Every time my wife & I get together with friends, they comment on our most recent Facebook travel pictures saying “I wish I could travel like you.”
Here is how I get to take my whole family on trips that cost less than what most people pay for just one person:
- For vacations, I watch every day for deals and I plan way ahead. I don’t just look for “good deals”… I only watch for AMAZING deals. When I find one that looks good, I book it well in advance and plan my family’s schedule around it. I’m talking about $110 flights to Cabo, $192 flights to Aruba, $154 flights to Cancun… $325 to London, $290 to Spain, and so on. (Those are all round-trip prices, BTW.)
- I also keep an eye out every day for cheap fares where I have friends/family who I like to visit. I’ve booked $29 weekend flights to Indianapolis (where my wife grew up), $39 flights to L.A to visit friends, $84 flights to visit my brother’s family in Raleigh… When I found $50 flights where some other friends lived, I invited them to visit us for a ski weekend. The list goes on. None of these trips are trips I would have planned. But when you can take a long weekend visiting friends/family for those prices… Why not?
Finally – I always keep a stash of at least 100,000 frequent flyer points for scenarios when I CAN’T find a cheap trip that fits my schedule. I know that sounds like a big hassle, but trust me – it’s nowhere near as big a hassle as beating your head against a wall trying to find a cheaper flight than that $600 per-person flight that you were hoping to pay $150 for. (Plus – when you can get 100,000 points with just a couple slight adjustments to your spending habits, there is never an excuse for not planning ahead so you have them when you need them.)
- For example:
- When my wife wanted to go to Hawaii, but my cheap ass refused to pay $1326 PER PERSON just to get there??? Points to the rescue. We went for $22 each.
- When friends from Indiana found a JGOOT deal to Turks and Caicos and invited our family to join them, we’d have had normally had to say no. (Flights were more than twice as expensive out of Denver at $600 each but by redeeming points, we went for $96. (And started an AMAZING “friendcation” tradition with friends from around the country.)
- When we had to fly to a friends’ Dad’s funeral and couldn’t find tickets less than $450 each, we used points and went for $11.