Jamaica

Playing ping pong with my kids while someone else made dinner and put it on the table
truly made me feel like I was on vacation.
— Courtney L.

Trip type: Family / any season

IDEAL TRIP LENGTH: 5-7 DAYS 

to & From:

  • Fly with as few stops as possible into Montego Bay.

  • If you are not staying within a property, hire a car with a driver for the week. They drive on the other side of the road and a driver is worth the little you will pay.

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Stay

  • Rent a house with access to private resort club through rental agency or VRBO. Look for properties with access to either Tyrall or Round Hill. We rented a house across the street from Round Hill with access to all the amenities including restaurant, beach and workout facilities.
  • Tryall and Round Hill are both have very nice villas and rooms you can rent directly from the resort.

Eat & Drink

  • Our house came staffed with a cook as many rentals do so we did not eat out as much as we usually do on vacation. The treat is to be served breakfast, lunch and dinner in your pj’s on your own veranda on your own time.
  • Lunch at the Seaside Terrace and dinner at The Restaurant at Round Hill are both worth enjoying but truly the extensive afternoon tea at Round Hill (free to all guests) is what made Jamaica feel unique to other beach vacations.
  • For FRESH lobster on the sand, try The Lobster Trap. Far from fancy, great food, gorgeous setting, no scene. Very limited menu—only for lobster lovers.

Do

  • Nothing. We called Jamaica our beach to bar vacation.... days spent on the beach followed by a drink at the bar.  The waters are the warmest of warm and the kids can swim all day. If you are not happy chilling on the beach all day, then Jamaica is probably not the trip for you. 
  • Jamaica is not a safe country to go exploring in. It is best to stick to resorts and tourist areas—though the tourist areas are just that… touristy.
  • Golf is available through the Tryal Club.
  • SKIP the snorkel cruise offered out of Montego Bay. Half of the time allotted is spent at Margaritaville where you are encouraged to buy drinks and spend money. Snorkeling is only so so.

the inside scoop

  • Groceries are limited. If there are special items you want, bring them. Gluten free bread and corn tortillas were among the items we wished we had and were not available.

  • Our house cook was a cook but not a chef.  Come with recipes and thoughts on what you want your cook to prepare, maybe even a cookbook. Ask your cook to source fresh fish... in our case the fisherman came to our house with their cooler.

  • Be prepared to tip your staff. Most rentals will outline the amount you are expected to tip.

  • Check in with Kingsley, the concierge at Round Hill, if you need anything.  He is an icon on the property and will truly point you in the right direction.

  • Say hi to Stewart at the Round Hill Beach Bar. He has been there forever and will forever be loved.

Your oliver guide: Courtney Leary