Friday
- 7:00 PM
Gloria's Seafood
Jamaican Seafood · $$ · Port RoyalPatio kickoff — Old pirate-town seafront — escovitch snapper, conch soup, sunset over the harbour.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Port Royal — short walk from your other stops
- ·A fall-perfect atmosphere
- 8:30 PMDrive-In MovieFamily · Outskirts
Pack snacks, park up and catch a double feature under the stars.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Outskirts — short walk from your other stops
- ·A fall-perfect atmosphere
Saturday
- 9:00 AMEmancipation ParkOutdoors · New Kingston
Iconic 'Redemption Song' bronze statues — joggers at dawn, lovers at dusk.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in New Kingston — short walk from your other stops
- ·A fall-perfect atmosphere
- 1:00 PM
Scotchies
Jerk · $ · Constant SpringOutdoor lunch — Pimento-wood-smoked jerk chicken, festival dumplings, Red Stripe — the benchmark.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Constant Spring — short walk from your other stops
- ·A fall-perfect atmosphere
- 3:00 PMTrampoline ParkFamily · Suburbs
Open jump, dodgeball courts and foam pits — chaotic kid energy or unironic adult fun.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Suburbs — short walk from your other stops
- ·A fall-perfect atmosphere
- 8:00 PM
Regency Bar & Lounge
Caribbean Fusion · $$$ · Terra Nova HotelOld-Kingston elegance — curry goat tasting, rum flights, live jazz Thursdays.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Terra Nova Hotel — short walk from your other stops
- ·A fall-perfect atmosphere
Sunday
- 9:00 AMKayak / Paddleboard RentalOutdoors · Waterfront
Hop on the water for an hour — beginner-friendly, great with a friend or date.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Waterfront — short walk from your other stops
- ·A fall-perfect atmosphere
- 1:00 PM
Devon House I-Scream
Ice Cream · $ · Devon HouseNational Geographic top-4-in-the-world — Devon Stout, soursop, grapenut on a cone.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Devon House — short walk from your other stops
- ·A fall-perfect atmosphere
Remix
Want a different vibe?
Every plan below is freshly built from Kingston's top curated picks.
- Classic 48 HoursOpen plan
- Foodie EditionOpen plan
- Romantic WeekendOpen plan
- Date NightOpen plan
- Boys' Night OutOpen plan
- Girls' Night OutOpen plan
- First-TimerOpen plan
- With KidsOpen plan
- Solo EditionOpen plan
- On a BudgetOpen plan
- Rainy Day RescueOpen plan
- Birthday CelebrationOpen plan
- Hidden Gems TourOpen plan
- Friends Night OutOpen plan
- Weekend GetawayOpen plan