Ultimate 5 Day Itinerary for Montego Bay Jamaica

by | Jan 16, 2022 | Caribbean, Jamaica | 11 comments

Affiliate Disclaimer: This post may contain affiliate links meaning if you click on them and make a purchase, I may earn a small commission at no extra cost to you. This helps me to continue making content and I couldnt thank you enough for your support!

Jamaica is a beautiful island rich with culture so I hope you’re ready to explore it using my ultimate 5 day Itinerary. This is perfect for those of you who enjoy both luxury resort vibes + local cultural vibes. 

How to Get Around

The 4 times my family or I have been to Jamaica, we always hire a driver. This is honestly the best thing to do since 1) in Jamaica you drive on the left side of the road so renting a car isn’t the best idea and 2) excursions can be hours away. We have a great driver Stanhope who I recommend booking with for your stay! 

Stanhope – 1-876-486-2172 | Book via What’s App 

Where to Stay

This guide is specific to staying in Montego Bay so here are some of the places I’ve stayed in:

Airbnb Pineapple Palms
Airbnb upscale 3 bed
Hyatt Ziva Rosehall

For this trip, my family and I spent half our time in an airbnb and the other half at our favorite all inclusive resort – Hyatt Ziva Rose Hall. This is my preferred way of traveling as I get to explore the island and also enjoy resort life. We typically do airbnb for the first half then resort the second half. Let’s get into the day to day itinerary!

Day 1 – Travel Day

Arrive and Get Settled

On travel day you typically want to rest, so that’s what we did. Once we arrived, Stanhope picked us up and took us to our airbnb. On the way we stopped to try the highly recommended KFC. Now I know what you’re thinking…”did you really travel to Jamaica to eat KFC?” YES I DID. Lol, ok I had the same thoughts but apparently it’s really good and better than the chains in the USA. We got 1 bucket of fried chicken and biscuits…I’ll give it a 7/10. Wasn’t the best I’ve ever had, but it was pretty good. I do recommend trying it out just to say you did it 😉 

KFC’s in Montego Bay

  • Allice Eldemire Drive, Montego Bay, Jamaica
  • Whitter Village Ironshore, Montego Bay, Jamaica

Since you’re staying in an airbnb, you may want to stock up on some basic food items like breakfast and snacks. Here are some grocery stores you can count on. 

Grocery Stores in Montego Bay

  • Progressive Foods Supermarket 
  • Mega Mart
  • Hi-Lo Food Stores

Restaurants in Montego Bay 

In case KFC isn’t up your alley…here are some fave restaurants to try out in the area.

  • Tastee’s – The Best Patties
  • Scotchies – Jerk Chicken / Pork galore  
  • Pier One on the Waterfront – really beautiful restaurant on the pier

After eating our late lunch/early dinner we played games, hung out at the pool and rested up for the next big day – Dunn’s River Falls. 

Day 2 – Dunn’s River Falls 

Our first full day was an excursion to Ocho Rios to climb Dunn’s River Falls. This was such a fun day and actually my second time being there. I was last at the falls in 2000 when I was just 4 years old! (Check out our then and now 20 yr difference pic below) On the way to the falls we stopped at Tastee’s to grab some patties for lunch – a must have when visiting Jamaica. 

Noon – 3pm Dunn’s River Falls
Location: Main St, Ocho Rios, Jamaica
Hours: 8:30am – 4pm
Price:  $3846 JMD Adults , $2615 JMD Kids | $25 USD Adults, $17 USD Kids 

Here are some notes & tips for visiting Dunn’s River Falls:

  • The falls are about 2 hours away from Montego Bay, so plan to leave early
  • The beginning of the falls actually begins down at the beach
  • Be sure to either bring water shoes or be prepared to purchase some on site ($10 USD)
  • Make sure you put on sunscreen and are hydrated before starting the climb
  • Guides are available to take you through the best path and I highly recommend doing this 
  • It can be scary when climbing up – but it is safe and you will be okay 🙂 Just listen to your guides and have no fear!

