Jamaica: Cherry oh Baby!

I had not been to Jamaica for 20 years and it was high time I checked back in! This island has an easy, happy and friendly vibe that encourages you to smile and let your hair down right away! Due to great air connectivity, we have families who rent fully staffed homes at Tryall Club and Round Hill year after year. It was wonderful for me to see some of the terrific homes and meet the lovely teams that take care of our clients! I also got the chance to travel to the north of the island and stay at the marvelous Golden Eye where Ian Fleming wrote all of his James Bond novels. After that, I headed up to the Blue Mountains where Jamaican coffee is grown and food is truly farm to table at the lovely Strawberry Hill. Jamaica Inn was also a real treat, a throw back to the glamorous 50’s and 60’s when every famous person vacationed here and likely sat at Teddy’s Bar with Teddy who still holds court!

Round Hill – Classic, elegant, old world

Checking into Round Hill
First sights of the Caribbean!
Protected beach at Round Hill
Water sports center at Round Hill
The spa pool at Round Hill
The iconic staff members, still in full coat and tie in the heat of the day
Round Hill has lovely hotel rooms in addition to their special multi-room villas.
Morning swim
Shady reading spot!


The villas at Round Hill are exceptionally well appointed and come with a dedicated staff during your stay. The below images are from one of their most luxurious villas – terrific for a large family or group of friends:


Next stop, Tryall Club!

Tryall Club is a very large property with a wide range of fully staffed spectacular homes – each completely different in design and decor. When families return year-after-year it is often because of the staff whom they have grown to love!

Given the vast range of choices, it is important for me to speak to my clients about what style decor they enjoy – whether they are looking for more of a classic or contemporary feel.  All of the homes are completely unique in size and amenities. We visited several with gorgeous views, welcoming staff, and terrific amenities including private pools, tennis courts, and entertainment areas.  All guests staying at Tryall have access to the beach club, golf course, and tennis courts.



Welcome to Half Moon

Half Moon is located just 10 minutes from the Montego Bay airport with a whirlwind of activities from golf, tennis, horseback riding, kids club, waters sports, fitness facilities, and many dining options. This property will appeal to families with varied interest and who want a lot of activities.

This is a very large resort spread out among many acres with varied options for hotel rooms, suites, and villas. The villa product is going to be more generic with hotel standard furnishings and art, not like an individually owned home. While the larger villas have many rooms, the public or shared entertainment space is not very large. Decent value but the decor will not wow those looking for a special home.


Jamaica Inn

What a wonderful throwback to a glamorous era of travel! This historic and iconic property really has a sense of place and is full of tales of the storied cast of characters who have enjoyed this escape.

Ocean Side Rooms are private and allow you to literally look over your balcony into the water
Outdoor living space in many of the rooms is so charming and enjoyable.


The main pool next to the croquet lawn and Teddy’s Bar.
Here is Teddy himself who will make your a drink, sing you a song, and tell you about the heads of state and famous actors he has served drinks to for a half century at Jamaica Inn.
The honeymoon villa is a stand alone unit
I loved my beach front room
My outdoor living area was my remote office during the day and cocktail lounge by night.
My friend Teddy, always ready with a cocktail!

Jamaica is a study in contradictions – Rastafarian reggae meets elegant old world. It is not unusual for staff to be in coat and tie – expect guests to also step up their dress at the traditional old guard properties such as Jamaica Inn and Round Hill.


The open air spa at Jamaica Inn – one of the best massages I have EVER had!

Golden Eye

Owned by Island Records founder Chris Blackwell and the site where Ian Fleming wrote all of the James Bond novels, Golden Eye is the place that helps you understand Jamaica and all of the legends who celebrated life here during the 70s and 80s. And today it remains a relaxing haven of cool! Golden Eye is a rustic eco-chic retreat with terrific food and relaxation. No sport coat expected here!


The private beach at the Ian Fleming Villa


Welcome cocktail delivered to my cottage shortly after arrival
Our Lagoon Cottage
The newer beach huts are a more affordable option at Golden Eye


Cocktail hour at Golden Eye with the fantastic GOLDEN EYE Rum cocktail and tasty organic appetizers – pumpkin seed dip and mango jerk chicken.


Heading to the spa by kayak (you can swim there too!)
Spaaaah bound!
Beachside lunch and what else but Blackwell Rum!
Glad this guy showed up to join me for a beach lunch and Blackwell Rum.
We barely made it to the spa without capsizing our kayak
The treatments were certainly a treat!

Strawberry Hill

Not many travelers go to Jamaica get up to the highlands but we wanted to visit the famous Blue Mountains in coffee country! We stayed at the ever so charming Strawberry Hill which is part of Island Outpost – the group that has Golden Eye.  This makes for a wonderful combination of coast and country!

Our view of the lush valley and hills far above Kingston
Charming bedroom


The Main House with a wonderful restaurant
Staying at Strawberry Hills feels like you are a guest in a great house from a bygone era.
Gracious hospitality and always a rum in sight!
Even in pouring rain, the views are stunning
Strawberry Hill sits in the Blue Mountains overlooking Kingston
Wonderful lunch on the porch
Lamb and Goat
Jamaican me happy, mon!

Strawberry Hill is not for the faint of heart, the roads leading up to the property are narrow and windy and in the rains can feel treacherous. I am glad we did not miss it though! Jamaica has soul and character and when visiting, I definitely suggest you get out and experience the land and the people rather than just staying resort bound. The people of Jamaica will raise your spirits from the start – a robust and confident smile – everything is going to be alright!

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