How I find great travel deals

Friends are always asking me how I find such great travel deals. While I don't always get great deals (domestic airfare is impossibly pricey during the holidays!), I'm always scouring the internet to find them. These travel deals tend to require flexible timing, which is easier for us to manage as DINKs  - I will miss that about DINK life if/when we have kids.

Here are some of the deals we've travelled on recently:

Positano, Italy, September 2014

• Deal: $685 per person for roundtrip airfare from JFK to Naples 
• Found through: Kayak

Hakodate, Japan, May 2014

• Deal: $1,075 per person for roundtrip airfare from Taipei to Hokkaido, 5 day guided tour through 3 cities within Hokkaido, and four nights of hotel accommodation
• Found through: Lion Travel

Moorea, French Polynesia, November 2013

• Deal: $1598 per person for roundtrip airfare from LA to Auckland, including a 3 day stopover in Tahiti, one night in a standard room at the Intercontinental Tahiti, and two nights in an overwater bungalow at the Intercontinental Moorea
• Found through: Travelzoo Top 20 deals (expired link here for your reference). 

Tips on getting good deals

Kayak: Whenever I find a great fare on Kayak, I always check the fare for the same flight on the airline's own website, as it doesn't always match the lowest fare on Kayak. This is particularly true with flights on EVA Air - I have no idea why. The limitation to Kayak is that it doesn't include certain airlines, so it's not a one stop shop.

Lion Travel: Lion Travel tours start in Taipei and only offer Mandarin language tours, so they probably aren't a convenient option for most people. However, if you can make it work, Lion Travel puts together some great packages. I always price out a package to see if I can get it cheaper on my own - just the roundtrip airfare from Taipei to Hokkaido would have been $700 per person, so their Hokkaido package was definitely legit.

Travelzoo: Travelzoo is where I find a majority of my combo (flight & hotel) deals, so I'm very diligent about checking the new deals of the week every Wednesday morning. You have to be patient though, because weeks or months will go by where I am not interested in any of the deals. Keep your eyes peeled for the combo deals to the intriguing destinations abroad - that's where I've found the best deals. Just like with the Lion Travel package to Hokkaido, I always price out the deal separately to see if it really is a good deal. With the New Zealand/Tahiti package, I knew that it was a good deal since one night in the overwater bungalow at the Intercontinental Moorea is close to $1,000/night!

Hope that helps! In the meantime, I'm daydreaming about this deal for a week long vacation in Japan...