First name is required!
Last name is required!
First name is not valid!
Last name is not valid!
This is not an email address!
Email address is required!
This email is already registered!
Please enter valid email address
Password is required!
Enter a valid password!
Please enter 6 or more characters!
Please enter 16 or less characters!
Passwords are not the same!
Terms and Conditions are required!
Email or Password is wrong!
Please select the captcha checkbox!
Please select the valid captcha!
Something went wrong! Try again later!

Jamaica Trips & Tours

All Jamaica tours, river cruises, expedition cruises, and adventure trips. Find the best guided trips and expert planned vacation and holiday packages from over 600 tour companies. 8 trips found. 45 reviews with an average rating of 4.6 for all Jamaica trips. See all Jamaica Reviews

Sign in to unlock private member deals up to $500 off.

Members save up to $500 per person on thousands of trips every day and get access to private deals up to 50% off. Log in or join to see eligible deals. It's free!

Sort By:

 
Cuba Cruise Adventure tour

Cultural, Education / Learning, Small Ship Cruise

4.9 | Excellent | 100+ Reviews
10 Days
$ 250 per day
Type: Small Ship Cruise
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, Jamaica, Havana, Santiago de Cuba
From
$ 2,499

Highlights

  • Enjoy a traditional dance performance (Santiago)
  • Enjoy Rum Tasting
  • Walking Tour of Old Havana
  • Visit Fine Arts Museum (Havana)
  • Casa Fuster (Havana)
  • Project Trazos Libres (Cienfuegos)
  • Teatro Tomas Terry (Cienfuegos)
  • Special exclusive experiences for smarTours travelers provided by your Tour Director
More
Jamaica Encompassed tour

Cultural, Nature & Wildlife

4.8 | Excellent | 100+ Reviews
10 Days
$ 200 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: Jamaica, Caribbean
From
$ 1,999

Highlights

  • Relax on world-class beaches around the island
  • Bargain at the local markets
  • Visit a rastafarian village
  • Learn to drum and dance with the locals at a maroon village
  • Experience a different side of this familiar island
More
Jamaica Encompassed & Reggae Sumfest tour

Cultural, Local Immersion & Homestays, Festivals & Special Events

4.8 | Excellent | 100+ Reviews
13 Days
$ 204 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: Jamaica, Caribbean
From
$ 2,649

Highlights

  • Relax on world-class beaches
  • Dance the night away to local music
  • Listen to local and international stars at reggae sumfest
  • Visit a rastafarian village
  • Watch cliff jumping at the famous rick's café
More
Best of Jamaica tour
4.7 | Excellent | 100+ Reviews
8 Days
$ 224 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:
Very Easy

Very Easy Physical LevelMinimal walking. Motor vehicles for all major parts of trip. Wheelchair friendly (check for individual trips). Most cruises.

Visits: Jamaica, Caribbean
From
$ 1,616

Highlights

  • Short and sweet, this eight-day trip hits the 'must-sees' of Jamaica while allowing you to explore and sample Jamaica's 'real' side
  • Impress family and friends with newly acquired skills in Jamaican cooking
  • A visit to the Bob Marley museum in culturally vital Kingston is essential to appreciating the musical background of this island nation
  • Practically untouched until the 1960s, the spectacular beaches and laid-back vibe of Negril have yet to be devoured by development
  • Enjoy a home-cooked meal at a private home with locals to get a ground-level sense of daily life in Jamaica
More
The Caribbean & Cuba tour

Cultural, Nature & Wildlife, Small Ship Cruise

4.2 | Great | 45 Reviews
13 Days
$ 114 per day
Type: Small Ship Cruise
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:
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: Antigua And Barbuda, Barbados, British Virgin Islands, Jamaica, Saint Lucia, Caribbean, Santiago de Cuba
From
$ 1,485

Highlights

  • Explore Bridgetown, Castries and Oranjestad
  • Visit Brimstone Hill Fortress to admire magnificent views across the island
  • Discover the subterranean environment of Harrison’s Cave
  • Visit Ocho Rios and Santiago de Cuba
  • Discover the natural beauty of Tortola
More
Want a custom trip?
We can help.
Custom Trip Expert
Cuba by Land & Sea tour

Cultural

by
4.8 | Excellent | 100+ Reviews
10 Days
$ 291 per day
Type: 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:
Strenuous

Strenuous Physical LevelFull day hiking or trekking over medium to long distances. Moderate expectation of physical fitness.

Visits: Cuba, Jamaica, Havana, Miami
From
$ 2,909

Highlights

  • Havana: Orientation tour; Revolution Square; ride in an Old Styler car, lunch and discussion at a paladar; guided walk and discussion in Old Havana; interact with children at a daycare center; Finca Vigia (Hemingway’s home); discussion and lunch at an organic farm; workshop at José Fuster’s studio; Hotel Nacional de Cuba; discussion with Cuban baseball players; farewell dinner
  • Cienfuegos: City orientation; performance by the Cienfuegos Orchestra; lunch and discussion with owner and staff at a paladar
  • Santiago de cuba: Historic center; Revolution Square; San Juan Hill; interact with workers at Jardín de los Helechos (Garden of Ferns); cruise to Granma Island; discussion with local fishermen
  • Shrouded in mystery for the last 50 years, you now have the rare opportunity to visit the captivating country of Cuba
  • Globus’ people-to-people program allows you to experience Cuba unlike any other destination
More
All Inclusive Colors of Cuba Cruise tour

Cultural, Small Ship Cruise

4.1 | Great | 38 Reviews
10 Days
$ 400 per day
Type: Small Ship Cruise
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, Jamaica, Havana, Santiago de Cuba
From
$ 3,998

Highlights

  • 2-nights at an all-inclusive beach resort in Montego Bay, Jamaica
  • 7-night cruise visiting 4 ports in Cuba
  • Visit the historical cities of Cienfuegos, Havana, and Santiago de Cuba
  • Full-time People-to-People Program of on-board activities and included shore excursions
  • Learn about and experience Cuba's culture, history, cuisine, nature, music, dance and the people
  • Enjoy the pristine beach of Punta Frances on the "Isle of Youth"
More
10-Day Jamaica Encompassed Bus Tour

Cultural

4.8 | Excellent | 11 Reviews
10 Days
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: Jamaica
From
$ 1,999

Highlights

  • <br/><br/>
  • Relax on world-class beaches around the island<br/>
  • Bargain at the local markets<br/>
  • Visit a Rastafarian village<br/>
  • Learn to drum and dance with the locals at a Maroon village<br/>
  • Experience a different side of this familiar island<br/>
More
Award winning travel
X
Unlock Member Savings

In order to see Stride Select deals you must sign in. We’ve negotiated with many of the world’s best travel companies to save you money! Get the best experiences, save up to $700 per person, and be a hero to your travel companions!

or
or
Provide email and Password

We respect your privacy and take great care to protect your information. By joining you agree to our Privacy Policy and Terms of Use.

Already a member?

With FREE membership you:

  • Save up to $700 per person!*
  • Access private deals and offers
  • See personalized trip recommendations
  • Save favorite trips
See member program details
 

 

Tours & Operators on Stride Awarded and Featured by:

  • National Geographic, Condé Nast Traveler, Travel + Leisure
  • Outside, The New York Times