Start your first Maui morning with a hearty island breakfast at Gazebo Restaurant in Napili-famous for macadamia-pineapple pancakes-then take a leisurely stroll along the nearby shoreline at Napili Bay, perfect for spotting sea turtles in calm waters. Afterward, pick up any groceries or beach supplies at Whalers Village Shopping Center so you're ready for afternoon pool time and sunset plans at the Sheraton.
After your Napili morning, ease into island time with a relaxed afternoon at Kāʻanapali Beach-rent snorkel gear from the beachfront stand and explore the reef near Black Rock for colorful fish and occasional honu (sea turtles). Later, pop into Whalers Village for a casual lunch at Leoda's Kitchen and Pie Shop or a shave ice stop, then return to the Sheraton for poolside lounging and a sunset cocktail at Sheraton's Whale's Tale bar before freshening up for evening plans.
After freshening up at the Sheraton, take a short walk to Lahaina Harbor for a gentle twilight stroll and to watch boats drift by as the sky softens. For dinner, head to nearby Fleetwood's on Front St. for rooftop cocktails and live music (reservations recommended), then finish the night with a relaxed drink on the Sheraton lawn while listening for surf and watching the sunset over the island.
Wake up slowly and head for breakfast at Kimo's Maui on Front Street for a laid-back oceanview meal (try the loco moco or fresh island fruit) before a peaceful morning paddle at Baby Beach in Lahaina, ideal for gentle swell and beginner stand-up paddleboarding. Afterward, stroll through the historic Lahaina Banyan Court Park to admire the sprawling banyan tree and local art booths, then grab a casual mid-morning coffee and pastry at All Day Donuts to enjoy on a bench overlooking the harbor.
Spend a leisurely afternoon alternating between the Sheraton's poolside cabanas and a sheltered swim at Honokōwai Beach Park, where tide pools make snorkeling easy and calm for all ages. Later, wander over to Whalers Village for a relaxed lunch at 808 Deli or a poke bowl from Ululani's Hawaiian Shave Ice and finish with a sunset stroll along the beachfront walkway toward Kapalua Coastal Trail to catch late-day light and coastal views before returning to the hotel.
As the sky softens, stroll to the nearby Kāʻanapali Skywalk (the beachfront promenade) and pause for sunset views from the grassy knoll by Pillbox Park before dinner; it's a quieter vantage point that still captures the golden light over the water. For a relaxed dinner without repeating earlier spots, reserve a table at Mala Ocean Tavern for fresh seafood and island-inspired cocktails, then finish the night with a stroll through Lahaina's Front Street to browse art galleries and pick up a kona coffee treat to enjoy back at the Sheraton.
Board the Quicksilver at Lahaina Harbor for check-in and a morning of expert-led whale watching-arrive early to grab good deck seating and enjoy a light continental breakfast from the boat's café while naturalists point out humpback behaviors. After the cruise, stroll through Front Street to stretch your legs and pick up a fresh poke bowl at Paia Fish Market Lahaina before settling in for a relaxing afternoon at Kahekili Beach Park, where calm bays and reef snorkeling are perfect for spotting tropical fish and resting after your sea adventure.
After your morning on the water, drift into a mellow post-cruise afternoon at Kapalua Bay-rent a clear-bottom kayak or snorkel from the beach shack and explore the protected coral gardens teeming with reef fish. Later, stroll the nearby Mokule'ia Bay shoreline for tidepool searching and settle in for a late-afternoon shave ice at Ululani's (Kapalua location) before returning to the Sheraton to freshen up for evening plans.
After freshening up at the Sheraton, head to Street Food Maui in Lahaina for a casual, flavorful dinner of local-style tacos and poke bowls-grab a table outside to enjoy the warm evening air. Follow with a sunset walk along Baby Beach to watch the colors deepen over the harbor, then finish the night with live Hawaiian music and cocktails at Down the Hatch, where the laid-back vibe is perfect for unwinding after a day on the water.
