Cracking the Caribbean: Three Islands, One Epic Journey | Outtraveler

Cracking the Caribbean: Three Islands, One Epic Journey

Cracking the Caribbean: Three Islands, One Epic Journey


Cracking the Caribbean: Three Islands, One Epic Journey



Photography by Brandon Presser.

No longer just a long-weekend escape or a brainless beach honeymoon, the Caribbean has been reimagined — a result of our collective obsession with small-batch charm. All-inclusive vacations are now being traded in for trips that offer an untapped reservoir of tropical appeal and a palpable sense of place. 

This new breath of life is largely due to the sudden increase in air routes (a by-product of the uptick in the economy), which provides an opportunity for younger airlines to broaden their demographics and scope. With additional direct flights being added each season, a new transit trend is emerging that pairs nicely with travelers’ rediscovery of the tropics: the island road trip.  

Consider the following as New Caribbean 101, an updated guide to seamless multi-stop vacationing: Fly directly down to Puerto Rico, jump over to St. Barth, continue on to Antigua, then zip back to the continental U.S. without ever having to backtrack.

Island Hopping Simplified

With a massive increase in connections and affordable tickets, the Caribbean should no longer be considered a constellation of singular getaways. Now it’s easy to hop between islands on reputable carriers like JetBlue (JetBlue.com), which not only provides rapid and regular service to several key destinations in the region but also offers in-house “Getaway” packaging services tying flights and hotels together. Pair JetBlue’s regular connections to its Caribbean hubs with scheduled-charter links by Tradewind Aviation (FlyTradewind.com), and you’ve got yourself a streamlined itinerary. 

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