4 – 6 pm Local Beach for Sunset
Location: Flavours beach St Ann | Google Address
Price: Free99

On our way back to the Montego Bay area, we stopped at a local beach front to watch the sunset. My mom and I walked along the shore and it was so beautiful. I don’t typically see local beach fronts that aren’t marketed for tourists so it was a nice change of scenery – very serene.

6pm – 7pm Dinner at Scotchies 
Location:  G4CP+GWR, Montego Bay, Jamaica
Hours: 11am – 7pm 
Price: $

Before heading back to the airbnb we stopped at our fav Jerk chicken restaurant – Scotchies. This is definitely the place you’ve got to try at least 3 times before leaving lol. I recommend ordering jerk chicken, rice & peas, festival and breadfruit.

Day 3 – Negril Village 

Our third day was the most packed and most fun. We started off with a yummy traditional breakfast trying red pea soup & peanut porridge at Stanhope’s family restaurant – Portions. Then headed off to Negril Village to hang at the beach, do bamboo rafting, and cliff jumping. 

9am – 10am Traditional Breakfast 
Location:  Portions | Airbnb Experience Link
Hours: 11am – 7pm 
Price: $

10:30am – noon Bamboo Rafting with Juicie’s Adventures
Location: Lethe District, Hanover, Jamaica 
IG Page: @Juicies_Adventures
Price $60 USD pp

Bamboo rafting is a go to activity to partake in when you go to Jamaica. It was a really cool experience to sail down the river in a bamboo raft! This 1 hour excursion includes: trip down the river, limestone massage, coconut water, and sugar can – yum. This specific raft activity is from a more local business rather than the popular touristy one. I prefer this one as it was more authentic. 

12:30pm – 4pm MargaritaVille
Location: Norman Manley Blvd, Negril, Jamaica 
Price: $FREE99 entry | $-$$ Food & Drinks (touristy prices)

Margaritaville is typically not my preferred choice of activity because of how touristy it is…BUT yall… it was a 10/10 experience. They had constant entertainment – music, fun games and free drinks (for the winners)! Great thing is that the chairs are free and the umbrellas are only $10 for rent. My favorite part was the Mango Spa – a little spa on the beach where you can get a massage for $1 per minute!! A beautiful price if you ask me. This was the best beach day.

This is a family friendly place to go and you should def add it to your list for a bit of fun. Enjoy this photo of my beautiful family and I.

4pm – 7pm Rick’s Cafe Negril
Location: W End Rd, Negril, Jamaica
Price: $$ Food & Drinks (touristy prices)

Ricks Cafe in Negril is a super popular restaurant that is on top of a cliff overlooking a blue lagoon. The sunset views are immaculate and the music matches the vibe. Whenever you visit here, be sure to go right before sunset so you can fully enjoy the scenery. I will say, the food is super expensive and tbh not great so don’t waste money here. Rather, head back to Scotchies like we did before going to your airbnb.

Ricks Cafe Montego Bay

Day 4 – Resort Day 

Our last full day was going to be spent at my favorite All Inclusive resort – Hyatt Ziva Rose Hall. You will not regret splurging here – unlimited drinks, food, beach front, pool vibes and more. 

All Day: Hyatt Ziva Rose Hall
Location: Rose Hall Road, A1, MontegoBay, Jamaica
Price: $250+ a night | 20K points via Hyatt or via Chase travel reward points (these prices can fluctuate throughout the year)

