Caribbean Tours in May 2025
4.5 stars on(7,100 reviews)- Choose from 46 Caribbean tours
- 1 verified reviews from TourRadar travelers
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10 best Caribbean trips in May 2025
Compiled by
MelissaCaribbean travel expert at TourRadar
- Tailor-Made Jamaica Trip with Daily Departure (Private Guide and Driver)
- Jamaica Highlights 7Days/ 6 Nights
- Tailor-Made Best Puerto Rico Tour with Daily Departure
- Dominican Republic has it all - 8 days
- Classic Dominican Republic - 8 days
- Puerto Rico Family Holiday 7Nights/6Nights
- PUERTO RICO – Natural Wonders & Adventure
- JAMAICA – Montego Bay Ocho Rios Negril Highlights
- Tailor-Made Jamaica Holiday with Daily Departure
- Customized Private Jamaica Tour with Daily Departure
- Explore Rasta Village and culture
- Climb Dunn's River Falls
- Boat to Monkey Island from Blue Lagoon
Duration 10 days Destinations Montego Bay, Ocho Rios, Blue Mountain National Park, Treasure Beach, Negril Age Range 1 to 99 year olds Operated in English Operator Agate Travel From
- US$6,729
Jamaica Highlights 7Days/ 6 Nights
1 Review by TourRadar travelers“The planning and organization were impeccable. Every detail was thoughtfully curated to ensure a seamless and enjoyable experience.”
Justus, traveled in October 2023
- Explore Kingston's rich history and culture
- Swim and hike at Island Gully Falls
- Climb the famous Dunn's River Falls
Duration 7 days Destinations Kingston, Ocho Rios, Montego Bay, Negril Age Range up to 99 year olds Operated in English, German, French, Spanish Operator Across Caribbean Excursions From $3,140
10% Off- US$2,826You save $314
- Explore Old San Juan's historic sites
- Discover El Yunque National Rainforest
- Experience bioluminescent kayaking in Fajardo
Duration 6 days Destinations San Juan, El Yunque National Forest Age Range 1 to 99 year olds Operated in English Operator Agate Travel From
10% Off- US$5,339
- Explore Santo Domingo's colonial zone
- Visit Santa María Cathedral and museums
- Relax in Jarabacoa's serene settings
Duration 8 days Destinations Santo Domingo, Jarabacoa, Cabarete, Las Terrenas Age Range 3 to 95 year olds Operated in English, Spanish Operator Receptivo Aborigen Tours From
10% Off- US$1,199
- Explore the colonial zone with a local guide
- Visit Santa Maria Cathedral and two museums
- Relax and enjoy optional activities at the hotel
Duration 8 days Destinations Santo Domingo, Santiago de los Caballeros, Cabarete, Las Terrenas Age Range 3 to 95 year olds Operated in English, Spanish Operator Receptivo Aborigen Tours From
10% Off- US$899
- Explore historic Old San Juan and its forts
- Zip through Toro Verde's aerial adventures
- Snorkel in Vieques' crystal-clear waters
Duration 7 days Destinations San Juan Age Range up to 1 year olds Operated in English, Italian, Spanish Operator Across Caribbean Excursions From $3,267
10% Off- US$2,940You save $326
- Explore historic Old San Juan at sunset
- Snorkel and relax at Flamenco and Culebra
- Hike and kayak in El Yunque and Bio Bay
Duration 6 days Destinations San Juan, Culebra, El Yunque National Forest Age Range 18 to 90 year olds Operated in English Operator Bucket List Group Travel LLC From
10% Off- US$2,790
- Explore the beaches and shops of Montego Bay
- Raft on the Martha Brae and swim in the Blue Hole
- Interact with dolphins and snorkel with stingrays
Duration 5 days Destinations Montego Bay, Ocho Rios, Negril Age Range 18 to 90 year olds Operated in English Operator Bucket List Group Travel LLC From
10% Off- US$2,990
- Explore Montego Bay on your first day
- Hike to the Blue Hole and Dunn's River Falls
- Ride horses through a plantation to Negril Beach
Duration 6 days Destinations Montego Bay, Ocho Rios, Negril Age Range 1 to 99 year olds Operated in English Operator Agate Travel From
10% Off- US$4,029
- Explore the Bob Marley Museum in Kingston
- Discover Blue & John Crow Mountains Park
- Raft and swim in the Rio Grande river
Duration 7 days Destinations Kingston, Ocho Rios, Negril, Montego Bay Age Range 1 to 99 year olds Operated in English Operator Agate Travel From
10% Off- US$4,729
