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Region
Caribbean
Multi-stop journeys with every stop from a real source and every day checked against a clock.
One journey from each of the six countries with the most here, longest first.
When these journeys are at their best
Most journeys in seasonFebMar11 of 11 journeysFewest journeys in seasonJunJulAugSepOct0 of 11 journeys
What travel in the quieter months is like
Havana to TrinidadMay–Nov
Heat, heavy rain and hurricane-season disruption add to current fuel, power and transport constraints. Keep the itinerary flexible and follow official weather and travel advice.
Roseau & Morne Trois PitonsNov–Jan · Jun–Jul
The route remains conditionally available with a current weather, road and trail check. Rain can make steep volcanic paths, river crossings and narrow roads unsafe, so the certified guide or authorities may require a fallback.
Santo Domingo to the North CoastMay–Jul · Nov
A wetter or storm-season shoulder month needs flexible days plus current INDOMET, COE, road and coastal checks.
Guadeloupe: Grande-Terre & Basse-Terre LoopMay–Jul · Nov
Wetter or storm-season shoulder travel needs flexibility, current Météo-France vigilance and alternatives for mountain, coast and marine activities.
What travel here actually looks like
- Journeys
- 11
- Countries and territories
- 7
- Typical distance
- 225 km
- Typical length
- 4 days
Every journey here
Dec–May
Caribbean Island Hopper: Guadeloupe to Saint Lucia
See the journey→
Nov–Apr
Holguín to Baracoa
See the journey→
Dec–Mar
Havana to Trinidad
See the journey→
Nov–Apr
Havana to Viñales
See the journey→Feb–May
Roseau & Morne Trois Pitons
See the journey→
Dec–Apr
Castries to the Pitons & South Coast
See the journey→Dec–Apr
Guadeloupe: Grande-Terre & Basse-Terre Loop
See the journey→
Dec–Apr
Martinique: Fort-de-France to Le Diamant
See the journey→Dec–Apr
Negril to Ocho Rios
See the journey→
Dec–Apr
Puerto Rico Island Loop
See the journey→Dec–Apr