Maui, Hawaii
Touchdown in paradise. We are kicking off a trip at The Westin Maui. The only thing better than the weather is getting in some daughter time.
You may have heard the phrase Maui No Ka Oi (Maui is the best). For us, this island holds a deeply personal place in our hearts. It was the very first trip we took as a couple outside the mainland US. We fell in love with the rhythm of the islands here. Every return visit feels like coming home. You feel it the moment the automatic doors open at Kahului Airport. The smell of plumeria and heavy tropical air hits you. Your shoulders instantly drop two inches.
That is why the devastating fires that destroyed Lahaina were so absolutely heartbreaking for us. We have decades of memories in that historic town. We remember walking Front Street, sitting under the Banyan Tree, eating at Fleetwood’s. Seeing it gone was a shock. However, on our recent visits, we found a community that is resilient and eager to welcome visitors back. Since the fire, tourism has been much slower. The message we heard from locals was clear. They want and need travelers to return.
The "Aloha Spirit" is as real as ever but come with an open heart. Drive slowly (it seems like nobody honks in Hawaii). Support the local businesses that are rebuilding. The island is healing. Being there now feels more meaningful than ever.
The Hotels
Maui is unique because the resort areas are distinct "neighborhoods" with very different vibes. Wailea in the south is polished, sunny, and serene. Ka'anapali in the west is vibrant, energetic, and famous for its sunsets.
Four Seasons Resort Maui at Wailea This is the gold standard of Wailea luxury. It manages to be both sophisticated and incredibly welcoming. You never feel out of place here whether you are in linen or board shorts. The open-air lobby is spectacular. It frames the ocean and the island of Lanai perfectly.
The Experience: There are no resort fees here. This is rare for Hawaii. But the real standout is the Serenity Pool. It is an adults-only infinity pool that offers one of the best views on the island. The silence there is golden. The service is anticipatory. Attendants circulate with Evian spritzes, frozen grapes, and cucumber slices for your eyes. It makes a day by the pool feel like a full spa treatment.
Comfort Note: Accessibility is excellent throughout the property. The pathways are wide and smooth. They have pool lifts available at the main pools. It is one of the most wheelchair-friendly luxury resorts we have visited. The staff is trained to assist discreetly.
Montage Kapalua Bay Located on the ruggedly beautiful northwest coast, the Montage feels less like a hotel and more like a private luxury residence. The surroundings are lush and greener than Wailea. The units are massive multi-bedroom suites with full gourmet kitchens and lanais that are bigger than most NYC apartments. It feels secluded and private.
The Experience: It is quieter than Wailea. You can access the Kapalua Coastal Trail directly from the property for morning walks along the cliffs. The Cliff House is a historic venue perched over the ocean. It is one of the most stunning spots on the island. We once watched a private dinner happen there at sunset. It looked like something out of a movie.
Comfort Note: Because these are residence-style units, you have the convenience of in-suite laundry and a full kitchen. This makes extended stays incredibly comfortable for those with medical needs or dietary restrictions who prefer to control their own environment.
Grand Wailea, A Waldorf Astoria Resort "Grand" is the only word for it. The grounds are lush, tropical, and massive. It feels like a tropical theme park in the best way. The lobby is filled with Botero sculptures and the gardens are impeccable.
The Experience: If you are traveling with a multi-generational family, this is the winner. The kids will never leave the pool system. It includes slides, caves, and a water elevator. Meanwhile, the adults can disappear into the newly reimagined Kilolani Spa. It is the largest spa in Hawaii and features a hydrotherapy circuit that reflects the phases of the Hawaiian moon. It is an experience in itself.
Comfort Note: Be aware that the property is huge. If walking long distances is an issue, request a room near the elevators or the lobby. Some wings, like the Napua Tower, are more central. Others can be a 10-15 minute trek from the main areas.
The Westin Nanea Ocean Villas, Ka'anapali Sitting right on the famous Ka'anapali Beach, this resort captures that classic Hawaiian vacation energy. It is vibrant and social. It puts you right in the heart of the action on the west side. The architecture honors Hawaiian culture with designs inspired by traditional basket weaving.
