Caribbean Island Hopping: How to Plan the Perfect Multi-Island Trip

The Caribbean is not one destination — it is over 700 islands, 13 independent nations, and a dozen overseas territories spread across 1,000 miles of the most beautiful ocean on Earth. Each island has its own personality, cuisine, music, and pace of life, which is exactly why island hopping is the best way to experience the region.

But combining islands requires more planning than a single-destination beach trip. Ferry schedules are limited, inter-island flights can be expensive, and choosing the wrong combination can mean wasted travel days and missed connections.

This guide breaks down how to island-hop efficiently, which islands to combine, and what kind of experience each destination delivers.

Understanding the Caribbean Geography

The Caribbean is divided into several island groups, and understanding this geography is essential for planning efficient combinations.

Greater Antilles (Northwest)

Cuba, Jamaica, Hispaniola (Haiti and the Dominican Republic), Puerto Rico. These are the largest islands, best visited as standalone destinations rather than island-hopping stops.

Lesser Antilles (Eastern Arc)

The chain of smaller islands arcing from the US Virgin Islands south to Trinidad. This is the prime island-hopping territory, divided into:

• Leeward Islands (north): US Virgin Islands, British Virgin Islands, St. Kitts and Nevis, Antigua, Guadeloupe
• Windward Islands (south): Dominica, Martinique, St. Lucia, St. Vincent and the Grenadines, Grenada

ABC Islands (Southern)

Aruba, Bonaire, Curacao — off the coast of Venezuela. A distinct group with Dutch colonial heritage and a drier climate than the rest of the Caribbean.

Other Notable Groups

• Bahamas: North of the Caribbean, technically in the Atlantic
• Cayman Islands: South of Cuba
• Turks and Caicos: Southeast of the Bahamas

Comparing Islands by Vibe

Party and Nightlife Islands

Aruba: The most developed ABC island with beach bars, casinos, and an active nightlife scene along Palm Beach's high-rise hotel strip. The island has a guaranteed-sun reputation (outside the hurricane belt) and a party-friendly atmosphere.

St. Maarten/St. Martin: Split between Dutch and French sides, offering beach bars (Maho Beach, where planes land meters overhead), casinos on the Dutch side, and sophisticated dining on the French side. The Heineken Regatta in March is a legendary sailing party.

Barbados: The most socially vibrant island in the Eastern Caribbean. Oistins Fish Fry on Friday nights, the Crop Over festival in August, and a rum culture that permeates everything. Rihanna's home island has a confident, celebratory energy.

Jamaica: Reggae, rum bars, and a music culture that defines the island. Negril's Seven Mile Beach has a laid-back party atmosphere, while Montego Bay is more resort-oriented.

Luxury and Romance Islands

St. Barts: The Caribbean's most glamorous island. Tiny, French, and expensive — designer boutiques, Michelin-quality dining, mega-yachts in Gustavia harbor. Minimum budget: USD 400-600/day for a couple.

Anguilla: Pristine beaches (Shoal Bay is regularly ranked among the world's best), excellent restaurants, and an understated luxury that favors privacy over scene. No cruise ships.

Turks and Caicos: Grace Bay Beach on Providenciales is consistently ranked the world's best beach. Resort-heavy, polished, and ideal for honeymoons.

Mustique: The ultimate private island in the Grenadines. Royal family vacation spot. Only accessible if you rent a villa or know someone.

Nature and Adventure Islands

Dominica: The "Nature Island" of the Caribbean. Volcanic peaks, boiling lakes, hot springs, and rainforest that feels primordial. The Waitukubuli National Trail is the Caribbean's premier long-distance hike (115 miles, 14 segments). Not for beach seekers — the coastline is rugged rather than sandy.

Saba: The smallest special municipality of the Netherlands. A single volcanic peak rising from the sea with no beaches at all — just world-class diving, cloud forest hiking, and a village accessible by a road nicknamed "The Road That Could Not Be Built."

Trinidad and Tobago: Trinidad offers the Caribbean's biggest Carnival and outstanding birdwatching (the Asa Wright Nature Centre). Tobago has quieter beaches and the oldest protected rainforest in the Western Hemisphere.

