Local bar in Vieques. Photo: supplied
Puerto Rico itself is a contradictory experience. Colonised in 1509, it retains its Spanish roots in the language and in the relentless crow of roosters puncturing the steamy air in the heart of the capital San Juan. They will bring a smile to your face until you remember- they could be fighting cocks.
And yet, Puerto Rico is American. There are no customs or border patrol if you arrive from the mainland. Between the tiny bars selling tostones (fried green plantains), $1 cans of local brew Medalla and $5 pina coladas (Puerto Ricans claim they invented this quintessentially Caribbean cocktail), there are United States Post Offices and Walgreens "farmacias". The currency is the greenback.
This is America and yet is is not. The locals fiercely guard their heritage from North American influence (cockfighting, which is illegal in all US states, is protected as an 'integral' aspect of Puerto Rican heritage). Unlike Mexico and South America, where the history of pre-colonisation is etched into the stones of Chichen Itza and Machu Picchu, little survives of the original Taino culture on this island paradise.
But the calm turquoise waters and wild palm trees can't quite hide the island's brutal history; Puerto Rico is where you realise colonialism never really ended.
As an official territory of the US, Puerto Ricans are US citizens and they are flocking to the mainland in record numbers to escape the dwindling economy. Yet, in many ways, I feel it is the Puerto Ricans who have the worse deal.
The "small" island of Vieques is a 75 minute ferry ride from the territory's main or "big" island.
Its even smaller neighbour, Isla de Culebra, has a number of mainland Americans running shops renting snorkelling gear and kayaks. And, at least to the casual observer, there is an easy mingling between the locals and the foreigners.
Vieques, however, is a different story. In the coastal town of Esperanza, where my partner and I recently stayed, the hub of tourist activity is along the Malecon, a boardwalk running along the coast. Across the road, with glorious views of the Caribbean Sea, there is a strip of guesthouses, open air bars and operators running group kayak tours to the nearby Bioluminescent Bay, boasting the world's highest concentration of phytoplankton.
Nearly all of these thriving business are owned by mainland American and British "expats". Expats. Even the name we give to Westerners who migrate to other shores signifies the lopsided relationship the West has with the rest of the world.
No one would call a Puerto Rican living in mainland US an "expat"; they are called "immigrants", a word loaded with the burden of poverty and lesser status. The racism and discrimination faced by Puerto Ricans in the US is well-documented.
No such disadvantages meet the"gringo" Americans in Vieques. They flourish by offering slightly overpriced drinks and food, and grossly overpriced accommodation. At Duffy's, a bar opposite the Malecon popular enough to sell its own line of singlets, you will be served a Duffy's Sunset (the bar's name for pina colada, because even this, it seems, has to be Americanised).
Every night, tourists get roaring drunk, while across the road on the Malecon, a few locals sit and silently watch tourists spend more money in a night of drinking than they earn in a week.
What do they make of the fact that mainland Americans come to their island, not merely to play but to make loads of money?
The unemployment rate in Vieques is worse than any US state. Walk a few steps away from the Malecon and it won't be long before you come across families living in squalor. Some capture the wild chickens and horses that populate the island to use as sources of food and transport (public transport is virtually non-existent outside the capital of San Juan). Every third house has boarded up windows and every door and window is hidden behind jail-like bars; the high unemployment, unsurprisingly, manifests itself in high levels of petty crime.
"Stay away from the locals", a fellow traveller warned me, regarding the crime. "And you'll be fine."
Stay away from the locals? What then, is the point of travelling?
This is modern colonialism in action- a thriving tourist trade that seems to bypass the locals almost completely. As a traveller, you at least hope the money you spend in poorer communities gets fed back into the local economy. In Vieques, the money seems to go straight into the pockets of the "expats".
I have felt a certain sense of guilt whilst travelling before, at the way us Westerners gawk at locals, taking endless photographs without bothering to seek consent, and at the privilege that is proven by the mere fact we have the means to travel.
Never before, however, have I felt like I was part of such an overtly exploitative force.
The gulf between the locals and the tourists and expats was cavernous. While a few islanders work in the bars and restaurants, it is by far mostly young "expat" Americans raking in the tips and older Americans pulling in the profits. I soon felt uncomfortable paying for my hostel (owned by a British expat) and we began avoiding the expat establishments, seeking out the one local (and far more run-down) bar, and local tour guides. I refused to buy a sarong that caught my eye because an American woman was selling the Indonesian-made garments for $15 a pop at a makeshift stall by the beach.
If the locals shared my resentment, they didn't show it. A few Puerto Ricans raised in mainland US I spoke to, however, were more forthcoming with their feelings about the uneven state of affairs. "The Americans are taking over," one of them half-joked.
Is it possible to avoid exploitation when travelling? In some ways perhaps, but not in Vieques. It is here that Western privilege shows his true reach, extending beyond his own borders to entrench himself in a tiny Caribbean island where the locals will smile with embarrassment as they ask you to spare a dollar.
We left Vieques after just four days, feeling like it was at least two days too late. Later this week, we move on to the US Virgin Islands, another Caribbean hotspot whose colonialist past is still so present, it is written into its name.
And so it continues.