JAMAICA || A Winter Getaway

WHAT \\ The crystalline waters, the lush green mountains, the pristine powder sand beaches, combined with rum cocktails and molten sunsets – make Jamaica the perfect spot for a Winter Getaway. It is a place where there are very little decisions to be made, it is all about relaxing in the warm sun, floating in the salt water, watching sunsets with a cocktail in hand, naps in the hammock, and maybe a visit or two to the spaaaaaaaah. All the details are mapped out here.

WHERE \\ Ocho Rios – Montego Bay – Negril are typically filled with all-inclusive resorts, and happen to be in some of the most beautiful parts of the Country. To break from the crowds, choose smaller boutique hotels or head further afield to places like Treasure Beach or towards Port Antonio. This trip takes in a little of both worlds. Starting in a small mid-range boutique in Negril, and then moving to top-end luxury accommodation in Oracabessa Bay.

WHO \\ A romantic getaway for two people. Celebrating a birthday & a wedding anniversary, however, you don’t need these as an excuse to enjoy a few luxury treats & experiences.

WHEN \\ December thru March are the months for peak season, weather is great low rainfall and temperatures are high without humidity. March tends to find Jamaica a little less crowded and still doused in sunshine filled weather with very little rainfall.

WHY \\ All in the name of R&R, giving a much needed break from the bleak cold snow laden winter filling us all with a serious case of the blues [and I am not talking skies].

DAY ONE || Getting there
Most of the day will be spent traveling to your destination. Be wise, book direct flights if you can to Jamaica. In the winter this is a must, with cancellation of flights & weather delays possible – it keeps things simple. Now let’s just hope the flight crew all remember their passports and set their alarm clocks so you can get this show on the road.

3:30PM || Arrive Montego Bay Once your plane touches down at MBJ Sangster International Airport – utilize the VIP Airport Service ‘Club MoBay‘to speed things up: getting through immigration & customs; and then getting you connected with your driver that you pre-arranged to collect and take you to your hotel in Negril. This service is a serious time saver. The lines for immigration twist & turn longer than a Disneyland ride at spring break, the Mo’Bay Club team gets you through the airport in under 30 minutes and on your way to the beach. Woo hoo!

5:00PM || Check into – Tensing Pen – Negril Tensing Pen is a secluded hideaway nestled into Negril’s west-end cliffs where the ocean kisses the rocks. It is made up of a collection of 17 stone, wood and thatch cut: cottages; studios; bungalows; & homes all neatly tucked into lush tropical gardens, providing privacy and a sense that you have the place to yourself. Access to the water is easy: jump off the bridge or cliffs into the crystal clear waters; or gently ease yourself in from a short ladder accessible via a serious of stairs & platforms artfully carved into the cliff.

5:30PM || Swim & Relax Quickly drop your bags, peel off the clothes, pull on a swimsuit, grab a beer and start to feel the stress slip away. Top it off with a refreshing swim as you watch the sun go down.

7:30PM || Cocktails & Dinner  At your leisure after a long day of travel enjoy dinner on premise with some crisp cool wine admiring all the stars in the open air restaurant. Later slip into bed and fall asleep listening to the sounds of the ocean.

DAY TWO || Meeting the Locals

Today everything is at your leisure: stay by the pool; find a hammock to spend the day with a book; or head out on foot to explore Negril.

7:00AM || Breakfast Swim After a peaceful night sleep wake up with some fresh coffee and a swim, followed by breakfast of fresh tropical fruits & juice, and then back for some more swimming. Maybe grab a quick nap in a hammock or on a lounger in the warm sun.

11:00AM || Explore & Meet the Locals Step out the gates and hit the road on foot to explore your surroundings. You can pop into Rick’s Cafe to watch some cliff divers, but if you wander a little further along the road you will find a more ‘local’ and authentic Jamaican experience at ‘Sir D’s Firewater Lovenest’. A family run business, with the loveliest people & locals you will ever meet. You feel like old friends in no time, and in no time you realize several hours have passed. The views are spectacular & if you are in luck you can watch dolphins playing in the cove as you sip your beer & share stories.

3:00PM || Naps & Swim Return to Tensing Pen for a relaxing swim and float in the ocean cove, or take an afternoon nap – after all you are on vacation and there are no rules and no expectations. Whatever you do, just make sure you replenish the sunscreen slathering from time-to-time and drink plenty of water to keep hydrated.

5:30PM || Traditional Jamaican Dinner When leaving Sir D’s organize for a local dinner to be cooked for you. Donnette, the owner of the bar can prepare & cook for you some of the best fried chicken & chips with local spiced sauce you will ever have. Arrive in time to watch the sunset and enjoy your meal, share some more great stories and meet more of the locals.

7:30PM || Dessert Once you return to Tensing Pen pop into the restaurant and grab some dessert and a digestif cocktail, return to your cottage to enjoy your sweet treats under the twinkling stars. Later be lulled to sleep once again to the sounds of the ocean crashing into the rocky cliffs. ZZZZzzzzzz – like a baby.

