This 7-day route covers the essential highlights of the Caribbean at a comfortable pace. It suits first-time visitors who want a balance of cultural sights, natural landscapes and time to eat well. Day 1 — Arrival in Santo Domingo Land in various area and settle into your accommodation. Walk the historic centre in the afternoon, then head out for dinner at a family-run restaurant to try jerk chicken (Jamaica). Ease into local rhythms; jet-lag recovery matters more than sightseeing on day one. Day 2 — Santo Domingo highlights Devote a full day to Old Havana (UNESCO) and the surrounding historic quarter. Include a museum visit and time to sit at a local café. Evening dinner featuring ropa vieja (Cuba). Day 3 — Travel to Havana Morning transfer (2-4 hours by train, bus or rental car). Afternoon exploration of Pitons in Saint Lucia or the Havana old town. Overnight in Havana. Day 4 — Havana day trip Visit Bioluminescent Bay Vieques on a day trip. Rental car offers flexibility; local guided tours are worth the money if you prefer no planning. Return to Havana for dinner. Day 5 — San Juan and coast/nature Morning transfer to San Juan. Depending on the season, spend the afternoon on Dunns River Falls Jamaica. Enjoy the region's specialty dish and take some downtime. Day 6 — Off-the-beaten-track Head to Colonial Zone Santo Domingo for a full day. This is the destination that rewards travellers who venture beyond the obvious. Return late afternoon or move on to your next base. Day 7 — Return and departure Morning shopping in Kingston for souvenirs, olive oil, wines or crafts. Head to your departure airport with time to spare. Reflect on the week with a final meal. Practical notes Currency is varies by island (USD widely accepted). Distances between destinations range from 100 to 400 km — plan accordingly. Best season for this itinerary: December to April for dry season and reliable sunshine. For accommodation at each stop, hotels, restaurants and daily activities, use the verified catalogue at caribbeanforall.net — each listing includes photos, contact details and honest reviews.