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Signature journey

Caribbean Grand Journey

Fifteen days through three of the Caribbean’s most distinctive countries: the colonial streets of Santo Domingo, Havana on foot and by vintage car, the tobacco valley of Viñales, Trinidad’s music, the beach at Varadero and a slow, open finish on the Riviera Maya. Built around contrast and rhythm rather than a checklist of airports.

  • 15 days
  • 14 nights
  • Small group journey

Journey route

  1. 1Santo DomingoDominican Republic · two nights
  2. 2HavanaCuba · two nights
  3. 3Viñales ValleyPinar del Río · one night
  4. 4TrinidadSancti Spíritus · one night
  5. 5VaraderoMatanzas · one night
  6. 6Cancún / Riviera MayaQuintana Roo, Mexico · seven nights
  • Best time to goNovember to April
  • Group size2 to 12 travellers
  • Activity levelModerate
  • Trip styleCulture · Beaches · Nature
  • CountriesDominican Republic · Cuba · Mexico
  • MealsDaily breakfast and 6 dinners

Trip highlights

  • Santo Domingo’s Zona Colonial, a UNESCO World Heritage site: the cathedral, the Alcázar de Colón and the oldest plazas in the Americas
  • Old Havana on foot, then Vedado and the Malecón from a classic vintage car
  • The mogotes of Viñales Valley and a working tobacco farm
  • Trinidad’s cobbled centre in late-afternoon light, with live music around Plaza Mayor
  • A deliberate change of pace on the white sand of Varadero
  • Seven open days on the Riviera Maya, with Tulum and the cenotes there if you want them

The route on the map

Distances and times are approximate

About 1,228 km by road and 2 flights, 3 h 30 min in the air. The longest drive is Viñales to Trinidad, about 7 h on day 6.

CUBAMEXICODOMINICAN REP.HAITIJAMAICACaribbean SeaGulf of MexicoSanto DomingoNights 1 and 2HavanaNights 3 and 4ViñalesNight 5TrinidadNight 6VaraderoNight 7Cancún · Riviera MayaNights 8 to 14TulumOptional, day 10

Swipe the map to see the whole route.

  • By road
  • Flight
  • Optional, quoted separately
  1. 1Santo Domingo Nights 1 and 2
  2. 2Havana Nights 3 and 4
  3. 3Viñales Night 5
  4. 4Trinidad Night 6
  5. 5Varadero Night 7
  6. 6Cancún · Riviera Maya Nights 8 to 14
  7. +Tulum Optional, day 10
  1. Day1Santo Domingo airport to Zona Colonial hotelArrival transfer≈ 35 minBy road · ≈ 30 km
  2. Day3Santo Domingo to HavanaRegional flight, plus transfers at both ends≈ 2 h 15 minFlight · ≈ 1,420 km
  3. Day3Havana airport to Havana hotelBy the Malecón≈ 30 minBy road · ≈ 18 km
  4. Day5Havana to ViñalesPrivate drive≈ 2 h 45 minBy road · ≈ 180 km
  5. Day6Viñales to TrinidadThe longest drive of the journey, with stops on the way≈ 7 hBy road · ≈ 500 km
  6. Day7Trinidad to VaraderoPrivate drive≈ 4 hBy road · ≈ 270 km
  7. Day8Varadero to Havana airportPrivate transfer≈ 2 h 15 minBy road · ≈ 150 km
  8. Day8Havana to CancúnRegional flight≈ 1 h 15 minFlight · ≈ 510 km
  9. Day8Cancún airport to Riviera Maya hotelArrival transfer; 20 to 60 minutes depending on the hotel≈ 45 minBy road · ≈ 40 km
  10. Day10Riviera Maya to TulumOptionalOptional day out, quoted separately≈ 1 h 45 minBy road · ≈ 130 km
  11. Day15Riviera Maya hotel to Cancún airportDeparture transfer≈ 45 minBy road · ≈ 40 km

What it is like there

Read Sun 11 Oct, 03:00, local time

  • A bright sun in a blue sky
    Sunny
    Santo Domingo24°ClearH 30° · L 23°90%
  • A bright sun in a blue sky
    Sunny
    Havana25°Partly cloudyH 33° · L 25°92%
  • A bright sun in a blue sky
    Sunny
    Viñales24°Partly cloudyH 33° · L 24°99%
  • A bright sun in a blue sky
    Sunny
    Trinidad24°ClearH 33° · L 24°95%
  • A bright sun in a blue sky
    Sunny
    Varadero26°ClearH 32° · L 26°89%
  • A heavy grey overcast sky
    Cloudy
    Cancún26°OvercastH 29° · L 26°89%

Cuba is warm all year: the dry season runs roughly November to April, and the wet, hotter months from May to October bring short heavy showers rather than whole grey days. On the Mexican Caribbean the dry months are December to April; the rain between June and October comes in the afternoon and passes. Beyond 15 days no forecast exists, so a date further out is shown as the average of the same day in past years.

Day-by-day itinerary

    • OvernightSanto Domingo
    • StayColonial-quarter hotel
    • ExperienceWelcome dinner · Evening in the Zona Colonial
    • TransferAirport to hotel
    • MealsDinner