Caribbean travel: practical tips for picking islands, flights and packing

Want sun, clear water and a stress-free island trip? The Caribbean has thousands of islands, but picking the right few makes all the difference. This guide gives quick, useful advice on when to go, which islands suit your style, how to find cheap flights, and what to pack. Read on and plan smarter, not harder.

First, decide what you want. Beaches and parties? Try Jamaica or the Dominican Republic. Luxury and calm? Think St. Barts or Turks and Caicos. Scuba and reefs? Bonaire and the Cayman Islands are top picks. Want culture and local food? Barbados, Puerto Rico and Trinidad deliver real island life beyond resorts.

When to go and weather

High season runs from mid-December to April. Expect higher prices and busy beaches then. The rainy season is June to November, with the real hurricane risk between August and October. May and late April are sweet spots: decent weather, fewer crowds, and lower prices. For diving, visibility often peaks after the rainy season clears the water.

Budget, flights and island hopping

Want cheaper flights? Fly midweek and check nearby hubs like Miami, San Juan or Panama City for connections. Use fare alerts and be flexible on dates. Low-cost carriers serve some islands, but watch baggage fees—they add up fast. Consider flying into a major island and island-hopping by short local flights or ferries. Ferries are cheaper and can be part of the fun, but check schedules—some run only a few times a day.

Book accommodation early for holiday weeks and festivals. Mix stays: a resort for a few nights and local guesthouses for the rest. That saves money and gives a fuller experience.

Getting around on islands varies. Small islands often rely on taxis and rented scooters. Larger islands offer buses and affordable car rentals. If you rent a car, check insurance and road rules—some islands drive on the left.

Is the Caribbean safe to visit? Most visits are trouble-free. Use common sense: avoid poorly lit areas at night, secure valuables, and use hotel safes. Check travel advice for your specific island before you go. When snorkeling or swimming, heed local warnings—strong currents can surprise you.

Health and paperwork: carry travel insurance that covers medical evacuation. Pack reef-safe sunscreen and a basic first-aid kit. Check passport validity and any visa rules. Some islands require proof of return travel or vaccination records—confirm ahead of time.

Packing tips: lightweight clothes, a light rain jacket, reef shoes, snorkel gear if you prefer your own, and a portable charger. Bring copies of important documents and a small dry bag for beach days. Leave room for local spices, rum, and handmade crafts.

Final quick picks: Bahamas for quick US getaways; Jamaica for music and food; Puerto Rico for culture with no passport for US citizens; Aruba and Curacao for near-guaranteed dry weather; St. Lucia for dramatic scenery. Pick one vibe and build your trip around it.

Ready to book? Compare flights, lock a few must-see spots, and keep extra days free for unplanned island finds. The Caribbean rewards slow travel—plan less, enjoy more.