Caribbean holidays
If you’re looking for white-sand beaches, fringed with palms and ringed by coral cays then, yes, Caribbean holidays have got the lot. And if you’re more inclined towards cycling in Cuba, bird watching in St Lucia or trekking in Dominica then our partners can sort that too. Set sail on your very own Caribbean adventure... but don’t just stick to the obvious.
31 Caribbean holidays found
Cuba holiday, small group
The best of old-world Cuba
From £1,640£1,279 to £1,980 15 days ex flights
Small group travel:
Departs selected Saturdays every month throughout the year
Up to £420 off selected dates.
Late availability on these dates: 22 Sep, 20 Oct, 10 Nov, 17 Nov, 24 Nov, 08 Dec, 22 Dec
Late availability on these dates: 22 Sep, 20 Oct, 10 Nov, 17 Nov, 24 Nov, 08 Dec, 22 Dec
Dominica holiday
Indulge on this adventure holiday in the Caribbean
From US $3,595 8 days ex flights
Small group travel:
2025: 5 Apr
Dominican Republic adventure tour
Explore this wild, rocky, rough, rugged, but beautiful area
From £1,955 to £2,295 8 days ex flights
Small group travel:
2024: 6 Oct
2025: 5 Mar, 5 Apr, 5 May, 5 Jun, 5 Jul, 5 Aug, 5 Sep, 5 Oct
2025: 5 Mar, 5 Apr, 5 May, 5 Jun, 5 Jul, 5 Aug, 5 Sep, 5 Oct
Small group backroads and beaches tours to Cuba
Explore off the beaten track locations
From £999£799 to £1,299 8 days ex flights
Small group travel:
2024: 12 Oct, 19 Oct, 2 Nov, 23 Nov, 21 Dec
2025: 18 Jan, 8 Feb, 15 Feb, 8 Mar, 22 Mar, 12 Apr, 26 Apr, 10 May, 24 May, 26 Jul, 16 Aug, 18 Oct, 1 Nov, 22 Nov, 20 Dec
2025: 18 Jan, 8 Feb, 15 Feb, 8 Mar, 22 Mar, 12 Apr, 26 Apr, 10 May, 24 May, 26 Jul, 16 Aug, 18 Oct, 1 Nov, 22 Nov, 20 Dec
Up to £200 off selected dates.
Late availability on these dates: 12 Oct, 19 Oct, 02 Nov, 23 Nov, 21 Dec
Late availability on these dates: 12 Oct, 19 Oct, 02 Nov, 23 Nov, 21 Dec
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
01273 823 700
Call us until 6pm
Calling from outside the UK
rosy@responsibletravel.com
Small group tour to Cuba
Discover the fascinating diversity of Cuba
From US $1,970 20 days ex flights
Small group travel:
2024: 4 Oct, 13 Dec, 27 Dec
2025: 10 Jan, 24 Jan, 14 Feb, 28 Feb, 14 Mar, 28 Mar, 4 Apr, 18 Apr, 2 May, 13 Jul, 18 Jul, 22 Aug, 12 Sep, 17 Oct, 7 Nov, 21 Nov, 5 Dec, 26 Dec
2025: 10 Jan, 24 Jan, 14 Feb, 28 Feb, 14 Mar, 28 Mar, 4 Apr, 18 Apr, 2 May, 13 Jul, 18 Jul, 22 Aug, 12 Sep, 17 Oct, 7 Nov, 21 Nov, 5 Dec, 26 Dec
Cuba adventure tours
Authentic Cuba using guesthouses and local guides
From US $705 8 days ex flights
Small group travel:
Departs every Thursday throughout the year
Scuba diving and tour in Cuba
Scuba diving and roundtrip Cuba with homestays and/or hotels
From €995 to €1,790 15 days ex flights
Tailor made:
This trip can be tailor-made and departures can be arranged all year. The sample itinerary below can be modified to your personal wishes including departure date, duration, accommodation used & how long you spend in each destination.
Holidays to Cuba
A comprehensive and intriguing tour
From £1,799£1,449 to £2,099 15 days ex flights
Small group travel:
2024: 19 Oct, 26 Oct, 9 Nov, 16 Nov, 21 Dec
2025: 11 Jan, 1 Feb, 15 Feb, 22 Feb, 8 Mar, 22 Mar, 29 Mar, 12 Apr, 26 Apr, 10 May, 24 May, 28 Jun, 19 Jul, 2 Aug, 16 Aug, 4 Oct, 11 Oct, 18 Oct, 25 Oct, 8 Nov, 15 Nov, 20 Dec
2025: 11 Jan, 1 Feb, 15 Feb, 22 Feb, 8 Mar, 22 Mar, 29 Mar, 12 Apr, 26 Apr, 10 May, 24 May, 28 Jun, 19 Jul, 2 Aug, 16 Aug, 4 Oct, 11 Oct, 18 Oct, 25 Oct, 8 Nov, 15 Nov, 20 Dec
Up to £350 off selected dates.
