We entered Jamaica with the goal of seeing everything from the dense tourist areas to densely forested cockpit country. We started and ended the trip in Negril (an easy taxi ride from Montego Bay). We lazed in the sun the first two days in Negril while waiting for an available rental from a local jeep rental company.
Upon attaining our island cruiser, the local Toyota version of a jeep, we immediately set off down towards Black River with every intention of seeing Jamaican "alligators" on the Black River Safari. Unfortunately we were waylaid by some local hustlers at "roaring river" and later caught by a torrential downpour. After many surprises from the flooded road, we finally found refuge at the end of the day at Astra Country Inn in Mandeville. The following morning we made for cockpit country instead of attempting a side trip to the Milk River and Alligator hole--considering our experiences on the road the prior day. The road to Windsor from Mandeville is an experience in itself--not recommended for the faint of heart. However, at the end of the road, every single pot hole was worth it to come to rest at Windsor Great House.
In Windsor we were taken care of by Sugarbelly and Franklyn. Sugarbelly kept us well fed and offered up suggestions on which trails to explore. Franklyn was a knowledgeable guide to Windsor Cave. In total we spent 2 nights and 3 days at Windsor hiking, caving, and birdwatching.
After roughing it, we were ready to relax on the beach away from hustlers and the mosquitoes. We found what we were looking for 5 minutes east of Falmouth at a little "resort" called Time 'n Place. These little Thai style huts on relatively undeveloped beach were a slice of heaven. The owners and staff were extremely friendly and helped find rides for all the guests to Rock, Oyster Bay to see the bio-luminescent waters.
After a relaxing night at Time 'n' Place we headed to Negril to return the jeep and arrange accommodations for our last night in Jamaica. Our flight left 12pm the next morning, so we had the luxury of sleeping in and taking a relaxing taxi drive to Montego bay the next morning.
Quick Tips:
Avoiding Hustlers: Hustlers are especially rampant at night in Negril on the Long Bay. Many will introduce themselves ask your origins and seem pretty congenial at first glance, but beware of getting talked into buying something you don't want or need out of guilt. They may even try to walk with you and give you a "friendly tour" while you are simply trying to enjoy the stars with your loved one. Nothing is for free from a Jamaican in or around Negril. A friendly walk and a chat could lead to much begging for money, hustling for ganja, etc.
Here are some tips when approached:
1. Remember NOTHING is free in Negril.
2. Always say no thanks, not interested firmly and persistently.
3. Do not continue a seemingly conversation, be polite but keep moving, eventually they will somehow try to get your money.
4. Do not take a hit off a joint even if "freely offered," later they will ask for money out of "respect."
5. Do not walk on the beach of Long Bay in Negril on a weekend night unless you expect hustling.
Best Way To Get Around:
Driving in Jamaica: if you plan to drive anywhere other than the well-populated tourist areas, I would recommend renting a 4wd vehicle. If you do this through the airport you will pay a hefty price to a day. I suggest Island cruisers in Negril for no more than a day plus insurance. Make sure to ask for a jack though.
Remember to drive on the left and don't be afraid to honk--especially in Negril. Honk if you're overtaking, passing a pedestrian, bicyclist, or just for the heck of it!
If you just want to stay in Negril, Montego Bay or around I highly recommend the route taxi service. Always agree on price before you get in though. Ask local hotel desks for reasonable prices.