Jamaica

I have been here 3 times.  Back in the mid 90s, in 2005 and with the whole Wardein clan in 2006.  There is a special laid back, rasta vibe here.  You can stay in a nice resort and still experience the culture.  I love it.

Top 5 Days

1. Beach time - totally relaxing to lay on this lovely beach.
2. Go where no locals go - My mom would get up and go into town to the early morning markets to help pick fresh fruits and seafood for dinner.
3. Snorkel and scuba - The underwater magic of the entire Caribbean is here.
4. Floyd's Pelican Bar - THE most UNIQUE bar in the world.  You have to take a boat the get here and it is made of sticks in a sandy area.  They only serve lobster and Red Stripe.  Near Jakes.
5. Go see a reggae show - The music makes this place all the cooler.

 

Top 5 High Style, Low Maintenance Hotels

1. Round Hill - Privately owned villas and homes on a hill overlooking a private beach.  I have rented a villa and a whole house with the family.  What is special here is that it is all part of resort - so you have full service, water sports, a water trampoline, a kids club, restaurants, etc... We had full service meals in the house every night - we ate on the deck by the pool overlooking the bay.  Near Montego Bay.  Ralph Lauren has a place there and the style screams high style, low maintenance.
2. Jakes - Part of the Outpost Island group, owned by Chris Blackwell, who owns Island Records. A chic, shabby group of villas on the sea.  Defintely a bit rustic - expect lots of critters around.  The beauty here is it is just locals around - not other tourist and resorts.
3. Strawberry Hill - Another Outpost Island resort up in the mountains for a totally different feel.
4. Rockhouse Hotel - On the water, but not on the beach in Negril.
5. Rent a villa - I looked at tons of places for my family and there is a ton of stuff, though we loved Round Hill.

 
Top 5 Foodie Finds

1. Lobster Everything - I order it in everything.
2. Jerk - Chickem, Steak, Pork.  I love the flavor.
3. The Caves - A really special spot in Negril right on the water.
4. Negril Beach - There are tons of special spots right on the water with reggae music and cheap eats out in the sun.
5. Red Beans and Rice - The local staple and a safe eat even from the side of the road.

Top 5 Misses

1. Big Resorts - There are so many where you would never leave and see anything.
2. Crime - You gotta watch it here.  The nice places have a guard around.
3. Airport - It is crazed with vendors and aggressive taxi drivers. 
4. Hurricanes - We followed one there with my family.  Make sure not to go during hurricane season.

Top 5 Tips

1. Great flight schedules - I think I have been 3 times because it is so much easier to get to than anywhere in the Caribbean.
2. Bring your patience - It is rasta time, so don't expect that marg you ordered to be there in 3 minutes.
3. Red Stripe - Drink the national beer.   A lot of it.
4. Build a good reggae mix for your iPod.  There will be lots of relaxing time.
5. Iriemon.