Top Central America & the Caribbean History Trips & Packages In 2025/2026

Our 96 most popular Central America & the Caribbean History Trips & Packages trips. Compare tour itineraries from 32 tour companies. 159 reviews.

96 Trips match your criteria (1 - 22 shown)

A Taste of Cuba
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5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a wide range of trip styles, Exodus caters to every type of traveler out there- even those with specific interests from cycling to winter hiking.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Caribbean, Havana, Trinidad, Vinales

Highlights

  • Experience the real Cuba, its complex story revealed by our expert tour leader
  • Cruise the streets of Havana in a classic car
  • See rural Cuba on a walk through tobacco plantations in the UNESCO-listed Viñales Valley
  • Learn to dance salsa in Trinidad – a local expert showing you the steps
  • Relax on the picturesque Caribbean beach of Playa Ancón
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Themes

Cultural, Nature & Wildlife, National Parks

What travelers are saying

"Excellent service"

Trip dates & details
Save this trip to your favorites or other list

Health Safety +

Generous cancellation

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Cuba: La Isla Grande
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4.7/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a wide range of trip styles, Exodus caters to every type of traveler out there- even those with specific interests from cycling to winter hiking.
Lodging level
Standard - 3 star
Physical level
Moderate

Visits

Baracoa, Caribbean, Havana, Santiago, Santiago de Cuba, Trinidad

Highlights

  • Cruise Havana in a classic car
  • Join Cuban cowboys for an immersive afternoon at a working farm
  • Explore isolated Baracoa on Cuba's eastern tip
  • Get moving on a drumming workshop led by local musicians
  • Shake things up with a cocktail-making class
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Themes

Cultural, Nature & Wildlife, National Parks

What travelers are saying

"Excellent service"

Trip dates & details
Save this trip to your favorites or other list

Health Safety +

Generous cancellation

More
Tropical Costa Rica  - 2024
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4.8/5 Excellent
100+ reviews
Group Tour
Why we love them
With a history that spans back to 1918, they have unparalleled expertise in the guided tour industry and can cater to all types of travelers.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Guanacaste

Highlights

  • Discover the history of coffee in Costa Rica during your visit to a coffee plantation.
  • Learn about local farming practices and learn to make tortillas while having lunch at Don Juan Finca Educativa.
  • Take your journey to new heights and explore the Monteverde Cloud Forest from the elevated treetop canopy.
  • Put your feet up and relax during a 2-night stay in Guanacaste known for the country’s most beautiful beaches.
  • Enjoy the breathtaking scenery surrounding Arenal Volcano.
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Themes

Cultural

What travelers are saying

"This was a tremendous trip. Nice mix of New Zealand s spectacular scenery and cultural highlights. In Australia Cairns was interesting for culture and great barrier reef, which is unfortunetely getting bleached due to rising ocean temps.The Sydney Opera house was amazing. Our Auastralian guide was knowledgeable and very organized. Only complaint was that at 37 folks the trip was too large in our opinion."

Trip dates & details
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Costa Rica: A World of Nature featuring Tortuguero National Park, Arenal Volcano & Manuel Antonio National Park - 2024
Save this trip to your favorites or other list
4.8/5 Excellent
100+ reviews
Group Tour
Why we love them
With a history that spans back to 1918, they have unparalleled expertise in the guided tour industry and can cater to all types of travelers.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Taste for yourself why cacao is called “the food of the gods” and observe the process of converting this seed from bean to bar.
  • Learn how to cook using a coconut before making some delicious local candy.
  • Learn about Costa Rica’s ecosystem and local culture.
  • Visit the world’s first sea turtle research station in Tortuguero National Park.
  • Explore Arenal during a captivating 3-night stay.
Show more

Themes

Cultural

What travelers are saying

"This was a tremendous trip. Nice mix of New Zealand s spectacular scenery and cultural highlights. In Australia Cairns was interesting for culture and great barrier reef, which is unfortunetely getting bleached due to rising ocean temps.The Sydney Opera house was amazing. Our Auastralian guide was knowledgeable and very organized. Only complaint was that at 37 folks the trip was too large in our opinion."

Trip dates & details
Save this trip to your favorites or other list
More
Tropical Costa Rica  - 2024
Save this trip to your favorites or other list
4.8/5 Excellent
100+ reviews
Group Tour
Why we love them
With a history that spans back to 1918, they have unparalleled expertise in the guided tour industry and can cater to all types of travelers.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Guanacaste

Highlights

  • Discover the history of coffee in Costa Rica during your visit to a coffee plantation.
  • Learn about local farming practices and learn to make tortillas while having lunch at Don Juan Finca Educativa.
  • Take your journey to new heights and explore the Monteverde Cloud Forest from the elevated treetop canopy.
  • Put your feet up and relax during a 2-night stay in Guanacaste known for the country’s most beautiful beaches.
  • Enjoy the breathtaking scenery surrounding Arenal Volcano.
Show more

Themes

Cultural

What travelers are saying

"This was a tremendous trip. Nice mix of New Zealand s spectacular scenery and cultural highlights. In Australia Cairns was interesting for culture and great barrier reef, which is unfortunetely getting bleached due to rising ocean temps.The Sydney Opera house was amazing. Our Auastralian guide was knowledgeable and very organized. Only complaint was that at 37 folks the trip was too large in our opinion."

