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Caribbean Island Hopping Guide: Sail, Swim, and Discover Paradise

Intro to Caribbean Island Hopping Guide

Start planning your journey with our complete Caribbean Island Hopping Guide — from white-sand escapes and volcanic adventures to hidden gems only reachable by boat or puddle-jumper.

The Caribbean is not just one destination — it’s a kaleidoscope of cultures, landscapes, and lifestyles scattered across turquoise seas. Island hopping here isn’t just a vacation idea; it’s a way to experience vibrant diversity, from French Creole markets and British colonial towns to Dutch dive hubs and Afro-Caribbean rhythms. Whether you’re cruising between calm beaches and coral reefs, flying between rainforest-draped peaks, or hopping ferries through archipelagos, this guide will help you build the perfect Caribbean escape — one unforgettable island at a time.

Explore immersive Caribbean tours and experience unforgettable things to do in the Caribbean — from sailing and scuba to volcano hikes, historic towns, and local rum distilleries.

Continent: North America (Caribbean Region)
Region Type: Geographical + cultural grouping of island nations and territories
Area: ~239,000 km² (collective)
Population: ~44 million (2024 est.)
Density: Varies by island – from ~30 people/km² (St. Kitts) to 1,300+ people/km² (Barbados)
Regional Hubs: San Juan (Puerto Rico), Nassau (Bahamas), Kingston (Jamaica), Bridgetown (Barbados), Port of Spain (Trinidad), Santo Domingo (Dominican Republic)
Language(s): English, Spanish, French, Dutch, Creole languages
Currency: USD, Eastern Caribbean Dollar (XCD), Euro, Peso, Guilder, etc. (varies by country)
Time Zones: Ranges from UTC–5 to UTC–4
Airports: 50+ major international airports across the region (see breakdown below)
Climate: Tropical – hot and humid with distinct dry and wet seasons
Known For: Beaches, coral reefs, music, festivals, rum, water sports, cruise ports, vibrant cultures, colonial history

Visa-free entry for short stays is common between Caribbean countries and for citizens of the U.S., EU, UK, Canada, and Commonwealth nations
Caribbean Community (CARICOM) allows easy travel among member states
Some islands (e.g., Cuba, Haiti) may require additional permits or tourist cards
U.S. citizens must follow entry protocols for non-U.S. territories (e.g., Jamaica, DR)
Always confirm via local immigration websites or Caribbean Travel Requirements

Recommended: Hepatitis A, Typhoid, Tetanus, COVID-19, Mosquito precautions
Dengue, chikungunya, and Zika virus risks present in tropical areas
Yellow fever vaccine required for travelers entering from endemic countries
Public hospitals exist on larger islands; private care recommended for travelers
Travel insurance with evacuation coverage is highly advised — get coverage here
Stay Informed with Official Updates: World Health Organization – International Travel and Health | Centers for Disease Control and Prevention – Global Travel Health

Most islands are Level 1–2 (normal to increased caution)
Petty theft is the most common issue in tourist zones
Hurricane season: June–November — check alerts and plan accordingly
Some islands experience political unrest or protests (e.g., Haiti, Cuba)
Stay Informed with Official Updates: US Travel Advisory | UK Foreign Travel Advice

Carnival: February or March, with major celebrations in Trinidad, Barbados, St. Lucia
Independence Days: Celebrated individually by country (e.g., Jamaica – Aug 6, Bahamas – Jul 10)
Christmas, Easter, and New Year’s Day widely observed
Other regional celebrations: Emancipation Day, Boxing Day, Junkanoo, Holi (in Indo-Caribbean communities)

Multiple currencies used across the Caribbean:
USD (e.g., U.S. territories, Bahamas, Turks & Caicos)
Eastern Caribbean Dollar (XCD) – used in 8 countries
Jamaican Dollar (JMD), Trinidad & Tobago Dollar (TTD), Cuban Peso (CUP/CUC)
ATMs available in cities; cash recommended for small purchases or rural areas
Tipping: 10–15% standard; check if service charge is included
Duty-free limits vary; typically 1 liter alcohol, 200 cigarettes, and personal items per entry

