Baileys Tours Jamaica
Discover Jamaica with a driver who calls it home
Private airport transfers from Montego Bay, island tours and cruise shore days with Mr. Winston Bailey. Cold drinks in the cooler, stories on the road, and no shared shuttles.
Loved by 500+ guests on Tripadvisor & Google
MBJ transfers from
$35
- Happy guests
- 500+
- On the road
- 8 yrs
- Resort routes
- 12
- Tripadvisor rating
- 5★
What we offer
From touchdown to your last sunset
One local team for the whole trip: the airport pickup, the day trips in between and the ride back for your flight home.
Airport transfers
Private rides from Sangster International (MBJ) to any hotel, resort or villa, with flight tracking included.
See faresIsland tours
Waterfalls, beaches, Nine Mile and Rick's Café, at your pace and with a guide who grew up here.
Browse toursCruise excursions
Docked in Falmouth or Ocho Rios? We plan your shore day around the ship and have you back early.
Plan a shore day
Airport transfers
Fixed fares from MBJ
Prices are per vehicle for up to 4 guests. Tap Book on your resort to see the total for your group.
Negril, Westmoreland
Negril Seven Mile Beach & West End
about 1 hr 20 min up to 4 guests
One way from$90
Ocho Rios, St. Ann
Sandals Dunn's River & Royal Plantation
about 1 hr 30 min up to 4 guests
One way from$90
Staying somewhere else? We drive everywhere in Jamaica, including Kingston airport and the cruise ports. Compare areas to stay or ask for a quote.
Island tours
Days out worth the drive
Private tours with hotel or cruise-port pickup, priced per person with a group rate for 5 or more. Or mix stops into your own day.
WaterfallsOcho Rios, St. Ann about 6 hrsDunn's River Falls Tour
Climb Jamaica's most famous terraced waterfall hand in hand, then cool off where the river meets the sea.
Per person$75$60 for 5+
AdventureSt. Ann hills, above Ocho Rios about 5 hrsBlue Hole Adventure Tour
Swim in jungle pools, swing on the rope and jump from the ledges into clear blue water.
Per person$65$50 for 5+
BeachNegril, Westmoreland full dayNegril Beach Day
A lazy day on Seven Mile Beach with jerk for lunch and a front-row seat for the sunset.
Per person$55$45 for 5+
CultureNine Mile, St. Ann full dayBob Marley Nine Mile Tour
Visit the village where Bob Marley was born and now rests, high in the hills of St. Ann.
Per person$70$55 for 5+
SunsetNegril, Westmoreland about 4 hrsRick's Café Sunset Experience
Watch the cliff divers, sip a rum punch and see the sun slide into the Caribbean.
Per person$50$40 for 5+
CruiseOcho Rios, St. Ann about 5 hrsOcho Rios Cruise Excursion
Make the most of your shore day from Ocho Rios port, with stops picked around your ship's schedule.
Per person$70$55 for 5+
- CruiseFalmouth, Trelawny about 5 hrs
Falmouth Shore Excursion
Step off your ship and into a hand-picked Jamaica day, with an expert local guide and a guaranteed return.
Per person$70$55 for 5+
Want shopping, rafting or a rum estate too? See everything we can plan.
Mr. Winston Bailey
Owner & lead guide
Our story
Born in Jamaica, built for travelers
Baileys Tours is privately owned and run by Mr. Winston Bailey, a Montego Bay local who has spent years showing visitors every corner of the island. Guests remember the history lessons on the drive, the cooler of cold drinks and the fact that he is always there early.
We keep things simple: modern air-conditioned vans for groups of any size, itineraries built around you, and a WhatsApp line that is answered from the day you book until the day you fly home.
- Safe & reliableLicensed, insured and always on time.
- Your itineraryNo cookie-cutter tours. Your trip, your pace.
- 24/7 WhatsAppFrom booking to your flight home.
- Honest pricingNo hidden fees. What you see is what you pay.
Mr. Bailey is the perfect person for your tours and airport transfers. Extremely reliable, very knowledgeable and great value. He even provides drinks in a cooler for guests. Can't recommend him enough!
Winston was great and very informative. He gave us a wonderful history of the island of Jamaica throughout the entire journey. A truly memorable experience from start to finish.
Good service and on time. Very sociable driver. I recommend Mr Bailey for your transfer from or to the airport and for your excursions.
The very best experience I've had traveling. Mr Bailey is a friendly and humble man, and driving us around while educating us about so many things was well appreciated.
Our island in pictures
Real guests, real memories
Airport pickups, Negril sign photos and plenty of smiles from our guests around Jamaica.
Travel guides
Insider tips for your trip
6 min readDocked in Falmouth? The Best Shore Excursions That Still Get You Back to the Ship
What to do on a cruise stop in Falmouth, Jamaica: drive times to Dunn's River, rafting, beaches and Montego Bay, plus how to plan around all-aboard.
5 min readBlue Hole Ocho Rios: What to Expect at Jamaica's Favourite Jungle Swimming Hole
Rope swings, cliff jumps and turquoise pools: everything you need to know before visiting the Blue Hole near Ocho Rios, from what to wear to when to go.
5 min readNine Mile: How to Plan a Day Trip to Bob Marley's Birthplace from Montego Bay
Visiting Bob Marley's birthplace and resting place at Nine Mile, St. Ann: the drive from Montego Bay, what the tour covers and how to plan the day.
FAQ
Questions before you fly?
Still unsure? Send Mr. Bailey a WhatsApp and you'll get a straight answer.
Get in touch
Plan your Jamaica adventure today
Planning a tour, need an airport pickup or just have a question? Reach out and we'll reply within a few hours.
Based inMontego Bay, Jamaica
Available7 days a week, 6am – 9pm