Montego BAY Itinerary

Crystal clear waters, all-inklusives & Jamaican city life

Duration: at least 5 days

Budget: $ 75 per day

Stay:  Cloud 9 Suite or Five Gabels

I was a little weary of Montego as it seems such a popular all-inclusive spot. However, the city quickly grew on me and
I found Montego to be the perfect starting point for my Jamaica itinerary.

Its touristic infrastructure lets you settle in quite quickly while downtown gives you glimpses into real Jamaican city life. As the island is relatively small, one can set out to do anything from MoBay.

Let’s divide Montego Bay into roughly two areas: Gloucester Avenue, aka the “Hip Strip,” lined by beaches, bars and restaurants. The “Hip Strip” is Montego’s main tourist area, and you can feel an American vibe.

The rest of Montego Bay and downtown feel a lot more real and offer an authentic feeling to those who venture out.

To experience the best of both worlds, I can only urge you to venture beyond the Hip Strip and get to know Mobay from an Airbnb in a more local neighborhood.
I loved my stay with Cerri and Jah B in Mount Salem.

As a touristic hub, Montego Bay welcomes most visitors to Jamaica. While tourism can significantly boost the local economy, it also imposes severe challenges on the local community. As such, it is vital to be aware of the implications and support small, locally-owned businesses as much as possible.

Beaches in Montego Bay

Harmony Beach Park

Coming from downtown, Harmony Beach is the first beach you’ll pass. It’s a free public beach that was just recently opened in 2021.

To my surprise, it’s a pretty large, very well-maintained park area with a beautiful sand beach. Even though Harmony Beach Park is free, you have pleasant amenities such as Lockers, Showers, and changing rooms. You’ll also find a booths that sell drinks and food.

Harmony Beach Park is almost empty during the week and becomes lively on the weekends. It is closed on Mondays for maintenance.


Harmony Beach Montego Bay
Doctors Cove

Doctor’s Cove

This stunning beach’s supposedly healing waters have attracted visitors since its opening in 1906. Today, it’s Mobay’s most famous beach offering visitors all kinds of amenities.

You’ll find the entrance next to Starbucks. The Entrance fee is $6. The beach area feels almost like you have entered a hotel complex. You have all the amenities: showers, changing rooms, bathrooms, a restaurant, and a bar onsite. 

The color of the water and the views of incoming and departing flights are unique.
Doctor’s Cove Beach is also the perfect spot to spend your last day before heading to the airport, as it’s close by.

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One Man Beach/ St James Hospital Beach

You’ll find a very quiet Bay with a beach located right behind the former St. James hospital. The water is super calm, and because it is so quiet, you can almost always find shade under an almond tree. The beach is seamed by a stone pier which is home to numerous colorful fish. Bring your snorkel mask to see them. 

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Dead End Beach/ Buccaneer beach

Dead End Beach is the famous beach where airplanes land right over your head, as the airport is right beside the beach! This relatively small stretch of beach located north of Gloucester Avenue is also known as Buccaneer Beach. It’s a free public beach with no facilities other than a small beach bar.

I love going there to “hold a vibe” for sunset as many Jamaicans do as well.


Montego's Gloucester ave, aka. "Hip Strip"

Mobay’s Hips Strip is the main party street in Montego Bay, with many bars, nightclubs, and restaurants. It is the center of tourism. It’s also where you’ll find Jamaica’s largest duty-free shopping area. 

While the hipstrip is not my favorite area to get food, the sunset views from one of the many Beach Lounges are beautiful. The lounge behind Island Strains Herb House is my favorite place to spend sunsets in MoBay!

Magarthiaville, the world-famous Usain Bolt Track record and restaurant, and Pier1 are other popular choices. 

Downtown Montego Bay

Downtown Mobay isn’t exactly pretty,  and pretty gritty on first sight. However, it is definitely worth exploring as it is Jamaica’s second largest city!

Chruch Street is Mobay’s “most picturesque” street. You’ll find Mobay’s Townhouse, Gregorian-style structures, and some pretty churches there.

downtown Montego Bay

Sam Sharpe Square

The square was named after Jamaican National hero Samuel Sharp. Samuel Sharp led the Christmas rebellion in 1831. In the afternoon hours, you’ll find tasty street food around, and it’s a good spot for hanging out and observing the crazy hustle of the city. Close by, you’ll also find the National heroes’ Monument.

sam harp square downtown montego bay

Montego Bay Cultural Center

You’ll find Montego’s Cultural Center southwest of Sam’ Sharpe Square. Home to a history museum, a small art gallery, and MoBay’s cultural events.