Late availability on these dates: 19 Oct, 26 Oct, 09 Nov, 16 Nov, 21 Dec
Late availability on these dates: 19 Oct, 26 Oct, 09 Nov, 16 Nov, 21 Dec
Small group tour to Western Cuba
Tour the 'Garden Province' of Cuba
From US $575 6 days ex flights
Small group travel:
2024: 18 Oct, 29 Nov, 13 Dec, 27 Dec
2025: 10 Jan, 24 Jan, 7 Feb, 28 Feb, 14 Mar, 28 Mar, 11 Apr, 18 Apr, 2 May, 16 May, 27 Jun, 1 Aug, 5 Sep, 26 Sep, 31 Oct, 21 Nov, 5 Dec, 19 Dec
2026: 9 Jan
2025: 10 Jan, 24 Jan, 7 Feb, 28 Feb, 14 Mar, 28 Mar, 11 Apr, 18 Apr, 2 May, 16 May, 27 Jun, 1 Aug, 5 Sep, 26 Sep, 31 Oct, 21 Nov, 5 Dec, 19 Dec
2026: 9 Jan
Cuba small group vacation
Cuba travel, legal, and local!
From US $2,500 to US $2,600 9 days ex flights
Small group travel:
2024: 9 Nov, 26 Dec
2025: 15 Mar
2025: 15 Mar
Women only tours to Cuba
Meet female entrepreneurs, artists, and change-makers in Cuba
From US $740 8 days ex flights
Small group travel:
2024: 7 Nov, 19 Dec
2025: 9 Jan, 13 Feb, 13 Mar, 3 Apr, 1 May, 12 Jun, 17 Jul, 14 Aug, 11 Sep, 16 Oct, 13 Nov, 18 Dec
2025: 9 Jan, 13 Feb, 13 Mar, 3 Apr, 1 May, 12 Jun, 17 Jul, 14 Aug, 11 Sep, 16 Oct, 13 Nov, 18 Dec
Cuba cultural tours
Experience authentic Cuba using local guides and guesthouses
From US $1,395 15 days ex flights
Small group travel:
Departs every Friday throughout the year
Best of Cuba holiday
A superb introduction to the fascinating island of Cuba
From £1,379£1,179 to £1,499 10 days ex flights
Small group travel:
2024: 12 Oct, 19 Oct, 2 Nov, 23 Nov, 21 Dec
2025: 18 Jan, 8 Feb, 15 Feb, 8 Mar, 22 Mar, 12 Apr, 26 Apr, 10 May, 24 May, 26 Jul, 16 Aug, 18 Oct, 1 Nov, 22 Nov, 20 Dec
2025: 18 Jan, 8 Feb, 15 Feb, 8 Mar, 22 Mar, 12 Apr, 26 Apr, 10 May, 24 May, 26 Jul, 16 Aug, 18 Oct, 1 Nov, 22 Nov, 20 Dec
Up to £200 off selected dates.
Late availability on these dates: 12 Oct, 19 Oct, 02 Nov, 23 Nov, 21 Dec
Late availability on these dates: 12 Oct, 19 Oct, 02 Nov, 23 Nov, 21 Dec
Cuba kayaking holiday
Rare chance to kayak Western Cuba's waterways
From US $3,390 to US $3,590 8 days ex flights
Small group travel:
2024: 3 Nov, 17 Nov
2025: 19 Jan
2025: 19 Jan
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
01273 823 700
Call us until 6pm
Calling from outside the UK
rosy@responsibletravel.com
Cuba multi activity holiday
Explore Cuba by kayak, bike and on foot
From US $3,690 8 days ex flights
Small group travel:
The group tour departs every Sunday, please enquire to discuss your dates
Antigua to Dominican Republic sailing holiday
Enhance your sailing in azure blue Caribbean Sea
From £2,699 12 days ex flights
Small group travel
Grenada sailing regatta holiday
Unforgettable sailing experience in the enchanting Caribbean
From £1,899 7 days ex flights
Small group travel
Dominica adventure holiday
Action and adventure in the Caribbean's nature island
From US $2,735 to US $2,959 12 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Cuba short break, Havana and Vinales
From the vibrant city to the lush countryside
From US $1,405 5 days ex flights
Small group travel:
2024: 17 Oct, 24 Oct, 31 Oct, 7 Nov, 14 Nov, 21 Nov, 28 Nov, 5 Dec, 12 Dec, 19 Dec, 26 Dec
2025: 2 Jan, 9 Jan, 16 Jan, 23 Jan, 30 Jan, 6 Feb, 13 Feb, 20 Feb, 27 Feb, 6 Mar, 13 Mar, 20 Mar, 27 Mar, 3 Apr, 10 Apr, 17 Apr, 24 Apr, 1 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 16 Oct, 23 Oct, 30 Oct, 6 Nov ...
