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Top Guided Trips to Cuba Trips & Tours

5 trips from 6 tour companies with 11 reviews

All Top Guided Trips to Cuba tours, river cruises, expedition cruises, and adventure trips. Find the best guided trips and expert planned vacation and holiday packages. Average rating of 5.0 for all Top Guided Trips to Cuba trips.

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Vintage Cuba tour

Cultural

4.7 | Excellent | 8 Reviews
9 Days
$ 113 per day
Type: Small Group Tour
Lodging:
Basic - 2 star

Basic - 2 star Lodging LevelYou'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Cuba, Havana, Trinidad
From
$ 1,020

Highlights

  • There’s a world of difference between Cuban life in the city and in the country, and you’ll learn all about it with a walking tour of Havana and strolls down the rural dirt roads of Vinales, watching the tractors, vintage cars and horse drawn carriages pass by
  • Discover the man behind the t-shirt with a visit to revolutionary Che Gevara’s Mausoleum and Museum
  • Music’s the fuel that makes Cuba move, so fill up on the rhythm and learn to move like a local
  • Get a hands-on experience with one of the country’s most famous exports; a tobacco farmer will teach you how to roll a cigar with his prestigious harvest
More
The Best of Cuba tour

Cultural, Education / Learning

4.9 | Excellent | 100+ Reviews
9 Days
$ 378 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Cuba, Trinidad & Tobago, Camaguey, Havana, Miami, Trinidad
From
$ 3,399

Highlights

  • A true “people-to-people” experience with cultural exchanges such as visits with artists, musical performances, and local organizations
  • Riding in American Vintage Automobiles (Havana)
  • Home of Ernest Hemingway (Havana)
  • Cigar Factory (Havana)
  • Casa Fuster (Havana)
  • Bay of Pigs Museum (Giron)
  • Walking Tour of Trinidad
  • Bici-Taxi Tour of Camaguey
  • Beaches of Guardalavaca (Holguin)
  • Meeting Local Fishermen (Gibara)
More
Cuba by Kayak tour

Family Friendly, Nature & Wildlife, National Parks, Scuba Diving, Rafting, Kayaking, Canoeing

4.9 | Excellent | 9 Reviews
8 Days
$ 448 per day
Type: Small Group Tour
Lodging:
Premium - 4 star

Premium - 4 star Lodging Level3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.

Physical:
Moderate

Moderate Physical LevelRegular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.

Visits: Cuba, Miami
From
$ 3,585

Highlights

  • Enjoy a walking tour through Colonial Havana’s plazas 
  • See former military fortifications lining the beach in sharp contrast to the paradisiacal shores.
  • Visit the Museo de Ernesto Hemingway, a somewhat recent development to Hemingway’s Cuban legacy. 
  • Explore the surrounding banks, and snorkel along the coral reefs.
More
Cuba Today: People and Society—Havana and the Countryside

50 plus, Cultural, Education / Learning

4.5 | Great | 30 Reviews
9 Days
$ 444 per day
Type: Small Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Cuba, Havana
From
$ 3,995

Highlights

  • Delve into US-Cuban Relations and the History of Cuban music with experts.
  • Attend a rehearsal by a Cuban dance company and speak with the dancers. Spend a day in the beautiful landscapes of the Vinales Valley to meet tobacco growers.
  • Enjoy interactions with a local Community Arts Project, an artisan farmer and a Cuban baseball player. Explore Ernest Hemingway’s farm, Finca La Vigia.
More
Cuba People-to-People Multisport Tour tour

Cycling & Biking, Hiking & Walking, Cultural, Transformative

5.0 | Excellent | 2 Reviews
8 Days
$ 975 per day
Type: Group Tour
Lodging:
Value - 3 star

Value - 3 star Lodging LevelMid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.

Physical:
Easy

Easy Physical LevelSome walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.

Visits: Cuba, Havana
From
$ 7,798

Highlights

  • Legally travel to Cuba on this special People-to-People Multisport Trip—the very first trip of its kind!
  • Explore Matanzas on foot, discovering caves and white-sand beaches, and meeting farmers and some of Cuba's famous artisans
  • Pedal alongside members of Cuba's National Cycling club through beautiful natural areas, rural villages and captivating colonial towns
  • Bike and hike the Viñales Valley, tobacco farm capital and World Heritage site, beloved for its geologically unique landscape dotted with mogotes
  • Be enchanted by the vibrant history, beautiful architecture and seductive vibe of Havana
More
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