The first thing to say about a seven-day Caribbean trip is what not to do. The region spans more than 4,000 kilometres from the Bahamas to Trinidad and the islands are separate countries with separate immigration halls, currencies and airlines. Havana to Santo Domingo is a 1,300-kilometre flight over open sea, usually with a connection in Panama City or Miami. Trying to combine two or three countries in a week means spending two of your seven days in airports.
Pick one island, or one tight cluster served by ferries. Below are three routes that genuinely fit into seven days, each with a different character. Distances and transfer times are the real ones.
Route 1 — Cuba: Havana, Vinales and Trinidad
The best route for anyone who wants architecture, music and a sense of somewhere genuinely unlike home. Everything moves by road; the Viazul coach network is cheap and reliable, and a private taxi colectivo costs perhaps three times more and halves the time.
- Days 1-2 — Havana. Arrive at Jose Marti, 25 minutes from the centre. Give Habana Vieja a full day on foot: the four colonial squares, the Malecon at sunset, a paladar dinner. Day two, the Museo de la Revolucion and Vedado, then live son at a neighbourhood venue rather than a hotel lobby.
- Day 3 — Vinales. Three hours west by coach. Limestone mogotes, tobacco drying barns, a horseback ride through the valley. Stay in a casa particular; there are hundreds and the family breakfast is part of the point.
- Day 4 — Vinales to Trinidad. A long transfer, roughly seven hours, usually via Havana. Break it with a taxi colectivo if the budget allows.
- Days 5-6 — Trinidad. The best-preserved colonial town in the Caribbean, cobbled and small enough to walk. Playa Ancon is 12 kilometres away for a beach afternoon. Take the steam train into the Valle de los Ingenios.
- Day 7 — back to Havana (four to five hours) for the flight, or fly out of Santa Clara, 90 minutes away, if the schedule allows.
Budget guide: casas at 25-40 euros a night, meals 8-15 euros, coach fares 10-20 euros a leg. Cash matters — bring euros and expect card payment to be unreliable.
Route 2 — Dominican Republic: Santo Domingo, Samana and Las Terrenas
The route for a first Caribbean trip when you want a genuine city, a proper beach and no ferry logistics. Distances are moderate and the roads are the best in the Greater Antilles.
- Days 1-2 — Santo Domingo. The Zona Colonial is the oldest continuously inhabited European settlement in the Americas, and its cathedral, from 1541, is the oldest in the hemisphere. Two days is right: one for the Zona on foot, one for the Museo de las Casas Reales, the Alcazar de Colon and an evening of merengue on Calle El Conde. Try la bandera — rice, beans, stewed meat — at a comedor rather than a hotel buffet.
- Day 3 — north to Samana. Two and a half to three hours on the Autopista del Nordeste, one of the smoothest drives in the region. Hire a car; buses exist but cost you half a day.
- Days 4-5 — Las Terrenas and El Limon. Long Atlantic-facing beaches, a French-Italian expatriate restaurant scene, and the El Limon waterfall a 40-minute ride inland. If you travel between mid-January and mid-March, book a humpback whale trip out of Samana bay — some 2,000 whales winter there and it is one of the most reliable sightings anywhere.
- Day 6 — Los Haitises National Park. A boat day among mangroves, karst islets and caves with Taino petroglyphs. Leaves from Samana or Sabana de la Mar.
- Day 7 — return. Three hours back to Santo Domingo, or fly out of Samana El Catey, 40 minutes from Las Terrenas, which has direct European connections in season.
Budget guide: mid-range hotels 60-110 euros, a hire car 45-60 euros a day, dinner 15-25 euros. The peso is the working currency; dollars are accepted but at poor rates.
Route 3 — The Grenadines by ferry
The route for sailors, divers and anyone who wants small islands without chartering a yacht. St Vincent and the Grenadines is a single country, so there is no immigration between stops, and the mail boat and ferries do the work.
- Day 1 — arrive St Vincent at Argyle International. Overnight in Kingstown; visit the botanical gardens, founded in 1765 and the oldest in the western hemisphere.
- Days 2-3 — Bequia. One hour by ferry from Kingstown, several sailings daily. Port Elizabeth, the Princess Margaret beach walk, and a boatbuilding tradition still alive in Paget Farm. This is the easiest of the Grenadines to like.
- Days 4-5 — Union Island or Mayreau. Two to three hours further south on the ferry. Union has kitesurfing at Clifton and a hike up Mount Taboi; Mayreau has 300 residents and one of the finest anchorages in the Caribbean at Salt Whistle Bay.
- Day 6 — the Tobago Cays. A day boat from Union to a marine park of five uninhabited islands inside a horseshoe reef. The best snorkelling on this route, with green turtles almost guaranteed.
- Day 7 — back north. Ferry to Kingstown, or a short hop by inter-island plane if you are tight on time.
Budget guide: guesthouses 50-90 euros, ferry legs 10-25 euros, day boats 60-90 euros a head. Check the ferry timetable before fixing anything — sailings drop to a few a week on the southern legs and the schedule is the constraint on this route, not distance.
Choosing between them
Cuba gives the most for the least money and the strongest sense of a place with its own logic, at the cost of patchy connectivity and long road transfers. The Dominican Republic is the easiest to organise and the best mix of city, beach and nature in a single week. The Grenadines are the most beautiful and the most restrictive — everything depends on a boat timetable.
Whichever you take, keep one day unplanned. The Caribbean runs on weather and boat schedules, and a week with no slack in it becomes a week of rearranging.