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Small Group Cuba Tours
Havana Cuba Alley with Colorful Buildings
10 Days / 9 Nights

HAVANA | SANTA CLARA | CAMAGÜEY | SANCTI SPÍRITUS | CIENFUEGOS 

No more than 12 guests

The intriguing island nation of Cuba is roughly 780 miles long. We wouldn’t blame you if you wanted to see it all.

SAVE UP TO $900 PER PERSON ON SELECT DATES

Next Available Date
June 29, 2020
Prices Starting at
$4095
church trinidad cuba landscape
7 Days / 6 Nights

HAVANA | PLAYA LARGA | PLAYA GIRON | CIENFUEGOS | TRINIDAD | SANTA CLARA

No more than 12 guests

Cuba’s most famous cities, Havana, Cienfuegos, and Trinidad, stir visions of brightly painted Colonial buildings, pounding mambo rhythms and barrios that bustle well into the night.

SAVE UP TO $900 PER PERSON ON SELECT DATES

Next Available Date
June 7, 2020
Prices Starting at
$3895
Cuba Architecture Havana
6 Days / 5 Nights

HAVANA | VIÑALES VALLEY 

No more than 12 guests

Steeped in mystique, Cuba creates legends. Uncover a history so rich, its legacy is memorialized in its architecture and its people. Learn why Hemingway and Sinatra felt an affinity for this island nation.

SAVE UP TO $700 PER PERSON ON SELECT DATES

Next Available Date
June 13, 2020
Prices Starting at
$2695
havana Cuba Jazz music travel club band salsa mambo
4 Days / 3 Nights

HAVANA

No more than 12 guests

For the traveler with little time but a lot of interest, insightCuba offers a jam-packed four day weekend with cultural highlights and authentic Cuban experiences in Havana.

SAVE UP TO $700 PER PERSON ON SELECT DATES

Next Available Date
June 18, 2020
Prices Starting at
$1895
Varadero, Cuba Beach
5 DAYS / 4 NIGHTS

VARADERO | HAVANA | CARDENAS

NO MORE THAN 12 GUESTS

Stick your toes in beaches once off-limits to Americans and experience Cuba's capital Havana. 

Next Available Date
May 21, 2020
Prices Starting at
$2995

Specialty Cuba Tours
Havana Marathon Package
4 Days / 3 Nights

HAVANA

Want a chance to see Cuba before it changes? InsightCuba offers U.S. runners the opportunity to legally take part in the Havana Half + Full Marathon + 10K race.

Next Available Date
November 20, 2020
Prices Starting at
$1195
20th-anniversary-celebration-tour-400x300
5 Days / 4 Nights

HAVANA

Join insightCuba president, Tom Popper, and many special guests for a 20th Anniversary Celebration Tour to Cuba. 

Next Available Date
November 11, 2020
Prices Starting at
$2795
7 Days / 6 night

HAVANA | MATANZAS

2021 DATES COMING SOON

Experience Cuba's iconic rhythm during the six-day tour centered around the country's annual Havana Jazz Festival. 

Next Available Date
January 19, 2021
Prices Starting at
$3995

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  1. 🇨🇺 Have you ever had a Hemingway Special? "This frozen daiquiri, so well beaten as it is, looks like the sea where… https://t.co/ofGRjxxSVU
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