Road Affair

It's not a tour, it's an experience

Join us on an experience of a lifetime and get ready to discover the real Jamaica. This is an experience that takes you beyond all-inclusive resorts and through Jamaica's best-kept secrets. Hike through lush rainforests, meet true Rastafarians, swim in surreal waterfalls and relax on some of Jamaica's most divine beaches. Immerse yourself in the Jamaican way of life on this 8-day adventure and get an intimate look into Jamaica’s vibrant culture and jaw dropping nature. What do you say, are you in?

Ya Man, I'm in!

This experience is for you if

+ You want to relax, go slow and have fun in one of the most gorgeous and worry-free places on earth.

+ You prefer simple and authentic adventures over luxurious and superficial vacations.

+ You want to connect with like-minded individuals who share the same passion as you.

+ You love the spirit of independent travel, but also enjoy the company of a small group of traveling friends.

+ You want to immerse yourself in the local culture and get an authentic feel of Jamaica.

+ You don’t mind getting your feet wet and stepping out of your comfort zone.

Where we go

After catching the sunrise on Jamaica’s highest point in the lush Blue Mountains, we head over to the beautiful underrated parish of Portland to explore some of Jamaica’s hidden gems. Here are some of the highlights included on this trip.

+ Blue Mountains
+ Reach Falls
+ The Blue Lagoon
+ Nanny Falls + Nanny Town
+ Boston Beach
+ Winnifred Beach
+ Cornwall Barracks
+ Restoration Village Farm
+ and much more

Request Itinerary

What's included

Mango Ridge in Port Antonio, Jamaica

Food & Accommodation

Our home away from home will be in locally-owned rustic style cottages and guesthouses. We will have awesome views, with simple but comfortable beds in shared rooms, as well as a shared kitchen for those who want to cook their own food. Six traditional Jamaican meals, a mixture of breakfast, lunch and dinner are on us!


Transportation to and from all included activities are covered in the price. Throughout this 8-day adventure we will only be using local transportation which means no private tour buses, no shuttle vans with A.C. and no chartered taxis. Because the best way to experience the real Jamaica is the local way!

Rasta at Winnifred Beach in Jamaica
Blue Lagoon in Port Antonio Jamaica


Entrance fees and guides for all included activities are covered by us! We made sure to not only include the “must dos” but also the lesser known, but equally fun, activities, like hiking to Cornwall Barracks or visiting charming local communities. However, this is YOUR experience so you have the freedom to choose what you want to do each day.

The Perks of traveling with us

+ You'll get to explore the real Jamaica with well-travelled individuals who know what it takes to have a hell of a good time without breaking the bank.

+ You'll get an amazing, once in a lifetime experience for a great price.

+ You’ll get a refreshing and unique alternative to the old worn out and crowded tourist places in Jamaica.

+ It’s so much more fun than traveling alone.

+ You won’t have to worry about being left high and dry. From helping you find a cheap flight to giving you suggestions on what to pack, we got your back.

+ You'll get to connect to the more carefree version of you while we proudly do all the dirty work! Just sit back and enjoy the Jamaica that most people never get to experience.

Ben & Jazzy from Road Affair

Meet Us

Hi, we are Ben & Jazzy. For the last four years we have been traveling full-time and helped thousands of people travel the world on a budget with our blog, Road Affair. We have backpacked, hitchhiked, and couchsurfed our way through many great countries, but no place has pulled on our heart strings quite like Jamaica. Not the Jamaica advertised in travel magazines or on TV, but the one rarely seen by tourists. That is why we started “Discover the Real Jamaica”, so you too can experience Jamaica beyond the guidebooks, all-inclusive resorts and tourist-catering places like Negril or Montego Bay. Join us on this unforgettable 8-day adventure to get a taste of the Jamaica we fell in love with.

Our Travel Style

Support Locals

Whether it’s using local transportation or eating at local restaurants, we make sure that every dollar we spend goes into the pockets of locals and not huge corporations.

