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.
101 Caribbean vacations found
St Lucia sailing holiday
Unforgettable sailing journey from St. Lucia to Martinique
From US $1,107 5 days ex flights
Small group travel:
2023: 16 Dec
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:
2023: 19 Nov, 26 Nov, 3 Dec, 10 Dec, 17 Dec, 24 Dec, 31 Dec
2024: 7 Jan, 14 Jan, 21 Jan, 28 Jan, 4 Feb, 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
2024: 7 Jan, 14 Jan, 21 Jan, 28 Jan, 4 Feb, 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 $2,400 9 days ex flights
Small group travel:
2023: 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
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Havana dance vacation in Cuba
Immersive salsa course in Cuba's capital city!
From £925 8 days ex flights
Small group travel:
2024: 25 Feb, 17 Nov
Cuba 5 day vacation, footsteps of Hemingway
Havana and Viñales: classic cars, rum and cigars
From US $1,845 to US $2,245 5 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
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 $3,190 to 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 €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
RORC Caribbean 600 sailing vacation
Classic Offshore Caribbean Race
From US $3,077 9 days ex flights
Small group travel:
2024: 16 Feb
Grenada sailing regatta vacation
7 days of fun Caribbean racing!
From US $2,338 7 days ex flights
Small group travel:
2024: 26 Jan
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
St Maarten Regatta sailing vacation
St Maarten Regatta: Exhilarating & Fun!
From US $2,504 6 days ex flights
Small group travel:
2024: 27 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
St Lucia & the Grenadines sailing holiday
The Windward Islands: St Lucia & the Grenadines
From US $3,323 12 days ex flights
Small group travel:
2024: 8 Jan, 22 Jan, 12 Feb
St. Lucia to Grenada, sailing mile builder
Immersive learning experience with plenty of adventure
From US $614 2 days ex flights
Small group travel:
2024: 22 Jan
Grenada to Antigua sailing vacation
Caribbean Short Cruise: Grenada to Antigua
From US $1,878 7 days ex flights
Small group travel:
2024: 5 Feb
Tobago yoga retreat
Vinyasa-style yoga retreat in the Caribbean
From £1,299 to £2,000 8 days ex flights
Small group travel
Dominican Republic authentic tour
Explore the authentic Dominican Republic
From £1,755 8 days ex flights
Small group travel:
2024: 13 Jan, 10 Feb, 16 Mar, 13 Apr, 15 Jun, 13 Jul, 17 Aug
Cuba small group tour with homestays
Authentic Cuba in 10 intensive days
From €1,782 10 days ex flights
Small group travel:
2023: 10 Dec
2024: 17 Jan, 25 Mar, 10 Jun, 15 Jul, 18 Nov
2024: 17 Jan, 25 Mar, 10 Jun, 15 Jul, 18 Nov
Women only tours to Cuba
Meet female entrepreneurs, artists, and change-makers in Cuba
From US $740 8 days ex flights
Small group travel:
2023: 7 Dec
2024: 4 Jan, 15 Feb, 14 Mar, 11 Apr, 2 May, 6 Jun, 4 Jul, 8 Aug, 5 Sep, 10 Oct, 7 Nov, 19 Dec
2024: 4 Jan, 15 Feb, 14 Mar, 11 Apr, 2 May, 6 Jun, 4 Jul, 8 Aug, 5 Sep, 10 Oct, 7 Nov, 19 Dec
Dominican Republic wildlife tour
Specialist rare mammal tour - solenodons, hutias & bats
From £1,995 5 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Dominica adventure vacation
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 birdwatching tour
Birding in Western Cuba's pristine natural parks
From US $1,680 9 days ex flights
Small group travel:
2023: 13 Dec
2024: 10 Jan, 7 Feb, 6 Mar, 3 Apr, 24 Apr, 23 Oct, 13 Nov, 11 Dec
2025: 8 Jan
2024: 10 Jan, 7 Feb, 6 Mar, 3 Apr, 24 Apr, 23 Oct, 13 Nov, 11 Dec
2025: 8 Jan
St Lucia resort accommodation, Anse Chastanet
One of a kind, environmentally conscious Caribbean resort
From US $430 to US $1,595 per accommodation per night
Accommodation
Cycling vacation in Cuba
Explore the highlights of Cuba on two wheels
From US $2,690US $2,490 to US $2,690 15 days ex flights
Small group travel:
2024: 2 Feb, 29 Mar, 25 Oct, 8 Nov
Up to US $200 off selected dates.
Late availability on these dates: 02 Feb
Late availability on these dates: 02 Feb
Havana long weekend in Cuba vacation
Fun weekend exploring beautiful, vibrant Havana!
From US $1,085 to US $1,150 4 days ex flights
Small group travel:
2023: 7 Dec, 28 Dec
2024: 4 Jan, 11 Jan, 18 Jan, 25 Jan, 1 Feb, 8 Feb, 15 Feb, 22 Feb, 29 Feb, 7 Mar, 14 Mar, 21 Mar, 28 Mar, 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 11 Jul, 18 Jul, 25 Jul, 1 Aug, 8 Aug, 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 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
2024: 4 Jan, 11 Jan, 18 Jan, 25 Jan, 1 Feb, 8 Feb, 15 Feb, 22 Feb, 29 Feb, 7 Mar, 14 Mar, 21 Mar, 28 Mar, 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 11 Jul, 18 Jul, 25 Jul, 1 Aug, 8 Aug, 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 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
Cuba vacation, Havana and Vinales
From the vibrant city to the lush countryside
From US $1,400 5 days ex flights
Small group travel:
2023: 7 Dec, 21 Dec, 28 Dec
2024: 4 Jan, 11 Jan, 18 Jan, 25 Jan, 1 Feb, 8 Feb, 15 Feb, 22 Feb, 29 Feb, 7 Mar, 14 Mar, 21 Mar, 28 Mar, 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 11 Jul, 18 Jul, 25 Jul, 1 Aug, 8 Aug, 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 17 Oct, 24 Oct, 31 Oct, 7 Nov, 14 Nov, 21 Nov, 28 Nov, 5 Dec, 12 Dec, 19 Dec, 26 Dec ...
2024: 4 Jan, 11 Jan, 18 Jan, 25 Jan, 1 Feb, 8 Feb, 15 Feb, 22 Feb, 29 Feb, 7 Mar, 14 Mar, 21 Mar, 28 Mar, 4 Apr, 11 Apr, 18 Apr, 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 11 Jul, 18 Jul, 25 Jul, 1 Aug, 8 Aug, 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 17 Oct, 24 Oct, 31 Oct, 7 Nov, 14 Nov, 21 Nov, 28 Nov, 5 Dec, 12 Dec, 19 Dec, 26 Dec ...
