Fodor's Expert Review The Old Wailuku Inn at Ulupono

2199 Kahookele St., Wailuku, Hawaii, 96793, USA See on Map Fodor's Choice

Built in 1924 and listed on the State of Hawaii Register of Historic Places, this home with knowledgeable innkeepers offers the charm of old Hawaii, including authentic decor and architecture. Each room is decorated with the theme of a Hawaiian flower. Other features include 10-foot ceilings and floors of native hardwoods. Some rooms have delightful whirlpool tubs, and first-floor rooms have private gardens. A newer cottage, Vagabond's House, has three well-appointed rooms, each with a standing spa shower and bed coverings by Hawaii's premier fabric designer, Sig Zane. A hearty breakfast (included in the price) is served at 8 am in the casual dining room. Guests often include attorneys and others with business in Wailuku town.

Book directly with the B&B if you want to choose your room (and get a good deal). Third party booking sites do not allow for room choice.


There are seven main guest house rooms and an additional three rooms in the Vagabond’s House cottage, creating 10 guest rooms at this inn. Decor is beautiful and charming and rooms in the guest house have a gorgeous traditional Hawaiian quilt on them. Rooms include TV with cable, coffee maker, complimentary snacks and soft drinks, ceiling fans, air conditioning, and free Wi-Fi. Bed configurations for many rooms include two twins that can be combined to make a king-sized bed.

YOU SHOULD KNOW Rooms have a very small capacity -- almost all of the rooms max out at 2, which makes this a less desirable option for traveling families, but great for couples who want a quieter stay.


Each room at the end has a private bathroom. The rooms in Vagabond’s House have a shower with wall jets, hand held shower head, and rainmaker showerhead. The Ulu, Ilima, and Mokihana rooms have whirlpool tub/shower combinations. All bathrooms are stocked with Aveda products.


There is no lobby at this small B&B-style inn.


Though there is no restaurant, the home cooked breakfast is a special treat at this inn, with many of the fresh fruits coming directly from trees in the yard. There are no kitchen or cooking facilities available, but there is a small refrigerator and a microwave in the common breakfast area available to guests.


Getting Around

It’s easy (and preferable) to explore Maui’s smaller towns by foot, but to get to them and around the island, you’ll need to rent a car. If you plan on exploring the Road to Hana, get something with a little extra horsepower (but not too big as the road can get very narrow).


Beloved Hawaiian chef Sheldon Simeon’s newest project, a contemporary take on his family’s Filipino food, takes diners through his personal story, ranging from his childhood to his time on “Top Chef.” The dishes at Lineage (44-min drive) are deeply personal, and the new interpretations of the food Simeon grew up with use incredible ingredients, including gorgeous vegetables from Oprah Winfrey’s Maui farm. The cocktail program at the beautiful bar is just as exceptional as the food, and the surprising amount of plant-based options is refreshing (but there are plenty of elevated traditional options for meat lovers).

Find fresh, vibrant food at Fork and Salad (17-min drive), featuring signature, as well as build-your-own salads, grain bowls, and sandwiches made with a wide variety of mostly local and organic ingredients. These healthy options make a great choice to pick up for a beach picnic or day of hiking.


The Four Seasons (34-min drive) is known around the world for its welcoming lobby bars, whether you’re a guest or not, and the gorgeous Maui hotel is no exception. The lobby bar recently underwent a facelift that included new furniture, new staff uniforms, and an entirely new cocktails menu that is arranged by the changing colors of the day, with plenty of twists on tropical classics. Enjoy with music and comfy views while relaxing on comfy, new furniture.

Though it may not be as popular as another Hawaiian brewing company, Maui Brewing Co. (27-min drive) deserves every bit as much respect, especially since it’s still local. Its newest brewery, tasting room, and pub in Kihei is super sleek and fun. Drop in for a brewery tour or grab a seat at the massively long bar and try out some of their seasonal beers that are only available at the brewery. Be sure to grab a crowler or growler to enjoy those special flavors during the rest of your trip.


This beautiful home, built in 1924, is so much a part of Maui history that it is also on the Hawaii State Register of Historic Places. The rooms are beautiful and charming, but still have modern amenities that travelers are looking for. Breakfast is a huge draw and wonderful time for guests to meet one another and chat with the very friendly hosts and staff. The nightly cookies left in guest rooms are also a very nice touch.


Residential Area
Local Flavor


Phones: 808-244–5897;800-305–4899

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