The Island Hopper’s Guide to Cheap Flights

Remote islands are expensive to reach. It’s the “Paradise Tax.” Limited runways, monopoly airlines, and long distances usually mean high fares. Flying to Tahiti or St. Helena can cost more than the accommodation.

But in 2026, flight hacking tools are smarter than ever. You can cut costs by 50% if you know how to search. Here is the playbook.

1. The “Greek Island Trick” (Positioning Flights)

Don’t search for “New York to Naxos.”

  • The Problem: The search engine tries to book you on one ticket (e.g., Delta -> Air France -> Sky Express). This protects your connection but costs a fortune.
  • The Hack: Book “New York to Athens” (Major Hub). Then separately book “Athens to Naxos” (Local Hop).
  • The Saving: Often $300-$500.
  • The Risk: If the first flight is late, you miss the second. Leave a 4-hour buffer or spend a night in Athens.

If you just want an island but don’t care which one.

  • Tool: Skyscanner or Google Flights.
  • Method: Set destination to “Everywhere” or region “Caribbean.” Select “Whole Month.”
  • Result: You might find that flying to Martinique is $400 cheaper than Barbados this month. Go there instead.

3. The “Hidden City” (Skiplagging)

  • Concept: A flight from A -> B -> C is sometimes cheaper than A -> B. You get off at B.
  • Example: You want to go to Charlotte (Hub). A flight NY -> Charlotte might be $300. A flight NY -> Charlotte -> Miami might be $200. You book the Miami flight and walk away in Charlotte.
  • Rules: NEVER check a bag (it will go to Miami). Do not use your frequent flyer number (airlines hate this). Use Skiplagged.com to find them.

4. Island Hopping Passes

  • Hawaii: Hawaiian Airlines often has inter-island passes.
  • Azores: SATA Azores Airlines offers a free stopover program. If you fly from Boston to Lisbon via Ponta Delgada, you can stay in the Azores for up to 7 days for no extra airfare.
  • French Polynesia: The Air Tahiti Pass creates a flat rate to visit multiple islands (Bora Bora, Raiatea, Maupiti). It is the only affordable way to do it.

5. Points and Miles (The Holy Grail)

Islands are the best use of points because cash prices are high.

  • Sweet Spot: British Airways Avios for short-haul flights.
    • Example: Miami to Grand Cayman or Bahamas on American Airlines (partners) can cost very few Avios despite high cash prices.
  • United Excursionist Perk: Allows a free one-way segment within a region. Great for island hopping in Micronesia or the Caribbean.

6. The “Reverse Season”

Flight prices follow school holidays.

  • The Hack: Go when others don’t. The Caribbean in May/June is perfect weather but half the price of Christmas. The Mediterranean in October is warm but cheap.

7. Monitor Price Drops

Don’t book and pray.

  • Tool: Google Flights “Track Prices.” Set it 6 months out.
  • Tool: Going (formerly Scott’s Cheap Flights). Sign up for alerts. They find “mistake fares” (e.g., US to Fiji for $600).

8. Local Airlines aren’t always on Google

  • The Issue: Tiny island hoppers (like in the Philippines or Indonesia) might not appear on Google Flights.
  • The Fix: Look at Wikipedia for the island’s airport to see which airlines fly there. Then go directly to the airline’s website (e.g., Air Juan or Wings Air).

9. Use the “Hub and Spoke” Model

  • The Concept: Fly to the cheapest major airport in the region, then use a budget airline.
  • Asia: Fly to Singapore or Bangkok. From there, AirAsia or Scoot can get you to Bali, Phuket, or Langkawi for $50.
  • Caribbean: Fly to Miami or San Juan (Puerto Rico). From San Juan, regional props fly to Tortola, St. Barths, or Anguilla.

10. The 24-Hour Rule

If you book a flight to/from the US, you legally have 24 hours to cancel for a full refund (if booked >7 days in advance).

  • The Hack: If you see a great fare but aren’t sure, BOOK IT. Think about it for 23 hours. If you can’t go, cancel. If you wait, the fare will be gone.

11. Be Ready to Move

The best deals happen fast.

  • Have the money ready: Keep a “Travel Fund” savings account.
  • Have the passport ready: Check your expiry date. Many islands require 6 months validity.

Getting to paradise shouldn’t require a second mortgage. With a little creativity, the island life is closer than you think.