Hawaii Itinerary: The Perfect 2 Weeks

Many vacations happen on the spur of the moment – a weekend jaunt to visit friends or family or a couple of days tacked onto the end of a business trip. But if you’re coming all the way to paradise in the middle of the Pacific Ocean, two weeks in Hawaii is the perfect amount of time to really feel like you’re on a vacation. With two weeks, you’ll have enough time to visit more than one island, perhaps even three if you’re feeling extra ambitious.

Here we will help you to craft your itinerary for your perfect two weeks in Hawaii, no matter what type of traveler you are. Follow the suggestions below, or mix and match elements of each to find the perfect Hawaiian vacation for you.

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Note that each itinerary is split between two islands. While you may be tempted to do more in order to squeeze in another island, be sure to weigh this against the extra time and expense it will eat up during your stay as you will need to allow for airport transfers, security lines, checking in and out of hotels, and ground transport once you arrive. Although some of the islands can be done as a day trip, to make the most of your time here, we would recommend slowing down and tackling one island per week, tops. Save the rest for your next trip, and slow down to island time.

Relax, you’re on vacation!

Two Perfect Weeks in Hawaii: Romance

Maui (10 days)

If you’re looking to getaway with your sweetheart, you’ll enjoy the relaxed pace on the island of Maui. While you’ll probably want to base yourself in Kihei/Wailea (in sunny South Maui) at the beginning of your trip, you will get to see much of the island with a week to explore.

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On your second day, when you’ll be up early due to the time difference, it’s a perfect day to watch the sunrise over Haleakala. Plan a full day to drive the famous, winding Road to Hana, with its miles of sharp curves, beautiful waterfalls and scenic points.

Instead of doing like most day-trippers, stay at least two nights at the beautiful all-inclusive Travaasa Hana Resort (formerly Hotel Hana Maui) in Hana town, where you can connect with nature as well as with each other. You won’t regret it! After your stay in Hana, it’s time to drive back, either the way you came or “the back way” around Haleakala, which will allow you to stop at Tedeschi Vineyards, Maui’s winery, on the way back.

Spend some time in Upcountry Maui and enjoy dinner at Haliimaile General Store or at one of the fine dining options near your next hotel, in Kaanapali or Lahaina on Maui’s West side.

>> Details on Getting from Maui to Lanai

Lanai (4 days)

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For your second stop, slow down even further and visit the secluded island of Lanai. Whether you arrive by ferry or by air, you’ll enjoy getting to know the natural beauty of Lanai. Here you’ll have just a few options for accommodation, but this is a good thing because two are luxurious Four Seasons properties. Most will opt for the Four Seasons Lanai at Manele Bay, with its location on Hulopoe Beach, although the Four Seasons Lodge at Koele is a completely different experience, up at a higher elevation in Lanai City, so you’ll get to snuggle together as the nights get a little chilly.

Lanai’s smaller size means you’ll be able to easily spend your days exploring beautiful beaches like Polihua Beach on the northwestern side of the island or Shipwreck Beach to the north. Other options include playing golf on world-class courses, going for a horseback ride, hiking, snorkeling, or scuba diving. Unwind with an oceanside massage or just relax at the pool.

Two Perfect Weeks in Hawaii: Active

Kauai (5 days)

For the adventurous, Kauai provides some of the islands’ best locations for getting outdoors and staying active. Experienced hikers looking for a challenge will tackle the 22-mile trail on the Na Pali Coast on Kauai’s north shore. Other great hikes include the Waimea Canyon, known as “The Grand Canyon of the Pacific.”

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Ocean activities include kayaking, surfing, body boarding, and land lovers will enjoy ziplines, helicopter tours, horseback riding, ATV Tours and some of the island’s best golf.

The Kauai Marathon takes place over Labor Day weekend in September and features both a Half and Full course that takes advantage of the natural beauty (and hilly terrain) of the southern side of the island, starting and ending in Poipu.

Two Perfect Weeks in Hawaii: Foodie

Oahu (9 days)

Honolulu is a foodie haven, featuring dining options ranging from hole-in-the-wall to five-star. A melting pot of cultures, here you will find a blending of the old and the new – both traditional Hawaiian foods and contemporary cuisine borrowing from every ethnic group that emigrated to the islands over the years.

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Start your foodie adventure in Waikiki, where you’ll have any number of fine dining options within walking distance. Be sure to check out the local food scene by consulting resources like Yelp.com, FoodSpotting.com, and even Twitter. Food trucks have seen a huge swell in popularity in recent years, and a monthly food truck rally is held on the last Friday of each month, allowing you to sample anything from gourmet burgers, fried spam musubis, local-made popsicles, and fanciful desserts.

Since food is more important than accommodation, you may opt to pad your food budget by staying a few blocks from the beach rather than across the street – this decreases hotel room prices dramatically so you can spend it where it really matters!

In between meals, work up an appetite by visiting Pearl Harbor, cruising the North Shore (hello, shrimp trucks and shave ice!), hiking up Diamond Head, or taking a surfing lesson.

>> Details on Getting from Honolulu to Maui

Maui (5 days)

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Maui is a great second stop for a food-lover’s tour of the islands. Upcountry Maui is a treasure trove of farms, a winery, and a dairy! You can take in a tour at Surfing Goat Dairy or a culinary class or luncheon at Alii Kula Lavender. Travel out to Ulupalakua to visit Tedeschi Vineyards, Maui’s Winery, which even makes a wine from pineapples!

In West Maui you can take a tour of coffee orchards or visit local foodie favorite Star Noodle in Lahaina. Mom and pop eateries showcase a blending of local comfort foods – reflecting an ethnic makeup of primarily Japanese, Chinese, Portuguese, Filipino, and Hawaiian cultures which came together as workers on Maui’s sugar plantations swapped foods and cultural practices over the years. Food festivals here include the East Maui Taro Festival in April and the Maui Onion Festival in August.

couple on beach