Top Central America &amp; the Caribbean Luxury Historic Sightseeing Tours &amp; Packages 2025/2026

Save this trip to your favorites or other list

Hola Cuba

premier

4.5/5

Small Group Tour

$2,881

9 days From$2,342

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.

$2,881

9 days From$2,342

Save this trip to your favorites or other list

Save this trip to your favorites or other list

Best of Costa Rica

premier

4.5/5

Small Group Tour

$3,266

10 days From$2,655

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.

$3,266

10 days From$2,655

See all 11 Central America & the Caribbean Luxury Historic Sightseeing Tours & Packages trips

Save this trip to your favorites or other list

Small Group Central America & the Caribbean Luxury Historic Sightseeing Tours & Packages Tours

Small Group Central America & the Caribbean Luxury Historic Sightseeing Tours & Packages Tours11 trips >

Save this trip to your favorites or other list

Beautiful Cuba

premier

4.5/5 Excellent

Small Group Tour

$1,909

8 days From$1,552

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.

$1,909

8 days From$1,552

Save this trip to your favorites or other list

Hola Cuba

premier

4.5/5 Excellent

Small Group Tour

$2,881

9 days From$2,342

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.

$2,881

9 days From$2,342

Save this trip to your favorites or other list

Best of Costa Rica

premier

4.5/5 Excellent

Small Group Tour

$3,266

10 days From$2,655

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.

$3,266

10 days From$2,655

Save this trip to your favorites or other list

Save this trip to your favorites or other list

Best of Mexico & Costa Rica

premier

4.5/5 Excellent

Small Group Tour

$10,258

24 days From$8,340

Highlights

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.
Discover the colourful, fantastical world of alebrijes – folk art sculptures of mythical creatures – during a visit to a women-run workshop outside Oaxaca. The artists will share their process and stories of how they came to specialise in these artworks.
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.
Get a taste of Maya culture during a homecooked Pibil lunch with a local family, sampling this traditional method of cooking which involves barbecuing food underground.
By travelling on this trip, you’ll directly support our Intrepid Foundation partner, Gastromotiva. Donations help them provide nutritious, balanced meals for vulnerable people in Mexico.

$10,258

24 days From$8,340

Save this trip to your favorites or other list

Costa Rica in 9 days - Pura Vida & Paradise in Tamarindo - Superior

Save this trip to your favorites or other list

Costa Rica in 9 days - Pura Vida & Paradise in Tamarindo - Superior

preferred

4.4/5 Great

Small Group Tour

9 days From$1,399

Highlights

Arenal
Guanacaste
San José
Tamarindo

9 days From$1,399

Save this trip to your favorites or other list

Dominican Republic in 5 days - All-Inclusive Escape to Samana - Luxury

Save this trip to your favorites or other list

Dominican Republic in 5 days - All-Inclusive Escape to Samana - Luxury

preferred

4.4/5 Great

Small Group Tour

5 days From$1,199

Save this trip to your favorites or other list

Costa Rica in 12 days - Tropical Rainforests & Beach Escape - Superior

Save this trip to your favorites or other list

Costa Rica in 12 days - Tropical Rainforests & Beach Escape - Superior

preferred

4.4/5 Great

Small Group Tour

12 days From$2,399

Highlights

Arenal
La Fortuna Waterfall
Monteverde
San José
Tamarindo

12 days From$2,399

Save this trip to your favorites or other list

Costa Rica & Panama in 12 days - Arenal, Puerto Viejo & Bocas del Toro - Superior

Save this trip to your favorites or other list

Costa Rica & Panama in 12 days - Arenal, Puerto Viejo & Bocas del Toro - Superior

preferred

4.4/5 Great

Small Group Tour

12 days From$1,799

Highlights

Arenal
Puerto Limón
San José
Bocas del toro

12 days From$1,799