If you have never though about riding St. Thomas or St. John you should give it a chance. The only reason I haven't been back is the cost of the flight (which obviously this cheap fare takes care of).


While I didn't really score the last time I was down there the clarity of the water, chill vibe and perfect weather are pretty hard to say no to. Plus I was the only one out. As an added bonus when you are on St. Thomas you are also just a ferry ride away from St. John which has additional spots (not to mention a really cool bar just off the Ferry downtown.)

The major plus from the surf perspective is that the trades are blowing all winter long and the islands aren't that big (easy to drive around) so its pretty rare to get totally skunked by a flat spell. You may have to take a quality hit to find dig up some size on some windward part of the island, but there are at least SOME waves SOMEPLACE.

Its a hell of a lot warmer than NJ during winter, definitely not world class, but it definitely IS worth checking out.


I didn't have my longboard skateboard last time I went but there are no shortage of spots. Watch out for on-coming traffic, people drive crazy and the roads are narrow, but there is some great pavement and some great views.

I would classify this one as a longboard travel bonus as opposed to a longboard travel destination, ie. if you are going bring your downhill / slide deck for sure but I wouldn't plan on shooting the worlds best video while I was there.

There is also plenty of flatland stuff and it never rained while I was there, so I suppose if thats your jam you could absolutely make a video trip happen.


You don't need a passport and the flights we found were direct from New York although we are researching other regions as well.

You will need to rent a car while you are there to get to the better spots, as mentioned above there is indeed a ferry to go check out St. John.

Lodging can be expensive but a cheap flight (this flight usually runs in the $550 range) during the height of winter swell season leaves room to cover expenses.

Dogfood? No one at HBWT is going yet, but we all wish we were.

New Riders sign up for our "For Fun" member package for $1 today and we will email you the exact dates we found for this deal and then send you every cheap flight we find your region for the next 30 days.

After that "For Fun" membership runs $6 per month. Alternately you can save yourself some money and sign up for the rest of the year for $5/mo

Pros, Ams and Brands

When you are serious about surf, skate or snow travel and sign up for $12/mo you get first dibs on all deals, plus we never stop searching.

We will keep an eye on this (and all of our cheap fare deals) then let you know when we pair an inexpensive flight with a positive probabilistic surf / skate / snow forecast once we approach the exact dates of availability.

We watch the weather 24/7, you dive on the deal when to forecast matches up with a cheap flight.

For $12/month Pro, Am and Brand travel becomes practically skunk proof.

As always: If you are searching for cheap surf travel flights yourself... You are Doing it Wrong.

Catch you guys next time.