Jamaica –The Land of Reggae and Rum


Round Hill Hotel & Villas invited a group of Travel Advisors out to their property for a few days to experience the ‘Timeless Elegance’ the property prides itself on.

As it’s the low season in the U.S. market, I found myself connecting through Philadelphia on the way to Montego Bay. On the way back, I connected through Miami to get back to Chicago.

Upon arrival at MBJ, Round Hill organized Meet & Greet Assistance through Club MoBay – a VIP service that includes fast track through customs, and VIP Lounge access for your departure flight. A representative meets guests right outside of the aircraft and guides them through customs, and onto the Round Hill desk in the Arrivals Hall.

We were informed the Montego Bay Airport will be expanding in the next year or two and, with this new space, Round Hill is seeking to create a lounge space in the Arrivals Hall – it’s sure to be a wonderful addition to the arrival experience!

Once at the Round Hills desk, you are then guided to a transfer van for your 30-minute drive to the beautiful Round Hill Hotel & Villas property. Opened in 1953 and situated on a hill, Round Hill Hotel & Villas features a collection of secluded and elegant luxury villas, ocean-view rooms, and suites, that are nestled in the one-hundred lush acres and surrounded by natural beaches. Fun fact #1: Ralph Lauren owns two homes on their property. Who knows, you may get lucky and see him hanging around the beachside bar during your stay!

Upon arrival to the classic lobby, you are greeted with a welcome drink which, of course, has a splash of rum in it! A true Jamaican welcome.

From the minute you step foot onto the property, you are met with smiles and warmth from all the staff. A true contrast from the airport staff who, to their confession, take their jobs very seriously and do not express the same Jamaican warmth one might expect right after touchdown on the Caribbean Island.

We were led to the main dining area – the Seaside Terrace which, as the name suggests, is located right next to the water, and has wonderful views of the beach and ocean beyond. Fun Fact #2: this terrace is featured in the rom-com ‘How Stella Got Her Groove Back.

After the delicious lunch, we were driven in golf carts to our accommodations during our stay – their 5 Bedroom Estate Villa located halfway up the hill – all ensuites. Pictures do not do this villa justice, but I can still try!

Once we were settled in, we were met by the villa butler and staff. At Round Hill, staff are always stationed at the same villa and therefore know the accommodation inside and out. Our Butler, David, and our Head of the House, Ms. Carmen welcomed us to what was truly their home. Ms. Carmen is now the longest-serving staff member at Round Hill with 30+ years of experience! Round Hill is excited to have just launched their new Butler Service – providing guests staying in villas with a kind staff member to help curate their experience during their stay. They can help with anything from restaurant reservations to spa appointments, to confirming water sports activities.

In the evening, the villa staff helped to put together a lovely Welcome Dinner at the villa. The head chef for the property even cooked for us!

We began our first full day with a site inspection of the property. Situated on the northern part of the property, the entry-level Ocean View Rooms are located on the second floor of a two-story building. Below on the main floor, you can find the Ocean Front Rooms, which have a nice-sized private patio off them. Between this building and the ocean, is the oceanfront pool. Fun Fact #3: Ralph Lauren helped to design the interior of both room categories.

We then headed up to see two other Villas on the property – #23 and 18, a 3-Bedroom and 6-Bedroom Signature Villa, respectively. It’s important to note that all villas on the property have different owners and therefore have their own unique decorative styling and charm. Personally, the interior design of Villa #23 was fantastic – comfy but with worldly furnishings.

For the newfound pickleball fans – you’re in luck! Round Hill has two tennis courts that can easily be turned into pickleball courts. Just up the hill a smidge, you can find the property’s organic garden which they use in all their cooking. If they can’t get the ingredients they need from this garden, they seek what is needed from local businesses. One of many things the property does to foster the connection between them and the surrounding community.


Ending our tour, we walked along the oceanfront wooded pathway to the spa and fitness center area. As it’s designated as an adult-only area, it’s a great option to hang around to escape from the families that may be enjoying the beach. There were plenty of children enjoying the resort facilities during our stay and you wouldn’t even know it! They could be enjoying the water or building sandcastles, but they didn’t take away from your blissful Caribbean vacation.

For the kids, there’s a fantastic children’s program on the property. From full days spent outside to organized activities like soccer, tie-dye sessions, board games, table foosball, reading, and painting, Round Hill offers kid-centric activities, clubs, and dining options, as well as an on-site nanny program.

Getting back to the fitness center, it’s a spacious and bright space whose walls are made up of windows. The A/C machines are running to help with the Jamaican heat! Next door, there’s a yoga pavilion where guests can schedule yoga classes as well as personal fitness classes with the onsite trainer.

After our tour, we were given the opportunity to go out and enjoy the facilities. I took time to swim in the ocean (bath water temperature!) and got a massage at the spa. Round Hill recently partnered with an Oceanographer to help them rebuild the coral reef just off the coast from the property. It seems to be working as the staff commented that the water is clearer than ever.

Every Tuesday, Round Hill throws a BBQ dinner on the beach and sets up food stations, tables, and tiki torches on the sand. It’s a great way for the hotel guests to get together and enjoy some great food and live music.

On our last full day, we ventured outside the property for a 2.5-hour drive to YS Falls – a destination that travelers go to in order to experience the seven waterfalls that cascade into natural swimming pools. The roads were a bit rough, but the joke goes that the potholes aren’t fixed very quickly to prevent drivers from speeding on the smooth asphalt! Here, you can venture into the pools and climb on the rocks (with the help of a guide) and go ziplining over the water. I’ve been ziplining a few times in my life, but it was unique to be zipping over a waterfall!

We then drove to Appleton Estate to take a tour of how this famous Jamaican rum is made. With the first distillation taking place in 1749, the estate has been around for longer than the U.S. has had independence! With a cocktail in hand (which had Appleton rum in it, of course) we took a group tour and had a rum tasting.

Arriving back to Round Hill, we were met by this spectacular sunset from our villa to close a wonderful trip to Jamaica.

With Club MoBay reserved, my time at Montego Bay Airport went by smoothly with a private line through security and lounge access.

Overall, it was a wonderful introduction to Jamaica, and I cannot wait to go back! Round Hill is truly the perfect location for a romantic escape, family getaway, or even a wedding (an entire property buyout is an option).