2025: 2 Jan, 9 Jan, 16 Jan, 23 Jan, 30 Jan, 6 Feb, 13 Feb, 20 Feb, 27 Feb, 6 Mar, 13 Mar, 20 Mar, 27 Mar, 3 Apr, 10 Apr, 17 Apr, 24 Apr, 1 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 16 Oct, 23 Oct, 30 Oct, 6 Nov ...
Highlights of Cuba cycling holiday
Explore Cuba on bicycle from Havana to Trinidad
From £1,699 to £1,799 10 days ex flights
Small group travel:
2024: 8 Nov
2025: 8 Feb, 8 Mar, 5 Apr, 18 Oct, 1 Nov, 20 Dec
2025: 8 Feb, 8 Mar, 5 Apr, 18 Oct, 1 Nov, 20 Dec
Late availability on these dates: 08 Nov
Cuba cycling tour
Cycle from Havana to Varadero through the Yumuri Valley.
From £2,180£1,984 to £2,570 14 days ex flights
Small group travel:
2024: 7 Oct, 21 Oct, 18 Nov, 9 Dec
2025: 6 Jan, 27 Jan, 17 Feb, 10 Mar, 7 Apr, 7 Jul, 6 Oct, 20 Oct, 3 Nov, 17 Nov, 8 Dec, 22 Dec
2026: 5 Jan, 26 Jan, 16 Feb, 9 Mar, 6 Apr, 6 Jul, 5 Oct, 19 Oct, 2 Nov, 16 Nov, 7 Dec, 21 Dec
2025: 6 Jan, 27 Jan, 17 Feb, 10 Mar, 7 Apr, 7 Jul, 6 Oct, 20 Oct, 3 Nov, 17 Nov, 8 Dec, 22 Dec
2026: 5 Jan, 26 Jan, 16 Feb, 9 Mar, 6 Apr, 6 Jul, 5 Oct, 19 Oct, 2 Nov, 16 Nov, 7 Dec, 21 Dec
Up to £240 off selected dates.
Late availability on these dates: 07 Oct, 21 Oct, 18 Nov, 09 Dec
Late availability on these dates: 07 Oct, 21 Oct, 18 Nov, 09 Dec
Exuma Cays kayaking holiday in The Bahamas
Explore Uninhabited Cays in the Islands of The Bahamas
From US $2,495 6 days ex flights
Small group travel:
2025: 27 Feb, 8 Mar, 17 Mar
Cuba on a Shoestring small group holiday
Discover Cuba, from historic Havana to Trinidad
From £860£731 to £965 8 days ex flights
Small group travel:
2024: 12 Oct, 9 Nov, 23 Nov, 7 Dec
Up to £120 off selected dates.
Late availability on these dates: 12 Oct, 09 Nov, 23 Nov, 07 Dec
Late availability on these dates: 12 Oct, 09 Nov, 23 Nov, 07 Dec
18-29 tour in Cuba
Go back in time on the streets of Cuba during this trip
From £530£424 to £580 8 days ex flights
Small group travel:
2024: 22 Oct, 19 Nov, 3 Dec, 24 Dec
Up to £100 off selected dates.
Late availability on these dates: 22 Oct, 19 Nov, 03 Dec, 24 Dec
Late availability on these dates: 22 Oct, 19 Nov, 03 Dec, 24 Dec
Active Cuba holiday
Explore Cuba's natural wonders on an outdoor adventure
From US $1,700 10 days ex flights
Small group travel:
2024: 26 Nov, 10 Dec, 17 Dec
2025: 7 Jan, 11 Feb, 18 Feb, 11 Mar, 25 Mar, 15 Apr, 22 Apr, 20 May, 14 Oct, 4 Nov, 11 Nov, 25 Nov, 9 Dec, 18 Dec
2025: 7 Jan, 11 Feb, 18 Feb, 11 Mar, 25 Mar, 15 Apr, 22 Apr, 20 May, 14 Oct, 4 Nov, 11 Nov, 25 Nov, 9 Dec, 18 Dec
Cuba activity holiday
Multi-activity holiday in Cuba: Cycling, trekking, kayaking!
From £1,399 8 days ex flights
Small group travel:
2024: 4 Oct, 8 Nov, 6 Dec
Caribbean Lionfish hunting in Carriacou, Grenada
Help nature in her fight against invasive lionfish
From US $875 to US $1,750 7 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Divemaster and instructor courses in the Caribbean
Eco-Divemaster course in Carriacou, Grenada.
From US $8,040 8 weeks ex flights
Small group travel
Caribbean coral reef conservation in Carriacou
Marine Conservation in the heart of the Caribbean!
From US $1,750 to US $2,270 14 days ex flights
Tailor made:
This project is available to start between May and September
Eastern Cuba kayaking tour
Kayak and hike in the wake of Christopher Columbus
From US $3,190 8 days ex flights
Small group travel:
This trip departs on Sundays, please enquire to discuss your dates.
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