It’s hard to think of anyone who has better distilled the dream of island living than Jimmy Buffett. And Buffett’s empire has expanded far beyond music, from the famous, ubiquitous Margaritaville restaurants and bars to a fast-expanding portfolio of branded resorts, including in the Caribbean. 

Margaritaville’s resort portfolio, which includes properties under several different sub-brands in the region, is a chance for travelers to experience the Margaritaville ideal in vacation form, from 5 O’Clock Somewhere bars to on-site breweries and splendid swim-up bars.

The latest expansion is the result of an alliance between Margaritaville and Karisma Hotels and Resorts, one that has led to a number of new brands (and several more new resorts currently in the pipeline).

We’ve gathered our five favorite Caribbean resorts under the Margaritaville umbrella for you, including the company’s freshest new all-inclusives, a unique boutique resort and even a vacation club. Whether you’re a full-fledged Parrothead, a beach seeker or a Caribbean aficionado, you’ll find a group of well-run, thoughtfully-designed resorts that exemplify the best of the beach life. 

Margaritaville Island Reserve by Karisma Cap Cana, Dominican Republic If there’s a “flagship” Margaritaville resort in the Caribbean, it’s this 228-stunner in the tony Cap Cana enclave of the Dominican Republic’s tourism hub of Punta Cana. The resort, which is also home to 40 villas (all of which have their own private balcony pools), is set on the spectacular Juanillo Beach, with a signature St Somewhere Spa, a Gourmet Village with a number of restaurants and bars in a walkable format and even the only Landshark brewery in the Caribbean.