Jamaica Blog Posts

Fresh cocktails prepared by your own bartender!
Fresh cocktails prepared by your own bartender!

Best Staffed Villas in the Caribbean



The only thing better than staying in a Caribbean villa is staying in a staffed Caribbean villa. After all, who really wants to cook on vacation? Some travelers like the idea of grilling their own fresh-caught fish, but being wined and dined while watching a tropical sunset is…

Tipping in the Caribbean: An Island by Island Guide

Tipping can be one of the trickiest parts of travel— some regions won’t accept tips at all, whereas others will tack on additional fees until you’re bone-dry. The Caribbean is made up of several different cultures and islands, and our team at WhereToStay wants to clear up any misconceptions or…

View from the massive pool at Silent Waters villa
View from the massive pool at Silent Waters villa

Best of the Week - Silent Waters Villa, Jamaica

Within minutes of stepping onto the grounds, you’ll feel like king or queen of the world. Perched atop one of Jamaica’s highest mountains, Silent Waters offers sweeping views of Montego Bay and the azure Caribbean Sea.
The stunning scenery doesn’t end there. This is easily one of the most…

Three Caribbean Hot Spots to Get Hitched

Destination weddings have become all the rage in rage in recent years. And with good reason – powder soft sand and the azure Caribbean Sea make for a pretty decent wedding photo backdrop. If you’ve dreamed of your impending nuptials taking place in an idyllic island setting, you might want…

Rick's Cafe, Negril, Jamaica
Rick's Cafe, Negril, Jamaica

Five Best Jamaican Beach Bars

Perhaps the only thing better than lounging around in your gorgeous Jamaica villa is chilling out on the beach with a drink in your hand and sand in your toes. Here are five beach bars you should definitely check out the next time you’re on the island.
1. Norma’s…

woman reading on Caribbean beach
woman reading on Caribbean beach

Top Ten Caribbean Themed Reads For The Summer

Summer will be here before you can say “cannonball!”.  You may not be headed to the Caribbean this summer (though you really should!). However, reading Caribbean-themed books by the pool or beach can transport you mentally – and that’s almost the same, right? Okay, so it’s not the same at…

You Miss A Lot When You Island Hop!

I sort of dig Caribbean cruises. I enjoy sampling different islands, I like the onboard activities, and I kind of love being able to eat every hour if I want to. That being said – there is one thing that will make me to rent an island villa over cruising…

Six Caribbean Islands - Six Family Friendly Ways to Enjoy Them!

Family vacations seem to have gotten more exciting since I was a kid. Though our annual 12-hour trek to the nearest beach was nothing short of monumental, today smaller world affords more realistic opportunities for family travel. Fleeing cold climates for a Caribbean escape is commonplace, and kid-friendly activities are…

Rose Hall Plantation in Jamaica
Rose Hall Plantation in Jamaica

Getting Spooky for Halloween In The Caribbean

Whether your visit to the islands coincides with Halloween, or you like to be creeped out any time of the year, the Caribbean is a good place to look for things that go bump in the night. Here are a few places to add to your haunted itinerary. You might…

Get up close and personal ocean views
Get up close and personal ocean views

Golden Clouds villa

Do you need a huge vacation home for your upcoming family reunion, corporate retreat, or annual couples’ getaway? Look no further!

Golden Clouds villa is a luxurious 9-suite estate situated in a 6-acre park. It is a spectacular oceanfront villa located on Jamaica’s fabled North Coast in the picturesque…

Haystack Villa

Do you love the great outdoors? Need a place to show your family that you’re the ultimate billiards champion? Want to come home with a golden tan, totally blissed out?

Haystack is a 8 bedroom, 8 bathroom villa located in the famous Tryall Club Estate. With attention to detail…

Where To Stay

Home Page
My Trip
My Favorites
Blog