Choosing which Caribbean islands to visit can be overwhelming. I have island-hopped across the region over several trips – from the all-inclusive resorts of the Dominican Republic to the quiet luxury of Turks and Caicos, from reggae bars in Jamaica to swimming with stingrays in Grand Cayman. Each island feels like a different country with its own personality, costs, and character. This guide helps you choose which one matches what you are looking for.
The Caribbean has hundreds of islands, each with its own character. Some are developed resort destinations; others remain quiet and relatively untouched. This guide covers the most visited islands and what makes each one different.
When to Visit
Dry season (December-April): Best weather, warmest sea temperatures, and peak prices. Book early.
Shoulder season (May-June, November): Fewer crowds, lower prices, occasional rain.
Hurricane season (June-November): Lowest prices but risk of storms, especially August-October. Many islands still fine to visit, but check forecasts and get travel insurance.
Island Comparison
| Destination | Best For | Budget Level | Vibe |
|---|---|---|---|
| Dominican Republic | All-inclusive value | £ | Resort beaches, Mayan ruins |
| Jamaica | Culture, music, adventure | ££ | Reggae, waterfalls, jerk chicken |
| Bahamas | Luxury, water clarity | £££ | Swimming pigs, blue holes |
| Barbados | Sophisticated escape | £££ | British heritage, good food |
| Cayman Islands | Diving, stingrays | £££ | Upmarket, Seven Mile Beach |
| Turks & Caicos | Pristine beaches | ££££ | Quiet luxury, Grace Bay |
Dominican Republic
The most affordable Caribbean option for UK and US visitors. Most tourists head to Punta Cana for all-inclusive beach resorts, while Santo Domingo has the oldest colonial city in the Americas.
Best for: All-inclusive value, beach holidays, colonial history
Daily budget:
- Budget: $50-80 USD
- Mid-range: $100-200 USD
- Luxury: $400+ USD
Key attractions: Punta Cana beaches, Santo Domingo’s Zona Colonial, whale watching in Samaná (Jan-Mar)
See our Dominican Republic Travel Guide for details.
Jamaica
Birthplace of reggae, with genuine culture beyond the resorts. Montego Bay and Negril have the main tourist beaches. Kingston offers music history and local food.
Best for: Music, culture, adventure, waterfalls
Daily budget:
- Budget: $90-100 USD
- Mid-range: $210-400 USD
- Luxury: $450+ USD
Key attractions: Dunn’s River Falls, Bob Marley Museum in Kingston, Seven Mile Beach in Negril, Rick’s Cafe cliff jumping
Note: Exercise caution outside tourist areas, especially at night.
See our Jamaica Travel Guide for details.
The Bahamas
Over 700 islands with some of the clearest water in the Caribbean. Nassau and Paradise Island have the main resorts. The Out Islands (Exuma, Eleuthera, Andros) are quieter.
Best for: Clear water, swimming pigs, diving, luxury
Daily budget:
- Budget: $150-200 USD
- Mid-range: $250-350 USD
- Luxury: $500+ USD
Key attractions: Swimming pigs at Big Major Cay, Nassau’s pirate history, Andros blue holes, pink sand beaches
Note: More expensive than most Caribbean destinations. Safety concerns in parts of Nassau after dark.
See our Bahamas Travel Guide for details.
Barbados
East Caribbean island with British heritage. The west coast (Platinum Coast) has calm water and upmarket resorts. The east coast has surf. Bridgetown is a UNESCO World Heritage site.
Best for: Sophisticated dining, history, rum, cricket
Daily budget:
- Budget: $150 USD
- Mid-range: $270 USD
- Luxury: $500+ USD
Key attractions: Harrison’s Cave, rum distilleries, Crop Over festival (July-August), Bathsheba surfing beach
Note: More expensive than Dominican Republic or Jamaica.
See our Barbados Travel Guide for details.
Cayman Islands
British territory known for diving and stingrays. Grand Cayman’s Seven Mile Beach is the main tourist area. Excellent restaurants – it’s called the “Culinary Capital of the Caribbean.”
