Caribbean vacations
If you’re looking for white-sand beaches, fringed with palms and ringed by coral cays then, yes, Caribbean vacations 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.
62 Caribbean vacations found
Jamaica highlights tour
Jamaica highlights tour in 12 days
From US $3,200US $2,930 to US $3,360 10 days ex flights
Small group travel:
2024: 14 Feb, 20 Mar, 24 Apr, 2 Oct, 30 Oct, 13 Nov, 27 Nov
2025: 22 Jan, 5 Feb, 19 Feb, 5 Mar, 19 Mar, 9 Apr, 1 Oct, 29 Oct, 12 Nov, 26 Nov
2025: 22 Jan, 5 Feb, 19 Feb, 5 Mar, 19 Mar, 9 Apr, 1 Oct, 29 Oct, 12 Nov, 26 Nov
Up to US $270 off selected dates.
Late availability on these dates: 14 Feb, 20 Mar, 24 Apr
Late availability on these dates: 14 Feb, 20 Mar, 24 Apr
Cuba cultural vacation
Immerse yourself in Cuban culture on this 8 day adventure
From €690 to €1,115 8 days ex flights
Small group travel:
2024: 11 Feb, 18 Feb, 25 Feb, 3 Mar, 10 Mar, 17 Mar, 24 Mar, 31 Mar, 7 Apr, 14 Apr, 21 Apr, 28 Apr, 5 May, 12 May, 19 May, 26 May, 2 Jun, 9 Jun, 16 Jun, 23 Jun, 30 Jun, 7 Jul, 14 Jul, 21 Jul, 28 Jul, 4 Aug, 11 Aug, 18 Aug, 25 Aug, 1 Sep, 8 Sep, 15 Sep, 22 Sep, 29 Sep, 6 Oct, 13 Oct, 20 Oct, 27 Oct, 3 Nov, 10 Nov, 17 Nov, 24 Nov, 1 Dec, 8 Dec, 15 Dec, 22 Dec, 29 Dec
Tobago beach accommodation
17 beautiful accommodations in unique eco resort
From £117 to £390 per accommodation per night
Accommodation
Dominican Republic adventure tour
Explore this wild, rocky, rough, rugged, but beautiful area
From £1,855 8 days ex flights
Small group travel:
2024: 10 Mar, 5 May, 9 Jun, 7 Jul, 4 Aug, 8 Sep, 6 Oct
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Dominica nature and culture vacation
Discover Dominica's Caribbean-island secrets and treasures
From US $2,415 to US $2,615 11 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Walking and sightseeing holiday in Dominica
An easy holiday on the rugged Caribbean island of Dominica
From US $1,600 to US $1,750 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Cuba tour, The Revolutionary Trail
Follow in the footsteps of the revolutionaries
From £2,450 to £2,850 10 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Small group tours to Cuba
Explore off the beaten track locations
From US $1,210US $1,020 to US $1,520 8 days ex flights
Small group travel:
2024: 10 Feb, 17 Feb, 9 Mar, 23 Mar, 27 Apr, 11 May, 25 May, 12 Oct, 19 Oct, 2 Nov, 9 Nov, 23 Nov, 21 Dec
Up to US $200 off selected dates.
