scatter a few rose petals around the place or something.
One concept that is consistently overlooked in the wedding proposal is spontaneity. You’re in a foreign land where everything looks, feels and smells special, different and exciting so, in truth, the streamers, bells and whistles are probably superfluous and unnecessary. Consider simply keeping the ring safe and close by for one of those travel moments where time stands still. Simplicity is underrated... and the less you've got going on means the less that can go wrong.
Before you book flights, brush up on the basics of the perfect proposal.