Stories
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April 3, 2025
How to Visit Cuba Today: Navigating Travel Bans, Family Ties, and a Timeless Culture
Traveling to Cuba, whether as a tourist or to visit family, offers a unique opportunity to experience its culture and connect with its people, despite economic challenges. Ensure compliance with travel regulations, bring sufficient cash, and engage respectfully with locals. For family visits, consider bringing practical gifts to support loved ones. The user’s emotional connection to Cuba, valuing its beauty and people, underscores the need for a more empathetic US approach, potentially lifting sanctions to alleviate economic hardships and foster better relations.
A few years ago, I stepped off a plane into the humid embrace of Havana, Cuba a place that instantly felt like stepping back in time. The air carried the sharp tang of diesel gasoline, vintage cars rumbled past, and the streets pulsed with a rhythm that’s hard to forget. I went as a tourist, but what I found was more than just a destination; it was a revelation. Cuba is an amazing country its people warm, its cities breathtaking, its spirit unbroken despite decades of hardship. Today, as I write this on March 31, 2025, I can’t help but feel a pang of sadness.
The island’s beauty stands in stark contrast to its struggles, worsened by policies like the U.S. embargo and, most recently, President Trump’s decision to slap Cuba back onto the state sponsors of terrorism list. Here’s what it’s like to travel there now—whether you’re a curious explorer or someone, like me, yearning to reconnect with family and why I wish we could do more for this incredible place.A Political Tug-of-War: Cuba’s Latest Chapter
Let’s start with the elephant in the room: Trump’s move in January 2025 to redesignate Cuba as a state sponsor of terrorism, undoing a brief reprieve granted by President Biden just days earlier (Reuters).
This isn’t new Cuba was on the list back in 2021 before Biden lifted it—but its return tightens the screws on an already strained economy. The U.S. State Department says it’s about holding the Cuban government accountable (Cuba Sanctions - United States Department of State), but critics argue it’s the people who suffer most, not the regime. Sanctions mean less trade, fewer dollars, and harder lives for Cubans already scraping by on an average of 4,648 Cuban Pesos a month—about $38.73 USD at the official rate of 120 CUP to 1 USD (Statista). I’ve heard tales of $20 monthly wages for educated folks, and while that might’ve been true years ago, today’s numbers still paint a grim picture when food and medicine are scarce.
Getting There: A Maze Worth Navigating Traveling to Cuba as a U.S. citizen isn’t straightforward, but it’s doable. There are no direct commercial flights from the U.S. thanks to tightened restrictions, so you’ll need to get creative. Charter flights from Miami exist. check with American Airlines (Cuba − Travel information − American Airlines)—or hop through a third country like Panama. I’ve done the Miami-Panama-Havana route myself; it’s a hassle, but the moment you see Havana’s skyline, it’s worth it. The U.S. allows travel under 12 categories, like family visits or “support for the Cuban people” (Legal Travel to Cuba Explained). No special license needed—just a valid passport, a tourist visa (grab it via the Cuban embassy or a travel agency), proof of return, and health insurance (U.S. Embassy in Cuba).
At Miami’s airport, expect a stop at the “Cuba Ready” booth to state your purpose—bring patience; it can take hours.The Cuban Reality: Beauty Amid StruggleLanding in Cuba feels like entering a living museum. Havana’s Old Town, a UNESCO gem, dazzles with colonial buildings and salsa beats echoing through the streets. Varadero’s beaches are postcard-perfect, and Trinidad’s cobblestone charm takes you centuries back (Condé Nast Traveler).
But beneath the beauty lies a harsh truth. The U.S. embargo, started in 1962, has left Cuba outdated—think crumbling infrastructure and limited tech (Council on Foreign Relations). Inflation’s soaring at 30% a year, and the ration system barely covers basics (BTI 2024 Cuba Country Report).
I remember walking past empty shelves and hearing stories of families stretching meals. It’s heartbreaking when you know how special these people are—resilient, educated, and kind despite it all.
My Journey: Tourist Meets Time Traveler As a tourist, I marveled at the 1950s Chevys and the faded grandeur of Havana’s Malecón. But it’s the personal moments that stick with me sharing coffee with locals who welcomed me like family, even with so little to give. Now, if I went back to visit relatives, I’d bring cash (Euros or USD, since U.S. credit cards are useless there) and essentials like clothes or non-perishables (Cuba Unbound).
The official exchange rate is 120 CUP to 1 USD, but there’s an 8% fee on dollars, so Euros might stretch further. Internet’s spotty plan on being offline and tap water’s a no-go; stick to bottled (State Department).Why Cuba Matters and What’s NextCuba’s not just a travel spot; it’s a testament to human spirit. The embargo and sanctions like those tightened in 2025 keep it trapped, unable to modernize or feed its people properly (The Conversation). I get it the U.S. and Cuba’s government don’t see eye to eye. But punishing an entire nation feels wrong when you’ve seen its heart. Obama’s 2015 thaw showed promise (CFR Timeline), so why not try again?
