Just over an hour apart by air, across the same sea, and about as different as two Caribbean countries can be. All-inclusive resorts, cenotes and Maya cities on one side; 1950s Havana, live son and rationed everything on the other.
Cuba is the more demanding half, and it's better appreciated once you've rested.
The Riviera Maya is easy: good hotels, reliable food, cenotes and ruins, and a beach. Cuba is not easy — patchy internet, shortages that affect restaurants and shops, and a currency situation that changes. It's also one of the most extraordinary places in the Caribbean and completely unlike anywhere else. Doing Mexico first means you arrive in Havana rested and ready for it, rather than trying to decompress in a country that doesn't really do decompression.
Thirteen nights with a short flight in the middle, and a home flight from Havana.
1Beach, cenotes and Maya cities, with the best-value all-inclusive resorts at this standard anywhere.
Where you stay: Playa del Carmen to walk out into a town, or the Riviera Maya resort belt for beachfront all-inclusive.
Getting there: 9h 45m direct to Cancún, then a transfer of 20 to 90 minutes depending on the resort.
2Five nights, because Havana rewards slowness and the day trips are worth doing.
Where you stay: A casa particular in Habana Vieja or Vedado — a licensed family home, and far better than most hotels here.
Getting there: 1h 15m from Cancún to Havana. Several flights weekly.
Everything below is quoted up front. Nothing appears after you've paid a deposit.
Guide prices per person, two sharing, outside school holidays. The hotel standard is the biggest single variable.
| Standard | What that means | Guide price pp |
|---|---|---|
| 4-star | Good all-inclusive in Mexico, casa particular or three-star in Havana | £2,149 |
| 4-star plus | Beachfront all-inclusive, boutique hotel in Habana Vieja | £2,799 |
| 5-star | Luxury Riviera Maya resort, best available Havana hotel | £3,899 |
Cuban hotels do not track international star ratings — a five-star in Havana is often a comfortable four elsewhere. A well-run casa particular frequently beats a mid-range hotel on food, warmth and reliability, and costs a fraction. We'll be straight with you about which is which.
November to April is dry season on both, and it avoids Mexico's seaweed window and the hurricane season.
December to March is the best weather on both legs and the busiest. Mexico's sargassum seaweed affects east-facing Riviera Maya beaches roughly April to August — if your dates fall in that window we'll steer you to Isla Mujeres or Cozumel's west coast. Hurricane season runs June to November across the whole region, peaking in September. Cuba is hot and humid in summer with far fewer visitors.
We'll come back with the right beach for the season, sort the Cuban tourist card, and write the payment plan out in full.
Shortages are real and affect restaurant menus and shop stock. Internet is limited and slow. None of it is dangerous — it just needs a flexible frame of mind, and it's part of why the place is remarkable.
A casa is a licensed family home, usually with better food and far more warmth than an equivalently priced hotel. We book good ones and tell you what to expect.
A tourist card, which we arrange with the booking. Cuba also requires health insurance, normally bundled into the airfare — we confirm it before you travel.
April to August on east-facing beaches. It's the commonest complaint about that coast, and we'll name the beaches that escape it if your dates fall in the window.
Similar shapes, and the ones people most often weigh up alongside it.
Same approach, different shape. All reshapeable around your dates.
