Doctor’s Cave is one of the best beaches in the world for swimming. By the time I first came here, I had lived in Asia and visited Boracay before it became a hotspot. I had already seen Bahía de las Águilas in the Dominican Republic and Grace Bay on Providenciales. My standards were high. Doctor’s Cave belongs in that company.
That is the first reason to consider S Hotel Montego Bay: it sits directly on this beach. The second is the freedom to walk out through the hotel’s gate onto the Hip Strip. Between the two, it offers a particularly appealing way to stay in Montego Bay.
It is also one of four Jamaican properties in Small Luxury Hotels of the World, alongside S Hotel Kingston, The Trident Hotel and Bluefields Bay Villas.
Doctor’s Cave and the Hip Strip
The beach is the hotel’s great advantage. Direct access makes swimming part of an ordinary hotel day, with no transfer or separate outing to organise. The hotel provides loungers and beach concierge service on Doctor’s Cave.
On the other side is Jimmy Cliff Boulevard, still widely known as the Hip Strip. I felt comfortable walking straight out from S Hotel and exploring the street. That ability to leave on foot mattered to me: I wanted a beach hotel with some life around it. Jamaica’s first Starbucks opened at Doctor’s Cave in November 2017 and is still here—a familiar coffee stop that adds to the street’s relaxed, approachable feel.
It is a town address, with restaurants, shops and other hotels nearby. Doctor’s Cave is an established bathing club, so the beach is shared with visitors beyond S Hotel’s guests. Its history goes back to 1906, when Dr Alexander James McCatty donated the property to found the club.
The next generation of the Issas
Before S Hotel came to Montego Bay, Spanish Court in Kingston had already made its name among well-to-do Jamaicans. I remember its reputation as somewhere worth going, even if you had no need of a hotel room.
Its owner, Christopher Issa, belongs to a later generation of the family that helped shape modern Jamaican tourism. His granduncle Abraham “Abe” Issa, often called the father of Jamaican tourism, opened Tower Isle in 1949 and became the Jamaica Tourist Board’s first chairman. Tower Isle later became the foundation of Couples Resorts and its pioneering couples-only, all-inclusive holidays.
Christopher brought a different emphasis to that inheritance. He opened Spanish Court in 2009, transforming a former shopping centre into a boutique hotel in the capital. Guests shortened its name to “the S”, after the letter on the building. As he explained in a Jamaica Observer interview, the attraction of a city hotel was the part it could play in the life of the city.
A decade later, that idea reached Doctor’s Cave. S Hotel opened in January 2019 on the former Breezes property, with red umbrellas, a glass-walled rooftop pool and a distinctly chic atmosphere. Coming from a family so closely associated with all-inclusive resorts, its original decision to open without that model was especially interesting. The hotel encouraged guests to go out into Montego Bay.
S Hotel has since become all-inclusive, while Spanish Court was renamed S Hotel Kingston in 2024. The Montego Bay hotel’s position still gives guests the same choice: stay by the water or step out into town.
Rooms with a Jamaican soundtrack
The record player was the detail that set the mood in our room. Bob Marley’s Legend was there beside it, with headphones ready. It gave the room a sense of Jamaica that went beyond its address.
For booking today, the distinction to watch is the view. The Mini King Room and Mini King Suite are explicitly sold as non-ocean-view categories. The current room selection also includes ocean-view doubles, Junior Suites, a Junior Suite with Cabana and upper-level Sky Suites. If the sea is central to your choice of hotel, choose a category that names it.
Eating at S Hotel
Breakfast beside the main pool places you close to the water from the start of the day. Marketplace is the hotel’s buffet restaurant, while the current dinner options give the all-inclusive stay several different directions.
Roots Rock serves Jamaican dishes; Rocksteady focuses on seafood; and Jamrock takes an Italian direction. These dinner restaurants require reservations and operate on selected evenings. Rocksteady is adults-only, even though the hotel now welcomes children aged eight and above.
There is also S Café for coffee and light bites, and Vibes Bar & Grill beside the pool. For more of the island’s food beyond the hotel, I have written separately about the flavours of Jamaica.
Pools and the Irie Spa
The main pool sits between the hotel and the beach. Above it, the Sky Deck’s glass-enclosed pool brings the view up to rooftop level. Check the access included with your room when booking, particularly if the rooftop is part of the attraction.
The Irie Spa offers treatments and subterranean plunge pools at different temperatures. Bath sessions and treatments have separate charges; an all-inclusive booking does not make every spa experience part of the room rate.
Beyond the beach
If this is your first visit to Jamaica and you want to take just two trips from Montego Bay, I would choose Martha Brae rafting and Rose Hall by night.
Bamboo rafting on the Martha Brae is the quieter outing: a raft for two, a captain guiding it downstream, and green riverbanks passing slowly by. For me, its appeal lies in both the surrounding nature and the encounter with Rastafarian culture. The private excursion linked here includes hotel transfers and rafting admission.
For the second trip, take Rose Hall’s haunted night tour with transport. The eighteenth-century plantation house opens a window onto Jamaica’s colonial past. After dark, actors and storytelling add the theatrical legend of Annie Palmer, the “White Witch of Rose Hall”, to the visit. This is the time to go for atmosphere, with the return journey to the hotel already arranged.
S Hotel Montego Bay is at 7 Jimmy Cliff Boulevard, a short drive from Sangster International Airport. It now welcomes guests aged eight and over, so older descriptions calling it an adults-only hotel no longer apply.
The reason I would return is still Doctor’s Cave. After the beaches I had already seen, this one made an impression—and S Hotel puts it directly outside the door.
Featured photograph: S Hotel Montego Bay.