Lift the restrictions, let trade flow, and give Cubans a chance to thrive—not just survive.For now, if you go, go with purpose. Support local artisans, eat at paladares (private restaurants), or visit family with love and supplies in tow. Cuba’s a paradox poor yet rich, old yet timeless. It’s sad, yes, but it’s also beautiful. And it deserves more from us than a label on a list.
A few years ago, I stepped off a plane into the humid embrace of Havana, Cuba a place that instantly felt like stepping back in time. The air carried the sharp tang of diesel gasoline, vintage cars rumbled past, and the streets pulsed with a rhythm that’s hard to forget. I went as a tourist, but what I found was more than just a destination; it was a revelation. Cuba is an amazing country its people warm, its cities breathtaking, its spirit unbroken despite decades of hardship. Today, as I write this on March 31, 2025, I can’t help but feel a pang of sadness.
The island’s beauty stands in stark contrast to its struggles, worsened by policies like the U.S. embargo and, most recently, President Trump’s decision to slap Cuba back onto the state sponsors of terrorism list. Here’s what it’s like to travel there now—whether you’re a curious explorer or someone, like me, yearning to reconnect with family and why I wish we could do more for this incredible place.A Political Tug-of-War: Cuba’s Latest Chapter
Let’s start with the elephant in the room: Trump’s move in January 2025 to redesignate Cuba as a state sponsor of terrorism, undoing a brief reprieve granted by President Biden just days earlier (Reuters).
This isn’t new Cuba was on the list back in 2021 before Biden lifted it—but its return tightens the screws on an already strained economy. The U.S. State Department says it’s about holding the Cuban government accountable (Cuba Sanctions - United States Department of State), but critics argue it’s the people who suffer most, not the regime. Sanctions mean less trade, fewer dollars, and harder lives for Cubans already scraping by on an average of 4,648 Cuban Pesos a month—about $38.73 USD at the official rate of 120 CUP to 1 USD (Statista). I’ve heard tales of $20 monthly wages for educated folks, and while that might’ve been true years ago, today’s numbers still paint a grim picture when food and medicine are scarce.
Getting There: A Maze Worth Navigating Traveling to Cuba as a U.S. citizen isn’t straightforward, but it’s doable. There are no direct commercial flights from the U.S. thanks to tightened restrictions, so you’ll need to get creative. Charter flights from Miami exist. check with American Airlines (Cuba − Travel information − American Airlines)—or hop through a third country like Panama. I’ve done the Miami-Panama-Havana route myself; it’s a hassle, but the moment you see Havana’s skyline, it’s worth it. The U.S. allows travel under 12 categories, like family visits or “support for the Cuban people” (Legal Travel to Cuba Explained). No special license needed—just a valid passport, a tourist visa (grab it via the Cuban embassy or a travel agency), proof of return, and health insurance (U.S. Embassy in Cuba).
At Miami’s airport, expect a stop at the “Cuba Ready” booth to state your purpose—bring patience; it can take hours.The Cuban Reality: Beauty Amid StruggleLanding in Cuba feels like entering a living museum. Havana’s Old Town, a UNESCO gem, dazzles with colonial buildings and salsa beats echoing through the streets. Varadero’s beaches are postcard-perfect, and Trinidad’s cobblestone charm takes you centuries back (Condé Nast Traveler).
But beneath the beauty lies a harsh truth. The U.S. embargo, started in 1962, has left Cuba outdated—think crumbling infrastructure and limited tech (Council on Foreign Relations). Inflation’s soaring at 30% a year, and the ration system barely covers basics (BTI 2024 Cuba Country Report).
I remember walking past empty shelves and hearing stories of families stretching meals. It’s heartbreaking when you know how special these people are—resilient, educated, and kind despite it all.
My Journey: Tourist Meets Time Traveler As a tourist, I marveled at the 1950s Chevys and the faded grandeur of Havana’s Malecón. But it’s the personal moments that stick with me sharing coffee with locals who welcomed me like family, even with so little to give. Now, if I went back to visit relatives, I’d bring cash (Euros or USD, since U.S. credit cards are useless there) and essentials like clothes or non-perishables (Cuba Unbound).
The official exchange rate is 120 CUP to 1 USD, but there’s an 8% fee on dollars, so Euros might stretch further. Internet’s spotty plan on being offline and tap water’s a no-go; stick to bottled (State Department).Why Cuba Matters and What’s NextCuba’s not just a travel spot; it’s a testament to human spirit. The embargo and sanctions like those tightened in 2025 keep it trapped, unable to modernize or feed its people properly (The Conversation). I get it the U.S. and Cuba’s government don’t see eye to eye. But punishing an entire nation feels wrong when you’ve seen its heart. Obama’s 2015 thaw showed promise (CFR Timeline), so why not try again?
Lift the restrictions, let trade flow, and give Cubans a chance to thrive—not just survive.For now, if you go, go with purpose. Support local artisans, eat at paladares (private restaurants), or visit family with love and supplies in tow. Cuba’s a paradox poor yet rich, old yet timeless. It’s sad, yes, but it’s also beautiful. And it deserves more from us than a label on a list.
