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Long Weekend in Hawaii…from the East Coast


Hawaii in four days? From the East Coast? Crazy, right?

Maybe not.

With non-stop routes between New York City and Honolulu, a time zone difference that works in East Coasters’ advantage, and airline prices hovering under $500 round-trip to Honolulu, a long weekend in paradise is easier than you think.

Okay, let me bring you up to speed—in my opinion, a trip to Hawaii is always a good idea. To prove my own point, I set out on a quick jaunt from NYC this past December and while my lazing-on-the-beach time was indeed short, I was able to see tons of fantastic Oahu sights in four days without losing any sleep. Here’s how I did it…

Day 1: Welcome to Hawaii


Don’t load up your itinerary too much today—the long flight (11 hrs from NYC, but who’s counting) and time difference, which, depending on the time of year, is five to six hours behind Eastern Time, are sure to wear even the most seasoned travelers down a little.

Instead, enjoy your introduction to the tropical breezes of Hawaii before jetlag sets in. After checking into your Waikiki hotel, hop down to dip your feet in the warm Pacific waters at Waikiki Beach. Walk down the sand to Duke’s, a popular surf-theme beach bar and restaurant, where you can sip a lava flow, grab a bite, and listen to music on the torch-lit patio.

Day 2: Hiking, Snorkeling, and Sailing


The time difference will likely wake you up early—a good thing since today’s a busy day. Try to catch sun rise over iconic Diamond Head from Waikiki Beach, or don your swimsuit for a morning swim.

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Continue with your early start by driving over to Diamond Head to climb to the top of the extinct cinder cone. Entry is $5 per vehicle. The trek to the top is hot and involves a lot of stairs but the views from the summit are worth some huffing and puffing. A round-trip hike will take you about one and a half hours, and is perfectly topped off with a refreshing shave ice from the truck in the parking lot.


From Diamond Head, continue east to Hanauma Bay, Oahu’s premier snorkeling spot. The protected cove is home to a huge variety of marine life, and you’re likely to spot colorful reef dwellers like the state fish, the Humuhumunukunukuapuaa (yep), and endangered sea turtles (don’t touch—there’s a fine for disturbing these creatures). Access to the bay plus parking costs $8.50, and you can rent equipment here as well.

As evening rolls in, a great way to unwind is to hop on one of the many sunset catamaran cruises that ply the waters off Waikiki. Many outfitters such as Na Hoku II ($30) and Maitai Catamaran ($39) leave right from the beach and include free drinks. (Said free drinks cause these cruises to fill up quickly so it’s best to reserve a spot in advance.)

Day 3: An Island Tour


Today you’ll head out of town to take a look at the wilder, more “local” part of the island. Strike out early in your rental car, taking the Pali Highway through the Koolau Mountains.

Be sure to stop at the Pali Lookout ($3 per car), which offers expansive views and a bit of history, as it was the site of a major battle in King Kamehameha’s I quest to conquer Oahu. Once you cross the mountains, travel north along the winding Windward Coast, taking in the rugged beaches and green cliffs as you drive.

As the Windward side rounds into the North Shore, you’ll start seeing (and smelling) shrimp trucks and roadside fruit stands. Stop for a fresh taste of authentic Hawaii.


Oahu’s famous North Shore will soon unfurl in front of you. For surf fanatics, this coast is a mecca of famous breaks; in winter you can beach-hop down the highway to check out famous waves, from Sunset Beach to Pipeline to Waimea Bay. In the summer the water’s much calmer, and many beaches, like Shark’s Cove offer superb snorkeling.

Before heading back to the South Shore for the night, be sure to check out charming Haleiwa town. After a long day at the beach, a shave ice at Matsumoto’s is the perfect treat.

Drive back down H2 through the central plains of Oahu to return to Honolulu for dinner. If you’re hankering for some ethnic food, you can’t beat Chinatown, which not only boasts some great Chinese eateries, but also Vietnamese, Indian, Filipino, and Malaysian restaurants as well as Asian fusion food.

Day 4: Waikiki, Pearl Harbor, or Manoa Valley


Before you bid goodbye to paradise, soak up some final Hawaii fun. You can spend the morning shopping in Waikiki or try a surf lesson on the famous beach. Hikers can head to Manoa Valley for a quick trek to a 150-foot waterfall. (Just beware—the trail can be muddy, so might not be ideal if you’ve checked out of your hotel and plan to go straight to the airport.) If it’s your first trip to Oahu, reserve tickets in advance and pay a visit to Pearl Harbor (entry fees vary by ticket type). It’s near the airport so you can go directly to your flight afterward.

Getting Around Oahu

If you plan to spend your whole trip in Waikiki and Honolulu you can get away without a car, but for this itinerary you’ll want your own set of wheels to explore farther afield. When heading to the airport, keep in mind that traffic around Honolulu is brutal.

Where to Stay

The famous Waikiki resort area is home to most of the island’s lodgings, and you can find something for any budget or travel style. A great central option is the Hyatt Regency Waikiki, perched atop a busy shopping center across the street from the beach. For a more historic option check out the Westin Moana Surfrider, which sits on the sand and has been open since 1901.


What to Eat

From haute Hawaiian cuisine to budget-conscious plate lunch there’s a huge variety of dining options around Waikiki and Honolulu. One lunchtime favorite is Hula Dog, which combines island flavored relishes and sauces with taro buns to make a uniquely Hawaiian hot dog. At dinner, Duke’s and RumFire offer unbeatable beachfront settings, while Uncle Bo’s lures locals with its expansive menu and off-the-resort-strip prices.

Photos courtesy of Jess Moss

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