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North Shore One Day Itinerary

Oahu’s North Shore is known for surfing and a thrill as much for the surfer as the spectator. Waimea Bay’s sparkling waters and dynamic waves heighten the adventure that awaits, in any form, shopping, seaside dining or sightseeing.

Start the day with a sunset hike along Waimea Bay Beach’s coastline, but watch your distance for crashing waves. You’ll see local and visiting surfers dotting the waters, one of the world’s most renown. If waking up early on vacation is not your idea of a vacation, sleep in but start the day later with a walk here before heading to breakfast. Surf-themed hearty breakfast items include omelets, sweet bread French toast, breakfast quesadilla and good coffee are on the menu at Café Haleiwa, a casual shack serving surfers and their admirers. While in Haleiwa town, explore the art galleries and shops. It’s the essence of old Hawaii and the laid-back atmosphere supports the need to leisurely stroll through art galleries (including that of the prominent ocean artist, Wyland) and shops. You’re certain to find a handcrafted souvenir to take home.

Planning a trip to the North shore of Oahu? Check out our wide selection of North Shore vacation rentals.

Poipu One Day Itinerary

Kauai’s South Shore town, Poipu, at first glance is an idyllic locale. A visit and further exploration reveal a sunny part of Kauai with enough things to do and see to last a month. Adventure, golf, water sports, nature, heritage, spa indulgence and incredible dining are a part of the scene. Narrowing it down will be the welcome challenge.

Every good day on the islands starts with an indulgent, comfort food breakfast. Kalaheo Café and Coffee Company is the place with a casual and friendly atmosphere and just about any kind of breakfast imaginable. The upcountry breakfast (hearty and a lot of everything—eggs with rice, bacon, ham, smoked turkey or sausage and toast. The list continues with waffles, omelets, anahola granola and plentiful fruit and coffee. After a substantial breakfast or brunch, head to Mahaulepu Beach, a significant part of the Mahaulepu Trail, a heritage trail you can explore in a myriad of ways, by car, on foot, or on a bike. The remote beach is as rich with character as activity, including fishing, snorkeling, swimming and windsurfing.

Planning a trip to the sunny south side of Kauai? Stay in one of our Poipu condos.

Lahaina Holiday Guide

A town that is on the National Register of Historic Places, the entire town, and one with enough culture to fill several days of exploration, plus an area that could easily be featured in a film with a New England town setting, this is the multi-faceted town of Lahaina. Whales and art are draws, eclectic and scenic are characteristics, and its former name, Lele, which means relentless sun, tells the tale of its personality today.

Visitors to the area will find that the holidays in Lahaina are an experience to mix among locals. The churches on Lahaina celebrate with concerts of sacred Christmas music from multiple cultures, caroling, Christmas stories, and candle lighting ceremonies and other holiday festivities in the name of fellowship.

Planning to spend your holiday on Maui? Stay in one of our Lahaina vacation rentals.

Hiking around Lanikai

Historic bunkers, steep inclines, invigorating hikes and seemingly endless views of perfection at any angle are features of the hikes around Lanikai. Make sure to dress appropriately, both attire and shoes; bring water and essentials; respect areas that intermingle with private residences and plan to hike according to your endurance and stamina.

Lanikai Beach is a great place to begin a hike and to top one off with a swim or picnic. Both rich in heritage and views, Lanikai Bunkers, fondly known as Pillboxes, is just past Kailua Beach Park. From Mokulua Drive, turn onto Kaelepulu Drive and find parking near the Mid-Pacific Country Club. Early morning or late afternoon times are optimal as there will be no shade along this hike. The Ka’iwa Ridge Trail is a mix of grass, red dirt and lava rock, which keeps the hike as interesting as the views reveal more of Oahu’s beauty. The key features of this trail are the World War II bunkers (pillboxes) and each one gives a glorious perspective of the island below. Hike down carefully as it can be slippery and a bit of an unwieldy walk.

Explore the windward coast of Oahu from one of our Lanikai vacation rentals.

Kona Shops – Can’t miss shopping treasures.

Any vacation has an element of shopping for yourself; coworkers, friends and family back home and sometimes just as an activity. When the atmosphere and experience are appealing, that’s when even those not very interested in shopping will be appreciative of their time not being wasted.

Kona offers a mix of open air markets, shopping centers and art galleries. The best shopping experiences are those that are unique to you. Visiting with locals, hearing chatter about the area, watching items being made and finding handcrafted and locally-made items are facets of a Kona shopping day.

Stay nearby all the great shopping found in Kona in one of our Kona vacation rentals.