Puerto Rico: SJU (Luis Muñoz Marín International)
Jamaica: MBJ (Montego Bay), KIN (Kingston)
Bahamas: NAS (Nassau), GGT (Exuma), FPO (Freeport)
Dominican Republic: PUJ (Punta Cana), SDQ (Santo Domingo)
Barbados: BGI
Trinidad & Tobago: POS (Port of Spain), TAB (Tobago)
Saint Lucia: UVF (Hewanorra), SLU (George F. L. Charles)
Aruba: AUA | Bonaire: BON | Curaçao: CUR
USVI: STT (St. Thomas), STX (St. Croix)
Martinique: FDF | Guadeloupe: PTP

Taxis, minibuses, and shuttles are common on most islands
Car rentals available but may require left-hand driving (e.g., Barbados, Jamaica)
Ferries and water taxis operate in multi-island nations (e.g., Bahamas, St. Vincent & Grenadines)
Public transit may be unreliable; tours often include round-trip transport
Domestic flights connect larger island groups like the Bahamas, BVI, and French Antilles

Mobile and 4G/5G access varies by island
Major regional carriers: Flow, Digicel, Claro, BTC, LIME
Wi-Fi widely available in hotels, cafes, and airports
eSIM support limited outside of main islands — verify in advance
SIM cards available at airports or local shops with passport

Legal drinking age: 18 (20+ in some territories)
Marijuana laws vary — legal in some (e.g., St. Vincent, Jamaica – decriminalized), illegal in others
LGBTQ+ protections vary — progressive in Dutch/French territories, conservative in others
Dress modestly in towns and sacred sites; beachwear is for the beach
Cultural respect is important; learn greetings and avoid making assumptions

Emergency Numbers:
Most islands use 911 or 112 for police/fire/medical
U.S. embassies and consulates are located in Kingston, Port of Spain, Bridgetown, Santo Domingo, and others
Travel insurance is recommended for all visitors — especially for water sports, hurricanes, and inter-island travel
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Tropical climate year-round:
Dry Season: December–May
Wet/Hurricane Season: June–November
Temps range: 24–31°C (75–88°F) with cooling trade winds
Best time to visit: Mid-December to April for low humidity and festival season
Forecast: Weather Forecast

Caribbean Territories

Anguilla (UK)

Aruba (Netherlands)

Bermuda (UK)

Bonaire, Sint Eustatius & Saba (Netherlands)

British Virgin Islands (UK)

Cayman Islands (UK)

Curacao (Netherlands)

French Guiana (France)

Guadeloupe (France)

Martinique (France)

Montserrat (UK)

Puerto Rico (USA)

Saint Barthelemy (France)

Saint Martin (France)

Sint Maarten (Netherlands)

Turks and Caicos Islands (UK)

US Virgin Islands (USA)

Independent Caribbean Countries

Antigua and Barbuda

Bahamas

Barbados

dominica

Dominican Republic

Grenada

Haiti

Jamaica

St Kitts and Nevis

St Lucia

Trinidad and Tobago

St Vincent and the Grenadines

Caribbean by Region – Where to Go

Greater Antilles
These are the largest and most populous islands, ideal for culture-rich travel, cities, and inland exploration.

Cuba: Classic cars, colonial cities like Havana and Trinidad, vibrant music scenes, and beach resorts.
Jamaica: Waterfalls, reggae culture, Blue Mountains, and world-class all-inclusives.
Hispaniola (Dominican Republic & Haiti): Beaches, history, and a contrast of resort life vs. raw authenticity.
Puerto Rico: U.S. territory with bioluminescent bays, historic San Juan, rainforest hikes, and island hopping to Vieques and Culebra.

Lesser Antilles – Northern Chain
Smaller islands perfect for short-hops, ferries, and boutique getaways.

US Virgin Islands: St. Thomas (duty-free shopping), St. John (national park beaches), St. Croix (heritage and diving).
British Virgin Islands: Ideal for yacht charters — explore Tortola, Virgin Gorda, and the Baths.
Anguilla: Luxe and laid-back, known for powdery beaches and chic villas.
Saint Martin/Sint Maarten: French and Dutch fusion, shopping, nightlife, and bay hopping.
St. Barts: Jet-set luxury, cliffside villas, and French-Caribbean charm.
Antigua & Barbuda: 365 beaches, English Harbour sailing scene, and pink-sand Barbuda.