Bonaire: The undisputed diving capital of the Caribbean. The entire coastline is a marine park. Shore diving is world-class and available 24/7 — simply wade in from the beach with your tank. Flamingos, salt flats, and a laid-back cycling culture round out the appeal.

Culture and History Islands

Cuba: Time-capsule architecture, vintage American cars, Afro-Cuban music, and a complex political history. Havana alone warrants 4-5 days. The most culturally distinct Caribbean experience.

Curacao: Willemstad's colorful UNESCO-listed waterfront, diverse cuisine reflecting Dutch, African, and Latin American influences, and excellent diving. More culturally complex than its ABC neighbors.

Guadeloupe and Martinique: Authentically French — baguettes, patisseries, and Creole-French fusion cuisine. Guadeloupe is shaped like a butterfly, with one wing of beach resorts and another of volcanic rainforest. Martinique offers the ruins of Saint-Pierre, the "Pompeii of the Caribbean," destroyed by a volcanic eruption in 1902.

Puerto Rico: Old San Juan's colonial fortress and cobblestone streets, the bioluminescent bays of Vieques, and El Yunque rainforest. US territory, so no passport needed for Americans.

Budget-Friendly Islands

Dominican Republic: All-inclusive resorts in Punta Cana offer some of the cheapest Caribbean beach holidays. Beyond the resorts, the Samana Peninsula and the colonial Zona Colonial in Santo Domingo offer genuine cultural depth.

Grenada: The "Spice Island" is affordable, authentic, and beautiful. Nutmeg, cocoa, and cinnamon grow everywhere. Grand Anse beach is stunning, and underwater there is a sculpture park. Daily budget: USD 80-150/person.

St. Vincent and the Grenadines: The main island of St. Vincent is affordable and undeveloped, while the Grenadines (Bequia, Mayreau, Tobago Cays) offer stunning sailing without the price tag of the BVI.

How to Get Between Islands

Inter-Island Flights

Regional airlines:

• LIAT (Leeward Islands Air Transport): Historically the main Eastern Caribbean carrier, though service has been unreliable. Check current status before relying on it.
• Caribbean Airlines: Connects Trinidad with several islands
• interCaribbean Airways: Connects Turks and Caicos, Dominican Republic, Jamaica, and several Eastern Caribbean islands
• Cape Air: Connects Puerto Rico with the US and British Virgin Islands
• Winair: Connects St. Maarten with Saba, St. Eustatius, and other nearby islands
• Air Antilles and Air Caraibes: Connect the French islands (Guadeloupe, Martinique, St. Barts, St. Martin)

Tips for inter-island flights:

• Book directly with regional airlines rather than through aggregators
• Flights are often in small prop planes (8-20 seats) — weight limits are strict
• Connections through San Juan (Puerto Rico), St. Maarten, or Barbados are common
• Expect delays and occasional cancellations. Build buffer days into your itinerary.
• One-way flights typically cost USD 80-250 between neighboring islands

Ferry Routes

Ferries are slower but cheaper and often more scenic. Key routes include:

US Virgin Islands and British Virgin Islands:

• St. Thomas to St. John: 20 minutes, frequent daily service (USD 7-14)
• St. Thomas to Tortola (BVI): 45 minutes (USD 30-50)
• St. Thomas to Virgin Gorda (BVI): 90 minutes
• Multiple operators run daily between USVI and BVI

French Antilles:

• Guadeloupe to Dominica: 2-3 hours (Express des Iles)
• Guadeloupe to Martinique: 3.5-4 hours
• Guadeloupe to Les Saintes: 45 minutes (a beautiful day trip)
• Martinique to St. Lucia: 1.5 hours

ABC Islands:

• Curacao to Bonaire: Fast ferry available (check current operator — service has been intermittent)
• Aruba to Curacao: No regular ferry service currently — fly (30 minutes)

Grenadines:

• St. Vincent to Bequia: 1 hour by ferry, multiple daily
• Bequia to Mustique, Canouan, Mayreau, Union Island: Various ferry and mail boat services
• Osprey Lines connects several Grenadines islands

Bahamas:

• Nassau to Harbour Island (Eleuthera): Water taxi from North Eleuthera after a short flight
• Nassau to Exuma: Fast ferry (several hours) or short flight

Sailing

The Caribbean was made for sailing, and chartering a yacht (bareboat or crewed) is the ultimate island-hopping method.

