Most Convenient Ways of Travel When Visiting Multiple Islands

Best Methods of Travel to Visit Multiple Islands

Island-hopping sounds like the dream vacation until you have to think about the whole ‘hopping’ part. For most U.S.travelers visiting places like the Caribbean and Hawaii, it almost feels obligatory to visit as many islands as possible. You’ve got to make the most out of what limited vacation time you get, right?

So, the way you organize your transfers between islands becomes a fundamental element of your trip. For most, it’s the sort of thing you trust your travel agent to take care of, but it can be pretty important to know how things work before you depart. In this guide, we’ll break down the most efficient ways to travel between islands, exploring private jets, seaplanes, regional ferries, and more.

Island Hopping in the Caribbean

There are over 7,000 islands in the Caribbean, and while you won’t be stopping off at all of them, there are more than a few that are commonly explored. No two island chains are the same, and while some are tightly grouped (like the U.S. and British Virgin Islands), others are separated by hundreds of miles of open ocean.

Commercial Flights

Several Caribbean airlines operate regional services, including LIAT, Caribbean Airlines, and InterCaribbean Airways. These work best for traveling between major islands, like from Puerto Rico to the Dominican Republic, or Jamaica to Grand Cayman.

Pros:

•       Affordable

•       Multiple flights daily on popular routes

•       Accessible for all travelers

Cons:

•       Delays and cancelations are common

•       You’ll often have to route through a hub (like San Juan or Miami), even if the islands are close together

•       Airport transfers and long check-ins eat into your day

•       Flights to smaller islands may be less frequent

Commercial flights make sense if you’re visiting places like Barbados, St. Lucia, and Antigua in one trip, where each island has a major airport and regular service.

Ferries

While ferries are a staple in places like the Greek Isles or Southeast Asia, they’re surprisingly under used in the Caribbean. However, a few routes are reliable:

●     British and U.S. Virgin Islands: Ferries between St. Thomas, St. John, Tortola, and Virgin Gorda are quick and frequent.

●     St. Martin– Anguilla – St. Barts: Fast catamarans and high-speed ferries make this triangle easily navigable.

Pros:

●     Scenic and affordable

●     No need for airport hassle

Cons:

●     Limited routes

●     Subject to weather disruptions

●     They can be rough for those prone to seasickness

PrivateJet Travel

When it comes to comfort and access, a private jet charter always takes top spot. With a jet, you’ll bypass commercial terminals, land at smaller regional airports, and operate on your own schedule. Jets are especially useful if you're visiting multiple countries or remote islands that aren’t well-connected by commercial routes.

Pros:

•       Direct flights between islands, even obscure ones

•       Tailored schedules that fit your itinerary

•       Room for luggage, family, and leisure gear like golf clubs or scuba equipment

•       Immigration and customs are often handled more quickly

Cons:

•       Expensive—particularly if you're flying solo or as a couple

•       Requires advance planning for availability and permits

•       The destination island must have an airport, or at the very least, an airstrip

Private jet travel is particularly useful in island groups like the Grenadines, Bahamas, and Turks and Caicos, where some islands have airstrips but no commercial service. U.S.-based private charter companies often fly out of Miami, Fort Lauderdale, and San Juan.

Seaplanes and Inter-Island Charters

If a full-sized private jet is too much, seaplanes or small charter aircraft can be a great middle ground. Carriers like Tropic Ocean Airways, Seaborne Airlines, and Cape Air connect smaller islands across the Caribbean with impressive frequency.

Seaplanes are especially popular in the Bahamas, where water landings make reaching boutique resorts or remote cays easy. In the Virgin Islands, small prop planes can hop between St. Thomas, St. Croix, and Tortola in under 30 minutes.

Pros:

•       Access to smaller islands and private resorts

•       Short flight times and scenic views

•       Often more affordable than private jets

Cons:

•       Limited luggage capacity

•       Susceptible to weather delays

•       Not ideal for large groups 

Island Hopping in Hawaii

While the Caribbean can be fragmented and inconsistent when it comes to island travel, Hawaii is a well-oiled machine. All major islands are part of one U.S. state, so border controls and customs checks are less invasive from island to island.

Commercial Flights

The most popular and convenient way to hop between Hawaiian islands is via commercial airlines. Hawaiian Airlines, Southwest Airlines, and Mokulele Airlines operate dozens of daily flights between Oʻahu, Maui, Kauaʻi, and the Big Island.

Pros:

•       Affordable and reliable

•       Multiple departures per day

•       Short flights (20–50 minutes)

Cons:

•       You’ll still go through security lines

•       Luggage restrictions can be tight

•       It can feel repetitive if flying often during your trip

For most travelers, especially families or couples, this is the most practical choice. It’s easy to book and usually only costs $50–$100 per segment.

Private Flights and Seaplanes

If you're traveling with a large group or want to avoid crowds, Hawaii has excellent private air charter options.Companies like Air Maui, Lanai Air, and Makani Kai Air offer chartered plane or helicopter experiences. These are especially useful for accessing Lanai or Molokai, which have more limited flight schedules. Also, if you’re coordinating group travel across islands, it can even be more affordable than a commercial flight on occasion.

Seaplanes, surprisingly, are rare in Hawaii due to airport restrictions, but small charters can land on the quieter airstrips of remote areas.

Pros:

•       Completely custom itineraries

•       Bypass busy airports like Honolulu

•       Excellent for multi-generational families or luxury travelers

Cons:

•       Cost can range from $2,000–$5,000+ per segment

•       Less flexible for last-minute bookings

Ferries

Another underused form of transport between islands is the ferry. At present, there is only one public ferry route in operation in Hawaii: between Maui and Lanai, operated by Expeditions Lanai Ferry. The journey takes about 45 minutes and runs several times per day.

There used to be a ferry between Oʻahuand Maui, but it was shut down due to environmental concerns and legal challenges. So, don’t plan your island-hopping trip around ferry services here.

Prioritize Time Over Price

When you're visiting multiple islands, your biggest enemy is wasted time. Sitting in long ferry lines or routing through distant hubs can burn entire days of your vacation. While private options come at a cost, they often add serious value by giving you back hours to spend at your destination.