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Guide to Montego Bay and Sandy Bay, Jamaica

Welcome to the first of my Central America & Caribbean posts! I'm so excited to finally talk about a trip that I took back in November of 2022 to Jamaica, and let me tell you, this country stole my heart! I think it's my favorite Caribbean country that I've visited to date, as it has some of the most stunning flora and fauna I've ever seen on an island.

But, the reason for this trip was what was most exciting to me, as mostly all of my mom's side of the family was there to celebrate my grandmothers birthday. We rented out a private villa at The Tryall Club and I would highly recommend it as an accommodation option if you're planning on visiting Jamaica with a group for a bachelorette party, birthday, etc. The staff at The Tryall Club is so hospitable (shout out to our staff at our villa, The Retreat!)

Here is your guide to visiting Montego Bay and Sandy Bay, to make the most out of your time in Jamaica. Yeah, mon!

Best Time to Visit Jamaica:

The best time to visit Jamaica is from November through April. This is when the island is experiencing its dry season, where the average temperature hovers around 82 degrees.

The island's northern coast experiences a slight increase in rain between September and November, so expect some comforting rainshowers that give life to the greenery and tropical plants surrounding you.

November really was a sweet spot for our family to visit - the resort that we stayed at was very quiet, and we only had a few overcast days during our week-long visit. Book your flights to Jamaica in advance for you and your group here to get the lowest prices.

Where to Stay Near Montego Bay:

Before we get into the activities that you can take part in Montego Bay and Sandy Bay, here's a little bit more information about The Tryall Club:

The Tryall Club

The Tryall Club is a set of private villas in Sandy Bay, Jamaica that offer a Caribbean country club experience along the north coast of Jamaica. With the luxury of a private villa, you and your group can enjoy the conveniences of a full staff that takes care of your standard three meals each day, housekeeping, laundry, and more.

The highlights of the villa and resort for me personally were:

  • Taking part in the watersports offered at the resort - you can choose from wakeboarding, water skiing, tubing, paddleboarding, glass-bottom boat tours, and for the kids, banana boat rides.

    • I went paddleboarding one morning and was out on the water for hours. I throughly enjoyed the tranquility of being out on the water all by myself, while peering into the crystal clear water looking for fish and coral.

  • Basking in the resorts infinity pool (I am a pool aficionado so I particularly loved spending time here!)

  • Walking around to see the other villas on a morning walk, and admiring their unique characteristics, while smelling the many varieties of tropical flowers along the way!

  • Seeing what the local vendors have to offer around the pool area.

  • Enjoying Tryall Nights at the resort, which are experiences such as Jamaica Nights offered on Mondays featuring reggae music and Jamaican cuisine, and Beach Reggae parties on Thursday nights, where you can jam out to Jamaican beats while feasting on a buffet. (Be sure to stay for the hermit crab races if they're offered - it's a great chance to connect with others who are staying at the resort and have some fun cheering on your favorite crab racer!)

  • Savoring an afternoon tea at The Great House - this starts at 4 p.m. each day, and is located at the veranda and terrace of The Great House. The staff serves incredible small bites, such as scones and finger sandwiches. It's a great chance to take in the views of The Great House while reflecting on your fun day in Jamaica.

As you can tell, I am a big fan of The Tryall Club, and I do believe that if you and your group are willing to splurge for a nice getaway, this is the place to do it as the resort is tucked away from the other resorts in Montego Bay and offers plenty of activities and something for every person that you travel with, while you don't have to worry about the upkeep of where you're staying, or even your meals!

The beautiful views of The Tryall Club

Activities to Enjoy in Montego Bay:

  1. Take a tour around the island's Caribbean waters, with tours such as a reggae catamaran cruise with snorkeling, which you can book here.

  2. Tour the Rose Hall Great House, which is an 18th-century historical site whose walls tell the story of Annee Palmer, otherwise known as the "White Witch of Rose Hall." I found this tour to be especially fascinating and I learned a lot about the lifestyle of the European bourgeoisie.

  • Rose Hall Great House is about a 45 minute drive from The Tryall Club. It's a perfect activity if you want to venture into Montego Bay for the day!

  • Tip: There will be vendors selling their items as you exit the tour - remember that you are not obligated to buy from them and do not let them haggle you into purchasing something. However, please support small, local businesses during your time in Jamaica if you have the opportunity to.

  • You can book a private tour of the house here!

3. Enjoy jerk chicken at just about any restaurant in Montego Bay, but my family opted for The Pelican Grill, which is a family-owned and operated restaurant serving up the tastiest Caribbean jerk chicken, oxtail, ackee and saltfish, curries, and more. The restaurant is comfortable, airy, and has a laid-back, family-focused feel to it. My grandmother and our van driver enjoying a slice of coconut pie!

While we only spent a day in Montego Bay during our week-long vacation, I believe that this was the perfect amount of time to spend in the city. I personally enjoyed the experience of time slowing down in Sandy Bay, where I could spend endless amounts of time in the water and laying out on the beach.

However, this vacation was not the most adventurous (and that's not the type of trip that it was supposed to be anyway!), but there's so many other places to explore and tropical activities to take part in while in Jamaica.

Ideas for Future Trips to Jamaica

For my next trip to the island, here are some of the items on my bucket list:

  • Visiting Reggae Sumfest, which is a music festival that celebrates reggae music on the island, and also features Jamaican cuisine and local arts and crafts vendors. The festival is running from July 14-20 this year. Early bird general admission ticket prices hover around $55 for each day.

  • A trip to Ochos Rios to explore waterfalls, rivers, and the rainforest.

  • Visiting Carnival in Jamaica which consists of fun festivities, vibrant costumes, and upbeat music and dance sessions! The next carnival is slated for Sunday, April 25, 2025. Take a closer look here.

  • Exploring Wickie Wackie beach and Cane River Falls in Bull Bay, Jamaica.

See you on my next adventure, this time in Central America! Hint: This country is home to the second largest coral reef system in the whole world!


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