We are planning on taking my first trip to a Caribbean island this December. I’ve always wanted to visit Jamaica but not for any real reason besides my love of Reggae and jerk chicken 
. I would appreciate any thoughts on islands to look into further as I’ve never even paid much attention to the area as a destination. I tend to gravitate towards less corporate properties if anyone has stayed at uniquely cool spot. TIA.
A bunch of years ago now, my daughter and a friend of hers and I went to Jamaica. We were not interested in a walled off resort and so we ended up staying a Jakes in Treasure Beach which was amazing. Run by the family of Perry Henzel who wrote The Harder They Come, it’s the southern coast of the island - you can fly into either Montego Bay or Kingston and they will help you arrange transport. There’s not a lot to do but as the folks of Treasure Beach would say, why would you want to do too much? Good local food, fun rooms, amazing ocean views, good beach, great bar where the town gathers in the evening for a few drinks and a lot of conversation … heaven. We also spent a few days in Negril which gave the younger folks a chance to go out clubbing etc but i found too busy after the relaxation of Treasure Beach.
Jakes - https://www.jakeshotel.com
Negril hotel - Home | Rockhouse Hotel & Spa
Jakes used to be part of Chris Blackwell’s of Island Records hotel group and he still has three Jamaica properties that are pricier but may be more classically luxe if you are looking for that - Jakes was very comfortable and amazing in so many ways but it’s not meant to be the St Regis.
My old business partner was from Jaimaica. His mom was the Super Chicken CEO. We went to some really splendid locations(mid 90s) that are still special. If you are a traveller that likes to see the real Jamaica vs. the AI Sandals/Montego style, go to Port Antonio side. Start in Kingston and get your Jerk fish fix in the port. Travel to Blue mountains and have brunch at Strawberry Hill (great Island Record stories there including U2 crashing car. Smoked Marlin yum). Go over the mountain to Ocho and go to the waterfall and stay on one of the incredible beaches. Stay at one of the condos where you get staff to fix your meals(true pepper pot and ackee and salt cod). Travel to Port Antonio and go to Walkers Wood to experience the real thing Jerk wise. Go to Frenchman’s Cove and see paradise. You can apparently go to Goldeneye now and stay where all the Bond books were written. I’ve given up my secrets.
Yep GoldenEye is one of Blackwell’s hotels along with Strawberry Hill.
As long as you avoid the AI scene, Jamaica is amazing.
We love Anguilla. Amazing beaches, great food, and not much else. Most of the big (by Anguilla standards, no AIs here) hotels are still closed but most of the small hotels, restaurants, and beach bars are open. Most of the beaches have great restaurants/bars that will loan or rent you a chair and umbrella for the day. No direct flights, you take a short ferry or 5 minute flight from St Martin. Can also ferry/fly to St Bart’s for day trip if you need more action for a day.
Have a plan B ready in case your plan A is affected by hurricane season.
Happened to me twice in the past 5 years.
Thanks for the initial thoughts especially on Jamaica, I think I’ll focus there since I’ve always wanted to do it. I have no interest in all inclusive as I want to get out to all the Jerk huts. I certainly Wouldn’t mind and will look for a nice ocean front bed though
Edit title to mainly reflect Jamaica, but if anybody has an incredible local getaway elsewhere I’d love to hear about it.
I think it depends on what you want to do. Going to the Caribbean for jerk chicken seems like a long way to go for naught. I am not a fan of Jamaica. There are some beautiful places like Siun mentioned but I think there are many other islands I would choose first depending on what you want to do outside of eating jerk.
Keep in mind that if you are booking for the holidays stuff books up way in advance and it is $$$. I am booked already on Bonaire for the week after xmas.
George
We love the Caribbean. Easy to get to, a variety of different cultures, variety of different types of terrain, food, things to do. We’ve visited around 15 islands and definitely have some favorites. Taking out the corporate type places which sound less interesting to you, so ignoring the Ritz and Four Seasons types, a few other ideas: 1) Mustique. This tiny island is in St. Vincent and the Grenadines. Technically a private island with 100+ villas (think island is owned by the homeowners), but also has a couple of small hotels/resorts that welcome guests year round. Cotton House is the biggest but still a small hotel by most standards. Firefly hotel is a cool boutique hotel with only a few rooms and amazing sunsets. Saw Paul McCartney on the island when we visited. Need a connecting flight from another island to get here. 2) Belle Mont Farm in St. Kitts. Newer resort set away from the touristy part of St. Kitts on a lush hillside. Beautiful views, rooms, pools, dining. Organic farms onsite for produce, a golf course. Direct flights available. 3) Sugar Beach in St. Lucia. Wonderful resort set between the Pitons which rise to the sky on either side of their private beach. Very dramatic setting. In Jamaica we stayed at a place called Round Hill which was nice. Wouldn’t call it boutique. Gets a fair amount of family traffic.
I’ve been to St Thomas and loved it. They (whoever they are) say Barbados is the other place to visit.
