Cuba's been on my radar for years and I finally went in November 2023 for three weeks. Honestly low-key one of the most extraordinary places I've travelled. Mean, you go expecting old cars and music and yeah, that's there, but you don't really get the depth of how the country works (or doesn't) until you're in it. Doris (the van) was in storage in Auckland and I was a bit lost without her but Cuba doesn't really have road-trip culture anyway.
[IMAGE: https://images.unsplash.com/photo-1500759285222-a95626b934cb?w=1600&q=80&auto=format&fit=crop | A vintage 1950s American car parked in front of pastel-painted colonial facades in Havana's old town at golden hour]
Real quick — what Cuba actually is
Largest Caribbean island. ~11 million people. Spanish colony until 1898, then American influence until the 1959 revolution, then closed-economy socialist republic for the next sixty years. Since around 2008 the country has been slowly opening — private restaurants and B&Bs (called casas particulares) became legal, the cuentapropista (self-employed worker) system grew, dual-currency was unified in 2021. Tourism is one of the few sectors that brings in hard currency so it's been pushed hard.
Practical visitor reality in 2024 is shortages of basic stuff are common (medicine, toilet paper, even fuel during 2022-2023 worst stretches), the internet is patchy, electricity blackouts happen, and you need to bring everything you might want in your luggage. None of that means don't go — but you should go knowing what you're walking into.
How to actually get there
For non-US passports it's straightforward — flights from Cancun, Toronto, Madrid, Frankfurt, Buenos Aires. Get a tourist card (tarjeta de turista) before flying — most airlines sell them at check-in for 20-30 USD. Visa-free for most Western passports for 30-90 days depending on nationality. NZ passport got 90 days, which I needed more of than I expected.
For US passports it's complicated. The US still technically bans tourism to Cuba; you need to travel under one of 12 categories (journalism, support for the Cuban people, etc.). Most US travellers go via Mexico or Canada and use "support for the Cuban people" — book casas particulares (private guesthouses, not state hotels), eat at private paladares, take guided tours from non-state operators. Keep your receipts for 5 years in case of audit. It IS doable, just requires planning.
Money — this is important
Cuba in 2024 is a dual cash economy. The CUP (peso cubano) is the official currency. USD is widely accepted at private businesses but technically you should change to CUP for state stuff. The MLC card (currency-equivalent) is for state-owned shops and hotels only.
Western credit cards mostly DO NOT WORK in Cuba — US-based banks are blocked, and even non-US Visa/Mastercard often fail because of the trade embargo affecting the SWIFT network. Bring CASH. EUROS or CAD or GBP exchange better than USD because there's a 10% surcharge on USD-to-CUP. I brought euros, got rid of them slowly, kept enough USD for emergencies.
Budget mental model: bring 100 EUR per day for two people, double if you want comfort/restaurants. Cash. In your money belt. Yes, all of it.
Where to go (this is what people really want to know)
I did Havana → Trinidad → Viñales → back to Havana over three weeks. With more time I'd add Santiago de Cuba in the east and Cayo Levisa for proper beach time.
Havana — 4-7 days. Old Havana (Habana Vieja) is UNESCO-listed and the most photographed neighbourhood; Centro Habana is rougher, more local; Vedado has the architecture and the famous Hotel Nacional; Miramar is the upmarket diplomatic-quarter area. Walk the Malecón at sunset. Eat at La Guarida in Centro Habana. Get cocktails at El Floridita where Hemingway drank daiquiris. Catch live music at the Buena Vista Social Club spinoff venues — yeah it's touristy, also brilliant.
Trinidad — 3-4 days. Small colonial town in the centre of the island, UNESCO-listed, cobblestoned, terracotta-roofed. Casa de la Trova for live son and salsa every night. Day trip to Topes de Collantes for waterfalls. Day trip to Playa Ancón for the nearest decent beach.
Viñales — 3-4 days. Tobacco-growing valley west of Havana. The famous limestone karst mogote hills. Cigar farms you can visit. Caves you can swim in. Horseback through the valley at sunset. Quiet. Slow. Best part of Cuba I went to.
Santiago de Cuba — would add 4-5 days. Far east. The Afro-Caribbean heart of Cuba — different vibe to Havana, more African heritage, hotter, more music. Didn't make it on this trip, going back.
