The Best of Jamaica
Two weeks is a good length for a trip to Jamaica and provides enough time to relax on the beach while also venturing beyond the sun and sand for a mix of adventure and culture. Highlights include Negril's West End, a few days in quiet Belmont, Kingston's culture and nightlife, and Portland's aristocratic history and lush natural beauty.
Day 1
Arrive at the airport in Montego Bay, check-in for two nights, and dine at the HouseBoat Grill or the more casual and every-bit-as-good Scotchie's. Hit up a bar for an evening drink to gauge the scene along the Hip Strip.
Day 2
Take tours of Rose Hall and Greenwood Great House in the morning. Then visit Doctors Cave Beach in the afternoon. Have dinner at Day-O Plantation followed by a play at Fairfield Theatre.
Day 3
Drive west to Negril for cliff jumping by late morning. Visit Royal Palm Reserve in the afternoon to fish and check out the waterfowl, then visit Bongo's Farm for sunset.
Day 4
In the morning, drive southeast to Savanna-la-Mar and then turn inland to Mayfield Falls. Spend the morning exploring the falls and gardens. On the return back to Negril, take the northern route stopping to visit Alexander Bustamante's birthplace at Blenheim before enjoying grilled lobster at Half Moon Beach in Hanover.
Day 5
Check out of your hotel and drive east toward Belmont, stopping at Blue Hole Garden and Roaring River along the way. Settle into a beachside cottage at Horizon Cottages and dine on fresh seafood or fried chicken across the road.
Day 6
Drive south to Parottee Point and head to Pelican Bar, a one-of-a-kind watering hole and ramshackle fried fish joint located a mile offshore on a sandbar. Go snorkeling and enjoy fried fish and a cold beer. On your way back to Belmont, stop in Black River for a boat trip into the morass.
Day 7
Drive inland and take a tour of Appleton Estate in the morning, followed by a stop on Bamboo Avenue for jelly coconut and a visit to Y.S. Falls in the afternoon. Pull over in Middle Quarters for fresh shrimp on the way back to Belmont, where you will spend another night.
Day 8
In Belmont, visit Peter Tosh Memorial Garden in the morning followed by a nature hike with Rasta Bryan. Depart in the afternoon for Kingston, arriving in time for dinner.
Day 9
Downtown sights in the morning could include the National Gallery, a stroll along Ocean Boulevard, and a visit to Liberty Hall. Visit Legend Café at the Bob Marley Museum for lunch and take a tour in the early afternoon. Stop by Hope Botanical Gardens for a juice at The Tea House before heading back down to Devon House for ice cream and shopping. Go out on the town at night in New Kingston.
Day 10
Visit one of Kingston's many private studios and then head out to Fort Charles in Port Royal by mid-morning, followed by lunch at Gloria's. Take a boat to Lime Cay for a swim in the afternoon. Dine at Fisherman's Cabin before returning to Kingston to go out on the town and hit the hay.
Days 11 and 12
Drive northeast from Kingston into the Blue Mountains for hiking in Holywell and two nights at Woodside. Stop at Strawberry Hill and splurge on a beer to check out the view--it's well worth it.
Start the next day with early-morning coffee and birding at Twyman's Estate, fueled by a fresh roasted pea-bean blend, the connoisseur's choice. Have lunch at The Gap Cafe, followed by an afternoon swim in the spring-fed pool at Woodside and then a home-cooked dinner.
Day 13
Leave for Port Antonio via Buff Bay immediately after breakfast. Check in to your hotel, take a swim and then a nap. Wake up for lunch at Cynthia's and a swim on Winnifred Beach. Hit Roof Club, La Best, or Cristal Night Club in the evening to scope out the local scene.
Day 14
Get up early to head west towards Montego Bay for departure with time to stop by Somerset Falls along the way.