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“No alien land in all the world has any deep strong charm for me but that one, no other land could so longingly and so beseechingly haunt me, sleeping and waking, through half a lifetime, as that one has done. Other things leave me, but it abides; other things change, but it remains the same. For me the balmy airs are always blowing, its summer seas flashing in the sun; the pulsing of its surfbeat is in my ear; I can see its garlanded crags, its leaping cascades, its plumy palms drowsing by the shore, its remote summits floating like islands above the cloud wrack; I can feel the spirit of its wildland solitudes, I can hear the splash of its brooks; in my nostrils still lives the breath of flowers that perished twenty years ago.”

– Mark Twain, on Hawaii.


Maui is one of the world’s most coveted vacation destinations and there is good reason why! Maui, the second most visited island in the Hawaiian Islands, has beautiful beaches, amazing volcanic mountain vistas, highland ranches, great dining, and entertainment. The reason we love Maui is that it has something for everyone and it is a great getaway during the cold winter months on the mainland.

Why Winter?

Since Maui has near perfect weather all year long, we figured you’d most want a warm, sunny paradise when you’re otherwise shoveling snow and ice in the middle of a dreary winter. Also, whale watching season is at its peak in the winter.


Special events

Winter events in Maui include the PGA Championship, Chinese New Year in Lahaina, the Ocean Arts and Whale Day Festivals, Jaws Surf Break surfing competition, and there are many Christmas-themed events in December, such as the Festival of Lights.


Must do

Snorkel in the submerged bowl of Molokini. Stroll along the streets of Lahaina Town. Take a drive to the highland ranch country for something completely different- ranches and cowboy country. Chill out, hang ten, or learn some new water sports at Ka’anapali Beach.


Must see

See the humpback whales during migratory season on a boat tour. See the sunrise at Haleakala, then bicycle downhill on the way back.  Partake in delicious food while watching Hula dancers perform at a Luau. Watch world-class surfers in Honolua Bay.


Must eat

Maui has a wide variety of dining options, ranging from fast-casual to fine dining, and representing cultures all over the world. The Maui specialties you should not miss are: Maui Onions (like a sweet Vidalia onion in a Maui onion soup, or raw!), a Hawaiian plate lunch of rice, macaroni salad, and fish/meat with gravy, purple Molokai sweet potatoes, tuna poke, spam sushi, and shave ice.


Must shop

There will be plenty of opportunities to get cheesy souvenirs while in Maui, but our favorite Hawaiian goods to shop for are: swim cover-ups (pareau), Hawaiian shirts (of course!), Kona coffee, Hawaiian sea salts, jewelry made from natural materials (fresh water pearls, Tahitian pearls, shells), macadamia nuts, and for the music lover and/or hipster in our lives, we love Hawaiian ukuleles.

Must stay

Maui has a wide variety of accommodations to match each budget level. Some of our favorites are the Grand Wailea for a family-friendly, luxury experience, the Travaasa Hana for a boutique hotel experience, and the Ka’anapali Beach Hotel for that “Aloha Spirit” and friendly staff.

Weather report

Maui has several microclimates, so temperatures may vary. (*Note – bring very warm clothes for any trip to Haleakala). In general, though, January and February temps are highs of 71°F/ 70°F and lows of 55°, respectively. We said near-perfect weather, right?!


Money matters

Maui is not a cheap destination for vacation. However, a vacation can be planned there on most price points (after airfare from the mainland, of course). In general, the cost of food and lodging is higher than most places in the United States. We typically work with four and five-star hotels in order to ensure our clients get the best service while traveling – expect to pay $400-700/ night for our recommended hotels in Maui.



Did you know that it is considered bad luck by locals to remove stones or sand from Hawaii? Some believe doing this encourages the wrath of volcanic goddess, Pele, to whom the sand and stones belong. As such, Hawaii visitor bureaus receive stones and sand in the mail from visitors citing bad luck as the reason! (Also, it’s just not a good idea to take sand and stones for ecological reasons!)


Getting around

Maui’s geography can make it difficult to navigate. If you plan to visit more than one part of the island, consider renting a car or hiring a tour to do so. Cabs are generally cost prohibitive.


Getting there

Unless you take a one-way cruise here, you’re going to have to fly. The main Maui airport is Kahului.


How long do I need?

Considering the cost and time it takes to fly there, we wouldn’t visit for less than four nights. To experience a nice combination of relaxation, site-seeing, and active pursuits, we recommend giving yourself at least one week.

Kiddos like…

Other than whale watching, surfing/ snorkeling, and attending a luau, kids will love the Maui Ocean Center, zip-lining, playing at the pool, and lots of Dole Whips and shave ice!

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