Late availability on these dates: 10 Feb, 17 Feb, 09 Mar, 23 Mar, 27 Apr, 11 May
Late availability on these dates: 10 Feb, 17 Feb, 09 Mar, 23 Mar, 27 Apr, 11 May
Cuba cultural tour, 9 days
Fun and legal tour for American travelers
From US $1,750 9 days ex flights
Small group travel:
2024: 11 Feb, 23 Mar, 7 Apr, 21 Apr, 5 May, 19 May, 2 Jun, 14 Jul, 18 Aug, 22 Sep, 13 Oct, 10 Nov, 24 Nov, 8 Dec, 15 Dec, 29 Dec
Cuba small group cycling vacation
Cycle adventure to Cuba's highlights and hidden gems
From US $1,495 9 days ex flights
Small group travel:
2024: 28 Apr, 19 May, 16 Jun, 21 Jul, 18 Aug, 15 Sep, 20 Oct, 3 Nov, 1 Dec, 15 Dec, 29 Dec
2025: 5 Jan, 19 Jan, 2 Feb, 16 Feb, 2 Mar, 16 Mar, 30 Mar, 13 Apr, 27 Apr, 11 May, 8 Jun, 20 Jul, 24 Aug, 21 Sep, 19 Oct, 2 Nov, 16 Nov, 30 Nov, 7 Dec, 21 Dec
2025: 5 Jan, 19 Jan, 2 Feb, 16 Feb, 2 Mar, 16 Mar, 30 Mar, 13 Apr, 27 Apr, 11 May, 8 Jun, 20 Jul, 24 Aug, 21 Sep, 19 Oct, 2 Nov, 16 Nov, 30 Nov, 7 Dec, 21 Dec
Skyline Trail cycling tour in Western Cuba
Cycle the spectacular Skyline Trail through Western Cuba
From £1,299 8 days ex flights
Small group travel:
2024: 11 Feb, 3 Mar, 7 Apr, 5 May, 14 Jul, 20 Oct, 10 Nov, 24 Nov, 8 Dec, 22 Dec
Cuba tailor made vacation, 8 days
Fantastic immersive 8 day trip, highlights and hidden gems
From US $2,250 to US $2,350 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Luxury resort in Saint Lucia
A cornucopia of organic architecture celebrating nature
From US $1,050 to US $3,050 per accommodation per night
Accommodation
Cuba adventure tours
Authentic Cuba using guesthouses and local guides
From US $705 to US $740 8 days ex flights
Small group travel:
Departs every Thursday throughout the year
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
10 day Cuba tour, small group
Group tour exploring the beguiling and captivating Cuba
From €840 to €1,325 10 days ex flights
Small group travel:
2024: 11 Feb, 18 Feb, 25 Feb, 3 Mar, 10 Mar, 17 Mar, 24 Mar, 31 Mar, 7 Apr, 14 Apr, 21 Apr, 28 Apr, 5 May, 12 May, 19 May, 26 May, 2 Jun, 9 Jun, 16 Jun, 23 Jun, 30 Jun, 7 Jul, 14 Jul, 21 Jul, 28 Jul, 4 Aug, 11 Aug, 18 Aug, 25 Aug, 1 Sep, 8 Sep, 15 Sep, 22 Sep, 29 Sep, 6 Oct, 13 Oct, 20 Oct, 27 Oct, 3 Nov, 10 Nov
Cuba small group vacation
Cuba travel, legal, and local!
From US $2,500 9 days ex flights
Small group travel:
2024: 9 Nov, 26 Dec
Walking vacation in Cuba
Cuba off the beaten track: Private guided walking holiday
From £2,725 to £3,125 14 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Havana and Eastern Cuba luxury tour
12 day journey through vibrant Havana & Eastern Cuba
From £6,599 12 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Western Cuba 8 day private tour
Cuba's culture, nature and adventure!
From £3,968 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Western Cuba tailor made vacation, 12 days
Cultural experience with Cuban people and their heritage
From US $1,983 12 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
9 day tour of Western Cuba
Delve into the African-Cuban heritage of Western Cuba
From £5,670 9 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Havana dance vacation in Cuba
Immersive salsa course in Cuba's capital city!
From £975 8 days ex flights
Small group travel:
2024: 26 Oct, 17 Nov
Cuba photography tour
World class photo tour through classic Cuba
From US $3,190 8 days ex flights
Small group travel:
This trip runs on any Sunday with a minimum of 4 people booked on. Please enquire to discuss available dates.
Cuba cycling and culture tour
Explore quintessential Cuba by bike
From US $4,190 8 days ex flights
Small group travel:
This trip departs with a minimum of 4 people every Saturday, please enquire to discuss dates.
National Parks of Cuba walking vacation
Explore a Cuba few visitors get to see
From US $3,390 8 days ex flights
Small group travel:
This group tour can depart on any Sunday, please enquire to discuss your dates.
Cuba kayaking vacation
Rare chance to kayak Western Cuba's waterways
From US $3,390 8 days ex flights
Small group travel:
This group tour departs on Sundays, please enquire to discuss your dates
Cuba multi activity vacation
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
St Lucia to Antigua sailing holiday
A relaxed sailing adventure in the Caribbean
Antigua
From £3,077 to £3,323 12 days ex flights
Small group travel:
2024: 26 Feb, 11 Mar, 1 Apr
Save $1000. Now only $2404 for Feb & Mar sailing
RORC Caribbean 600 sailing vacation
Classic Offshore Caribbean Race
From US $3,077 9 days ex flights
Small group travel:
2024: 16 Feb
Antigua to Dominican Republic sailing vacation
Enhance your sailing in azure blue Caribbean Sea
From US $3,381 12 days ex flights
Small group travel:
2024: 15 Apr
