Montego Bay vs Portland

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.

Portland

Portland has a cool marine climate — famously rainy, but not in the way visitors expect. The rain is a persistent drizzle, not heavy downpours. Portland actually receives less annual rainfall (about 36 inches) than New York or Houston, but it is spread over 150+ rainy days from October through May. Summers (July through September) are gloriously dry, sunny, and warm. Winter brings occasional snow that typically melts within a day or two.

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 — sidewalks are inconsistent, traffic is aggressive, and distances to attractions are too far for comfortable walking.

Portland

Portland has the most useful public transit of any city its size on the West Coast. MAX light rail (5 lines) connects the airport, downtown, and key suburbs. The Portland Streetcar loops through downtown, the Pearl, and east side neighborhoods. TriMet buses fill in the gaps. Within individual neighborhoods — Pearl, Hawthorne, Alberta, Mississippi, NW 23rd — walking is the right answer. Portland is also one of the best US cycling cities with protected lanes and a cyclists-first culture.

Walkability: Portland is one of the most walkable large cities in the American West — grid-patterned, flat on the east side, and most interesting neighborhoods (Pearl, NW 23rd, Hawthorne, Division, Alberta, Mississippi, Belmont) have dense commercial strips. Downtown blocks are short (only 200 ft) which makes walking feel quicker. Expect rain 9 months of the year — a good waterproof shell is more useful than an umbrella in the Portland wind.