Planning the perfect Lahaina vacation means balancing beach time, adventure, culture, and relaxation. After years of helping visitors plan their West Maui trips, we've put together this day-by-day itinerary that hits every highlight without feeling rushed. Whether you're a first-timer or returning for another dose of aloha, this seven-day plan will make sure you don't miss a thing.
Day 1: Arrive & Settle In — Check into your hotel and resist the urge to do too much. Jet lag is real, even when you're flying to paradise. Grab a casual lunch at Aloha Mixed Plate — their kalua pig plate is legendary and the oceanfront picnic tables set the tone for the whole trip. Spend the lazy afternoon at Ka'anapali Beach, getting your toes in the sand and your body on island time. As the sun dips, walk to Black Rock at the Sheraton to watch the nightly cliff-diving ceremony. A torch-lit diver leaps into the ocean as the sky turns orange and pink — it's a genuinely magical way to start your vacation. For dinner, keep it simple with fish tacos at a beachside spot.
Day 2: Snorkel Morning — Set your alarm early (you'll be up anyway thanks to the time change) and head to Kapalua Bay before 8am. The morning water is glass-calm and the visibility is incredible — you'll see parrotfish, humuhumunukunukuapua'a (Hawaii's state fish), and probably a few sea turtles. Spend the morning alternating between snorkeling and lounging on the sand. After lunch, drive five minutes to Napili Bay for a change of scenery — it's a perfect crescent of sand with its own resident turtles. End the day with dinner at Monkeypod Kitchen in Whaler's Village, where the happy hour (3-5:30pm) is one of the best deals in West Maui with half-price flatbreads and craft cocktails.
Day 3: Road to Adventure — Book a morning surf lesson in Lahaina (Maui Surfer Girls and Goofy Foot are both excellent for beginners). There's nothing like catching your first wave with the West Maui Mountains as your backdrop. After your lesson, explore the Kapalua Coastal Trail — a 1.76-mile paved path along dramatic sea cliffs with views of Molokai. The trail is easy enough for all fitness levels and the scenery is postcard-perfect. Cap off the day with the Old Lahaina Luau, widely considered the best luau in Hawaii. The traditional Hawaiian feast, hula dancing, and fire knife performance are worth every penny. Book well in advance — this one sells out weeks ahead.
Day 4: South Maui Day Trip — Rent snorkel gear for the day and drive to Ma'alaea Harbor for a morning Molokini Crater snorkel trip. This partially submerged volcanic crater has 150-foot visibility and hundreds of fish species. Back on land, grab lunch at Monkeypod Kitchen in Wailea (yes, it's that good — they have two locations), then spend the afternoon at Wailea Beach. The crescent-shaped beach is stunning, and the adjacent Wailea Beach Walk connects five beaches along a beautifully landscaped path. Drive back to West Maui for a quiet sunset dinner.
Day 5: Culture & Food — Start the morning with the Lahaina Food Walk — a walking tour through town sampling local favorites while learning about the area's rich history. Lahaina was once the capital of the Hawaiian Kingdom and a major whaling port, and the stories are fascinating. After the tour, explore what's open along Front Street — galleries, shops, and the famous Banyan Tree (one of the largest in the country). Spend the afternoon at Baby Beach, a calm, shallow stretch perfect for floating and reading. For the sunset splurge, book a rooftop table at Fleetwood's on Front St. The nightly drumming ceremony at sunset is unforgettable, and the food (owned by Mick Fleetwood of Fleetwood Mac fame) lives up to the setting.
Day 6: Ocean Day — If visiting between December and April, book a whale watch cruise out of Lahaina Harbor. Maui's waters are a major humpback whale breeding ground, and seeing a 40-ton whale breach just a hundred yards from your boat is a life-changing experience. Outside whale season, book a Lanai snorkel trip instead — the short boat ride to this neighboring island offers pristine reefs, spinner dolphins, and crystal-clear water. Spend the afternoon resting by the pool (you've earned it). For your last big dinner, head to Merriman's Kapalua for farm-to-table Hawaiian regional cuisine with an oceanfront sunset view.
Day 7: Relaxation & Departure — Wake early for a final sunrise at Launiupoko Beach Park, where the sky lights up behind the West Maui Mountains. Have breakfast at Gazebo Restaurant in Napili — get there when they open at 7:30am because the line gets long fast. Their macadamia nut pancakes with pineapple are famous for a reason. Spend your last hours at whichever beach stole your heart this week, then head to the airport with sand still between your toes. The drive back to Kahului takes about 50 minutes — leave extra time so you're not stressed.
Packing Tips for This Itinerary: Reef-safe sunscreen (required by law), rash guard for snorkeling, water shoes for rocky entries, a light rain jacket for surprise showers, and a nice outfit for the luau and Fleetwood's. Don't overpack — you'll live in swimsuits and flip-flops.
Local Knowledge
This article is written with local Lahaina knowledge and updated regularly to stay current.