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Top 10 Vacation Destinations Of The Rich And Famous

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Written by Timothy Sykes
Updated 3/20/2023 7 min read

UPDATE: Here’s a little birthday surprise from me to you: use coupon code TIM32 HERE on any annual subscription and see what happens for a limited time only though 🙂

My trading challenge students have had great success the past few months with over a dozen of them up $50,000+ in the first three months of 2013 already…it’s no wonder they’re getting more interested in how to put some of their profits to use whether its paying off their mortgages, their children’s college educations or my favorite, luxury travel!

Thanks to this great female penny stock trader and student who you should follow on Twitter for putting together this list of vacations spots of the rich and famous 🙂

Check it out:

Tim loves to travel to exotic places, and other wealthy individuals are no different. Check out ten of the most popular get-away destinations of the celebrities, millionaires and billionaires. Tim has been to a few of them, so check out his YouTube Channel to see videos and find out which ones.

First we have Vegas. Tim actually holds his annual pennystocking conference here, so you can go to the popular destination if you sign up! With drinking, gambling and strippers, this place is great for those who want to get their minds off of everything. The city of sin is home to 13 of the world’s 20 largest hotels, with famous restaurants, shopping, theatre shows, night clubs and more. As always, remember that what happens in Vegas, stays in Vegas.

Image via Expedia
Image via Expedia

Next we have Monaco. Since it is tax free, it is a great spot to really go all out. The individuals making the visit are met with rich history. Located on the French Riviera in Western Europe, this gorgeous city overlooks the blue waters of the Mediterranean. Not only is it gorgeous, but there are yachts, casinos, and some of the world’s top hotels. You can also taste food and champagne from some of the best restaurants in the world.

Image via miriadna.com
Image via miriadna.com

Third we have Dubai. Luxury and Dubai go hand in hand. With a seven-star property, the world’s tallest tower, manmade islands, underwater hotels and buildings that spin like a Weeble with an inner-ear infection, the city of Dubai is bar none the best at making headlines. It has built an entire tourist industry out of people’s curiosity. If you find yourself with 24 hours in the city, you’ll have no shortage of things to do. This United Arab Emirates destination is on every billionaires list.


Up next is Ibiza. Sometimes called the “clubber’s heaven,” this place is extremely popular among celebrities. Although it is famous for having some of the best nightclubs in the world, the island also has more than 100 miles of stunning coastline with dozens of tiny coves and more than 50 beaches to explore. You’ll have to fit in time to visit some of the exquisite restaurants and area culture. You’ll also have the option of staying in some of the most sophisticated hotels in the Mediterranean.

Image via paradiseintheworld.com
Image via paradiseintheworld.com

St. Barts is fifth on the list. The Caribbean get-away draws in billionaires to immaculate beaches, especially during the winter months. The island of just eight square miles offers a fair amount of privacy as well. You’ll find luxury yachts, designer boutiques, and celebrities, including the likes of Alicia Keys, Mariah Carey, and Jay-Z.

Image via saint-barths.com
Image via saint-barths.com

The Maldives is a rather popular destination for our very own Tim Sykes. Last year he actually took two trading challenge students to the island as a reward for working so hard. It has been reported that Sir Philip Green flew 100 guests in two private jets to the island for his 55th birthday. The gorgeous water, unrivaled seclusion and tranquil beaches draw in big names like Naomi Campbell. Who can blame them when websites like visitmaldives.com say “Welcome to the Maldives, where sands are white as the smiles of the locals, where fish swim happily in the warm waters of the Indian Ocean, where the weather is a dream, and the deep rays of the sun wait to engulf you their arms.”


Hvar has made it on the list even though I have not heard of it before. Some call it the new St. Tropez of Europe with the mega-rich flocking to the Mediterranean coastline. Bill Gates, Steven Spielberg and Eva Longoria are among the big name stars that like to visit. With lush vineyards, hills covered in blooming flowers, gorgeous beaches, secluded coves, restaurants, boutiques, and a vibrant nightlife, I can see why it is the ideal get-away.


Bora Bora is definitely one of the destinations that I had heard of. Located in the French Polynesia, this “Pearl of the Pacific” draws in honeymooners and the high-end crowd alike. Surrounded by a lagoon and a barrier reef, this gem is a major international tourist destination, famous for its aqua-centric luxury resorts. Snorkeling and scuba diving in and around the lagoon of Bora Bora are popular activities, and if you’re feeling adventurous, many species of sharks and rays inhabit the surrounding body of water.

Image via destination360.com
Image via destination360.com

Next we have St. Tropez. Everyone shows off here. You can find everything from toddlers decked out in haute-couture outfits to glamorous grannies zapping around town on vintage Vespas. Also located on the French Riviera, the names aren’t the only big things here, some of the secretive yachts are bigger than a typical house.