Hyatt Ziva Rosehall
Hyatt Ziva Rosehall

Here are some tips for staying in an All-Inclusive Resort

  • 💸𝗕𝗿𝗶𝗻𝗴 𝘀𝗺𝗮𝗹𝗹 𝗯𝗶𝗹𝗹𝘀 𝗳𝗼𝗿 𝘁𝗶𝗽𝘀: You may think it’s backwards to tip at an all inclusive resort BUT I can tell you from experience it will enhance your stay. Tipping throughout your time —> staff giving you above & beyond service. ⁣
  • 🔝𝗔𝘀𝗸 𝗳𝗼𝗿 𝗰𝗼𝗺𝗽𝗹𝗶𝗺𝗲𝗻𝘁𝗮𝗿𝘆 𝘂𝗽𝗴𝗿𝗮𝗱𝗲𝘀: Closed mouths don’t get fed! When you check in, ask if there are any available upgrades. Maybe you want an ocean facing room? Just ask! Worst they can say is no.⁣ 
  • ⁣🗣𝗟𝗲𝗮𝗿𝗻 𝘀𝗶𝗺𝗽𝗹𝗲 𝗽𝗵𝗿𝗮𝘀𝗲𝘀 𝗶𝗻 𝘁𝗵𝗲 𝗹𝗮𝗻𝗴𝘂𝗮𝗴𝗲: I follow this rule wherever I travel but it’s especially nice when at a resort when often the guests only speak English. ⁣
  • If your flight leaves later than your checkout time, the lobby can hold your bags however long you need and you can still enjoy the resort. 
  • Did you know Hyatt resorts usually offer free photography sessions? All you have to do is pay for the photos! My family and I did this for our Christmas photos (see below 😉 )
  • Some restaurants require reservations ahead of time for dinner – so when you check in go ahead and ask for the schedules and make your reservations.  

List of Restaurants at Hyatt Ziva Rose Hall

  • ChoiceZ Buffet Restaurant: This offers a plethora of cuisine options everyday for breakfast, lunch and dinner. 
  • FuZion Asian Grill: Here you can have Hibachi show for dinner or order A la Carte from the menu. This was one of my favorite places because I loveee Asian cuisine. It’s only open for dinner.
  • Barefoot JerkZ AKA JerkHut: This is an outdoor walk up restaurant where you can get some good jerk chicken/pork, rice & peas and festival. Its right next to the pool too!
  • Blue Grill at CalypZo: This outdoor restaurant offers seafood, sandwiches, pizza, and more. They are open for Lunch and Dinner. 
  • Di RoZa Italian Restaurant: They serve traditional Italian cuisine so all the pasta and pizza you can eat. Only open for dinner.

My favorite drinks to order

  • Pina Colada + Rum Floater 
  • Miami Vice 
  • Lemon Drop Martini
  • Strawberry Daiquiri

Day 5 – Last Day

On our last day, we spent the morning (8am – 3pm) at the resort since our flight was later in the evening. Tip: Book a later flight on your last day because you can still enjoy all of the perks of the hotel before you leave. Here is how I recommend you spend your last morning:


7am – 8am Have a gourmet breakfast at ChoiceZ 
8am – 9am Do a yoga or aquatic class (scheduled by the hotel)
9am – 11am Enjoy the pool or beach and make sure to grab a drink too 😉 
11am – noon Get dressed, pack your bags & drop them off at the lobby 
Noon – 2pm Have lunch at your choice of restaurant! Afterwards head to the airport to fly home

I hope this itinerary will help you have an EPIC trip to Montego Bay! 

Montego Bay Family Trip


  1. Carmyn

    amazing itinerary, will use for next Jamaica trip! 🤍

  2. Makala

    Can’t wait to visit. 🤩

  3. Decontee Gbahay

    I really appreciate this well put together blog with great info. Also On Day 3: Negril Village in your family photo, your mom had a lil slip up just wanted to let you know.

  4. Char

    This is one of the best and informative breakdowns for vaca I’ve ever read!!!! Thank you, I feel more confident to plan my itinerary.

    • Nylah Akua Adjei

      Yay! I’m so glad it was helpful. I hope your trip planning was successful 🙂

  5. Njoki Rose

    Your parents have not aged a day , beautiful vacation.I will visit after reading this

    • Nylah Akua Adjei

      Thank you so much! I hope you have a great trip 🙂

  6. Mona

    A well organized vacation. thanks for sharing. Heading to Jamaica the end of this month. Thanks for listing your drivers name and number. I know trips are cheaper than booking through the hotel. Mona

  7. Mona

    forget to mention. Beautiful family!!


Leave a Reply

Who is Simply Nylah?

I’m a travel influencer + content creator based in Los Angeles, CA. I love sharing my life experiences through creative content! I am especially passionate about discovering all that the world has to offer. Whether it is a vlog, photo or fun story, I enjoy connecting with others and I want to encourage YOU to live your life to the fullest.