As you know, your kids are ticking time bombs who must be entertained. You sort of devote your whole life to it. Somewhere in the daily blitz of media, the idea of a resort somewhere with kids’ activities and daycare got planted like a seed in your brain garden. Now you have reached the point where curiosity turns into Googling. Before stepping a virtual foot on any slick websites, look over this cheatsheet I made for you:  

  • Tuesday nights around midnight are the best times to book a flight. According to one source, flights are about 6% cheaper.
  • Ever notice how a fare you checked yesterday went up overnight? It didn’t go up for everyone. Try going to a different computer and searching again — you’re likely to find the original fare. Airlines sometimes use cookies and browser history to determine their prices online. In Chrome, there is a feature called Incognito Mode that allows you to shop…incognito. Always search for flights in Incognito Mode!
  • It’s usually cheaper to arrive mid-week and stay over a weekend.
  • Go to where your friends are! Save on hotels and catch up with your chosen family — just don’t sleep walk into their kitchen and eat everything. Just saying.
  • Look at what’s available at Airbnb,, or VRBO to save on accommodations.
  • Pack lightly so you don’t have to pay for checked bags — you can always do laundry while you are there.
  • Try not to eat or get mimosas at the airport.
  • If you’re driving, gas up before you hit the highway. Regular unleaded was $4.69 a ($%#!) gallon on the New York Thruway the other day.
  • Wherever it is you are going, stray from the beaten path a bit to find authentic restaurants. They’re not just better, they’re cheaper than the places that cater to tourists.

Flying cheap gets easier every day, but the seats are torture devices. Even if you’re driving, don’t forget to take breaks from sitting for long periods of time. I hope you’re successful in booking your next vacation — whether you’re a single guy or girl in the city; or a family in Aspen who just accidentally introduced three kids to the most expensive hobby imaginable.