Lesser Antilles – Southern Chain
Lush volcanoes, rich culture, and quieter gems await here.

Dominica: Hiker’s paradise with boiling lakes, waterfalls, and no mega resorts.
St. Lucia: Iconic Pitons, luxury resorts, Sulphur Springs, and boat tours.
Martinique & Guadeloupe: French islands with Euro-Caribbean flair, rum, and culture.
Grenada: Spice Island with waterfalls, chocolate farms, and quiet beaches.
St. Vincent & the Grenadines: Yacht anchorages, coral cays, and the Tobago Cays marine reserve.

ABC Islands (Leeward Antilles)
Arid and Dutch-influenced, these are great year-round options south of the hurricane belt.

Aruba: Resorts, nightlife, desert dunes, and snorkeling.
Bonaire: World-class shore diving, eco-tourism, and pink salt flats.
Curaçao: Colorful architecture, beach coves, and a thriving art scene.

Top Places to Visit in the Caribbean

Nature & Adventure

Dominica – Rainforests, canyoning, and hot springs
Puerto Rico – El Yunque, caves, and surfing beaches
St. Lucia – Piton hikes and volcanic mud baths
Bonaire – Protected reefs and desert landscapes

Cultural Capitals

Havana, Cuba – Salsa, cigars, and colonial streets
Willemstad, Curaçao – Dutch Caribbean design and street art
San Juan, Puerto Rico – 500 years of history and fortresses
Santo Domingo, Dominican Republic – First city of the Americas

Secluded Escapes

Barbuda – Pink sand and minimal crowds
Bequia – A Grenadine gem with beach bar bliss
Vieques – Horses on the beach and bioluminescent bays
Saba – Tiny island with towering hiking trails

Best for Island Hopping Base

St. Maarten – Fly or ferry to Anguilla, Saba, St. Barts, and Statia
Antigua – Quick hops to Montserrat, Barbuda, and Guadeloupe
Grenada – Sail north to Carriacou, Union Island, and the Grenadines
USVI – Combine with BVI or Puerto Rico easily

How to Choose Your Caribbean Island Hopping Route

Short Island Hops (by Ferry or Boat)

St. Maarten → Anguilla → St. Barts → Saba
USVI → BVI Loop
Guadeloupe → Dominica → Martinique

Fly-In Chains (via regional air)

Grenada → St. Vincent → Bequia → Mustique → Canouan
Puerto Rico → Culebra → Vieques → USVI → BVI
Aruba → Curaçao → Bonaire

Combo by Theme

Adventure & Nature: Dominica, St. Lucia, Puerto Rico
Luxury & Relaxation: Anguilla, St. Barts, Mustique
Culture & Food: Cuba, Guadeloupe, Martinique, Trinidad
Diving & Water Sports: Bonaire, Saba, Roatán, USVI

How to Get Around the Caribbean

Ferries & Water Taxis
Best for close-island travel (esp. around USVI, BVI, Guadeloupe chain, Grenadines, and Dutch/French islands). Be prepared for weather-related changes.

Inter-Island Flights
Caribbean airlines like LIAT, interCaribbean, Silver Airways, and Winair offer regional routes. Book early for peak season.

Yacht Charters & Cruises
Ideal for multi-island trips in the Grenadines, BVI, or French West Indies. Bareboat or crewed options available.

Fly + Ferry Combos
Many start in a flight hub (e.g., San Juan, St. Maarten, Antigua) then hop via ferries to nearby smaller islands.