The museum is especially interesting as it tells the story of Montego Bay from the Time of the Arawaks to the present day.


Greenwood Great House

This 18th century plantation was once awarded to Hersey Barrett, a British officer, after he was stranded in Jamaica following a failed raid on Hispaniola.
The former plantation is one of the few that survived the Christmas Rebellion unscathed. Today, the Greenwood Great House houses an antique museum, which also displays many historical musical instruments. The guided tour costs $20 and there is also a pub, which I find insensitive to the past.

Rose Hall Great House

This 18th-century plantation was once owned by Annie Palmer, the so-called “White Witch of Rose Hall”.
Today, it is a museum where you can learn about Annie Palmer’s dark past and Jamaica’s history.

In addition to the museum, the huge estate is also home to a golf club and a wedding and event location. Given its historical background, I find ungraceful.

Cinnamon Hills

Another Great House that is said to be haunted, is also located on the grounds and can be visited as part of a tour. Music legend Johnny Cash once lived on the estate. The tour lasts around 45 minutes and costs $25.

The property is located around 20 minutes outside of Montego Bay.

Montego 1

Green Grotto Caves

This 1.5 km-long cave system is famous for being the filming location for the James Bond movie Live and Let Die, but it also has a rich history.

The caves were a hiding place for enslaved people fleeing the plantation owners.

Today, the caves are open for tourists and offer a moving glimpse into Jamaican history. You can explore the cave system on their own or take a guided tour, and there is also a small museum on site.

Jamaican Food Tours

I love getting to know a country by its food! 

The culinary adventure starts with you meeting with your guide and exploring Montego. On the way, you will get to try Jamaica’s most traditional dishes while learning more about the food culture and the country itself. 

Ackee in Jamaica

Walk with the hooligans

Are you looking for something unusual to do and love dogs? You will love the special tour Montego Bay Animal Haven has put together!

This tour allows you to explore the hills with a huge pack of rescued dogs! 

The walk starts at the shelter and leads you through Jamaica’s lush green hills towards a small river. It’s a beautiful hike, and seeing how the dogs are enjoying it is wonderful!

Hike Hours: 9 am – 10 am
Visiting Hours: 9 am – 12 noon
Costs: $65 excluding transport

Take in Jamaica's lush side: Animal Farm & Nature Reserve

Things to do in Montego Bay go beyond the busy nightlife typically associated with this paradise island.

Animal Farm and Nature Reserve is just a 30-minute drive away, but it gives you a completely different experience! From birdwatching across the fields to floating down the roaring Great River on a raft, there are plenty of ways to explore the area.

The Animal Farm and Nature Reserve also offers solar-powered eco-cottages with stunning views!



Hummingbird in Jamaica

Visit Rocklands Bird Sanctuary

Visiting Rocklands Bird Sanctuary is absolutely mind-blowing and heartwarming.

As you visit, you get handed a feeder, and after five minutes, the birds will start coming by. They are super human-friendly and will even sit on your finger.

The story behind Rocklands Bird Sanctuary is also truly Beautiful.

Way back in the early 1900s, the original “bird trainer” decided to make a home in these remote Jamaican hills.

Every day, she would embark on these serene strolls through the hills, taking in the beauty and sharing some of her food with these extraordinary feathered creatures.

After about five years of these daily adventures, it seems the birds became quite attached to her. They began to follow her all the way back to her home, and, well, her house soon turned into their absolute favorite hangout spot!

The Bird Sanctuary is located just 20 minutes outside Montego Bay. The ride is bumpy. The tour takes one hour and costs $20.

Visit a dispensary

Exploring a dispensary can be an exciting experience, especially for cannabis enthusiasts or those intrigued to delve into the world of “the herb.” Montego Bay boasts a variety of dispensaries tailored to diverse preferences. Personally, I am drawn to the diverse strains offered by Starbuds, coupled with their relaxed and hassle-free shopping atmosphere. Conveniently situated adjacent to the Usain Bolt track records, it’s easily accessible and hard to miss. Consider stopping by before heading to Dead End Beach for a breathtaking sunset view.

me at starrbuds in Montego bay

Practical travel tips for Montego Bay & Jamaica

Which language is spoken in Jamaica?


