Charter 101: Private Jet Travel to the Caribbean

Photo taken in Baraterre, Bahamas. Photo Credit: EyeEm Mobile GmbH, iStock / Getty Images Plus

Autumn in the 21st century is a time beloved by marketers. Pumpkin spice, cozy sweaters, vivid leaves – it’s not just the relief from the summer heat that appeals to the public. However, hidden behind the bright exterior is the knowledge that (to coin a phrase) winter is coming. Grey days, bare trees, chilly rain or sleet – we’re headed for the season that inspires daydreams of being elsewhere.

For those seeking a contrast, what better place to fantasize about than the Caribbean? Pristine beaches, palm trees, pleasantly warm weather, blue skies – all sound much better than slogging through day-to-day winter life in North America or Europe. For those in the U.S., getting away from it all without jet lag is an added bonus. The only fly in the ointment is the travel process – long flights with stops or plane changes that run the risk of delays or cancelations due to weather.

There is another option for the Caribbean dreamers, though – private jet travel. Rather than fighting your way through cranky masses at large airports, you and your loved ones can set a custom-made itinerary that lets you make the most of your sojourn in paradise. If this sounds like a tempting possibility, read on.

A Little Bit Here, A Little Bit There

The first thing to keep in mind about the Caribbean is that it is most definitely not one amorphous, homogenous travel destination. Wikipedia – which defines the region as “a subregion of the Americas that includes the Caribbean Sea and its islands” – has a “Countries and territories list” that includes about 40 different entities in the area.

While some are their own countries -- such as The Bahamas, Cuba, Jamaica and Panama -- many others are territories of larger nations, including Turks and Caicos (U.K.) and the U.S. Virgin Islands. And, while Bermuda is technically in the Atlantic Ocean rather than the Caribbean Sea, it often is considered as part of the Caribbean for travel planning purposes. Each place has its own character.

“Every little island and every little spot is totally different,” says Jason Firestone, president of the Private Client Group for private aviation company FlyHouse. “People think of it as an extension of Florida, but it’s not.”

While some distinctions are relatively superficial – such as which side of the road vehicles drive on – others may be more relevant to travelers. Those journeying to the Caribbean cannot assume that the visa and customs requirements in one location apply to another. What works smoothly for one location may gum the works up in the other.

Bermuda. PHoto Credit: Matt Henry Gunther, The Image Bank / Getty Images

And there can be other, less common complications. “If you’re going to Bermuda, one of the challenges is that there are dead radio zones in the Atlantic between the U.S. and Bermuda,” says Marcela White, co-founder of charter operator Tavaero Jet Charter in Houston, Texas. “You have to use high-frequency radios, which aren’t typically how aircraft communicate anymore.” (She has no reports of flights mysteriously disappearing in the Bermuda Triangle, however.)

Selecting a charter broker or operator familiar with the region can help smooth your way. “You really need to pay attention to all of the details when you’re doing this,” Firestone advises. “If a passport number is off, if you don’t file for the right destination, you’re going to be denied and have to re-file.”

Island Time

Selecting your preferred Caribbean destination is only the start of the process. There are certain aspects to life in the region that travelers must consider when figuring out how to get from point A to point C. “You really need to think carefully about departure times, because in a lot of these places, you find that a 9 to 5 customs office is literally only open from 9am to 5pm, with no overtime,” Firestone mentions. “They’re really strict on it.”

In some locations, short runways will limit the types of aircraft that can land. While travelers to larger destinations such as Puerto Rico or Sint Maarten will have a range of options for their chariot in the air, those headed to smaller locations may need to rely on seaplanes or turboprops.

Soufriere, Saint Lucia. Photo Credit: David C Tomlinson,
The Image Bank / GETTY IMAGES

In some cases, it may make sense to mix and match flights if seeking to minimize the travel time involved. “A lot of my New York clients would fly directly down from New York to Marsh Harbor or take a commercial flight to West Palm Beach and then take a seaplane,” says Samantha Middlestead, trip coordinator for FlyHouse Private Client Group, of her time coordinating travel for a resort in The Bahamas. “They could land directly on the island and head straight to the resort rather than relying on a boat ride.”

For those looking to explore multiple Caribbean destinations, charter flights can be invaluable. Commercial flights have limited options for point-to-point travel in the area. Flying private is typically a lot faster and easier than taking a boat and will likely give you more room for luggage as well, along with allowing you to use smaller island airports that don’t necessarily have room for commercial jets.

“There are a lot of logistics and moving parts that have to be considered,” Firestone says. “There are some perks to going private and working with a team well-versed in it.”

Stormy Weather

Unfortunately, even in paradise, some rain must fall – and sometimes, the amount is overwhelming. The high levels of humidity and warm air that draw travelers to the Caribbean also provide a nigh-perfect environment for hurricanes, which can range from inconvenient to outright dangerous for visitors. Caution around tropical storms is the primary reason that the “slow season” for travel to the Caribbean spans roughly June to November, the time period during which almost all major hurricanes have occurred in recorded history (with activity typically peaking in August and September).

For those hoping to spend July 4 or Labor Day in the Caribbean, there can be some advantages – fewer fellow tourists crowding the beach and lower resort rates, to name a few. Hotels may close for a time for annual maintenance, but rarely stay shuttered during the entirety of hurricane season.

Divers explore coral reef in dominica. Photo Credit: Dsabo, iStock / Getty images plus

Calle Reina Isabel Street in Puerto Rico. Photo Credit: Maremagnum, Corbis Documentary / GEtty Images

For those willing to take a bit of a risk, travel insurance can mitigate the impact of a storm on a vacation; however, no insurance can magically stop commercial airlines from canceling flights when bad weather approaches. If you’re flying private, you usually have many more options. Your charter broker or operator can work with you to reschedule your trip home on the fly (pun intended), with no worries that the flight will leave without you if you’re delayed by packing or traffic.

Middlestead was in The Bahamas when Hurricane Matthew hit in 2016. While The Bahamas wasn’t as badly hit as Haiti, which experienced nearly $3 billion in damage, the Category 5 storm hit Grand Bahama hard, with trees, power lines and homes all taking the brunt of the wind and rain.

Middlestead’s employer regularly used a Challenger 850 aircraft to shuttle guests to and from New York. The club loaded all of its expatriate employees onto the plane for an escape to Florida, with six of their pet dogs going along for the ride. “They could bring all of their stuff and didn’t have to stress out about what they were going to pack,” Middlestead recalls.

Parrots, Palms, Shells and More

Caribbean travel experts caution would-be private jet travelers to remember that one commonality among local regulations is the requirement that passports must be valid for at least six months for those looking to enter from other nations. Your charter broker or operator may be able to work with you to get a passport renewal expedited but don’t leave this part of travel planning until the last minute.

However, those familiar with the region say that all of the details and planning are worth the effort to leave the mundane world for a tropical idyll, be it a honeymoon in St. Lucia, a beach hang-out in Anguilla, diving in Dominica, historic sites in Puerto Rico or whatever catches your fancy. “It’s a fabulous place to go,” Firestone says.

Take a look here for your charter operators in the Caribbean.