Top Central America & the Caribbean Luxury Historic Sightseeing Trips & Packages 2025/2026

Our 39 most popular Central America & the Caribbean Luxury Historic Sightseeing Trips & Packages trips. Compare tour itineraries from 19 tour companies. 40 reviews.

39 Trips match your criteria (1 - 22 shown)

Costa Rica Nature Adventure (San Jose)
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By Trafalgar
preferred
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
Their travelers enjoy 24/7 travel expertise and dedicated service throughout the trips - everything is taken care of.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Themes

Cultural, 50 Plus, Education / Learning, Small Ship Cruise

Trip dates & details
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Monkeys, Jungles and Volcanoes
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By Trafalgar
preferred
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
Their travelers enjoy 24/7 travel expertise and dedicated service throughout the trips - everything is taken care of.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Themes

Family Friendly

Trip dates & details
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Costa Rica Nature Adventure (Liberia, Guanacaste Beach)
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By Trafalgar
preferred
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
Their travelers enjoy 24/7 travel expertise and dedicated service throughout the trips - everything is taken care of.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Themes

Cultural, 50 Plus, Education / Learning, Small Ship Cruise

Trip dates & details
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Costa Rica Nature Adventure (Liberia)
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By Trafalgar
preferred
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
Their travelers enjoy 24/7 travel expertise and dedicated service throughout the trips - everything is taken care of.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Themes

Cultural, 50 Plus, Education / Learning, Small Ship Cruise

Trip dates & details
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Monkeys, Jungles and Volcanoes
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By Trafalgar
preferred
4.8/5 Excellent
100+ reviews
Group Tour
Why we love them
Their travelers enjoy 24/7 travel expertise and dedicated service throughout the trips - everything is taken care of.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Themes

Family Friendly

Trip dates & details
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Beautiful Cuba
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4.9/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Caribbean, Havana, Soroa, Trinidad, Vinales

Highlights

  • Walk around Old Havana, which sheds lights on the difference between the lifestyle of city and rural life in Cuba.
  • Take in all the colours and aromas of Soroa, the stunning valley area known as the 'rainbow of Cuba' and immerse yourself in local culture.
  • Stroll along the rural dirt roads of Vinales as tractors, vintage cars and horse-drawn carriages pass you by.
  • Step back in time in Trinidad – a real Cuban treat. Explore its old-world streets, then hit some fine palm-flanked beaches for a bit of rest and relaxation.
  • Marvel at the unique architecture of Palacio del Valle in Cienfuegosand ask your local leader for all the best local (and secret) spots.
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Themes

Cultural, Local Immersion & Homestays, High Adventure

What travelers are saying

"I went on the Intrepid 15 day "Best of Morocco" tour in 2025 and had such an amazing time that I wasn't ready to leave by the time the trip finished! It exceeded my expectations in so many ways: value for money, itinerary, a lot of included activities balanced with lots of rest stops on longer travel days, very caring & attentive local guides, and lots of optional activities. As a company, Intrepid was very easy to communicate with before the trip started (I had sent a few questions about optional activities). The website is also easy to navigate and simple for updating travel & health information. If you are considering doing a tour with Intrepid - make sure you read the Essential Trip Information they have on each tour page. It describes everything in detail so you'll know what to expect. While I LOVED my tour, I can see some people signing up for this without reading the description and then being surprised at some of the 2 star hotels (in this case it was the "Original" tour style). Overall, I am impressed at how this tour managed to simultaneously get us closer to Moroccan culture AND feel like an adventure AND feel like a vacation from day-to-day life back home. I would travel with Intrepid again."

Trip dates & details
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Hola Cuba
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4.7/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Caribbean, Havana, Trinidad, Vinales

Highlights

  • Learn the local customs, folklore and beliefs behind Afro-Cuban religion as you’re welcomed into the homes of devoted residents on a colourful and unconventional Urban Adventure in Havana.
  • Relish a real garden-to-plate dining experience at a privately-owned organic eco-farm in picturesque Vinales – indulge in a variety of fresh produce all while gazing across sweeping views of the valley.
  • Receive a fascinating insight into the rise and fall of the charismatic and highly celebrated Cuban revolutionary Che Guevara at his mausoleum and museum in Santa Clara.
  • Experience Cuban hospitality and old-world charm in the coastal town of Trinidad. Wander through cobblestone streets among colourful colonial buildings and relax on the picturesque Playa Ancon.
  • Support the Cuban community by staying at privately-owned guesthouses, dining at home-grown restaurants, and gaining insider knowledge into Cuba’s history, thanks to the expertise of local guides.

