Sure there are other Hawaii deals out there, but HBWT Trips get you there on an airline that doesn't hate you for bringing your surfboard along, namely Alaska Airlines.

Boston to Kauai runs easily $1100 (including boards) most of the year. These Trips have a Single Stop, with super-low board fees to save you 45%.

For all of us on the East Coast not lucky enough to fly many places with Air New Zealand or Quantas (neither charges for surfboards, small ones at least), Alaska Airlines $75 board coffin is damn near as good as we can do (stuff one for everyone going and be out the door cheap).

Getting to Kauai is almost always an additional $200-$300 compared to Honolulu, so this deal is pretty nuts.


Hanalei Bay has got to be one of the all time classic point breaks. Sadly one that remains on my personal to-do list.

I don't think I can make it make sense to drive to Boston to catch this flight, but rest assured we have our eyes out for Kauai trips from NY/NJ as well.

There is availability starting in August and running through the winter, that means you can jump on something now and head to the south side of the island, or wait for the first winter swells to start rolling in on the North Shore later in November.

Free Trips

Here are a couple of dates for those of you from Boston / North East that haven't subscribed as Email Supporters (free for life!) yet.

Alternately if you travel more than once a year, your best bet is to jump on a Pro/Am Supporter subscription from $6/mo to get a head start on every deal, more cheap flights, and the full list of available trips.

  • Dec 4 - Dec 11 | 7 Day Kauai Surf Trip

  • Dec 4 - Dec 13 | 9 Day Kauai Surf Trip
  • Note the long stop-over (overnight!) in San Diego. Personally I don't mind these that much (since I get a nap in the hotel, or in the airport haha), but if you prefer there are some American flights that have short stops, but more on bags and WAY more on boards.