25. Jimmy Buffett - $600m

25. Jimmy Buffett - $600m

You've probably seen the term 'island escapism' used to describe Jimmy Buffett's musical style through the years. With the money it's earned him, he could probably afford to go out and buy one. His fans, who are for some reason known as 'Parrotheads', have bought Buffett a lifestyle worthy of a tropical paradise.

One of his most well-known hits is the song 'Margaritaville', and he liked the title so much he turned it into a business empire. You can visit the Margaritaville Cafe or the Margaritaville Retail Store, listen to Radio Margaritaville, read his novel 'Tales from Margaritaville' or risk your money at the Margaritaville Casino. If you're lucky, the music in the background may have been recorded by Margaritaville Records. There's also Margaritaville themed real estate available, and even an online game! Branding is important in business, and Buffett seems to have the theme nailed.

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Did You Know...

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Wondering where to go in 2020 for an amazing deal, to beat the crowds, or for a truly once-in-a-lifetime travel experience? These destinations are on travel addicts’ radar for rightfully hyped 2020 events, new offerings, and recent developments that make them a must-visit right now.

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On top of the majestic scenery its long been known for, Montana is a newly trendy nature getaway celebrated for its expanding luxury hotel scene, culinary offerings, and shop-local boutiques, according to an American Express study detailing where cardholders are traveling in 2020. But Montana is also about to get more accessible than ever before thanks to emerging flight routes sure to stir up competition. Launching two brand-new seasonal routes to Big Sky country, American Airlines will fly from New York’s LaGuardia Airport to Bozeman and Kalispell, Montana, beginning mid-year and continuing through Labor Day. Take advantage of the new direct route before the secret gets out, and so that they’ll continue next year.

III

One of the cities featured in Booking.com’s travel trends for 2020, Urugay’s capital Montevideo is a stable and LGBT-friendly destination to visit in South America—a continent that’s seen dips in tourism of late thanks to political instability in travel destinations like Brazil, Chile, and Argentina. Travelers identified the city as a trending travel destination for anyone seeking an immersive, one-stop escape; according to the study, “over half (54 percent) of global travelers say they want to go on one long trip to a place that has all of their favorite activities and sights close together.” Montevideo’s offerings include beaches, nightlife, markets, theaters, culinary prowess, and festive Gay Pride Day celebrations in September.

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Europe’s intensely overtouristed spots (Venice, Barcelona, Santorini) have new Eastern European hotspots to thank for stealing away some of the spotlight: Romania is making a name for itself as one of the top five most trending Airbnb booking destinations for 2020. The nation that’s home to Transylvania, Dracula’s castle, and well-preserved medieval towns nestled among rolling hills has seen a 298 percent annual increase in Airbnb bookings.

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