Fly With Me to South Africa

Fly With Me to South Africa

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Do you want to live the fly life for yourself? Do you want to connect with places, people, and yourself in life-changing, long-lasting ways? Do you want to transform your life and become a true world citizen?

Then FLY WITH ME: Ernest White II, host and creator of FLY BROTHER.

FLY WITH ME experiences are all about exploration and transformation. Join Ernest as he revisits some of his favorite destinations and combines cultural exploration with personal growth and empowerment. Featuring lifestyle and business coach Michelle Lynn Adderley, local language and culture experts, and specially curated experiences, these week-long adventures—each limited to ten carefully selected participants—help you reinvent yourself in unexpected, life-affirming ways.



Fly with me to SOUTH AFRICA

18-27 October 2018
Cost: USD 3,999*

Connect with a people, a place, and yourself on this week-long adventure to bustling Johannesburg and breathtaking Cape Town.

On this experience, EVERYTHING will be taken care of—from airport pick-up to drop-off. Three meals per day, guides, ground transportation, admission, accommodation, tips, everything.

You don’t even need to bring any money with you at all if you don’t mind skipping souvenirs and alcohol, because those are the only things not included in the package. Well, maybe we’ll throw in a couple of cocktails. 😉

There’s only one word to describe this adventure: FLY.


The People

There will be up to 10 spots open on a first come, first served basis (initial deposit payment secures your spot—see Cost below). Participants must be at least 21 years of age.

You’ll be accompanied for the extent of the experience by Ernest White II and Michelle Lynn Adderley. We will be joined at varying intervals by a local assistant, a driver/guide, language and culture instructors, the housekeeper, cook, and security staff.

We will be with each other every day on a semi-fixed schedule. There is plenty of free time for exploration and relaxation away from the group, if you so desire, though there will be no refunds or discounts for skipping an included activity.

Accommodation in Johannesburg and Cape Town will be in double rooms, and you’ll be paired with another participant of the same sex, or of your choosing (single room supplements available—see Cost for more information).

Remember that part of the beauty of travel is connecting with new people. Lifelong friendships, romances, and business relationships can all form on this adventure. Be open and connect!

FLY BROTHER and South Africa

My first trip to South Africa was in 2014, as part of a press excursion to experience South African luxury and the glamour of Cape Town Fashion Week. I formed one of a group of eight journalists, all sponsored by South Africa Tourism. We spent a few days in the “City of Gold,” Johannesburg, before crossing the breathtaking wilderness aboard The Blue Train, a 19th-century passenger train in the style of the Orient Express. We finally arrived in Cape Town and stayed at luxury hotels, ate gourmet meals, and had near-front-row seats at the fashion shows. And I hated it. I couldn’t take the pretense, the over-hyped showmanship, and the shallowness that comes baked into the cake of Fashion Week. I also met some warm and wonderful people in both the fashion and tourism industries who I can count among my best friends, and they encouraged me to come back and give Cape Town another try.

On my second trip to the city, I spent more time interacting with local Capetonians of all backgrounds, and I fell in love the place as it grew to love me. In fact, I vowed to at least spend a couple of months in the Cape every year and even filmed an episode of the upcoming Fly Brother television show there. Then, there’s the exhilarating buzz and thrill of Johannesburg, Africa’s leading business hub and financial capital of the country; you’ll love it! I want to share the beauty and majesty of the place and its people with everyone.

Won’t you come with me to South Africa?

-Ernest White II


In Johannesburg and Cape Town, we will spend eight nights at two spacious, but tranquil villas near the heart of both cities. A hot breakfast is included at the villas each morning, and you will share a comfortable double room with a participant of the same sex or of your choosing. You can, however, arrange for a private room for a supplemental cost (see Cost, below). Aside from three meals per day, there will be plenty of healthy snacks and beverages available as well.


The total cost for this experience—excluding airfare and medical insurance—is $3,999 per person. Remember, this trip is about elevating, upgrading, and living a life of reasonable recklessness. The lifelong connections and endless possibilities you create for yourself will be beyond any price tag.

There will be 10 spots open for this trip. In order to secure your spot there will be a non-refundable $500 deposit required by 1 March 2018. First come, first served. (The deposit will be applied to the trip balance.)

A second payment of $500 will be due on 31 March 2018.

The balance for the entire trip—a final payment of $2,999—will be due 60 days before the start date of the trip (19 August 2018). If your payment is not received by that day you may lose your initial deposit/place on the trip (we will inform you when the date is approaching if we haven’t heard from you).

Pricing will be raised to $4,190 at 12:00am ET on 31 March 2018.

All prices are quoted in United States Dollars.

What the full payment includes:

  • 9 days/8 nights of accommodation in Johannesburg and Cape Town (see Accommodation above)
  • Rooms are double occupancy. If you are not traveling with a companion you will be matched up according to gender. If you want your own room this can be arranged for an extra $600.
  • One-way, economy-class flight from Johannesburg to Cape Town
  • Airport pick-up/drop-off
  • 3 meals per day
  • Unlimited bottled water
  • Guided tours to Soweto, Maboneng, Table Mountain, Robben Island, the Cape Peninsula, and a two-day Hop-on/Hop-off bus pass in Cape Town
  • A professional photographer during part of the journey
  • A community service project in a township in Johannesburg
  • A murder mystery dinner experience at a wine estate in Cape Town
  • Souvenirs, keepsakes, and swag
  • Guide, instructor, and staff gratuity
  • All taxes and surcharges
  • Smiles, laughter, and amazement

What the full payment does NOT include:

  • Flights to/from South Africa
  • Travel medical insurance (required)
  • Alcohol, except during the murder mystery dinner experience
  • Souvenirs

Payment methods include cash, check, money order, or PayPal (you assume fees). Please email us if you need information for sending cash or mailing a check or money order. You must provide proof of medical insurance that will cover you in South Africa for any emergencies at least 30 days before the start date of the trip.

