February is one of those months on island that feels extra special. The winter air is a little cooler, the sunsets stay soft and golden, and whale season is in full swing. Even a simple beach walk can turn into a whale watching moment.

A fun event this month is the Paint Maui Plein Air Invitational 2026 in Lahaina, happening February 14 to 22. Artists will be painting outdoors all week, with a few public demos, then the event wraps with an Awards Presentation and Grand Art Sale at Village Gallery Lahaina. A portion of proceeds supports the Lahaina Restoration Foundation.

Maui County recently released draft design guidelines intended to help streamline the complex rebuilding process in the historic business district, including Front Street. More clarity is a meaningful thing for local businesses that are ready to rebuild.

One planning note for your trip. Hawai‘i’s Green Fee is now in effect, and it is built into the statewide Transient Accommodations Tax that already exists. The TAT increased by 0.75%, and it is now 11%, which helps fund climate resilience and environmental protection statewide. Another reason to find ways to skip those pesky booking fees charged by Airbnb and Booking.com!

Below you’ll find February events, our newest blog posts, and welcoming places to stay across Maui!

Safe Travels,
Tiffany

Tiffany Rose, Publisher, Maui Accommodations Guide

Royal Lahaina Launches Kuraya Magic Series

Royal Lahaina Resort & Bungalows is launching Kuraya, a new weekly oceanfront magic show starring Maui-born magician David Kuraya, beginning Tuesday, January 27, 2026. Held every Tuesday evening in the newly renovated Hale Piʻilani Room, the intimate show blends close-up magic, storytelling, and humor for an engaging, all-ages experience.  Photo Credit: David Kuraya via MauiNow

Maui Songwriters Festival Returns to Kapalua

The Maui Songwriters Festival returns to The Ritz-Carlton Maui from February 11–14, 2026, for its 11th year, featuring country, pop, and rock songwriters in both intimate showcases and larger concerts. Led by Gavin Adcock and Hudson Westbrook, the multi-day event highlights the stories behind hit songs while supporting local causes. Proceeds benefit the Boys & Girls Clubs of Maui, continuing the festival’s strong community impact. Photo Credit: Maui Songwriters Festival via @mauisongwritersfestival's Instagram

Lahaina Food and Wine Festival 2026

The Lahaina Food & Wine Festival returns February 18–22, 2026, for its second annual celebration, bringing together acclaimed chefs, winemakers, and local culinary leaders for five days of dinners, tastings, and community events across Lāhainā. Hosted at venues like Māla Ocean Tavern, Coco Deck, Sale Pepe, and Lāhainā Jodo Mission, the festival blends elevated dining with family-friendly and charitable experiences that support local organizations. Photo Credit: Lahaina Food & Wine Festival

Best Places to Stay on Maui for First-Time Visitors

If you or a loved one are planning your first trip to Maui and feel overwhelmed about where to stay, this guide makes it simple. It breaks down the island’s most visitor-friendly areas and highlights standout accommodations by budget, from luxury resorts to great-value condos, so you can find a place that fits your travel style. Dive in to discover which regions and stays offer the best mix of beaches, convenience, and first-timer-friendly vibes.

All About Iao Valley Inn Cottage

Staying at Iao Valley Inn Cottage feels like a peaceful step into old Hawai'i, surrounded by lush greenery, mountain views, and the calming sound of the Wailuku River just outside your door. This detached private 1-bedroom, 1-bathroom cottage features a fully equipped kitchen, covered lanai, private gazebo, and an American Whirlpool hot tub. Perfect for couples and honeymooners, it offers a quiet, authentic Maui experience far from busy resort areas, with space to relax, cook, meditate, and truly slow down.

Maui Whale Watching Q&As

Every winter, humpback whales migrate to Maui’s warm waters, making whale watching one of the island’s most unforgettable seasonal experiences. Peak sightings happen in February, but whales are commonly seen from December through April, often right from shore along Maui’s south and west coasts. From boat tours and kayaking to spotting spouts from your lanai, there are plenty of safe, respectful ways to enjoy Maui’s most beloved visitors.

All About Maui Rainbow Condo Kahana E705

Experience the ultimate West Maui getaway at the Maui Rainbow Condo E705, a beautifully remodeled 3-bedroom, 2-bathroom retreat just steps from S-Turns Beach and minutes from Napili, Kapalua, and Ka’anapali. Enjoy resort-style amenities like a pool, jacuzzi, tennis and pickleball courts, or relax on your lanai with stunning ocean views while cooking in your fully equipped kitchen. With nearby dining, shopping, hiking, and golf, this condo offers the perfect mix of adventure and island serenity.

February Hot Picks: Where to Stay on Maui

February is a beautiful time to experience Maui, with warm days, gentle trade winds, and a romantic energy that lingers all month long. This month’s hot picks highlight standout places to stay across South Maui, Ma'alaea, and West Maui, from walkable Kihei condos and peaceful harbor-side retreats to upscale Wailea villas and beachfront Ka'anapali homes. Each featured stay focuses on comfort, location, and book-direct value, making it easy to plan a memorable winter escape.