DAY THREE || Negril to Oracabessa Bay
Time to change locations and head to the other side of the island to experience some serious luxury and pampering.

9:00AM || Swim & Tropical Breakfast Wake up and take a dip. Grab a light breakfast. Stuff your things into your suitcase, make sure you don’t leave your shoes or any belongings behind. Today you hit the road for new adventures on another part of the island.


10:30AM || Drive to Oracabessa Bay Having arrived via the ocean road to Negril take a different route, and have your driver shuttle you through the mountains to see the real Jamaica. Pass through parishes & small towns to observe life as the Jamaicans do daily. Ask your driver questions about the history and it’s people to get a little education about the country. Stop to sample the local fruits and have lunch on the road. The patties are tasty – coming in chicken + beef + soy + beef&cheese as options, a thin flaky-pastry savory-turnover, tinted golden yellow with turmeric and often with a hint of spice.

2:30PM || Check into – Goldeneye – Oracabessa Bay Once the home if Ian Fleming who wrote all 14 James bond Novels here, Goldeneye is now, thanks to Chris Blackwell, a laid-back five star resort where the A-list come to unwind. Attracted by the privacy that is offered, along with the magical setting, once you arrive you will never want to leave. The property offers a selection of villas and cottages, take your pick opting for the beach front or lagoon. We say – take the Lagoon option offering kayaks as your mode of transport to get around the resort.

4:15PM || Spaaaaah After the plane and road travel it is time to get a massage and iron out some kinks. Take a kayak from your lagoon cottage to the ‘Field Spa’. Here you will be greeted with a foot soak and cold cucumber water before being taken for your massage. The massage rooms have incredible views over the lagoon and tropical gardens, this alone will get you relaxed.

6:30PM || Drinks at Bizot Bar After freshening up in your outdoor shower, wander over to the beach front bar for a cocktail and enjoy the remains of the setting sun.

7:30PM || Dinner at the Gazebo Once your are finished with cocktail hour, take a stroll over to the Gazebo restaurant for dinner. Passing through the gardens, and over the bridge where the ocean flows into the lagoon, to dine in the treetops. Feast on fish caught by the local fisherman that morning, all whilst sipping some delightful french rose. A perfect ending to an adventurous day.

DAY FOUR || Wedding Anniversary
Enjoy your first full day at Goldeneye exploring all the amenities and activities that are on offer, and celebrate life or a special occasion with the assistance of the resort staff.

7:00AM || Breakfast – Bizot Bar Once you have refreshed yourself with a dip in the lagoon-pool-beach [there are many options], dry off a little in the sun before heading to the Bizot Bar for breakfast. Feast on an array of dishes ranging from continental to local. When in Jamaica you have to try the local options – like the national dish of ackee & salt fish. Ackee when prepared and cooked is like scrambled eggs – delicious, especially washed down with coffee or fresh squeezed juice. Yum!

09:15AM || Tour Ian Fleming’s Home If the actual home of Ian Fleming [that is available to rent] is not occupied, ask the front desk if you can get a tour. The Villa & encompassing cottages offer some serious private & luxe accommodations for up to 10 people, including a private beach. Stunning. See where the likes of Jay-Z & Beyonce slept, and where Sting wrote ‘every breath you take’.

11:00AM || Poolside Lunch Take a dip in the signature Goldeneye pool, while the staff keep you refreshed with beers & cocktails. They will even take your lunch order and come collect you when it is about to be served. Phew! Just-in-time you are starting to look like a prune from your long relaxing soak.

02:00PM || Nap-Spa-Swim It’s Jamaica Mon! Do whatever you please: take a nap; visit the spa; swim; eat; read a book. It is not hard to while-away the hours in shear blissed out relaxing nothing. You are here to relax, and relaxing is so not hard to do around here. Take a deep breath and soak it all in.

07:00PM || Private Dinner The staff will help you set-up a private dinner anywhere on the Resort. They will prepare a custom menu and provide you with your own server for the evening. A romantic table setting, candle lit of course, and the evening is all yours, take-your time everything and everyone is on island time.

DAY FIVE || Birthday Breakfast & Picnic!

Ready to explore, once again work with the Resort staff to organize an excursion further afield. They will take care of all the details: from the driver, the food, to the location, leave it to them and just turn up and be whisked away on your adventure.

8:00AM || Tropical Breakfast & Mimosa Naps Arrange with the resort to have breakfast delivered to your Lagoon Cottage. Saunter out of bed and plop yourself into a sun filled chair to enjoy a fruit filled meal with ‘ahem – the locals’. Dip your feet into the water from your dock as you finish your mimosa, and then layback on the lounge chair for a nap before making any decisions.

