Havana
Cuba
Montego Bay
Jamaica
Havana
Montego Bay
π° Budget
π‘οΈ Safety
Havana
Cuba is generally one of the safest countries in Latin America. Violent crime against tourists is extremely rare. The main annoyances are persistent jineteros (hustlers) offering everything from cigars to restaurant recommendations on commission.
Montego Bay
Montego Bay has a high crime rate in certain areas, but the tourist zones (Hip Strip, resort areas, Rose Hall) are generally well-policed and safe. Gang violence occurs in downtown neighborhoods like Canterbury and Norwood but very rarely affects tourists. Stick to tourist areas, use reputable transport, and exercise standard precautions.
β Ratings
π€οΈ Weather
Havana
Havana has a tropical climate with a dry season (November-April) and a wet season (May-October). Temperatures are warm year-round. Hurricane season runs from June to November, with September and October being the highest-risk months.
Montego Bay
Montego Bay has a tropical maritime climate with warm temperatures year-round. There is no true cold season. The "dry" season (December-April) has lower rainfall but rain is possible any time. Hurricane season runs from June to November, with peak risk in September-October.
π Getting Around
Havana
Havana's transport is a fascinating mix of vintage American cars, Chinese buses, coconut-shaped taxis, and horse-drawn carts. There's no ride-hailing app that works reliably. Getting around requires a mix of walking, negotiating with taxi drivers, and patience.
Walkability: Old Havana, Centro Habana, and the Malecon are all walkable, though sidewalks are uneven and sometimes missing. The 3-4 km walk from Habana Vieja to Vedado along the Malecon is one of the great urban walks. Beyond central areas, distances become too large for walking.
Montego Bay
Getting around MoBay involves taxis, route taxis (shared minibuses), and resort shuttles. There is no Uber or ride-hailing in Jamaica. Public transport is cheap but can feel chaotic for first-time visitors. Most tourists use hotel-arranged taxis or licensed JUTA drivers.
Walkability: The Hip Strip (Gloucester Avenue) is walkable for about 2 km along the coast with beaches, bars, and shops. Beyond this strip, MoBay is not pedestrian-friendly β sidewalks are inconsistent, traffic is aggressive, and distances to attractions are too far for comfortable walking.
The Verdict
Choose Havana if...
you want a time-warp to 1959 β vintage Chevys on the MalecΓ³n, Old Havana plazas, rum mojitos, son cubano clubs, and crumbling colonial grandeur
Choose Montego Bay if...
you want Jamaica's resort coast β Doctor's Cave Beach, Rose Hall Great House, Martha Brae rafting, Negril day-trips, and reggae at Margaritaville
Montego Bay