A few years ago, I stepped off a plane into the humid embrace of Havana, Cuba a place that instantly felt like stepping back in time. The air carried the sharp tang of diesel gasoline, vintage cars rumbled past, and the streets pulsed with a rhythm that’s hard to forget. I went as a tourist, but what I found was more than just a destination; it was a revelation. Cuba is an amazing country its people warm, its cities breathtaking, its spirit unbroken despite decades of hardship. Today, as I write this on March 31, 2025, I can’t help but feel a pang of sadness.
The island’s beauty stands in stark contrast to its struggles, worsened by policies like the U.S. embargo and, most recently, President Trump’s decision to slap Cuba back onto the state sponsors of terrorism list. Here’s what it’s like to travel there now—whether you’re a curious explorer or someone, like me, yearning to reconnect with family and why I wish we could do more for this incredible place.A Political Tug-of-War: Cuba’s Latest Chapter
Let’s start with the elephant in the room: Trump’s move in January 2025 to redesignate Cuba as a state sponsor of terrorism, undoing a brief reprieve granted by President Biden just days earlier (Reuters).
This isn’t new Cuba was on the list back in 2021 before Biden lifted it—but its return tightens the screws on an already strained economy. The U.S. State Department says it’s about holding the Cuban government accountable (Cuba Sanctions - United States Department of State), but critics argue it’s the people who suffer most, not the regime. Sanctions mean less trade, fewer dollars, and harder lives for Cubans already scraping by on an average of 4,648 Cuban Pesos a month—about $38.73 USD at the official rate of 120 CUP to 1 USD (Statista). I’ve heard tales of $20 monthly wages for educated folks, and while that might’ve been true years ago, today’s numbers still paint a grim picture when food and medicine are scarce.
Getting There: A Maze Worth Navigating Traveling to Cuba as a U.S. citizen isn’t straightforward, but it’s doable. There are no direct commercial flights from the U.S. thanks to tightened restrictions, so you’ll need to get creative. Charter flights from Miami exist. check with American Airlines (Cuba − Travel information − American Airlines)—or hop through a third country like Panama. I’ve done the Miami-Panama-Havana route myself; it’s a hassle, but the moment you see Havana’s skyline, it’s worth it. The U.S. allows travel under 12 categories, like family visits or “support for the Cuban people” (Legal Travel to Cuba Explained). No special license needed—just a valid passport, a tourist visa (grab it via the Cuban embassy or a travel agency), proof of return, and health insurance (U.S. Embassy in Cuba).
At Miami’s airport, expect a stop at the “Cuba Ready” booth to state your purpose—bring patience; it can take hours.The Cuban Reality: Beauty Amid StruggleLanding in Cuba feels like entering a living museum. Havana’s Old Town, a UNESCO gem, dazzles with colonial buildings and salsa beats echoing through the streets. Varadero’s beaches are postcard-perfect, and Trinidad’s cobblestone charm takes you centuries back (Condé Nast Traveler).
But beneath the beauty lies a harsh truth. The U.S. embargo, started in 1962, has left Cuba outdated—think crumbling infrastructure and limited tech (Council on Foreign Relations). Inflation’s soaring at 30% a year, and the ration system barely covers basics (BTI 2024 Cuba Country Report).
I remember walking past empty shelves and hearing stories of families stretching meals. It’s heartbreaking when you know how special these people are—resilient, educated, and kind despite it all.
My Journey: Tourist Meets Time Traveler As a tourist, I marveled at the 1950s Chevys and the faded grandeur of Havana’s Malecón. But it’s the personal moments that stick with me sharing coffee with locals who welcomed me like family, even with so little to give. Now, if I went back to visit relatives, I’d bring cash (Euros or USD, since U.S. credit cards are useless there) and essentials like clothes or non-perishables (Cuba Unbound).
The official exchange rate is 120 CUP to 1 USD, but there’s an 8% fee on dollars, so Euros might stretch further. Internet’s spotty plan on being offline and tap water’s a no-go; stick to bottled (State Department).Why Cuba Matters and What’s NextCuba’s not just a travel spot; it’s a testament to human spirit. The embargo and sanctions like those tightened in 2025 keep it trapped, unable to modernize or feed its people properly (The Conversation). I get it the U.S. and Cuba’s government don’t see eye to eye. But punishing an entire nation feels wrong when you’ve seen its heart. Obama’s 2015 thaw showed promise (CFR Timeline), so why not try again?
Lift the restrictions, let trade flow, and give Cubans a chance to thrive—not just survive.For now, if you go, go with purpose. Support local artisans, eat at paladares (private restaurants), or visit family with love and supplies in tow. Cuba’s a paradox poor yet rich, old yet timeless. It’s sad, yes, but it’s also beautiful. And it deserves more from us than a label on a list.
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Not All Who Wander Are Lost / Some of Us Are Just Unbothered.
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For inboxes that prefer one-way tickets
For inboxes that prefer one-way tickets
© OMG BYE!
2025
Not All Who Wander Are Lost
●
For inboxes that prefer one-way tickets
© OMG BYE!
2025