Travel Budget & Costs in the Caribbean

Average Daily Budgets

Budget: $80–$150 (guesthouses, ferry travel, street food)
Mid-range: $200–$350 (island hotels, tours, short flights)
Luxury: $400+ (resorts, yachts, fine dining)

Sample Inter-Island Transport Costs

Ferry (St. Maarten–Anguilla): ~$20
LIAT flight (Grenada–St. Vincent): ~$100–$180
Water taxi (Union–Tobago Cays): ~$40 round-trip
Yacht day charter: $400–$1,000 (group split)

Tips for Saving

Island-hop shorter distances
Travel in shoulder seasons (May–June, Sept–Nov)
Stay longer in fewer places to cut transport costs

Best Time to Go Caribbean Island Hopping

Dry Season (Dec–April)
Ideal weather, peak prices — book early. Great for sailing and festivals (e.g., Carnival, Junkanoo).

Shoulder Season (May–June, Sept–early Nov)
Fewer crowds, better prices, lush landscapes — light rain likely.

Hurricane Season (June–Nov)
Most active in Aug–Oct. Southern Caribbean (ABC Islands, Trinidad, Grenada) typically avoid direct hits.

Must-See Experiences in the Caribbean

Snorkel the Tobago Cays, a remote reef-strewn paradise
Dive shipwrecks off Bonaire or walls off Saba
Ride horseback on the beach in Vieques
Hike the Boiling Lake in Dominica
Party at Junkanoo in Nassau or Carnival in Trinidad
Sail through the BVI, stopping at Jost Van Dyke and Virgin Gorda’s Baths
Tour Havana in a classic car, then sip mojitos at sunset
Watch turtles hatch under a full moon in Barbados

Book immersive Caribbean tours and experience unforgettable things to do in the Caribbean — from steel pan rhythms and island feasts to volcano climbs and reef explorations.

Sample Caribbean Itineraries

7-Day Easy Hop (Dutch/French Islands)

Day 1–3: St. Maarten (base)
Day 4: Ferry to Anguilla
Day 5–6: Ferry to St. Barts
Day 7: Return via St. Maarten

10-Day Adventure Island Chain (South)

Day 1–3: Grenada
Day 4–5: Carriacou
Day 6–7: Union Island + Tobago Cays
Day 8–10: St. Vincent mainland + waterfalls

14-Day Grand Explorer

Puerto Rico → Culebra + Vieques → USVI → BVI
Combo of culture, beach, rainforest, and sailing

Local Cuisine & Culinary Experiences

Must-Try Flavors

Jerk Chicken & Ackee (Jamaica)
Fungee & Pepperpot (Antigua)
Flying Fish & Cou-Cou (Barbados)
Callaloo Soup (Trinidad/Dominica)
Lionfish Ceviche (Bonaire)
Accras (Guadeloupe/Martinique)

Foodie Experiences

Rum tastings in Barbados, Martinique, Grenada
Street food in San Juan or Port of Spain
Seafood grills on the beach in Bequia or Tobago
Chocolate tours in St. Lucia and Grenada

Taste your way through the Caribbean with plantain stews, rum cocktails, and open-air grills that define the region’s flavor.

Travel Safety & Island Etiquette

Safety Tips
Most islands are safe, but petty theft can occur. Avoid isolated beaches at night and follow local advice in lesser-traveled areas.

Cultural Etiquette

Greetings matter — always say “Good day” or “Hello” before asking questions
Respect island time — things may run a bit slower
Dress modestly in towns (not just swimwear)
Support local businesses, especially in small-island economies

Where to Go Next – Regional Add-Ons

Belize – Reef meets rainforest for diving and Maya ruins
Colombia’s Caribbean coast – Cartagena and the Rosario Islands
Mexico (Yucatán) – Combine with Cozumel or Holbox
Panama – Explore San Blas islands and Caribbean culture in Bocas del Toro

Explore more:

Final Planning Checklist for Caribbean Island Hopping

• Choose 2–4 island bases with ferry or flight access
• Book inter-island transport (LIAT, Winair, ferries) in advance
• Bring waterproof gear, reef-safe sunscreen, and motion sickness remedies
• Confirm passport + entry rules (some islands differ, even nearby ones)
• Download maps, ferry schedules, and travel insurance confirmation
• Budget for hidden costs like exit taxes or baggage fees
• Travel light — ferries and small planes have strict weight limits
• Leave space in your bag for rum, spices, or local crafts

Explore the Caribbean with confidence using our trusted tips, local insights, and region-by-region planning tools.

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