Weather and Clothing

October is a spring month in the Southern Hemisphere, and average temperatures in Johannesburg are mild-to-warm during the day (75°F/24°C) and cool at night (52°F/11°C). Jozi is located on the highveld plateau at 5,750 feet (1,750 m) above sea level, with a subtropical highland climate. It rains some late afternoons and evenings during this time of the year, but daytime usually means sun.

Cape Town is also generally mild during the day (70°F/21°C) and a bit cool at night (52°F/11°C). Cape Town has a Mediterranean climate with air that tends to the drier side in the spring, with many days of sun and an average of 9 cloudy days during October. Typically, late October sees days warm enough for the first of the coming summer’s beach-goers to venture out into the water, but, being spring, there’s no guarantee.

What to wear? Johannesburg is a center of commerce and industry, so attire trends towards business casual. A collared shirt may look more appropriate than a T-shirt, even in daytime in Johannesburg. Conversely, Cape Town is a very casual city, but also very fashion-forward in the smarter parts of town, so bring clothes that are the right combination of comfortable and stylish. A windbreaker jacket and hoodie or fleece is recommended for nighttime, but during the day jeans, khaki shorts/pants, T-shirts, etc. are all fair game. Four dinners and the murder mystery experience will be in upscale venues, so please bring attire suitable for a three-course meal. We’ll send you a full packing checklist to make sure you don’t forget anything—no worries there.


You take a risk leaving your house every morning and it pays to be street smart everywhere in the world. South Africa is no exception. Sadly, Johannesburg is known for street crime, much like Miami, Baltimore, or Detroit. The point, however, is to be aware without being afraid. Stick with the group as much as possible and leave all valuables at the villa.

Cape Town, on the other hand, is one of the most stable, crime-free cities in Africa. In the rare event crime does happen, it is almost solely crimes of opportunity by the poor to make some extra money—e.g. grabbing your bag or camera when you’re not looking. Violent crime is exceedingly rare, especially against tourists.

Even still, theft is not a major concern, as most employees in the service and tourism industries wouldn’t risk their jobs stealing anything. Sometimes have to watch out for baboons though… (Only half-joking.)

That said, you are required provide proof of travel health and trip protection insurance at least 30 days before the start of the trip.

As far as animals go, there is the very small chance that we really might encounter some baboons, especially while touring the Cape Peninsula. Please familiarize yourself with these techniques in case of a baboon encounter.

Visas and Immunizations

Visas to enter South Africa as a tourist are not required for U.S. citizens. However, you should have a minimum of six months’ validity in your passport and at least two blank pages. Tourists are typically allowed 90 days to travel within South Africa every 180 days.

If you are not a U.S. citizen then please check here for visa information regarding your nationality.

South Africa doesn’t really have any more communicable diseases than many of the other spots you might travel.

There is a slight risk of malaria, however it is more along the northeast of the country than the far southwest where we will be. Please talk to your travel medical specialist if you would like to bring anti-malarial medication with you (there are a few different types, but they all have their side effects—I choose to go without and just use longer clothing at night, though mosquitoes aren’t as prevalent in Cape Town).

Zika prevalence is low (lower than the U.S.). Ebola is virtually non-existent (there have only ever been two confirmed cases of the disease in South Africa, back in 1996, when a medical professional from Gabon traveled to Johannesburg after treating infected patients; he was hospitalized and the nurse who took care of him became infected and died).

If you’re coming straight to South Africa from a yellow fever-endemic country (click here for a list), you will be required to show proof of vaccination upon arrival at the airport.

As far as immunizations go, just make sure you are up-to-date on your usual foreign travel stuff—tetanus, typhoid, diphtheria, meningitis, etc. (Most of us should have already gotten the Hepatitis A+B vaccine in childhood.)

Getting There

The airport you will be flying into—arriving 19 October 2018—is OR Tambo International Airport in Johannesburg (JNB) and the airport you will be flying out of on 27 October 2018 is Cape Town International Airport (CPT).

From North America, the most direct routes to South Africa are on South African Airways from New York-JFK or Washington-Dulles to Johannesburg, and on Delta Air Lines from Atlanta. It is also possible to connect via major African, European, or Middle Eastern airline hubs.

From Europe, there are several nonstop flights, while travelers from South America, Asia, and Oceania will most definitely have one or two stopovers. Antarcticans, you’re SOL at the moment.

If paying for the flight (as opposed to using air miles), you can expect to pay between $800 and $1,900, depending on the date, departure city, and number of stopovers. A great tool to check all of the options available is Google Flights.

If leaving the U.S., it will take you a minimum of 19 hours to arrive in South Africa, so look for flights leaving no later than Thursday 18 October 2018. (Just make sure to get in at the very latest the evening of Friday 19 October 2018.)

We will meet each of you at the airport personally and manage your transfer to the villa in Johannesburg.

Fine Print

This is travel, and unexpected things may happen. Although we will do everything in our power to assist if something goes wrong, you get sick, etc, we are in no way legally responsible for your well-being during the duration of the trip. By signing up for this trip you are acknowledging this fact. You are required to show proof of travel medical insurance no later than 30 days before the start of the trip.

In addition, although we are pretty set as far as the schedule because the guesthouse and food are pre-booked, there may be things we may not get to see because of weather, bad luck—who knows. The schedule may be changed due to inclement weather, but a suitable replacement activity will be arranged in the case of an activity being canceled. All activities are voluntary, but no discounts or refunds will be issued for those who choose not to participate in the planned activities.


Image credit: South African Tourism



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