Freedom to Explore

This is YOUR experience! You are welcome to join included activities or wander off on your own. The choice is yours.

Small Groups

We travel in small intimate groups of no more than 8 people, which means making friends will be that much easier!


"Thank you!! Oh how I wish all travel sites could be this easy, straightforward and user-friendly to navigate. Your guide to Jamaica, has been a lifesaver. I am your faithful follower from this moment on! Keep up the great work guys! :)"

Gill's comment on one of our Jamaica posts

Frequently Asked Questions

+ Unfortunately, I can’t join you guys on the dates listed above, do you have other dates available?
We are sorry to hear that you can’t make it with us this time around, however if you sign up for our newsletter here you will be the first to know when we are offering new adventures, as well as discount deals.
+ How is Road Affair able to offer such competitive prices?
To give you the most authentic Jamaican experience, we travel locally and away from the worn-out tourist trail. By traveling this way, we are able to keep the trip cost low while at the same time supporting locals and their businesses.
+ Why should I book with you and not with one of those big tour companies out there?
We are not a tour company. We are not traveling at the speed of light, shuffling you from sight to sight and giving you a superficial perspective on a country. We are travelers just like you, looking to share a great experience with a small group of travelling friends. Book with us if you want a personal and intimate non-tour experience.
+ How do I know you are not going to scam me out of my hard earned money?
Well to be completely honest with you, you don't. We could tell you all kind of lies; after all, this is our website. However, if you take a look at our blog, you will notice that we have built enough street cred to be considered trustworthy. Not to mention that we are way too pretty for prison, don't you think? :D
+ Can I invite a friend?
Of course you can, the more the merrier! Actually, if your referred friend successfully books a trip with us, you AND your friend will both receive $50.00 off your trip! And no there is no limit to how many friends you refer, as long as you promise not to stick to your friend(s) like glue and make new friends while on the trip!
+ I'm a single traveler, can I still join the trip?
Yes of course! Most of our guests are solo travelers, so this trip would be perfect for you to meet other solo travelers and make new friends.
+ How dangerous is Jamaica really?
Jamaica is a beautiful country and should not be missed because of what you hear on the news. Are there areas where you shouldn’t go? Of course, just like in every other country in the world. But in general, Jamaicans are known to be very laid-back and friendly individuals, who don’t mind starting a conversation with you on the street or inviting you to a game of Dominos. So rest easy and turn off the news.
+ Do I need to join the group for all included activities?
We are independent travelers too, so we completely understand the need for the freedom to do what you want. If you feel like wandering off or doing something on your own, you're more than welcome to do so. After all this is YOUR experience, and you should have the choice to choose what you want to do!
+ Why doesn’t this trip include a visit to Negril, Montego Bay or Ocho Rios?
Because if we were to include these areas, we would have to rename this trip to “Discover the touristy side of Jamaica”. But with all seriousness, Negril, Montego Bay and Ocho Rios are not a real representation of Jamaica and don't have much to offer besides all-inclusive resorts, and overcrowded beaches and waterfalls.
+ What if I want to stay in a private room?
We get it, sometimes you need a little privacy, which is fine! If you would like your own room, we can arrange one for you for an additional $400 USD.
+ I still have some unanswered questions. How can I contact you?
If you still have questions that haven’t been answered here, feel free to send us an email to [email protected]
+ OKAY. I’m sold, and can’t wait to discover the real Jamaica, how do I pay?
Yay!!! We can’t wait to hangout with you! To pay, you can click here and it will lead you to PayPal, from there you can either pay via your PayPal or pay as a guest with any major credit card. Because we are using PayPal, you can rest assured your information is safe and secure!

Discover the real Jamaica

July 15 - 22, 2017 (5 spots left)
August 19 - 26, 2017 (7 spots left)
September 16 - 23, 2017 (7 spots left)

$1,390 USD*

*Special Offer. Price won't stay this low.

Reserve Your Spot

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