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.
60 Caribbean vacations found
Cuba salsa dance holiday
Learn to salsa in Santiago de Cuba
From £1,875 to £1,975 15 days ex flights
Small group travel:
2024: 28 Apr, 30 Jun, 24 Nov, 15 Dec
2025: 12 Jan, 10 Mar
2025: 12 Jan, 10 Mar
Jamaica highlights tour
Jamaica highlights tour in 12 days
From US $3,200US $3,000 to US $3,360 10 days ex flights
Small group travel:
2024: 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 upcoming trips
Late availability on upcoming trips
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: 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
2025: 5 Jan, 12 Jan, 19 Jan, 26 Jan, 2 Feb, 9 Feb, 16 Feb, 23 Feb, 2 Mar, 9 Mar, 16 Mar, 23 Mar, 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr
2025: 5 Jan, 12 Jan, 19 Jan, 26 Jan, 2 Feb, 9 Feb, 16 Feb, 23 Feb, 2 Mar, 9 Mar, 16 Mar, 23 Mar, 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr
Dominican Republic adventure tour
Explore this wild, rocky, rough, rugged, but beautiful area
From £1,855 8 days ex flights
Small group travel:
2024: 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 vacation
Indulge on this adventure holiday in the Caribbean
From US $3,595 8 days ex flights
Small group travel
vacations to Cuba
A comprehensive and intriguing tour
From US $2,290US $2,080 to US $2,550 15 days ex flights
Small group travel:
2024: 5 Oct, 19 Oct, 26 Oct, 9 Nov, 16 Nov, 21 Dec
2025: 11 Jan, 25 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, 25 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 US $340 off selected dates.
Late availability on upcoming trips
Late availability on upcoming trips
Small group tours to Cuba
Explore off the beaten track locations
From US $1,340 to US $1,610 8 days ex flights
Small group travel:
2024: 12 Oct, 19 Oct, 2 Nov, 9 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
Cuba cultural tour, 9 days
Fun and legal tour for American travelers
From US $1,750 9 days ex flights
Small group travel:
2024: 5 May, 19 May, 2 Jun, 14 Jul, 18 Aug, 22 Sep, 13 Oct, 10 Nov, 24 Nov, 8 Dec, 15 Dec, 29 Dec
2025: 5 Jan, 19 Jan, 26 Jan, 2 Feb, 16 Feb, 23 Feb, 9 Mar, 16 Mar, 30 Mar, 13 Apr, 20 Apr, 27 Apr, 11 May, 25 May, 8 Jun, 22 Jun, 13 Jul, 27 Jul, 10 Aug, 24 Aug, 7 Sep, 21 Sep, 19 Oct, 26 Oct, 9 Nov, 16 Nov, 23 Nov, 7 Dec, 21 Dec, 28 Dec
2025: 5 Jan, 19 Jan, 26 Jan, 2 Feb, 16 Feb, 23 Feb, 9 Mar, 16 Mar, 30 Mar, 13 Apr, 20 Apr, 27 Apr, 11 May, 25 May, 8 Jun, 22 Jun, 13 Jul, 27 Jul, 10 Aug, 24 Aug, 7 Sep, 21 Sep, 19 Oct, 26 Oct, 9 Nov, 16 Nov, 23 Nov, 7 Dec, 21 Dec, 28 Dec
Small group tour to Cuba
Discover the fascinating diversity of Cuba
From US $1,970 20 days ex flights
Small group travel:
2024: 14 Jun, 12 Jul, 23 Aug, 6 Sep, 4 Oct, 1 Nov, 15 Nov, 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 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
Eastern Cuba biking vacation
Cycle Eastern Cuba and experience the serene Yumuri Valley.
