Jamaica Uncovered: The Perfect Getaway Itinerary

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Advisor - Desiree Raymond
Curated By

Desiree Raymond

  • Adventure Travel

  • Arts & Culture

  • Beaches

  • Couples Travel

  • Group Travel

  • Nature Escapes

  • Jamaica

  • Mountains

  • Relaxation

  • Local Culture

Advisor - Jamaica Uncovered: The Perfect Getaway Itinerary
Curator’s statement

From the rhythmic beats of reggae music to the warm hospitality of the people, Jamaica offers an unforgettable experience with a blend of relaxation and adventure. Jamaica is such a vibrant island known for its stunning beaches, mountains and heritage. No matter what kind of experience you are searching for, Jamaica is a destination like no other.

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Day 1: Arrive in Montego Bay

Arrive in Montego Bay at the Sangster International Airport and check into your resort or hotel. Some popular choices would be Sandals Montego Bay, Half Moon or S Hotel. After getting settled, kick off your trip by visiting Doctor's Cave Beach, with beautiful crystal-clear waters. This is a perfect spot to swim and unwind. Enjoy a unique floating restaurant offering seafood and romantic sunset views at Houseboat Grill. If you like a more local vibe, visit the Hip Strip for bars, shopping and Jamaican patties at Juici Patties.

Day 2: Ocho Rios and Dunn's River Falls

On this day, visit Ocho Rios (1.5 hour drive from Montego Bay) and check out Dunn's River Falls. It is Jamaica's most famous natural attraction. Climb the waterfall and cool off in its refreshing pools. Enjoy a must-visit authentic Jamaican jerk chicken and pork lunch at Scotchies. A wonderful hidden gem is Blue Hole. It has beautiful turquoise waters and waterfalls. There are even opportunities for cliff-jumping for those who enjoy a thrill. Bring water shoes for both Dunn's River Falls and Blue Hole to make climbing and exploring much easier. At the end of the day, you can either choose to stay overnight at Ocho Rios or head back to Montego Bay. If you choose to stay, there is a cozy, loved spot for Jamaican cuisine called Miss T's Kitchen, a perfect place to have dinner.

Day 3: Seven Mile Beach in Negril

Start your morning by heading to Negril and visiting Seven Mile Beach. Soak up some sun, relax and swim. Have lunch at Pushcart Restaurant, it is known for their modern twist on traditional Jamaican flavors. Around the late afternoon, visit Rick's Cafe, famous for cliff diving and stunning views. Arrive at Rick's Cafe early to get the best spot for sunset viewing because it does get crowded quickly.

Day 4: Boat tour to Pelican Bar

Today enjoy yourself taking a boat tour to Pelican Bar, a wooden bar in the middle of the sea. Here you can enjoy a nice cold Red Stripe and watch the fishermen go to work. Take a trip to YS Falls, this is a less crowded alternative to Dunn's River. Unlike Rick's Cafe, YS Falls has a rope swing that is suitable for beginner's for those who want a thrill without cliff diving. Later in the evening, head back to Montego Bay and relax with a nice dinner at Margaritaville. This spot is super fun with live music and Caribbean vibes.

Day 5: Rose Hall Great House

The last day, but still some last-minute things to experience before heading home! Visit Rose Hall Great House, which is a historic plantation house with tales of the White Witch of Rose Hall. Do some shopping at Old Fort Craft Market or The Shoppes at Rose Hall for souvenirs, Blue Mountain coffee and crafts. If you have the time, enjoy a cocktail at your resort or a beachfront cafe. A little tip: It's best to buy a coffee at a local supermarket instead of the airport-it's cheaper!

Day 6: Additional days

Any extended days in Jamaica allow you to explore beyond the usual spots, and discover more hidden gems. From Kingston that offers the Bob Marley Museum, a historic mansion called Devon House and a fun nightlife experience at Dub Club! Or a visit to Portland, experiencing a private beach at Frenchman's Cove, and a bamboo raft ride down the Rio Grande! Jamaica has plenty of unforgettable places to offer!

Need to know

  • I recommend visiting in December–April. It offers the best weather. Visiting in the off-season has fewer crowds and lower prices! (May–November)

  • Hiring a private driver for longer day trips is a good idea for a stress-free experience.

Advisor - Desiree Raymond

Travel Advisor

Desiree Raymond

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