US Virgin Islands 🏝️ in $290s-$330s RT

US Virgin Islands 🏝️ in $290s-$330s RT

When my family visited St. Thomas, they were worried it would feel too American-ized. None of us wanted a resort vacation at a tourist town.

We were pleasantly surprised — despite being a US territory, St. Thomas feels nothing like the states. The whole island is utterly soaked in Caribbean vibes, and we met surprisingly few non-locals despite it being peak season. Unless you dive into the little pockets of resort traffic, you can easily settle into a slower life here among the winding mountain roads and lush jungle. They come with some pretty stellar views, after all.

For example: Skip right past touristy Margaritaville and climb along the eroded, vine-covered path to Sun & Sea. They served us some best fish tacos we've ever had (and we're from San Diego!) while we sat back and watched the sun set over the cove.

Plus, if one island simply isn't enough, there's a second (very different) island just a quick hop away...

Taking off ✈️

Tip Published: Oct 13, 2025

To

  • Saint Thomas (STT) (nye)
From

  • Boston (BOS) - $302 (up to $330, only until April)
  • New York (JFK) - $296 (peak summer)
Flight Details

Travel Dates

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Airline

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Standard Fare

From $600 (non-stop, NYE)

Bags & Fees

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Flight Notes

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How to Book

    This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.