From US $1,665US $1,498 to US $1,890 8 days ex flights
Small group travel:
2024: 16 Jun, 13 Oct, 27 Oct, 10 Nov, 24 Nov, 15 Dec, 29 Dec
2025: 12 Jan, 2 Feb, 23 Feb, 16 Mar, 13 Apr, 13 Jul, 12 Oct, 26 Oct, 9 Nov, 23 Nov, 14 Dec, 28 Dec
2025: 12 Jan, 2 Feb, 23 Feb, 16 Mar, 13 Apr, 13 Jul, 12 Oct, 26 Oct, 9 Nov, 23 Nov, 14 Dec, 28 Dec
Up to US $160 off selected dates.
Late availability on these dates: 16 Jun
Late availability on these dates: 16 Jun
Cuba cultural vacations, 15 days
Fun and legal way to experience Cuba's diversity
From US $2,525 15 days ex flights
Small group travel:
2024: 1 Jul, 12 Aug, 9 Sep, 2 Oct, 18 Nov, 9 Dec, 23 Dec
2025: 13 Jan, 10 Feb, 10 Mar, 14 Apr, 12 May, 16 Jun, 14 Jul, 11 Aug, 15 Sep, 20 Oct, 24 Nov, 22 Dec
2025: 13 Jan, 10 Feb, 10 Mar, 14 Apr, 12 May, 16 Jun, 14 Jul, 11 Aug, 15 Sep, 20 Oct, 24 Nov, 22 Dec
Cuba holiday, West to East
Cuba travel 24 days from West to East, best places
From US $2,829 to US $3,662 24 days ex flights
Small group travel:
2024: 20 Nov
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
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
Biking vacation in Cuba, 7 days
Explore Cuba on two wheels in one week
From US $1,355US $1,287 to US $1,660 7 days ex flights
Small group travel:
2024: 1 Jul, 7 Oct, 21 Oct, 4 Nov, 18 Nov, 9 Dec, 23 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
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
Up to US $140 off selected dates.
Late availability on these dates: 01 Jul
Late availability on these dates: 01 Jul
St Lucia sailing holiday
Unforgettable sailing journey from St. Lucia to Martinique
From US $1,107 5 days ex flights
Small group travel
Highlights of Cuba cycling vacation
Explore Cuba on bicycle from Havana to Trinidad
From US $2,290US $2,080 to US $2,420 10 days ex flights
Small group travel:
2024: 25 Oct, 1 Nov, 8 Nov, 20 Dec
2025: 18 Jan, 8 Feb, 8 Mar, 5 Apr, 18 Oct, 1 Nov, 20 Dec
2025: 18 Jan, 8 Feb, 8 Mar, 5 Apr, 18 Oct, 1 Nov, 20 Dec
Up to US $210 off selected dates.
Late availability on upcoming trips
Late availability on upcoming trips
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: 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
2025: 5 Jan, 12 Jan, 19 Jan, 26 Jan, 2 Feb, 9 Feb, 16 Feb, 23 Feb, 2 Mar, 9 Mar, 16 Mar, 23 Mar, 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr
2025: 5 Jan, 12 Jan, 19 Jan, 26 Jan, 2 Feb, 9 Feb, 16 Feb, 23 Feb, 2 Mar, 9 Mar, 16 Mar, 23 Mar, 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr
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
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 £3,323 12 days ex flights
Small group travel
RORC Caribbean 600 sailing vacation
Classic Offshore Caribbean Race
From US $3,077 9 days ex flights
Small group travel
St Maarten Regatta sailing vacation
St Maarten Regatta: Exhilarating & Fun!
From US $2,504 6 days ex flights
Small group travel
Grenada sailing regatta vacation
7 days of fun Caribbean racing!
From US $2,338 7 days ex flights
Small group travel
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
St Lucia & the Grenadines sailing holiday
The Windward Islands: St Lucia & the Grenadines
From US $3,323 12 days ex flights
Small group travel
St. Lucia to Grenada, sailing mile builder
Immersive learning experience with plenty of adventure
From US $614 2 days ex flights
Small group travel
Grenada to Antigua sailing vacation
Caribbean Short Cruise: Grenada to Antigua
From US $1,878 7 days ex flights
Small group travel
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