Five Ways to Travel Like a Boss

Wailea Beach Villas

Everyone likes to enjoy the finer things in life, but there are certain experiences that transcend even mere luxury. Experiences that are so special, unique and expensive that only a true Boss will be able to enjoy them. Here are just a few of the many travel experiences anyone can partake in, as long as they’re a Boss.

Disclaimer – No one paid me anything for these mentions and I doubt they will. I’m also not angling to be invited on these experiences, though I certainly wouldn’t say no if offered. Rather, I chose these because they truly are exceptional experiences perfect for the true Boss.

1. Four Seasons Private Jet Experience So you want to do an around-the-world trip but can’t be bothered with commercial aviation? Well the Four Seasons Resorts has a deal for you. Over the course of 22 days guests visit 8 countries around the world, from Hawaii to India all on a specially designed private aircraft. A luxury outfitted Boeing 757 whisks 56 luxury-minded souls around the planet as they enjoy the best in air-based comfort. Once on the ground passengers stay at some of the best Four Seasons Resorts in the world, enjoying prime concierge service along the way. The staggering $62,950 per person fee covers everything from flights to hotels and even excursions and meals. With all of those pesky details out of the way you can truly travel like the boss that you are.

 Wat Arun

2. The Ultimate Cruise – One of the world’s top cruise lines announced last year what must be the most expensive cruise on the planet. For a mere $1.5 million guests may board the Silversea Silver Whisper for an incredible 124-day adventure around the planet. If they’re leaving from Europe, passengers are flown on a private jet to the US where a Rolls Royce Phantom will deliver them to their ship and home for four-months, the massive 1,000-square-foot Royal Suite. The ship visits 28 countries all around the world and there are plenty of extra perks associated with this package including helicopter pick up from home (because we all have a helipad) pre- and post-cruise accommodations worth tens of thousands of dollars and I’m sure many little surprises along the way. So if you’re a boss who likes to be pampered on the high seas, this is the trip for you.


3. Route 66 in Style I think most of us dream of doing a great road trip one day, and one of the most famous is Route 66. Stretching from Chicago to Los Angeles, Route 66 came to define American post-war wealth and expansion and for many Americans it truly is the personification of the American dream. That doesn’t mean you have to drive like a schlub though, you’re a boss after all! I found a company that doesn’t just facilitate Route 66 tours, they do it in style. For between $7,000-$11,000 depending on what options you choose, you can drive a vintage 1967 Camaro SS, 1964 Corvette Sting Ray or 1955 Chevy Bel Air along the route that came to define America. These aren’t old clunkers either, they’ve been completely restored and even retrofitted with the latest amenities. Even if you manage to get into some mechanical trouble, they provide on-call professionals along the way to repair your car for you. This is the ultimate American dream trip and perfect for the ultimate boss who wants to travel in style.

 Rose Island, Bahamas

4. Private Island – The ultimate dream for any boss must be living a luxury lifestyle on a private island. These vacations don’t have to be crazy expensive though, in fact some island getaways around the world start anywhere from $100-$500 per night. One that particularly caught my eye is Calivigny Island in Grenada. This beautiful private island situated in the Caribbean can be rented out completely for a mere $14,000 a week, which actually isn’t that bad given the fact that it can sleep up to 50 people. Traveling with your extended family isn’t a boss thing to do though, so make sure it’s just you and your love when you book this island retreat for your next vacation.

Treasury at Petra

5. Visit Every UNESCO World Heritage Site – So you love history and culture and want to visit a few UNESCO World Heritage sites? How about visiting every one of them, all 962 them in nearly every corner of the world. That’s what the high-end company has put together at the competitive price of $575,000. Granted the itinerary is TWO YEARS LONG and covers all travel costs in at least business class accommodations, excursions, tours and accommodation in luxury hotels. Given how long this trip is and how very much it costs, you have to be one hell of a boss to tackle this adventure.


Honorable Mention: Space – Space tourism is slowly advancing and before long we’ll all be able to enjoy a suborbital flight around the planet. Until that time it will just be reserved for the most wealthy amongst us, especially since prices start at $200,000 to join Virgin Galactic as a Pioneer Astronaut. This includes a guaranteed seat on one of their first ships to launch into space where guests will get to enjoy zero-gravity fun with four other fantastically wealthy passengers. This is all still a fanciful dream at the moment, but I wager we’ll be there before we know it.

What other ways can people travel like a Boss?

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

7 thoughts on “Five Ways to Travel Like a Boss”

  1. Love the idea of the unesco sites. I had not heard of it before. When touring Angkor Wat I decided I wanted to see all the unesco sites, but, boy that list is a lot longer than I originally thought!

  2. Zaid -

    4 months on board a cruise ship? I don’t consider that luxurious. I just spent 3 weeks on a ship and below deck you are breathing in air conditioned air and the cruise only has a limited (yet large) selection of food to choose from. At some point you want to be sleeping in a different environment.

    Perhaps travelling like a boss would be having your own team of porters accompanying you on your trip, assisting you wherever you go (I have seen Arab families travel like this)

  3. Maybe I’m nuts, but $575K to visit every UNESCO site in business class accommodations actual sounds pretty reasonable. I still can’t afford it….

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