Depart Kāʻanapali early and head to Paia Town for a quick coffee and island pastry before your winding drive; grab picnic supplies at Mana Foods and fuel up for the road ahead. Stop at Twin Falls for a short, shady walk and a dip beneath a welcoming cascade, then continue to the dramatic sea cliffs and black sand of Honokalani Beach (Waiʻānapanapa State Park) to explore lava tubes and coastal vistas before pressing on toward Hāna.
After savoring the highlights nearer Hāna, spend the afternoon exploring the lush inland pockets: take a short hike to Puaʻa Kaʻa State Wayside for a refreshing waterfall swim and picnic by the cascades, then drive a few minutes to the tranquil pools and rope swings at Three Bears Falls (Kahanu Garden area) for a fun, photo-ready stop. Finish the afternoon with a slow walk through the historic Hāna Town-pop into Hāna Farms Store for fresh banana bread and kona coffee, and stroll the shoreline near Hāna Bay to watch tidepools and rest before the drive back toward Kāʻanapali.
After the long coastal drive back toward West Maui, unwind with dinner in the relaxed village of Kīpahulu-enjoy fresh, locally sourced fish and farm-to-table sides at Kīpahulu Kitchen while recounting the day's waterfalls. Finish the evening with a short stroll through the moonlit grounds at Kīpahulu Visitor Center to listen for native birds and the surf, then stop at Hāna Ranch Store & Cafe for a take-home banana-bread treat to enjoy back at the Sheraton.
Start the morning with a coastal walk and coffee at Kula Lodge (Kāʻanapali outpost) before heading to the nearby Kapalua Coastal Trail for gentle clifftop views and early light perfect for photos. After the walk, visit the peaceful tidepools and snorkel-friendly cove at DT Fleming Beach Park for a short snorkel session and beachside picnic featuring fresh poke from Aloha Mixed Plate to keep the pace relaxed after your Road to Hāna and whale-watching days.
Spend a relaxed afternoon strolling the waterfront boardwalk toward Front Street to browse boutique galleries and stop for a casual lunch at Paia Fish Market Lahaina for fresh fish tacos. Afterwards, rent a stand-up paddleboard at Kahekili Beach Park for a gentle paddle among sheltered reefs, then take a short drive to Napili Point to watch surfers and settle on the grassy headland for golden-hour views before returning to the Sheraton for sunset preparations.
Wind down the day with a sunset sail departing from Lahaina Harbor aboard a small, local charter for close-up views of the coastline and a chance to spot spinner dolphins while sipping a craft cocktail. After returning, stroll through Front Street's evening market stalls and dine at Lahaina Grill for refined island cuisine-finish with a nightcap on the Sheraton lawn listening to the surf.
Ease into your last full day with a relaxed breakfast at Honolua Store & Cafe (grab their signature breakfast sandwich and a cold brew), then head to Baby Beach at Kapalua for mellow snorkeling in calm, clear water and a chance to spot reef fish close to shore. After a leisurely morning in the sun, stroll the nearby Kapalua Farmers Market (check for local fruits, artisan jams, and hand-crafted souvenirs) to pick up edible gifts and last-minute keepsakes before returning to the Sheraton to freshen up for an afternoon of final shopping and Merriman's dinner.
Spend a leisurely afternoon exploring the quieter coves of West Maui with a snorkel session at Honolua Bay Marine Preserve, where clear water and thriving coral gardens make for excellent late-day sighting of reef fish and occasional sea turtles. After snorkeling, wander the boutique shops and galleries at Whalers Village for last-minute souvenirs, then relax with a seaside cocktail and pupu plate at Duke's Beach House on the Kāʻanapali shoreline before returning to the Sheraton to freshen up for your Merriman's reservation.
As the sun begins to dip, take a short drive to Kapalua Bay Club Lawn for a relaxed pre-dinner stroll and sunset photo ops overlooking the crescent beach, then pause at The Banyan Tree House for a cocktail on the patio and live acoustic music if it's playing. For dinner, savor farm-to-table Hawaiian cuisine at Merriman's Kapalua, arriving early to enjoy their lanai seating and order the nightly fish special with local sides; after your meal, wander the moonlit paths of Kapalua Coastal Trail back toward the Sheraton for a quiet seaside finish to your trip.