Immerse yourself in the real Cuba

Nine days to experience the enthralling history of this seductive Caribbean island


While Intrepid has had a legal trip to Cuba for over a year, Americans are getting closer than ever to having all tourism requirements lifted. While this change seems to be just around the corner, the time now is ripe to visit Cuba before the masses. How? Our completely legal trip for Americans lets you travel worry-free, as we've already organized all the required cultural and educational elements. With plenty of availability in the coming months, you can be one of the firsts to experience Cuba's rich culture, breathtaking landscapes, and friendly people. Don't wait, visit Cuba now. 

Roger, a Cuban guide speaks with us about Americans traveling to Cuba.



Cuba Image Gallery


Detailed Trip Itinerary


Day 1-2

Settle into your privately owned guesthouse and soak up some of Havana’s faded charm. Meet your local leader at a welcome meeting, then head out for a classically Cuban dinner at a local paladar. Tonight ends with a bang: a famous cannon ceremony that dates back to the 17th century.

Begin the next day with a walking tour of Havana’s gloriously decaying Old City, a World Heritage site since 1982. The streets are lined with colonial architecture, 16th-century fortresses and crumbling churches by the dozen. After lunch, visit 'Fusterlandia', an entire neighborhood into a lively and colorful series of mosaics.


Day 3-4

Leave Havana behind and head east to a UNESCO designated biosphere reserve in Las Terrazas. Meet up with a local community leader and learn about the reforestation and ecological research being done here. It’s on to Vinales, a quiet town among the tobacco fields and valleys of Pinar del Rio. Stop off at a local organic farm for a real farm-to-fork dinner.

Spend the morning learning about Cuban agriculture with a visit to a nearby tobacco farm. Get an insight as to how the communist system works, how much tobacco the farmers keep, how much produce they give back to the government and how they make ends meat. In the afternoon, learn to cook a few classic dishes in a cooking demonstration with a local chef.


Day 5

The journey from Vinales to Cienfuegos takes us past the Korimakao Cultural Project in Cienaga de Zapata, an area famous for its wetlands, as well as the beautiful Bay of Pigs – the spot where US-backed counter revolutionaries landed in 1961. Cool off in a nearby waterhole before moving on to the European boulevards of Cienfuegos, the ‘Pearl of the South’.


Day 6-7

If Havana is the heart of Cuba, Trinidad would be its soul. It is a beautiful colonial town with long stretches of white-sand beaches nearby and a vibrant nightlife. Take a guided tour of the World Heritage Old Town. Meet a local dance group and learn about the city’s Afro-Cuban roots before trying your hand (and feet) at a salsa class.

Stray off the cobbled path in Trinidad and discover the area’s rural side. Enjoy a short hike to a waterfall in the National Park "El Cubano". Visit 'Casa de Santander', a prestigious family who has been making pottery for generations.


Day 8-9

It’s time to head back to Havana. But on the way, stop off at Manaca Iznaga in the Valle de los Ingenios, the centre of colonial slavery in the region, where a 44-metre tower was built to watch over the slaves as they worked in the sugar fields. Visit Santa Clara, a key city in the Cuban Revolution and the site of the statue of Ernesto Che Guevara that was built after his death. Tonight, say farewell to your group with a goodbye dinner in Havana.

There are no activities planned for today, and you are able to depart Havana at any time. Wave goodbye to the city’s warm waters, colonial palaces and vintage Cadillacs before boarding your flight back to the US.


Get Going

Trip name Days Total
price from
Galapagos Encounter - Central Islands (Queen Beatriz) 6 Book trip
Beijing to Delhi 32 Book trip
Expedition Morocco – Walking with Berber Nomads 8 Book trip
Hike & Kayak Yellowstone 7 Book trip
USA Eclipse - Cascades and Coast (Northwest) 9 Book trip
Kimberley Trail Broome to Darwin 14 Book trip
Explore the Camino Way 10 Book trip
Grand Galapagos - (Queen Beatriz) 17 Book trip
Ushuaia to Santiago 23 Book trip
West Africa Overland 70 Book trip
Cape Town to Vic Falls 22 Book trip
Xi'an to Bishkek 27 Book trip


Cuba Inspired Blogs

Travel season guide: when to visit our favourite destinations

Posted on Mon, 22 Aug 2016

Travel. It's all in the timing.

Read more

An American in Cuba: everything you need to know before you travel

Posted on Wed, 6 Apr 2016

The President just went there. The Rolling Stones just toured. What do improving relations with Cuba mean for US travelers?

Read more

The most famous US Presidential trips of all time

Posted on Mon, 21 Mar 2016

With Obama touching down in Cuba for the first presidential visit in over 50 years, we're looking back on how Air Force One helped shape the 20th century.

Read more

Havana who? 5 reasons Trinidad is Cuba’s real star

Posted on Fri, 11 Dec 2015

Quick, think of words that best describe Cuba. “Rum”, “cigars”, “Havana” probably come to mind, right? Not anymore.

Read more

Cuba through an iPhone lens: you’ve never seen it like this before

Posted on Wed, 18 Nov 2015

Cuba has a reputation for being pretty photogenic, but can an iPhone handle all that crumbling 60s nostalgia? All signs point to yes.

Read more

Meet the ridiculously talented family that travels for a living

Posted on Mon, 21 Sep 2015

Meet the Bartholomews, aka You Can't be Serious.

Read more