The Experience: It feels incredibly fresh right now. The property completed a comprehensive villa refresh in 2024. The rooms feel brand new. One of our favorite things here is the grilling culture. The resort has immaculate gas grills poolside. There is something special about grilling your own steaks with a Mai Tai in hand while the sun sets over the ocean.
Comfort Note: The boardwalk that runs along Ka'anapali Beach is paved and flat. It is one of the best places on the island for a wheelchair user to enjoy a long oceanfront stroll without dealing with sand.
The room’s have been recently renovated and are practical and spacious. We appreciated the comfortable beds after the long flight to the island.
The Dining Scene
Maui's culinary scene has evolved way beyond tiki drinks and hotel buffets. The island is leading the charge in "Hawaii Regional Cuisine." It focuses on fresh, local ingredients grown in the rich volcanic soil Upcountry. Here are our favorites.
Monkeypod Kitchen This lively open-air spot by culinary pioneer Peter Merriman is casual, fun, and always packed with a mix of locals and visitors. There is almost always live music, usually a slack-key guitar player, which sets the perfect island tone.
Drink This: They are famous for their Mai Tai. It is topped with a signature house-made lilikoi foam. It is widely considered the best on the island. The foam adds a tart and creamy finish that balances the rum perfectly.
Eat This: Do not skip the Pumpkin Patch Ravioli or the fresh catch Fish Tacos. It is comfort food done perfectly using local ingredients.
Humuhumunukunukuāpuaʻa Named after Hawaii’s state fish, this "floating" restaurant at the Grand Wailea is set on a saltwater lagoon filled with tropical fish. It recently underwent a major renovation. This elevated the design from "tiki kitsch" to modern Polynesian luxury.
The Vibe: It is one of the most romantic spots in Wailea for a sunset dinner. Request a table near the edge of the lagoon. Watching the sun dip below the horizon while torches light up around the water is the quintessential Hawaii moment.
Morimoto Maui Located at the ultra-chic Andaz Maui at Wailea, this is Iron Chef Masaharu Morimoto’s beachfront masterpiece. The design is modern and sleek. It maximizes the ocean views with floor-to-ceiling glass.
The Meal: Expect world-class sushi and Japanese fusion with a view. Watching the sunset turn the sky purple while eating otoro sashimi is a core memory for us.
Eat This: The Tuna Pizza is a standout playful dish that is absolutely delicious. The presentation here is art.
Tin Roof Owned by Top Chef fan-favorite Sheldon Simeon, this is a humble lunch spot in a strip mall near the airport. Do not let the location fool you. This is some of the best food on the island.
Eat This: Order the Mochiko Chicken or the Pork Belly Kau Kau Tin. It is casual, affordable, and explodes with flavor.
Advisor Tip: We usually stop here immediately after landing or right before our flight home. There is no seating. Be prepared to eat in your rental car or take it to a nearby park. It is worth it.
Ululani’s Hawaiian Shave Ice You cannot come to Hawaii and not have shave ice. Ululani’s is widely considered the best because the ice is shaved so fine it feels like fresh snow rather than crunchy ice.
Order This: Try the Haleakala combo (coconut and leche) and definitely add the Snow Cap (sweetened condensed milk) on top. It is the ultimate cooldown on a hot afternoon. We have stood in line for 20 minutes for this, and we would happily do it again.
The view from our balcony. We loved that you can see the layers of the resort from here. You have the lush gardens, the pool complex, and then the open ocean beyond.
The Culture & Sights
The Old Lahaina Luau Miraculously, this iconic venue survived the Lahaina fire and reopened in early 2024. By visiting, you are directly supporting local employees and families who are still rebuilding their lives.
The Experience: This is considered the most authentic luau on Maui. There are no fire dancers here. Instead, the focus is on genuine Hawaiian history, hula, and storytelling. They have recently added new programming that specifically honors Lahaina’s history and recovery journey. Sitting on a mat right by the ocean while watching the sunset as the story of Hawaii unfolds feels respectful and deeply moving.
The Feast at Mokapu If you want a more upscale and intimate luau experience, head to the Andaz Maui. It feels less like a production and more like a dinner party.
The Difference: Unlike the massive buffet lines at other shows, this is a plated and sit-down dinner with craft cocktails delivered to your table. The food is excellent and elevated. It definitely costs more.
