You Can Still Go to Cuba as an American — But There's a Catch
If you're in despair that the Trump administration dashed your lifelong dreams of drinking daiquiris at La Floridita and finding true love — at least for the week — along the Malecón, then wipe away your tears. Because there's still a way you can make it to the long-forbidden Caribbean island that's perfectly legal. (For now.)
The adventure tour company Intrepid Travel is tweaking its Hola Cuba trip so that it stays within the bounds of the recent ban on most US travel to Cuba, which effectively ended the majority of trips by Americans, stopped cruise visits and upended the plans of countless businesses — both US and Cuban — that had counted on the thawing of relations between Washington and Havana.
"As Intrepid Travel is committed to providing opportunities for its US customers to freely explore the world through sustainable, experience-rich travel, the company has been diligently working to create another option for American citizens to continue to visit Cuba," Michael Edwards, managing director of the Americas and Europe, said in a statement.
An Intrepid spokesperson told The Points Guy they would not comment on the matter beyond the press release.
Before June 5, when the ban took effect, Intrepid's clients went to Cuba under the State Department's "People to People" travel category, which largely let Americans visit the country without an explicit governmental, humanitarian, educational or business purpose. The loophole that the company is exploiting now? The new ban included a vaguely worded exemption for Americans traveling to Cuba under a license called "Support for Cuban People."
The catch is that American tourists now have to stick to a strict plan under the new license — and be able to prove it if confronted by US authorities upon their return. Thus Intrepid's tweaked Cuba trip includes nine days in Havana, Viñales, Cienfuegos and Trinidad — and help documenting participants' interactions with the Cuban people, keeping track of their activities in the country and a diary that they can hand over to federal officials back in the States. (The tour will include scheduled time at the end of every day for travelers to journal.)
Intrepid is offering a 15% discount on its Hola Cuba tour through June 27, or from $2,338 per person.
TPG featured card
at Capital One's secure site
Terms & restrictions apply. See rates & fees.
| 5X miles | Earn 5X miles on hotels, vacation rentals and rental cars booked through Capital One Travel |
| 2X miles | Earn unlimited 2X miles on every purchase, every day |
Pros
- Stellar welcome offer of 75,000 miles after spending $4,000 on purchases in the first three months from account opening. Plus, a $250 Capital One Travel credit to use in your first cardholder year upon account opening.
- You'll earn 2 miles per dollar on every purchase, which means you won't have to worry about memorizing bonus categories
- Rewards are versatile and can be redeemed for a statement credit or transferred to Capital One’s transfer partners
Cons
- Highest bonus-earning categories only on travel booked via Capital One Travel
- LIMITED-TIME OFFER: Enjoy $250 to use on Capital One Travel in your first cardholder year, plus earn 75,000 bonus miles once you spend $4,000 on purchases within the first 3 months from account opening - that’s equal to $1,000 in travel
- Earn unlimited 2X miles on every purchase, every day
- Earn 5X miles on hotels, vacation rentals and rental cars booked through Capital One Travel
- Miles won't expire for the life of the account and there's no limit to how many you can earn
- Receive up to a $120 credit for Global Entry or TSA PreCheck®
- Use your miles to get reimbursed for any travel purchase—or redeem by booking a trip through Capital One Travel
- Enjoy a $50 experience credit and other premium benefits with every hotel and vacation rental booked from the Lifestyle Collection
- Transfer your miles to your choice of 15+ travel loyalty programs
- Top rated mobile app


