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5 of the Best Small Towns on Maui

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Maui, Hawaii, is a melting pot of cultures and communities. While it’s tempting to explore the tourist towns, consider visiting the island’s diverse, lesser-known villages instead. You’ll get a better feel for the Hawaiian way of life! Check out our favorite small towns on Maui below and use our carefully curated Travel Guide for additional trip-planning tips.

Experience the Best Small Towns on Maui

1. Wailuku: Peaceful & Historic

First up on our list is, of course, Wailuku! This ancient community sits at the mouth of the Iao Valley on the western side of the island. Wailuku played a large role in Hawaii’s history; it was the birthplace of the sugar industry, the site of King Kamehameha’s victory against the Maui Army, and where New England missionaries brought their beliefs in the mid-1800s.

Today, you can visit historic sites like Ka’ahumanu Church and the Bailey House Museum. Or, get outdoors and explore the incredible Iao Valley State Park. Wailuku’s downtown area is another must-see, with quaint coffee shops, restaurants, and boutiques.

Distance from our inn: 1 mile

2. Paia: “The Windsurf Capital of the World”

If you’re looking for a cool town with a laidback vibe, head to Paia. It’s nestled on Maui’s North Shore and attracts windsurfers, hippies, and yogis of all ages. Here, Ho’okipa Beach and Baldwin Beach Park provide a scenic backdrop for surf shops and specialty stores. We recommend strolling Baldwin Ave in search of unique, one-of-a-kind treasures.

Local Tip: Keep your eyes peeled for part-time Maui resident, Willie Nelson! When in town, he’s known to play at Charley’s Restaurant & Saloon in Paia.

Distance from our inn: 10.9 miles

3. Makawao: Cowboy Country

Did you know that there’s such thing as a Hawaiian cowboy? Well, you do now! Paniolo settled in Upcountry Maui in the 1800s and formed a distinct culture. In the center of Makawao, you’ll find an art gallery, hypnotherapist, and the Rodeo General Store. There’s also a 100-year-old family bakery. On the 4th of July, the town hosts a small parade with awesome Paniolo crews and fancy restored cars. Be sure to check it out if you’re in the area!

Distance from our inn: 15 miles

4. Lahaina: A Maui Hotspot

Lahaina is the most popular town to visit on the island. That’s because there are so many things to do and see! The historic whaling village boasts top-notch art galleries, shops, eateries, and live entertainment. There’s also a wide range of events to attend throughout the year. One of our favorites is the family-friendly Banyan Tree Craft Fair, held every weekend in the shade of one of the largest trees in the United States.

Distance from our inn: 21.6 miles

5. Hana: “Real Hawaii”

The Road to Hana is the most popular attraction on Maui, and for good reason! The final destination, Hana Town, is a gem of the island. This town is quiet, beautiful, and full of history. It’s the perfect place to relax and recharge. Feel free to grab some food at one of two excellent restaurants. Then, visit the Cultural Center and take an easy walk along the ocean. There’s no better way to end a day of adventure!

Distance from our inn: 53.5 miles

Discover These Towns and More When You Stay at The Old Wailuku Inn

The Old Wailuku Inn at Ulupono offers easy access to some of the best small towns on Maui. Whether you’re interested in history, art, food, or outdoor recreation, you’ll find it all just minutes from our B&B! Plus, our innkeepers were born and raised on the islands. We can provide you with a map of Maui and help you plan the ultimate Hawaiian vacation!

When it’s time to book your stay, choose from one of our gorgeous guest rooms. All of our accommodations feature private bathrooms and modern amenities. Your stay also includes a delicious, homemade breakfast each morning.

Check our availability and book your Hawaiian vacation today! We look forward to hosting you.

The Old Wailuku Inn

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  • 808-244-5897
  • 2199 Kaho'okele Street Wailuku
    Maui, Hawaii 96793