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Wall Street’s vacation hot spots for the winter

"You're out next week?" my trading assistant asked during lunch. "Where are you going?"

"Nevis," I said. "The Four Seasons."

"Where's that?"

"The Caribbean," I said. "I think..."

The truth was I didn't really know where Nevis was. But I wasn't worried. A friend of mine who owned his own brokerage firm and was worth north of $50 million had recommended it to me. How bad could it be?

Perhaps I should have done a little more due diligence when I was planning my trip, but that's how most vacations are conceived on Wall Street—word of mouth. We take suggestions from our peers and superiors. And this is what we want to know: Where to stay, how's the nightlife, what are the dining go to spots and what is there to do during the day like a day trip or something? An added bonus is a hookup to a local. Like I was told that Jimmy, the guy behind the bar at Sunshines, could get me anything I wanted—anything. And the bar just happened to be conveniently located next door to the Four Seasons in Nevis. And my friend was right—Jimmy could — and did — get me everything I wanted.

Wolfgang Kaehler | LightRocket | Getty Images

But Nevis is so 10 years ago. I spoke with traders, sales traders, bankers and analysts recently to find out where they're vacationing in 2016. The majority of them were traveling to a new destination, but places that were recommended by someone they work with.

I had to make the distinction between a vacation and a "real" vacation. Within the Wall Street vernacular the world "real" has significant meaning. The difference is about $20,000 or so.The Vegas, South Beach and Deer Valley trips are more of a jaunt — weekend getaways. A "real" vacation requires dropping about $25,000 for first-class plane tickets, a week's stay in a five-star hotel and no expense spared once they're on the ground.

"Let all the accountants and ad executives use TripAdvisor," one hedge-fund trader told me. "I just listen to the guys at my shop. They know how to vacation." He told me he's got a trip coming up in March. "My boss told me to go to Eden Rock in St. Barts. He says it's sick."

Here's a list of this year's most popular vacation spots and feedback from people who've been there:

If you want everyone to think you're getting engaged, then go to…

Katikies Hotel in Santorini, Greece

Katikies Hotel in Santorini, Greece
Source: Katikies
Katikies Hotel in Santorini, Greece

"I'm going to Santorini to score points," a portfolio manager told me who has an upcoming trip. "The way I see it, this outing will get me about six months of no nagging from my girlfriend when I'm out entertaining clients all year."

The Katikies Hotel oozes romance. Many of the people I spoke with had already been there. It's kind of a go-to spot for Wall Street, but it's hard to get in trouble on this island. You need a day trip to Mykonos if you're looking for signs of nightlife. The most popular activities are sailing, shopping and sight-seeing. Well at least the traders I know won't have to worry about smuggling Xanax on the plane.

If you don't care what the island is really called then go to:

Eden Rock in St. Barts

Eden Rock in St. Barts
Source: Eden Rock Hotel
Eden Rock in St. Barts

"Dude… I've heard it called St. Bart, St. Barthelemy, St. Bart's and St. Barth's," a senior sales trader told me. "I have no idea, but I'm going anyway. Me and the wifey heard it's got killer spots to dive."

You need to come in by twin-engine prop plane from St. Maarten or by boat. And the island has been able to keep it's old-world charm by limiting hotels to only one and two-story buildings.There are no signs of any Caribbean Islands eyesores that you'll find on other islands like time-share salesman and poorly built and poorly managed fast food chains. Seriously, if you're craving a Whopper on vacation then you should probably plan a different trip.

If you want to do what everyone has already done, then go to …

One & Only Ocean Club Resort in the Bahamas

One & Only at Ocean Club Bahamas
Source: One and Only Resort
One & Only at Ocean Club Bahamas

"I'm going because it's convenient," a hedge-fund trader told me. "I've been five or six times before, but it's so easy to get to and everything is taken care of by the time I land."

This is probably one of the most popular Wall Street destinations. I'd be hard-pressed to find someone who's been in the business for 10 years and had some success that has not been here.The hotel is peaceful, but the nightlife gambling is a quick taxi ride away. And when you're sick and tired of the beach and or pool, it's easy to charter a yacht for the day—just don't forget your American Express black card.

If you want to get off the grid then go to …

Four Seasons in Bora Bora

Four Seasons in Bora Bora
Source: Four Seasons
Four Seasons in Bora Bora

"I don't want to see anyone from Wall Street," a senior analyst told me. She said she was going away with her husband for two weeks. "It's unlikely that I'll be able to avoid New Yorkers, but hopefully I won't see anyone from the business."

Most people choose the Tahiti vacation for rest and relaxation, but this island is also on the adventurous side. There are all of your typical water sports and 4x4 safaris — you can even watch shark feedings and swim with the turtles if you're into that kind of thing.

If you are looking to get deviant then you should get a …

House rental in Costa Rica

House rental in Costa Rica Dream Makers
Source: Dream Makers
House rental in Costa Rica Dream Makers

"I'm going with a bunch of clients and friends," a sales trader told me. "We're going for the surfing and the girls." He told me he takes clients to exotic locations about twice a year and they're always looking for new spots.

Costa Rica is like Vegas on the beach, but without the gambling.

Honorable Mentions:

Jashitatotel in Tulum, Mexico. Going to Tulum is like graduating from Cancun. It's the next step.

Capjuluca in Anguilla. Capjuluca is referred to as the No. 1 resort in Anguilla for luxury resorts and hotels. And sometimes even the Caribbean, but in recent years it's been considered a predictable trip and not as easy to get to as the Bahamas.

Aman in Turks & Caicos. Aman checks almost all of the boxes — convenience, airline options, turquoise water, activities and culture. It's a great place to be pampered.

Wall Streeters don't vacation like normal people. They just want confirmation from someone who has gone before them. Cost isn't really an issue. And if they end up booking the trip before actually know where it is – it's a small matter. They'll just Google it before they get on the plane!

Commentary by Turney Duff, a former trader at the hedge fund Galleon Group. Duff chronicled the spectacular rise and fall of his career on Wall Street in the book, "The Buy Side." He's also a consultant on the upcoming Showtime show, "Billions," starring Damian Lewis and Paul Giamatti. Follow him on Twitter @turneyduff.