Cayo beaches — Cayo Levisa, Cayo Coco, Cayo Santa Maria. The white-sand turquoise-water Caribbean beaches that the postcards show. All-inclusive resorts dominate (mostly state-owned). Tag a few days on the end of a longer cultural trip if you need beach time.
Where to sleep
Casa particulares. Always. Forget the state hotels — they're overpriced, run-down, and the staff are paid in CUP which means they can't really invest in service. Casas are private homes that rent rooms (and usually breakfast/dinner). The owner is your host, your tour-booker, your local fixer. Quality varies hugely. Cost: 25-40 EUR per night per room.
Book the first 2-3 nights before flying (via Airbnb or directly through casa networks). After that, your first host will phone or message ahead to the next town's casa they recommend. This network is how Cuban tourism actually works. Trust it.
What to eat (Cuban food is better than its reputation)
Paladares (private restaurants) — way better than state restaurants. Lookup recommendations on Tripadvisor or Foursquare BEFORE you fly because internet in-country is unreliable.
The food itself: rice, beans, slow-roasted pork (lechón), tropical fruit, fish from the coast, mojitos and daiquiris. Comfort food. Not nuanced cuisine but properly good when it's done right. Trinidad's paladar Sol y Son and Havana's La Guarida and Atelier are the standout meals I had.
Skip state-run restaurants (mediocre), buffets at all-inclusive resorts (depressing), and beef ANYWHERE (Cuban beef is rare and bad due to limited cattle stock).
Internet, phones, and being unreachable
Cuba in 2024 has limited mobile internet. ETECSA is the only carrier. Buy a SIM card on arrival (about 30 USD for 6 GB / 30 days). Speed is fine in cities, patchy in villages, nonexistent in Viñales valley after dark. Wifi at casas is increasingly common but slow.
Honestly though — the disconnection was part of the experience. Three weeks without Instagram or work emails was excellent. Tell people back home you'll be off-grid.
Combining the trip
Cuba pairs naturally with Cancun/Yucatan (one-hour flight, easy onward leg) — the Akumal Bay snorkel area or the Yucatan cenote country make a beachy contrast to Cuba's harder travelling. The Caribbean category page collects more from across the region. If you'd rather not handle Cuban logistics solo, browse tours in Cuba for guided options.
Official sources
Cuba.travel, the official tourism site, has visa info and current advisories. UNESCO's pages for Old Havana and Trinidad have the architectural background.
Last thing
Cuba is a difficult place in 2024. The economy is genuinely struggling. People queue for things you take for granted. The government is repressive. The infrastructure is patchy. None of that is invisible to a visitor.
But the music, the architecture, the warmth of ordinary Cubans, the quality of light over a Havana street at 7am — that's real too. Go with humility. Bring cash. Stay in casas. Tip generously (it goes directly to families). Don't lecture anyone about politics. Listen.
Three weeks felt right. I'd happily go back for a month. Yeah nah, this one's stayed with me.
A note on photography
Cuba is the most photogenic country I've travelled. The colours alone — pastel facades, vintage cars, sea light, the particular Caribbean glow at golden hour. The temptation is to spend the whole trip with a camera glued to your face.
Resist it. Or at least ration it. Lots of Cubans are tired of being photographed by tourists — especially in Old Havana where every visitor seems to want to capture the same "authentic" street scene. If you want to photograph people, ask first, learn three words of Spanish, offer to send them the picture. Old men playing dominos in Centro Habana have been photographed by 10,000 tourists this year and most of them never sent the picture they promised.
If you want to photograph well, get out before 7am. The light is best. The streets are empty. The people who are awake are working and don't mind a camera. The same light comes back at 5-6pm. The four middle hours of the day are dead for photography in Cuba anyway — too harsh, too contrasty.
On safety
Cuba is one of the safest countries I've travelled solo. Violent crime is rare and police presence is heavy. Petty theft does happen in tourist areas (pickpocketing in Old Havana, occasional bag-snatching on quiet streets at night). Standard precautions — no flashy jewellery, money belt for the cash, leave the passport in the casa safe — apply. Solo women travellers have a generally positive time but verbal harassment from men in the street is common; ignoring it is the standard response.
Final practicalities
Bring an extra pair of glasses (eyewear is hard to replace). Bring tampons or pads if you need them. Bring any prescription medications with a doctor's note. Bring earplugs (Havana is loud). Don't drink the tap water (bottled only). Eat where the locals eat. Tip in CUC if you can. Smile a lot. Cuba responds.
