Hawaii or the Caribbean: how do you choose?

Turquoise seas, white-sand beaches, palm trees and fruity drinks – both Hawaii and the Caribbean Islands have all the ingredients for a dreamy, tropical getaway. For travelers in North America looking for island escapes, this is a common travel conundrum – but even if you're coming from further afield, how do you choose?

Decisions, decisions

With 65 major islands in the Caribbean and 6 in Hawaii – not to mention heaps of smaller and private islands – deciding on a spot for your warm-weather escape may seem daunting. We can help! There are many ways to filter the list of possible islands by your interests, budget, time of year, etc. all of which can be found in our free Hawaii or the Caribbean? ebook, but first, you need to decide between the Caribbean and Hawaii.

Practical concerns

Where you’re coming from may be the biggest consideration – the Caribbean is easier for East Coasters to visit, while Hawaii has frequent flights from the West Coast. If you're American and don’t have a passport, Hawaii is the obvious option, though Puerto Rico and the US Virgin Islands are also open to passport-less US citizens.


Resorts offer package deals for both Hawaii and the Caribbean, but the Caribbean will typically put less of a dent in your wallet. Puerto Rico and the Bahamas are especially affordable.


Both Hawaii and the Caribbean have distinct ‘off’ seasons. For the Caribbean, that's the hurricane season, which lasts from June through November. Cheaper prices and thinner crowds are pros; the chance of an actual hurricane blowing away your vacation is the definite con. Things start hopping again with the winter holidays, and go crazy during March and April for American Spring Break. In Hawaii, winter is busy, while spring and fall are more peaceful and still offer gorgeous weather to boot.

How much time do you have?

If you're on the East Coast, a weekend Caribbean jaunt is totally doable – the flight from New York to Nassau, Bahamas is only about three hours, for example. Plenty of companies offer long weekend packages to best take advantage of your limited time. A Hawaiian getaway is a longer commitment – the trip from Los Angeles to Honolulu takes nearly six hours.  So once you're there, you'll want to spend at least four or five days to make it worth the journey.

Your interests

While both regions offer sand, sun and waves, each has its own standout features:


A few Caribbean islands, including Martinique and Guadeloupe, have volcanoes, but nothing compares to the lunar landscapes and flame-spitting peaks of the volcanic Hawaiian islands. Kīlauea, the world's most active volcano, is a pilgrimage in and of itself, as is neighboring Mauna Loa, the world's biggest volcano. See both with a trip to the awe- and terror-inspiring Hawai'i Volcanoes National Park. Truly one for the ‘bucket list.’

Colonial cities

The Caribbean takes the cake here, with the oldest cities in the New World. Amble down the narrow cobblestone streets of Santo Domingo’s Zona Colonial (Dominican Republic), check out 17th century pirate haunts in Nassau, Bahamas, or admire the filigreed balconies and fluted columns of San Juan, Puerto Rico's Spanish mansions. Whether you're sleeping in a monastery-turned-hotel, dining in a former 18th century plantation house, or touring tumbledown Colonial forts overgrown with hibiscus and climbing vines, the past never seems far away.


Please, don't make us pick! The Caribbean has pink sands. Hawaii has black sands. Both have sugar-white sands stretching for miles into an infinity of cyan water. Many Caribbean beaches are family-friendly, with shallow waters and little surf, but Hawaiian waters are better for water sports.


If it's waves you want, Hawaii's tops. The sport, in its modern form, was first popularized here in the early 20th century, and the islands continue to attract the biggest names in surfing from across the globe. It's not uncommon to see Hawaiian kids surfing when they barely look big enough to walk – it's less a sport here than a religion, a way of life.


For sailing, the calmer, shallower waters of the Caribbean make for a smooth ride, and the close proximity of many of the islands make island-hopping a breeze. Most of the upscale resorts in the region offer marinas to dock your mega-yacht. If you're yacht-less, you can always rent – boats are available both with and without captain and crew.


The level topography of most of the Caribbean islands makes hiking a bit...flat. Hawaii presents no such problems. Whether you're picking your way across fields of dried lava or traversing the rim of Waimea Canyon en route to jungle-ringed Waipoo Falls, the islands offer hikes for all levels.


Hawaiian music is great, but the Caribbean offers a vast breadth and depth of danceable beats, from Cuban salsa to Bahamian goombay to Jamaican dancehall, reggae and ska to the calypso of Trinidad and Tobago to the zouk of the French West Indies. You can't walk down the street without hearing the sound of a steel drum or a tinny soca beat coming from a transistor radio, and you can hardly help shaking your hips.