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BEST ISLANDS GUIDE
27 islands, 7 years in the travel industry

Pick the right island, then plan it properly.

Honest, region-by-region island travel guides — Caribbean, Hawaii, and beyond — with real ferry times, real prices, and the bit nobody tells you, whether you're going for two weeks with the kids or four nights on your own.

Find your islandHow we research
Budget-friendlyWith kidsJust the two of youWorth the splurge
A person walking a dusty footpath that curves down toward a quiet turquoise bay, soft mid-morning light

Start with a region

Every guide written after a real visitAll regions →
A curved white sand beach in the Caribbean, palm trees framing clear turquoise water
CaribbeanDozens of islands, wildly different budgets — which one actually fits.1 guide
A traditional Hawaiian hale surrounded by palm trees on the Big Island's lava rock coastline, clear water nearby
HawaiiFour islands, four different trips — pick the right one first.1 guide
An elevated view of Charlotte Amalie harbor, St. Thomas, with anchored boats, hillside homes, and tropical flowers
US Virgin IslandsNo passport, US dollars, some of the best beaches in the Caribbean.1 guide
Santorini's famous blue-domed churches overlooking the volcanic caldera and the Aegean Sea below
Greek IslandsFerry-hop the Cyclades without wasting a day on the wrong island.1 guide
A horse-drawn carriage carrying visitors down Mackinac Island's Main Street, past shops and hanging flower baskets
USA IslandsNo passport needed — Mackinac's no cars, the San Juans' whales, and more.1 guide

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Recently published and updated
A curved white sand beach in the Caribbean, palm trees framing clear turquoise water
Caribbean & BahamasBest Caribbean Islands

Aruba, Turks and Caicos, Puerto Rico or somewhere else — the Caribbean island that's right for you depends on what kind of trip you're actually taking.

Santorini's famous blue-domed churches overlooking the volcanic caldera and the Aegean Sea below
Greek Islands & MediterraneanBest Greek Islands

Santorini gets the postcards, but it's rarely the island that actually fits your trip — here's how to pick between the Cyclades, the Ionian, and the rest.

A traditional Hawaiian hale surrounded by palm trees on the Big Island's lava rock coastline, clear water nearby
HawaiiBest Hawaiian Island to Visit

Oahu, Maui, the Big Island, or Kauai — each Hawaiian island does a genuinely different trip, and picking the wrong one is the most common Hawaii mistake I see.

Four ways in, none of them wrong

Tell us how you travel and we'll point you at the islands that suit it.

On a budgetFerries, guesthouses, market food
Two of youQuiet coves, long dinners
With familyShort transfers, shallow water
Going all outWhere the price is justified