Best sailing grounds:

• British Virgin Islands: The world's most popular sailing destination. Protected waters, short distances between islands, and reliable trade winds.
• Grenadines: More adventurous sailing with longer passages and less crowded anchorages.
• Bahamas Exumas: Island-hopping through the stunning Exuma Cays with swimming pigs, nurse sharks, and deserted beaches.

Costs: Bareboat charter (you captain) starts around USD 3,000-5,000/week for a 38-42 foot catamaran. Crewed charters with captain and cook run USD 10,000-25,000/week for a group.

Recommended 2-Week Itineraries

The Classic USVI + BVI Combination (14 days)

Best for: Beach lovers, snorkelers, beginner sailors

• St. Thomas (2 nights): Arrive, explore Charlotte Amalie, Magens Bay beach
• St. John (3 nights): Ferry over. Virgin Islands National Park covers 60% of the island. Trunk Bay, Cinnamon Bay, and the Reef Bay Trail are highlights.
• Tortola, BVI (2 nights): Cross to the BVI. Cane Garden Bay, Sage Mountain National Park
• Virgin Gorda (3 nights): The Baths — massive granite boulders forming sea-level grottos and pools. One of the Caribbean's most unique beaches.
• Jost Van Dyke (2 nights): Tiny island famous for the Soggy Dollar Bar (birthplace of the Painkiller cocktail) and White Bay beach
• Return to St. Thomas (2 nights): Final beach day and departure

Getting around: Ferries connect all islands. No flights needed.

Budget: USD 150-300/person/day depending on accommodation level.

Lesser Antilles Cultural Explorer (14 days)

Best for: Culture seekers, foodies, nature lovers

• Guadeloupe (3 nights): Split time between Grande-Terre beaches and Basse-Terre volcanic rainforest. Day trip to Les Saintes.
• Dominica (3 nights): Hike to Boiling Lake, soak in hot springs, explore Titou Gorge, snorkel Champagne Beach (volcanic bubbles rise from the sea floor)
• Martinique (3 nights): Visit Saint-Pierre ruins, hike the Route de la Trace through rainforest, explore Fort-de-France, eat extraordinary Creole-French cuisine
• St. Lucia (3 nights): The Pitons, Sulphur Springs, Marigot Bay, snorkeling at Anse Chastanet
• Grenada (2 nights): Grand Anse beach, underwater sculpture park, spice plantation tour, rum distilleries

Getting around: Express des Iles ferry connects Guadeloupe, Dominica, Martinique, and St. Lucia. Fly Grenada. Or fly between all islands via regional carriers.

Budget: USD 100-250/person/day.

ABC Islands Beach and Culture (10-14 days)

Best for: Guaranteed sunshine, diving, cultural variety

• Curacao (4 nights): Willemstad's colorful waterfront, Shete Boka National Park, beach hopping (Cas Abao, Playa Kenepa, Klein Curacao day trip), excellent dining
• Bonaire (4 nights): Shore diving (bring or rent gear), flamingo reserve, Lac Bay windsurfing, cycling around the island, Washington Slagbaai National Park
• Aruba (4 nights): Palm Beach resort area, Arikok National Park, Natural Pool hike, California Lighthouse, nightlife and dining along the hotel strip

Getting around: Fly between Curacao and Aruba (30 min). Curacao to Bonaire by fast ferry or short flight.

Budget: USD 120-280/person/day. Aruba is the most expensive; Bonaire is the most affordable.

