Celebrating his father’s 75th birthday last fall, our very own James d’Silva let us set him up with travel plans to Jamaica’ with his wife and infant son, his parents, and his sister and family. With two luxury villas lined up for their stay, world-class service across the board, and a list of fun local activities, the trip was on. Even though they traveled in October, with its reputation as hurricane season, James and family loved the island. His advice for travelers? “Roll the dice and go in the offseason.”
What to do in Montego Bay
Top of the bucket list in Montego Bay is a nighttime boat ride around the Luminous Lagoon. This little cruise takes you from a small community called Rock through Trelawny Parish’s marshlands on glowing green water and settles at Jamaica’s 18th century historic sugar port, Falmouth. As your tour boat settles on the water, the magic begins. When the lagoon’s water is disturbed, its microscopic organisms (it contains millions of dinoflagellates) cause it to turn an eerie green and expose the fish and other marine life existing down below. The same halo effect happens to your body when you jump out of the boat and swim. This rare phenomenon is something you have to experience for yourself – and if you get to do it during a full moon, all the better!
To enjoy the water in daylight hours, try Dreamer Catamaran Cruises for a memorable (and possibly rambunctious) experience. Your friendly crew will welcome you on board and take you out to a snorkeling location. Once that’s done, the bar opens up, and it’ll be full of Red Stripe and Jamaican rum, vodka, and rum punch. Then it’s a quick stop at Margaritaville for water slides followed by sailing along the coastline and ending with a dance lesson from the crew.
If relaxation is more your style, Deep Drop Fishing offers some of the best deep sea fishing on the island. Your four-hour trip with them is packed with opportunity, with the chance to catch marlin, tuna, mahi-mahi, wahoo, barracuda, and mackerel. Refreshments are included (water, Red Stripe, soda, and snacks), but you don’t want to fill up too much – they sport a 100% catch rate, and they encourage guests to eat what they catch.
Where to stay in Montego Bay
D’Silva was so taken by Flower Hill that he had a hard time finding the words to describe it. Eventually, he came up with two: massive and opulent. Tucked into a prestigious gated community, this property is downright lavish both inside and out. With room for up to 17 guests, Flower Hill is best suited for couples with families, each enjoying privacy in the form of their own room with an adjoining suite, making it possible to get away within your getaway.
You could spend days and days at Flower Hill without ever getting bored. Where do we begin? Pinball and PacMan machines can keep one person occupied for hours on end. If you’re looking to compete in groups, try pool, ping pong, shuffleboard, foosball, or cards. If R&R is more your thing, settle down in the spa room with massage table (a masseuse can be requested) or the cedar steam room to sweat it all out. Not to be forgotten are its Instagram-worthy ocean views.
Just next door, Villa Rosa is another masterpiece down to every last detail. Whether it’s the bedrooms practically nestled into the trees, sporting magical ocean views or spa-like bathrooms that invite you to stay a little longer, Rosa’s owner Margaret Kerr has thought of everything. She’s even thought of things most people would never think of, like the outdoor shower. This al fresco waterfall, like nothing you’ve seen before, is built right into a tree. You have to see it to believe it.
If you do feel the need to leave either of these villas, your stay grants you membership at Half Moon, a resort just a few walkable minutes away, allowing you access to the beach and its lounge chairs, water sports, and a swimming pool. You’ll also get to play the resort’s 18-hole golf course at no cost.
Where to Eat in Montego Bay
No matter where in the world you go, food is an important part of any vacation. Your private, world-class chef service along with al fresco dining at Flower Hill and Villa Rosa will make you reluctant to eat anywhere else. World-class butlers and chefs are at your beck and call, and they are big on local cuisine, serving dishes like ackee and saltfish as well as breadfruit, making sure you get the Jamaican experience you’re looking for. With fruit trees surrounding the villa, ask one of the staff members for a coconut, and a coconut you shall receive. Drinks are aplenty as well, and entertaining is at its finest on Flower Hill’s second floor, where a portrait of Ernest Hemingway hangs over the bar in a room named after the author.
For those days and nights you decide to venture off, we’ve put together a list of restaurants for you to consult so that when your stomach starts grumbling, you’ll be ready to satisfy it. For fine dining, head to The Sugar Mill at Half Moon resort, where you’ll find Jamaican cuisine with a twist. Try Solomon’s Brochette, a meat and seafood brochette dish flamed with rum. Julia’s, in the hills of Montego Bay, serves up Italian-style seafood with a view. Located right on the water off St. James’ coast, right next door to Margaritaville, Marguerites is the place to go in MoBay for their signature Caesar salad, seaside dining, and sunset views. Full stomachs, happy travelers.