Image via tumblr.com
Image via tumblr.com

Finally, we have Aspen. Celebrities obviously go for the best when they are looking to hit the slopes. This city in Colorado is most popular for its legendary ski resorts. The Aspen landscape is now home to celebs such as members of the Kennedy family, Goldie Hawn and Kurt Russell, Kevin Costner and Maria Shriver. The posh city offers handsome historic red-brick downtown and giant slopes that are certainly alluring, but many say Aspen’s greatest asset is its scenery. The magnificent alpine environment adds eye candy to an already glittering jewel.

Image via asyouwishcolorado.com
Image via asyouwishcolorado.com

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Timothy Sykes

Tim Sykes is a penny stock trader and teacher who became a self-made millionaire by the age of 22 by trading $12,415 of bar mitzvah money. After becoming disenchanted with the hedge fund world, he established the Tim Sykes Trading Challenge to teach aspiring traders how to follow his trading strategies. He’s been featured in a variety of media outlets including CNN, Larry King, Steve Harvey, Forbes, Men’s Journal, and more. He’s also an active philanthropist and environmental activist, a co-founder of Karmagawa, and has donated millions of dollars to charity. Read More

* Results are not typical and will vary from person to person. Making money trading stocks takes time, dedication, and hard work. There are inherent risks involved with investing in the stock market, including the loss of your investment. Past performance in the market is not indicative of future results. Any investment is at your own risk. See Terms of Service here

The available research on day trading suggests that most active traders lose money. Fees and overtrading are major contributors to these losses.

A 2000 study called “Trading is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors” evaluated 66,465 U.S. households that held stocks from 1991 to 1996. The households that traded most averaged an 11.4% annual return during a period where the overall market gained 17.9%. These lower returns were attributed to overconfidence.

A 2014 paper (revised 2019) titled “Learning Fast or Slow?” analyzed the complete transaction history of the Taiwan Stock Exchange between 1992 and 2006. It looked at the ongoing performance of day traders in this sample, and found that 97% of day traders can expect to lose money from trading, and more than 90% of all day trading volume can be traced to investors who predictably lose money. Additionally, it tied the behavior of gamblers and drivers who get more speeding tickets to overtrading, and cited studies showing that legalized gambling has an inverse effect on trading volume.

A 2019 research study (revised 2020) called “Day Trading for a Living?” observed 19,646 Brazilian futures contract traders who started day trading from 2013 to 2015, and recorded two years of their trading activity. The study authors found that 97% of traders with more than 300 days actively trading lost money, and only 1.1% earned more than the Brazilian minimum wage ($16 USD per day). They hypothesized that the greater returns shown in previous studies did not differentiate between frequent day traders and those who traded rarely, and that more frequent trading activity decreases the chance of profitability.

These studies show the wide variance of the available data on day trading profitability. One thing that seems clear from the research is that most day traders lose money .

Millionaire Media 66 W Flagler St. Ste. 900 Miami, FL 33130 United States (888) 878-3621 This is for information purposes only as Millionaire Media LLC nor Timothy Sykes is registered as a securities broker-dealer or an investment adviser. No information herein is intended as securities brokerage, investment, tax, accounting or legal advice, as an offer or solicitation of an offer to sell or buy, or as an endorsement, recommendation or sponsorship of any company, security or fund. Millionaire Media LLC and Timothy Sykes cannot and does not assess, verify or guarantee the adequacy, accuracy or completeness of any information, the suitability or profitability of any particular investment, or the potential value of any investment or informational source. The reader bears responsibility for his/her own investment research and decisions, should seek the advice of a qualified securities professional before making any investment, and investigate and fully understand any and all risks before investing. Millionaire Media LLC and Timothy Sykes in no way warrants the solvency, financial condition, or investment advisability of any of the securities mentioned in communications or websites. In addition, Millionaire Media LLC and Timothy Sykes accepts no liability whatsoever for any direct or consequential loss arising from any use of this information. This information is not intended to be used as the sole basis of any investment decision, nor should it be construed as advice designed to meet the investment needs of any particular investor. Past performance is not necessarily indicative of future returns.

Citations for Disclaimer

Barber, Brad M. and Odean, Terrance, Trading is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors. Available at SSRN: “Day Trading for a Living?”

Barber, Brad M. and Lee, Yi-Tsung and Liu, Yu-Jane and Odean, Terrance and Zhang, Ke, Learning Fast or Slow? (May 28, 2019). Forthcoming: Review of Asset Pricing Studies, Available at SSRN: “https://ssrn.com/abstract=2535636”

Chague, Fernando and De-Losso, Rodrigo and Giovannetti, Bruno, Day Trading for a Living? (June 11, 2020). Available at SSRN: “https://ssrn.com/abstract=3423101”