The Cuba trip planning guide

1. Yes, it’s legal. Here’s the category.

Americans travel to Cuba legally under the U.S. Treasury’s “Support for the Cuban People” general license. There’s no application. What the category asks is that your trip is a full schedule of activities that support independent Cubans: staying in private homes, eating at family-run restaurants, visiting private farms and artists. That is exactly what our tour is, day by day.

Keep your receipts and itinerary for five years. We give you a written itinerary that documents your activities.

2. The paperwork, step by step

1. Passport valid for your whole trip.
2. Cuba e-visa (90-day tourist card), about $60, bought online at eVisaCuba.com at least a week before you fly. It can no longer be bought at the airport. It includes access to Cuba’s health system.
3. D’Viajeros form, online, within 7 days before departure, using your e-visa number.
4. Travel insurance, required, that covers Cuba, cycling, snorkeling and emergency medical evacuation.

Once you’ve booked, we send links and a walkthrough for each one. The whole thing takes most people about twenty minutes.

3. Your timeline

4. Money

Bring US cash. US-issued credit and debit cards do not work in Cuba. All your meals, lodging, bikes, activities and flights from Miami are already paid for, so cash is for drinks, tips, souvenirs, cigars and rum. Small bills are best. If you’d like Cuban pesos, we’ll exchange some for you at the best available rate.

Each traveler may bring home 2 boxes of 25 cigars and 2 bottles of rum bought at the airport, plus gifts and souvenirs.

5. Phones and internet

Get a Cuban eSIM before you go or buy a SIM on arrival; we’ll send instructions. Most casas have Wi-Fi. You’ll be able to text, email and video-call home most of the time. It’s slower than you’re used to and it drops during blackouts. Download maps, music and anything you want to read before you leave Miami.

6. What the headlines mean for you

You’ve read that Cuba has blackouts, fuel lines and empty shelves. Some of that is true some of the time. Here’s what it means on tour: our homestays have solar backup for lights, fans and charging; our support vehicle starts every tour fueled, with reserve on board; your meals come from private hosts who buy from farmers and fishermen; we provide bottled water throughout. Bring a headlamp and a power bank, and you’ll barely notice.

Read Herschel’s full, honest write-up from his village.

7. Getting ride-ready

This tour is for people who are generally fit and active, not racers. Rides are 5–6 riding days, 10–25 miles each, done by noon, with a stop every hour and the van always close by. Eight weeks of easy riding is plenty:

Any health questions about whether this trip is right for you belong with your doctor; logistics questions belong with Herschel.

8. Packing list

9. Gifts that mean the most

Riders often ask what to bring for host families. Leave a little room in your suitcase for any of these:

• Over-the-counter vitamins and pain relievers
• Reading glasses
• School supplies: pens, notebooks, crayons
• Toiletries: toothpaste, toothbrushes, soap, shampoo
• Bike parts and tools for the Bamboo Bike Project
• Fishing line and hooks for coastal families
• Kids' clothes and shoes

10. The tour at a glance

• Eastern Cuba Culture & Cycling Tour: 9 days, 8 nights, Miami to Miami
• Route: Miami → Holguín → Gibara → Guardalavaca → Santiago de Cuba → Miami
• $3,895 per person, all-inclusive from Miami; 35% deposit
• Groups of 8–12; private departures for 8–14
• 2027 dates: January 13–21, 2027 · February 10–18, 2027 · March 10–18, 2027 · April 7–15, 2027 · May 12–20, 2027