Best for: Diving, stingrays, luxury beach, food
Daily budget:
- Budget: $150-200 USD
- Mid-range: $300-400 USD
- Luxury: $600+ USD
Key attractions: Stingray City sandbar, Seven Mile Beach, diving and snorkelling, Crystal Caves
Visa: No visa for UK/US citizens for stays up to 6 months.
See our Cayman Islands Travel Guide for details.
Turks & Caicos
British territory with some of the Caribbean’s best beaches. Providenciales (Provo) has Grace Bay Beach, consistently rated among the world’s best. Very quiet and upmarket.
Best for: Pristine beaches, luxury, snorkelling, tranquillity
Daily budget:
- Budget: $200 USD
- Mid-range: $400 USD
- Luxury: $800+ USD
Key attractions: Grace Bay Beach, snorkelling the barrier reef, Chalk Sound lagoon, iguana island
Note: No public transport on Providenciales – you’ll need taxis or a rental car.
See our Providenciales Travel Guide for details.
Practical Tips
Currency: Most islands accept US dollars in tourist areas, but local currency often gets better rates.
Flights: Direct flights from the UK to many Caribbean islands (9-10 hours). US East Coast is 3-4 hours.
Safety: Most tourist areas are safe. Exercise normal precautions. Some destinations (Jamaica, parts of Nassau) require more awareness.
Driving: Left-hand side in British territories (Bahamas, Cayman, Turks & Caicos, Barbados, Jamaica). Right-hand side in Dominican Republic.
All-inclusive: Particularly popular in Dominican Republic, Jamaica, and Cancun. Less common in Bahamas and Turks & Caicos.
Frequently Asked Questions
Do I need a visa to visit the Caribbean islands?
Visa requirements vary by island and nationality. UK and US citizens typically receive visa-free entry for 30-90 days to most Caribbean destinations including Jamaica, Bahamas, Barbados, and British territories (Cayman Islands, Turks & Caicos). Dominican Republic requires a tourist card ($10 USD), often included in airfare. Always check specific requirements for your nationality before travel.
What is the best time to visit the Caribbean?
The best time is during the dry season (December to April) when you’ll enjoy warm weather, minimal rain, and calm seas. However, this is also peak season with highest prices and most crowds. Shoulder months (May-June, November) offer good weather with lower prices. Avoid September-October if possible, as these are peak hurricane months.
What currency should I use in the Caribbean?
The US dollar is widely accepted across most Caribbean islands, particularly in tourist areas. Some islands use their own currency (Eastern Caribbean Dollar, Jamaican Dollar, Barbadian Dollar), while British territories like Cayman and Turks & Caicos use their own dollars pegged to USD. Credit cards are accepted at most hotels and restaurants, but carry some cash for smaller establishments and tips.
How much does a Caribbean vacation cost?
Costs vary significantly by island. Budget destinations like Dominican Republic can cost $50-80 USD daily for accommodation and meals at all-inclusive resorts. Mid-range islands like Jamaica and Barbados run $150-300 USD daily. Luxury destinations like Turks & Caicos and Bahamas can exceed $400-800 USD daily. All-inclusive packages often provide the best value, especially in Dominican Republic and Jamaica.
Is the Caribbean safe for tourists?
Most Caribbean tourist areas are safe, but safety levels vary by island and location. Resort areas and tourist beaches generally have good security. Exercise normal precautions: avoid isolated areas at night, don’t display expensive items, and stay aware of your surroundings. Some destinations (parts of Jamaica and Nassau) require extra caution outside tourist zones. British territories and upmarket islands like Turks & Caicos and Barbados have lower crime rates.
Which Caribbean island has the best beaches?
Turks & Caicos’ Grace Bay Beach consistently ranks among the world’s best with pristine white sand and turquoise water. The Bahamas offers exceptionally clear water and pink sand beaches. Barbados has beautiful beaches on both calm Caribbean and dramatic Atlantic coasts. For value combined with excellent beaches, consider Dominican Republic’s Punta Cana or Jamaica’s Negril Seven Mile Beach.
Related Guides
- Dominican Republic
- Jamaica
- The Bahamas
- Barbados
- Cayman Islands
- Providenciales, Turks & Caicos
- Cancun, Mexico
