Historically, Hawai‘i has been a popular port of call for whalers and military vessels. Prior to Western contact, Hawai‘i was colonized by some of the greatest seafarers the world has ever seen: Polynesian wayfinders who traversed the Pacific in double hull outrigger sailing canoes.

Today, air travel has all but replaced sea travel in Hawai‘i. Outside of Honolulu, the state’s busy capitol, you won’t find many bustling marinas competing for your business. In fact, you’re lucky to even find a marina on the less populous islands, such as Lana‘i, where refueling requires a trek up the hill. But a little inconvenience shouldn’t dissuade you from exploring this untrammeled locale. From big city lights to unspoiled wilderness, each Hawaiian island offers its own magic to the intrepid visitor.

If you’re sailing from the west coast of North America, the Island of Hawaii (or the Big Isle, as it’s called locally) is the first you will encounter. Two impressive peaks, Mauna Kea and Mauna Loa, tower above the clouds on the horizon. While most people associate Hawai‘i with palms and balmy weather, these high elevation mountains are often capped with snow. From the summit to the shoreline, Hawai‘i boasts of seven major climate zones and countless microclimates. At sea level, the temperature is a tropical 85 degrees year round. Venture inland and you’ll find everything from wine and coffee growing regions to subalpine shrubland.

The Big Isle is the youngest in the chain. In fact, it’s still being born. Pele, the volcano goddess, is busy adding more landscape daily at Kiluaea, the active volcano on the island’s east side. Keep a safe distance in your vessel, and you can watch lava spilling into the sea. Truly an impressive sight to behold! Hawai‘i’s largest island has few sandy beaches, though many have dramatic black sand.

The next island over, Maui, is slightly more cosmopolitan and has twice as many posh resorts and restaurants. Provisioning in Lahaina on Maui is probably as easy as on 'Oahu.Still, the Valley Isle, as it’s called, is mainly rural. Waving green sugar cane covers the central isthmus and rows of pineapple criss-cross the west side. You’re best off tying up in Lahaina, once the rowdy haunt of whalers. You can easily cruise Front Street’s bars and shops on foot, though you’ll want to rent a car to explore the island’s golden sand beaches, waterfalls, and hiking trails. If you’d like to attend a traditional Hawaiian luau (and you should), do so here. The award-winning performers at Old Lahaina Luau put on a terrific, authentic show, complete with hula dancing, chanting, and a huge feast. Book your tickets well in advance, since it sells out regularly. (www.oldlahainaluau.com)

Time seems to have stood still on the Islands of Moloka‘i and Lana‘i. Home to small communities (populations 8,000 and 2,800, respectively), these islands offer a taste of what island life was like before the advent of jet travel. Neither island has a stoplight.
With two Four Seasons resorts to chose from, Lana‘i has become the secluded playground of celebrities and newlyweds. The small boat harbor is adjacent to Holupoe Bay, a marine preserve frequented by Hawaiian spinner dolphins, famous for their ballerina-like leaps from the water. Nearby is majestic Cathedrals, one of the state’s top dive sites.

Moloka‘i remains truly Hawaiian—no resorts or restaurants to speak of. Many of its residents are subsistence fishers and farmers. But this is no reason to pass Moloka‘i by! Some of the friendliest people and most dramatic landscape can be experienced here. At the very least, you’ll want to tour the world’s tallest sea cliffs on the island’s wild windward side.

‘Oahu is Hawai‘i’s hub of action, with just under one million residents. Glitzy resorts front Waikiki beach, the birthplace of surfing, where longboarders catch rides from dawn to dusk, just as their Hawaiian predecessors did centuries ago. At the luxurious, three-story Ala Moana Shopping Center and Kalakaua Avenue boutiques, shoppers can find everything from pineapple oven mitts to diamond-crusted bikinis. Foodies should avail themselves of Honolulu’s numerous five-star restaurants and the best sushi outside of Japan. Visiting history buffs will want to tour the Arizona Memorial, dedicated to the lives lost during the WWII attack on Pearl Harbor.

Honolulu’s Ala Wai harbor is all about location. From the docks, it’s a 3-minute stroll to shopping at Ala Moana and surfing at Waikiki. Still, savvy yachts favor the full-service slips at Ko Olina, the private marina west of Honolulu, over the public docks. It remains one of the only places able to handle vessels up to 200’ in length with water depths to 15’ at low tide. For more information visit www.koolinamarina.com/. You’ll find plenty of amenities at Ko Olina. The adjacent resort offers a spa and several restaurants, including Roy’s—a fine example Hawai‘i Regional Cuisine.

Honolulu, the state capitol on 'Oahu is your best--perhaps only--bet for provisions and hardware. Grocery stores and farmer's markets are easily accessible from Ala Wai harbor and Ko 'Olina Marina. The personal concierge company on Maui is Concierge Connection: www.mauiconcierge.com/vacation. Their employees provision for $35/hour and 15% gratuity added to the grocery bill. In addition, they provide normal concierge services (booking restaurants, activities, etc.) free of charge. Should you need spare parts, West Marine on Sand Island is a quick taxi ride away from Ala Wai harbor, but a 45-minute drive from Ko 'Olina. (Ko 'Olina does have resident mechanics on hand to lend assistance.) On Maui and the Big Isle you will find numerous groceries and farmer's markets, but limited marine supplies.

‘Oahu has an easy-going, rural side, too. Public transit—affectionately known as The Bus—can deliver you from Waikiki to sleepy Haleiwa for just two dollars. ‘Oahu’s north shore isn’t always sleepy, however. In winter, it’s the home of the world-famous Triple Crown of Surfing, a big wave surfing tournament that takes place during December’s biggest swells.

Kauai, at the northwestern tip of the chain, is the oldest of the main islands. Eons of rain have chiseled once-tall volcanic mountains into lush green cliffs overflowing with waterfalls. Those who like to tick off birding and wildlife checklists will find ample opportunity here. The majority of Hawai‘i’s plants and birds exist nowhere else on earth. It’s well worth a hike into the forest to view the Hawaiian honeycreepers’ colorful plumage and long, curved bills—though make sure to take a guide (human or paperback will suffice) since the birds can be difficult to spot and identify.

Thanks to Hawaii’s isolation, twenty percent of reef fish in the Islands are endemic. (For an awesome marine identification guide, check out: www.marinelifephotography.com.) Deeper waters abound with megafauna. The rare Hawaiian monk seal can be glimpsed on occasion and green sea turtles are abundant. Humpback whales, spinner dolphins and manta rays are favorites with boaters and divers. Big game fishers can try their luck in thrilling sporting events, such as the Maui Jim tournament series held each summer. Marlins topping 800 pounds can be seen hanging from the scale at Honokohou harbor in Kona, on the Island of Hawai‘i.

Before cruising around Hawaiian waters, it pays to study your NOAA navigation chart for prohibited areas to avoid. The entire island of Kaho‘olawe is restricted, due to unexploded ordinance in the water and on land. Stray too far west of the entrance to Pearl Harbor and you’ll be dodging bullets and accruing hefty fines. The U.S. military operates a rifle range onshore and boating traffic has been diverted for safety’s sake. Also be on the lookout for state-managed Natural Area Reserves, or NARs. These pristine environments are typically open to visitors, but carry special restrictions on fishing and commercial activity.

For more information, contact the U.S. Coast Guard at 808-541-2477 or the DOBOR office at 808-587-1963. Free maps are available at the DOBOR office at 333 Queen Street, Suite 300 in downtown Honolulu.

Photos by Shannon Wianecki, except for Hula Girl courtesy of Old Lahaina Luau