Themes

Cultural, Local Immersion & Homestays, High Adventure

What travelers are saying

"I went on the Intrepid 15 day "Best of Morocco" tour in 2025 and had such an amazing time that I wasn't ready to leave by the time the trip finished! It exceeded my expectations in so many ways: value for money, itinerary, a lot of included activities balanced with lots of rest stops on longer travel days, very caring & attentive local guides, and lots of optional activities. As a company, Intrepid was very easy to communicate with before the trip started (I had sent a few questions about optional activities). The website is also easy to navigate and simple for updating travel & health information. If you are considering doing a tour with Intrepid - make sure you read the Essential Trip Information they have on each tour page. It describes everything in detail so you'll know what to expect. While I LOVED my tour, I can see some people signing up for this without reading the description and then being surprised at some of the 2 star hotels (in this case it was the "Original" tour style). Overall, I am impressed at how this tour managed to simultaneously get us closer to Moroccan culture AND feel like an adventure AND feel like a vacation from day-to-day life back home. I would travel with Intrepid again."

Trip dates & details
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Best of Costa Rica
Save this trip to your favorites or other list
4.5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Arenal Volcano, La Fortuna

Highlights

  • Visit a local indigenous community and meet the Terraba people – a matriarchal community who have lived along the Terraba River for the last 500 years – and learn how to make a traditional wooden mask.
  • Hike through the scenic landscapes of Manuel Antonio National Park with a local naturalist guide and learn all the hidden secrets of the rainforest, looking out for local wildlife like sloths and iguanas.
  • Tuck into a super fresh garden-to-table lunch of Costa Rican favourites, including fresh tortillas that you’ll learn how to make from a skilled local woman, with ingredients from her orchard.
  • Meet the family who run the Tierra Amiga organic coffee farm, and learn the whole process of the coffee bean, from planting to harvesting to tasting. Enjoy a cup fresh from the grinders and tuck into a locally made lunch.
  • Wander through the incredible Monteverde Cloud Forest Reserve, home to more than 100 species of mammals and over 400 species of birds. Learn about the biodiversity of the region and look out for quetzal birds and howler monkeys.
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Themes

Cultural, High Adventure

What travelers are saying

"I went on the Intrepid 15 day "Best of Morocco" tour in 2025 and had such an amazing time that I wasn't ready to leave by the time the trip finished! It exceeded my expectations in so many ways: value for money, itinerary, a lot of included activities balanced with lots of rest stops on longer travel days, very caring & attentive local guides, and lots of optional activities. As a company, Intrepid was very easy to communicate with before the trip started (I had sent a few questions about optional activities). The website is also easy to navigate and simple for updating travel & health information. If you are considering doing a tour with Intrepid - make sure you read the Essential Trip Information they have on each tour page. It describes everything in detail so you'll know what to expect. While I LOVED my tour, I can see some people signing up for this without reading the description and then being surprised at some of the 2 star hotels (in this case it was the "Original" tour style). Overall, I am impressed at how this tour managed to simultaneously get us closer to Moroccan culture AND feel like an adventure AND feel like a vacation from day-to-day life back home. I would travel with Intrepid again."

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

Health Safety +

More

Central America & the Caribbean Luxury Historic Sightseeing Trips & Packages Reviews

T

Trusted Customer

Apr 2025

Written on

Monkeys Jungles and Volcanoes

Beautiful trip, one we've done in the past and revisited last month.

K

Kelsey Ekeberg

Apr 2025

Written on

Monkeys Jungles and Volcanoes

We covered so much of Costa Rica! I saw so many different ...

S

Steven Ekeberg

Apr 2025

Written on

Monkeys Jungles and Volcanoes

Packed with action. Great multi-generational adventure. ...

C

Carol Venn

Mar 2025

Written on

Monkeys Jungles and Volcanoes

Excellent guide. REALLY promoted the Trafalgar family. We were never left "alone" during the daytime for the tours. They stuck to the itinerary and kept us going...

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