The official language is English, but you'll also hear Jamaican Patois spoken throughout the country. It's a colorful and vibrant mix of English, West African languages, and Spanish influences. Don't be afraid to interact with locals and try out some basic phrases in Patois - they'll appreciate the effort and you may even learn a thing or two.

What is the offical currency in Jamaica?


The Jamaican dollar is the official currency and is accepted everywhere on the island. However, US dollars are widely accepted as well, so it's always a good idea to have some cash in both currencies. You can easily exchange your money at banks or ATMs throughout the city. Just be aware that the exchange rate may vary, so it's best to check before making a transaction. Also, don't forget to tip - it's customary in Jamaica and greatly appreciated by service industry workers. So make sure you have some small bills on hand for tipping at restaurants, bars, and hotels.

What is the best time to visit Montego Bay?


Montego Bay is really an all-year-round destination. As anywhere in the region, hurricane season starts in June and lasts till November.

Is Montego Bay safe for travelers?


As a female traveler, I felt safe. Obviously, there are some hustlers you'll be fine with as long as you are friendly and walk with a purpose.
Montego's SoZo's
Zones of Special Operations were established about 10 years ago around Jamaica's cities after crime escalated. You'll notice the military around as soon as you enter a ZoSo. Salem is such a SoZo in MoBay. Be aware, but don't let it scare you. Flankers, Canterbury, and the area around the dump up beach are best avoided at night, though.

Public Transport in Montego Bay, Jamaica


Route Taxis are the way to move around Jamaica. Official route taxis have a red license plate. In MoBay, you'll see the route they are catering written on the doors. Route taxis are the cheapest and most flexible way to move around. Just be careful to enter/exit on the route. Otherwise, you'll be charged as a charter taxi.

Public Bus: The bus stop is downtown. I couldn't find a schedule. They seem to go more frequently than the Knutsford.
Knutsford: Leaving Moby Airport, Jamaica's luxury bus connects more significant destinations. Be aware that the time stated refers to calculated driving time and not the actual time to reach a destination. Adding to the driving time are stops and bus switches which are not apparent when buying the ticket. Due to Covid, there are fewer buses than usual, and it is better to buy the ticket online.


Arriving at MoBay Sangster International is quite picturesque as the airport is located right by the beach. The airport is also only 10 minutes from the HipStrip, 15 to downtown, and 20 minutes up Mount Salem. Sangster International Airport is also small making it extra comfortable to move around.

Can I drink tap water in Jamaica?


Even though Jamaica is considered a third-world country, it provides the best water quality in the region. You are, therefore, safe to drink tap water. This is especially true in the cities. However, if it makes you feel uneasy, bring a water purifier.

What's the biggest challenge for the conscious traveler?


Tourism leakage: Jamaica is a tropical paradise that's adored by tourists worldwide, but it has a problem that's hidden from sight - tourism leakage. This phenomenon refers to the loss of revenue that occurs when international hotel chains capture a large chunk of tourist dollars, leaving very little money behind to benefit the local economy. If you're among the millions of visitors who flock to Jamaica every year, there's a simple way to help mitigate the effects of tourism leakage: support Jamaican-owned hotels, shops, and restaurants. By doing so, you can put your money where your heart is - and give the people of Jamaica a chance to thrive. So don't be shy about seeking out local businesses on your next vacation. Your decision to keep tourism dollars within Jamaica could make a world of difference.

Beach access

While Jamaica is known for its beautiful beaches, there have been some issues with access to these public spaces. In recent years, many resorts and private properties have restricted access to certain parts of the beach, making it incredibly difficult for locals to maintain their life and right to the sea. Support public beaches and say no to all-inclusive tourism!


Make sure to bring a foldable food container and cutlery with you! The amount of waste caused by food sold on the street is incredible.


Make sure to protect Jamaica's marine life and bring reef-friendly sunscreen!

tanzania travel Zanzibar beaches

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As you see, there are plenty of things to experience in Jamaica. To come fully prepared, check out my packing list for Jamaica, which includes everything from eco-friendly toiletries to sustainable fashion and even the coolest travel gadgets!

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