I haven’t been to Jamaica mon. Check out this video from the SNL wanna be called Friday’s. It was a Friday night show on ABC. The Rasta Gourmet - YouTube
I haven’t traveled to other parts of Jamaica but heading to Negril for jerk chicken at Three Dives might be the answer … sooooo good (though I love their lobster so much too!)
y-KpoUe_V_I
A great source of info on traveling to Jamaica avoiding the AI scene is http://www.jamaicans.com discussion boards … great folks, great discussions by the diaspora
Certainly not going just to eat Jerk, but I will enjoy a lot of it. My point is I want to get out and see real local island life, not interested in the best sushi or whatever the four seasons has imported on the menu when I’m in a place with its own culture just outside the doorstep. There could be a time/place for that, but I’d like to explore a bit more.
Thanks all for the continued thoughts/recommendations.
I think you will be mostly disappointed with the local Jamaican culture. It is hard to find buried under the massive amounts of poverty IMO. Jamaica was the one island I have been to where I was not overly comfortable going anywhere. Certainly at all their tourist spots there is “local culture”.
Look at Barbados or St Lucia, Cuba. Mexico in terms of culture has some of the best IMO.
George
I have visited Jamaica regularly since the early 80’s. My daughter is married to a man whose family has been in Jamaica since the late 1700’s. They owned over 25k acres of farmland on the North Coast near Trelawny and Falmouth that has now been leased back to Jamaicans. If you saw "Stella Got her Groove Back " you saw that area in the mountains.
I reject the claim that Jamaican culture is difficult to find and be welcomed into. If you stay at resorts, you will feel this way but I have been all over this island and have been welcomed by all. In addition, I have been to virtually every other island in the Caribbean except for Grenada and Trinidad. The depth of cultural beauty is unmatched in Jamaica.
My daughter and her husband spent almost a year in Treasure Beach training farmers to grow organically and to promote the local foundation. TB is unlike any other area of Jamaica. First off, it is the bread basket of Jamaica with 80% of the produce grown in the valley. Fields of melons, bananas, other fruits everywhere along the hills and sold along the roads.
There are no resorts in TB as Siun mentioned which is a major advantage. You can easily rent a great house right on the beach at reasonable prices. You can buy fish right on the beach and cook at home or you can eat at any of the small places in TB. Jack Sprats and Jakes are more American in style but still tasty. If you go to TB , you have to drive to Little Ochi -http://littleochie.com/ . IT’s the best seafood restaurant in Jamaica right on the black sand beach. You walk in and are greeted by a staff member who shows you all the fresh fish , lobster, etc in the coolers. You select the style you want, Escabeche, jerk, etc and get some beers and go sit in a marooned boat that is now set w tables. On a weekend night, there is live music or a DJ , Reggae booming in your belly. Not only is the food great but the ride there is an adventure.
Other things to do in TB -
Take a cruise w Captain Dennis to a beachside lunch and then to the Pelican Bar in the middle of the bay on stilts. Or drive up to Black river and take a boat ride on the river and see crocs and other animals.
2 Summers ago, My daughter got married on the Beach in TB. Since they had lived there, they knew everyone in the area and were treated like family. My Daughter and her Husband produced the entire event. They invited over 100 friends and family to come down for 10 days . Not a single person’s plane was delayed nor were there any delays in the transit to TB. We rented a car but most people took Vans from Montego Bay Airport (@ 2.5 hrs) but worth the ride.
We rented virtually every house on the beach in Calabash bay. We were able to walk to every house and had big pot luck dinners at our house, Doubloon. This was in early July which is offseason and we rented doubloon for 4 couples for under $3000 for the week including the staff. Food costs are extra but reasonably priced. Hio, our cook made great meals and responded to virtually every request.
We were all there for 10 days and participated in a different event every day including dedicating a day to help rehab the local school, painting all the classrooms and giving drama and music workshops to the kids.
One of the biggest differences between TB and other more touristy areas of Jamaica is that there are never people on the beach trying to sell you stuff. None of our guesst ever felt challenged by anyone or felt unsafe.
If Jerk is your thing, make sure to stop on the way from Montego bay at Border Jerk. We have tried a lot of local jerk places in the course of 30 odd years visiting Jamaica and the Border Jerk is the real thing . It’s halfway between TB and Mobay so it helps break up the ride.
One other note, if you want to buy wine, there isn’t much except for supermarket Chilean wines that have been roasting on the shelves. Drink Rum or beer although for me Red Stripe tastes like soda water.
Finally, Jamaica has reformed their marijuana laws recently. Possession of less than an ounce is legal now. Resist the urge to buy from anyone you meet outside of your rental house or hotel. In full disclosure, we didn’t want any on the wedding guests to procure ganja by themselves. Since we knew locals, we were able to buy a pound of organically grown bud for @$100 US and provided a supply to all the guests.
Please feel free to ask me more about TB. We can introduce you to a number of the locals and fill you in more about TB and the entire San Pedro valley.
Can I join your family?
I’ll just add that as a single mom, I never felt unsafe in Jamaica and my daughter and her friend were able to go out and have fun -including touring with some ganja growers -with no worries at all. I felt welcomed into the community at Treasure Beach and local life.
Negril was different but not unsafe - we just had to learn to be very clear we did not want aloe massages or braids, etc on the beach. One time, that was persistent enough to be irritating but unsafe … nope.