Trip dates & details
Save this trip to your favorites or other list
More
Guatemala: See & Experience it ALL in 8 Days, 1st Class Custom Tours
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By Charlie The Traveler
Local Expert
Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.
5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
Travelers report that traveling with CharlieTheTraveler is a life-changing experience, in the best possible way.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Full schedule

Highlights

  • A Helicopter Ride Over Ancient Temples Found Deep in the Jungle
  • Watching an Active Volcano Erupt in the Middle of the Night (optional)
  • Hanging Out with Hippies in the Village of San Marcos
  • A Visit to the Country’s Biggest Indigenous Market
  • A Full-Day & Private Tour of Guatemala’s Showcase City, Colonial Antigua
Show more

Themes

Family Friendly, Nature & Wildlife

What travelers are saying

"Thank you for reaching out! This trip was absolutely phenomenal—truly the best 10 days of my life. I’m incredibly grateful for everything you arranged. Cindy, in particular, took such good care of me. It felt like she was supporting me around the clock, and I really appreciate her dedication. I’m already eager to recommend your services to my friends and colleagues. On top of that, I realized how much I love the South Island—I’m hoping to visit Queenstown and Mount Cook National Park next, perhaps while participating in some business-related community events. I’d be thrilled if your company could help me plan that trip as well. Thank you again for everything. I look forward to traveling with you in the future!"

Trip dates & details
Save this trip to your favorites or other list

Health Safety

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Belize: See & Experience it ALL in 10 Days, 1st Class Custom Tours
Save this trip to your favorites or other list
By Charlie The Traveler
Local Expert
Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.
4.9/5 Excellent
100+ reviews
Small Group Tour
Why we love them
Travelers report that traveling with CharlieTheTraveler is a life-changing experience, in the best possible way.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Full schedule

Highlights

  • Great Blue Hole Flight-Seeing Tour (optional)
  • Swimming with Sharks & Sting Rays
  • Snorkeling in the World’s Second Largest Barrier Reef
  • Visiting Impressive Archaeological Sites
  • Coming in Contact with Black Howler Monkeys
Show more

Themes

Cultural, Family Friendly, Nature & Wildlife

What travelers are saying

"Thank you for reaching out! This trip was absolutely phenomenal—truly the best 10 days of my life. I’m incredibly grateful for everything you arranged. Cindy, in particular, took such good care of me. It felt like she was supporting me around the clock, and I really appreciate her dedication. I’m already eager to recommend your services to my friends and colleagues. On top of that, I realized how much I love the South Island—I’m hoping to visit Queenstown and Mount Cook National Park next, perhaps while participating in some business-related community events. I’d be thrilled if your company could help me plan that trip as well. Thank you again for everything. I look forward to traveling with you in the future!"

Trip dates & details
Save this trip to your favorites or other list

Health Safety

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The Best of Panama
Save this trip to your favorites or other list
5/5 Excellent
14 reviews
Group Tour
Why we love them
They create highly personalized trips across all needs from family travel to luxury, food, diving, adventures and more.
Lodging level
Luxury - 5 star
Physical level
Moderate
Trip pace
Full schedule

Highlights

  • Panama City & Miraflores Locks
  • Embera Indians Village at Chagres Tour
  • Soberania National Park & Gamboa
  • Baru Volcano
  • Gulf of Chiriqui
Show more

Themes

Cultural, Nature & Wildlife, Education / Learning, Photography

What travelers are saying

"The brilliant excursions! Dear Richele! I am writing you with gratitude for organizing the brilliant excursions for our group of 16 people! They came back from Brazil very happy and really satisfied! So, many-many thanks to you and your wonderful team! Looking forward to our next cooperation) Kind Regards, Anna Zboranska Exotic Department TRAVEL PROFESSIONAL GROUP"

Trip dates & details
Save this trip to your favorites or other list

Health Safety

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Central America & the Caribbean History Trips & Packages Reviews

J

Jeff

Jul 2023

Written on

baez

Nice trip

A

Anonymous

Jan 2018

A great insight into a rapidly changing country

I'm really pleased I got to see Cuba before it changes too much. While you can see the commercialism is starting to creep in, it still feels like it has been stuck...

B

Brianna M.

Feb 2023

Written on

The company was well-organized and I enjoyed every activity they planned for this trip!

Although I have a friend from Guatemala who has told how magnificent the country is, I had never gone. One night I was doing research when I came across CharlieTheTr...

J

Jon H.

Feb 2023

Written on

The Guatemala trip through CharlieTheTraveler had so much packed into 6 days.

The Guatemala trip through CharlieTheTraveler had so much packed into 6 days. I had such a good time on each daytrip and going to each attraction. I was intrigued by...

R

Rachel G.

Feb 2023

Written on

I don’t think I can ever take a vacation without this assistance from this company again!

I don’t travel a lot, but after booking through CharlieTheTraveler, the company kept in contact with me to answer any questions and let me know how to prepare for my...

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