Best Island Getaways & Island-Hopping Gateways
Most island trips start on the mainland or at a major island hub, so the cheapest way to plan one is to book the long flight to the gateway city and arrange the short island hop separately. These destinations are the gateways that open up the world's best island regions, and each has its own hotel and flight page on Tripile.
Who this collection suits
Best for travelers combining a city stopover with beach or island time. Expect two stages: a long-haul flight into the gateway, then a ferry or short regional flight. Build in a night at the gateway city in each direction so a delay never costs you the island connection.
Island Getaways: destinations to compare
Athens: The gateway to the Greek islands, with ferries and short flights to Santorini, Mykonos and Crete.
Bangkok: The hub for Thailand's islands — Phuket, Krabi and Koh Samui are all short flights away.
Honolulu: Oahu's base for inter-island flights to Maui, Kauai and the Big Island.
Singapore: A spotless stopover city with fast links to Indonesian and Malaysian islands.
Cancun: Ferries to Isla Mujeres and Cozumel plus the whole Riviera Maya coast.
Lisbon: Direct flights to Madeira and the Azores for Atlantic island hiking and coastline.
How to plan and price this trip
Book the long flight and the island hop with a buffer of at least one night in each direction.
Compare hotels at the gateway city for arrival and departure nights — they are usually cheaper than resort rates.
Ferry schedules shrink outside high season; check them before you fix your dates.
Pack light: regional island flights often have stricter baggage limits than the long-haul carrier.
Frequently Asked Questions
What are the best island getaways destinations? Popular picks include Athens, Bangkok, Honolulu, Singapore. Each has its own Tripile page with live flight and hotel prices, so you can compare them for your exact dates.
How do I build a island getaways package on Tripile? Search flights for your dates first, then add a hotel in the same destination and a rental car if you need one. Tripile shows each element's live price and cancellation terms before checkout, so you build the package yourself instead of paying for a fixed bundle.
When is the cheapest time to book a island getaways trip? Shoulder season — the weeks either side of peak — is almost always the best value. Search with flexible dates and compare mid-week departures, which are usually cheaper than weekend ones.
Who are these island getaways ideas best suited to? This collection suits travelers combining a city stopover with beach or island time. Expect two stages: a long-haul flight into the gateway, then a ferry or short regional flight. Build in a night at the gateway city in each direction so a delay never costs you the island connection.