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I got the opportunity a few years ago to travel to Negril, Jamaica with my best friend of 25 years, Ashley. The trip of a lifetime is putting it mildly, and getting to experience it with her was the best choice ever!

We first got the idea when one of those phony faxes came to me at work. The ad says you can get a luxury vacation for super cheap. DO NOT fall for this! I did my research and the dates and locations are not guaranteed, and you will have to sit through hours of time share meetings. It really is not worth the hassle, especially when you can utilize my travel deals and tips!


The first thing we made sure to do was make sure we had our passports! Then we got online on a Tuesday (the best day to look for deals) and put in our desired travel dates to see what our options were for pricing. The prices came out over $600 for a round trip flight from Chicago O’Hare Airport. Flying out of a main hub such as O’Hare is always going to be a better deal with less connections (we didn’t have any layovers!). If the prices seem a bit too much for you, enter your email and Skyscanner will send you updates about price changes!

Stay patient and you will get prices like we did, we got our tickets for approx. $425 a piece for round trip with all the extra fees included! We flew into Montego Bay which is the best option for tourists. Kingston, in my humble opinion, can be a little dangerous for tourists and people not from the Island. If you know people in Kingston, it’s fine, but Montego Bay Airport was great and super easy to get through. Seriously though, the best advice I can give you is to be patient and jump on deals when they are presented to you!!

Location Location Location

I cannot stress enough that Negril is THE best place to go for a true Jamaican experience and the sunsets are to die for!

Montego Bay will be your option if you want the really touristy experience. If you choose Negril like we did, the drive from the airport is a couple hours. We took a free shuttle provided by our hotel, and most hotels should provide transportation. Do your due diligence and make sure your transportation needs are taken care of. Fair warning- cabs are cheaper during the day, but at night they can up their prices however much they want! Negril has fanstastic nightlife and superb restaurants!


We stayed at the Traveller’s Beach Resort. The prices were spot on for our week long trip, and they had a pool and are beach front. The rooms had safes so we could store cameras, our passoorts, and anything else of value. Make sure the hotel you pick has safes! Also, do not bring fancy purses and such. The local peddlers will think you are loaded and will bug you a lot or steal. If you carry a purse around, always hold onto it! The beds were SUPER comfortable, and we probably took more naps than needed! 😂😂

The security at the hotel was fantastic too! The gates closed by 10pm every night and only hotel guests could get in afterwards. The security guards kept pesky peddlers away on the beach. The peddlers are constant, but my advice is to buy the fruit if you want and stay away from hair braiding! The lice there can be rampant, and I’m betting you don’t want lice to attack during your leisure time! The guards will sit and chat with you, and they are super friendly. They ended up taking us clubbing at The Jungle. The native dances were super fun and they made sure we were safe all night. Life tip, don’t go before 11pm…we did one night and that’s when the prostitutes are full swing with middle aged+ men. 😳

But back to the hotel facts, there is a bar and restaurant that is great as well. The staff really goes above and beyond to keep you comfortable during your stay! Just make sure whatever you pick, whether it be hotel or hostel or hut on the beach, that you choose safety first.


There is SO much to do in Negril!! There are many bars to choose from, including the infamous Margaritaville! But the best part about experiencing a new country is going to local bars. Our favorite was Bourbon Beach Bar. They had reggae bands, dj’s, and even a ocean party!

The bartenders are fantastic, and really personable. We asked for fruity drinks, and he blended up fresh fruits with rum and they were SO good! The “national beer” is Red Stripe, and it is similar to Budweiser. The prices were cheap, and the atmosphere was great.

You may be wondering about the ganja policy! As a visitor, you have to have a medicinal card. BUT, everyone around was smoking even where there were signs saying no MJ smoking. The bartender actually came up and asked if the seeds and stems on the bar were ours. We stuttered and said no, and he just shrugged his shoulders, smiled, and cleaned it up. 😂 It IS safe to buy from randoms who walk up with baggies. It is SUPER cheap and SUPER good. Sorry mom! 🙊🙈😅

Definitely take cabs where you go, as at night it can get dicey walking. We took the beach route to Bourbon Beach one night, and got offered parties and drugs of all kinds. We had to walk away fast, and really convince them we were NOT interested (you’re welcome Mom, lol).

Some other fun things to do are waterfall tours, cave tours, the Dolphin Cove Swim (can be pricey), and the iconic Rick’s Cafe! There is a spot where you can cliff dive, and even if you don’t want to, watching the locals do flips is really a superb experience! Then make sure to get a good seat to watch the sunset, it is GORGEOUS. On the beach, locals will bring their horses and offer rides in the ocean. There is not really a “price on it”, but it’s not free. Tip them what you feel is fair. They will most likely try to sell you bracelets and other things too, don’t feel bad for saying no! But definitely take advantage of the locals and their tips!

Fooooood and Shopping

Only one tip: take full advantage of local restaurants and food carts. Jamaican Jerk Chicken is so darned good, and you will NOT regret buying it off a cart.

Go to the duty free shops for souvenirs. The shop owners will often barter too. I got a bracelet and a t shirt and traded my headband from Walmart that she loved! Give your money to the locals, and keep their economy thriving!!

Last Tip

If you want that dress, that drink, that chicken, or even a swim with a dolphin, DO IT! Experience trumps money every single time. You can always make more money, but each day you spend is another one you can’t get back! I have budgeted this trip out for some friends and am going to start vacation planning for people. With my experience and planning, I was able to make it under $2k a person for an entire week! Message me if you want more info on my Instagram AmandaJo_OnTheGo!

Remember, always take pictures of yourself smiling!


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