12:30PM || Tour Noel Coward’s Home Meet at the Gazebo to be taken on a road-trip 30 minutes away high in the mountains for the best view on the Island. It is no wonder that Sir Noël Peirce Coward made this spot his home, and his muse, inspiring him to write, paint & compose. Wander around the grounds and admire the garden, and feel the cooling mountain breeze as you gaze at the coastline below, sharing in the same view as Sir Coward’s final resting place. It is truly divine.

1:30PM || FireFly Picnic After a tour of the grounds and home, settle into the shade of the huge tree that gracefully shadows the wooden stage, where many a wedding / party has been thrown – including for royalty. Refuel on a picnic lunch that Goldeneye has thoughtfully curated for a special occasion. When you leave you will be feeling like you ‘went to a marvelous party‘.

3:30PM || Ocean Kayak Return from your excursion and when ready, get in a little exercise, although it won’t feel like exercise. Take a kayak out of the lagoon into the ocean to explore the coral reef, don’t worry ask the staff for the route that takes you with the current so it is less work and more leisurely. Breathe in the fresh ocean air, float with your feet dangling over the sides.

7:30PM || Gazebo Dinner After freshing up with a bath in your claw footed tub, eventually make your way to the Gazebo for another delicious meal. Select from the specials of the day or savor one of your favorite dishes you have already grown to love, like the fish tea. A deliciously light broth with delicate pieces of fish and sprinkling of vegetables.

9:30PM || Sleep Fall into the freshly turned down huge bed, the one that you have struggled to get out of the last few mornings. Snuggle in for a peaceful sleep, trying not to think about having to leave tomorrow.

DAY SIX || Saying Goodbye
It’s time to head back to reality, but there is still time to grasp onto a few last minutes of swimming and enjoying the tropics.

6:30AM || Final Swim & Tropical Breakfast Gather your belongings and pack your suitcase, jumping in the lagoon for a final swim before showering and heading to breakfast. Savor every last bite of fresh tropical fruit and blue-mountain coffee.

9:30AM || Drive to Airport Your driver arrives promptly to collect you and shuttle you back to the airport in an air-conditioned van. Taking about two hours to get to Montego Bay, it gives you a last chance to marvel at the madness on the roads, Jamaican drivers are crazy. At the Airport, once again utilize the Mo’Bay Club to fast track you past the security lines and provide you with a departure lounge to relax in. Grab one last red stripe & a pattie before you go.

1:00PM || Depart for Home Climb aboard your direct flight, settle into your seats and sadly, but fondly, watch the jewel tone blue water disappear from sight. As you head high into the clouds and return to the remains of a dreary winter, you are hoping – just hoping – your thoughts of Jamaica can keep you warm until spring rolls around.


Here are a few pointers that are good to know about Jamaica to help you plan for your trip:

COMMUNICATION \\ Everyone speaks English so communication is very easy for those of us that don’t speak the local language ‘patois’. We found that response time to emails and phone calls, regardless of level of service/price, is done on ‘island time’. Typically, they are slow to respond – but they do respond and are reliable to sticking to plans. No worries man!

CUSTOMS & IMMIGRATION \\ Check to see if you require a visa before traveling to Jamaica, most countries do not require a visa, but check to be sure. To avoid the long [and I mean long] lines during peak seasons at immigration & customs utilize the VIP Club-MoBay services to express-lane you through the process and get you to the beach faster. It is worth every penny.

TRANSPORTATION & TOURS \\ Very few Jamaican’s make any money from working with large tour companies. Where possible try and select ‘local’ small independent drivers & tours guides. Arrange travel ahead of time, most hotels will assist you with transfers. We organized our transport directly with Dale Hudson – a great & reliable driver – email him for details hudson.dale@ymail.com

PACKING \\ Jamaica is very laid back and relaxed. Pack more than one swimsuit as you will be living in them. Don’t forget sunscreen and a hat to protect you from the suns rays. In the evenings the weather can get a little chill in the air so add some light layers. And most importantly PACK FOR A PURPOSE – take with you some much needed supplies for local schools & charities, check with your hotel to see what program they participate in and the supplies they collect.

FOOD & DRINK \\ Groceries: Fresh fruit & vegetables are dirt cheap, and seafood can be purchased direct from the fisherman. Rum & Beer is free flowing and the least expensive options, Champagne & Wine however, along with other packaged food is mainly imported to the Island and the prices are reflected accordingly. Dining-Out: Vegetarians – there are a decent selection of options on most menus. Lots of fresh fish & shellfish to be found, with plenty of jerk: chicken & pork. Try the patties, curried goat & fish tea, along with ackee with salt fish for breakfast or the plantain porridge.

MONEY \\ Cash is the best form of payment in most places, especially once you step outside your hotel/resort. Everyone will accept US dollars, change will be given in Jamaican dollars. There are plenty of ATM’s in the large cities, some even dispense US dollars, if heading to smaller towns make sure you have cash.

Happy Travels!