Grenadines Sailing Adventure (10-14 days)

Best for: Sailors, snorkelers, off-the-grid seekers

• St. Vincent (1 night): Provision the boat, explore the Botanical Gardens
• Bequia (2 nights): The Grenadines' social hub. Admiralty Bay, Princess Margaret Beach, turtle sanctuary
• Mustique (day stop): Anchor and dinghy to Macaroni Beach
• Tobago Cays (2 nights): Marine park with the Caribbean's best snorkeling. Swim with sea turtles in impossibly clear water.
• Mayreau (1 night): Salt Whistle Bay, one of the Caribbean's most perfect crescents of sand
• Union Island (1 night): Kitesurfing, hiking, local Grenadines culture
• Carriacou (2 nights): Grenada's sister island. Quiet, authentic, excellent diving
• Grenada (2 nights): End the trip with culture, food, and Grand Anse beach

Getting around: Sailing charter or a combination of ferries and small boats.

Budget: USD 200-500/person/day including charter costs split among group.

Best Time for Caribbean Island Hopping

Peak Season (December-April)

• Best weather: dry, sunny, 26-30C
• Trade winds keep humidity manageable
• Highest prices and biggest crowds (especially during Christmas, New Year, and February/March spring break)
• Book accommodation and ferries well in advance

Shoulder Season (May-June, November)

• Excellent value — 20-40% cheaper than peak
• Weather is still good, though rain increases
• Fewer tourists, more authentic local experiences
• Some resorts offer significant discounts

Hurricane Season (July-October)

• The lowest prices but the highest weather risk
• Peak hurricane months are August-October
• The ABC islands (Aruba, Bonaire, Curacao) sit below the hurricane belt and are safe year-round
• Trinidad and Tobago are also largely outside the hurricane zone
• Travel insurance covering hurricane disruption is essential during these months

Practical Tips for Caribbean Island Hopping

Passports and Entry Requirements

• US citizens need a passport for all Caribbean nations except US territories (Puerto Rico, USVI)
• BVI requires a passport even for US citizens
• French islands (Guadeloupe, Martinique, St. Barts, St. Martin) follow EU rules — free entry for EU citizens, visa-free for many nationalities
• ABC islands follow Dutch Caribbean immigration rules
• Cuba requires a tourist visa (tourist card) for most nationalities

Currency

Different islands use different currencies, which adds complexity to multi-island trips.

• US Dollar: USVI, Puerto Rico, BVI (officially), Turks and Caicos, Bonaire
• Euro: Guadeloupe, Martinique, St. Barts, St. Martin (French side)
• Eastern Caribbean Dollar (XCD): Antigua, Dominica, Grenada, St. Kitts, St. Lucia, St. Vincent
• Netherlands Antillean Guilder/Florin: Curacao, Aruba (Aruban Florin), St. Maarten

Tip: US dollars are widely accepted throughout the Caribbean, even where they are not the official currency. ATMs are available on most islands but can be scarce on very small ones.

Packing Tips

• Reef-safe sunscreen (many islands are banning oxybenzone-based sunscreens to protect coral)
• Snorkel gear (bringing your own saves rental fees across multiple islands)
• Quick-dry clothing
• Waterproof bag for electronics during boat transfers
• Light rain jacket
• Insect repellent
• Power adapter (varies by island — US, UK, or European plugs depending on colonial heritage)

Health and Safety

• Mosquito-borne illnesses (dengue, Zika, chikungunya) are present across the Caribbean. Use repellent, especially at dawn and dusk.
• Water safety varies by island. Tap water is safe on most developed islands but not on all. Ask locally.
• Currents can be strong, especially on Atlantic-facing beaches. Swim at beaches with other people present.
• Travel insurance is essential for island-hopping trips. Missed connections, cancelled ferries, and medical evacuations from small islands are all real possibilities.

The Bottom Line

Caribbean island hopping rewards those who plan ahead but remain flexible. The region's beauty lies in its diversity — no two islands feel the same, and the contrast between a morning hiking through Dominica's volcanic rainforest and an afternoon lounging on Anguilla's white sand is what makes a multi-island trip so extraordinary.

Start with a proven combination from the itineraries above, book your inter-island transport early (especially in peak season), and leave room in your schedule for the unexpected — a local festival, a fisherman who offers to take you to a hidden beach, or simply an island you like so much you decide to stay an extra day. Those are the moments that turn a beach vacation into a genuine Caribbean adventure.