The Show: This performance does feature thrilling Polynesian fire knife dancing. It offers a high-energy contrast to the more traditional Old Lahaina Luau. The backdrop of Mokapu Beach is stunning.
Haleakalā National Park Driving up to the summit of this dormant volcano to watch the sunrise above the clouds is a spiritual experience. It feels like you are on Mars. The landscape is red, rocky, and silent.
Advisor Tip: Arrive early enough to see the stars before the sun breaks. The sky is incredibly clear at 10,000 feet. Seeing the Milky Way fade as the sun rises is unforgettable.
Wellness Note: It is freezing up there (often 40°F). Bring layers, hats, and gloves. Also, the air is thin. Move slowly. Reservations are required for sunrise entry, so plan ahead.
The Road to Hana This winding drive through lush rainforests and waterfalls is beautiful, but it is a long day with 600 curves. It takes commitment.
Advisor Tip: You do not have to do the whole thing. We often recommend driving just to Twin Falls or the Garden of Eden Arboretum to get the rainforest vibe without the 10-hour commitment. Stop for banana bread at a roadside stand. It is warm, moist, and delicious.
Comfort Note: If you are prone to motion sickness, take medication beforehand or skip this. The curves are relentless. Trust us. We barely survived the motion sickness on our last attempt and we travel all the time!
Whale Watching If you are visiting between December and April, this is non-negotiable. The Auau Channel between Maui and Lanai is one of the best places in the world to see Humpback whales breaching.
Advisor Tip: Book a smaller boat (like a catamaran or Zodiac) for a more intimate experience rather than the massive double-decker tourist barges. Being at water level with these giants is humbling. Also, if you stick your head underwater while snorkeling during whale season, you can often hear them singing. It is a haunting and magical sound.
Beyond the Beach: Day Trips
Molokini Crater: Take a boat trip out to this crescent-shaped volcanic crater partially submerged off the coast. The water clarity is insane. It often offers 100+ feet of visibility. It is a snorkeling paradise where you float in an aquarium. The morning trips are best before the trade winds pick up.
Upcountry Maui: Leave the beach for a day and head up the slopes to find cooler air, rolling green hills, and a totally different vibe. You must do lunch or dinner at Haliimaile General Store. It is an island icon set in the middle of pineapple fields. Chef Bev Gannon put Hawaii Regional Cuisine on the map here. Her Sashimi Pizza and Crab Dip are legendary. It is the perfect savory stop after exploring the lavender farm or Makawao town.
We drove up to the summit of Haleakalā. The landscape up here is otherworldly. It looks more like the surface of Mars than a tropical island. And bring a sweater, it’s cold!
The Essentials
Travel Notes: Things to keep in mind
Embrace "Maui Midnight": Do not fight the jet lag. Most visitors from the mainland wake up at 5:00 AM and are asleep by 9:00 PM (which some locals jokingly call "Maui Midnight"). Use those early mornings! The wind is calmest, the snorkeling is clearest, and the beaches are empty before 8:00 AM.
The "Book Ahead" Reality: Spontaneity is tough on Maui right now. For top-tier dining, luaus, or the Haleakalā sunrise, you need to book 3–6 months in advance. Treat your dinner reservations with the same urgency as your flight bookings.
Car Rental: A car is 100% essential on Maui. Uber is not reliable for exploring the island. Rent something comfortable (like a Jeep or SUV) as you will be spending time on the road.
The "Pau Hana" Traffic: Be aware that traffic on the main road (the Pali) between the West Side (Lahaina/Kaanapali) and the airport/Wailea can be brutal around 3:00 PM - 5:00 PM. The road hugs the cliffs and offers great views, but sitting in gridlock there is no fun. Plan your movements accordingly.
Malama (Respect): The concept of Malama means to care for the land. Use reef-safe sunscreen (it is the law), do not touch the sea turtles (honu), and never take rocks or sand home with you.
Accessibility: The Good & The Reality
The Good: Because Hawaii is in the US, ADA compliance is generally excellent. Hotels like the Four Seasons and Grand Wailea have pool lifts, ramps, and accessible rooms that are far superior to what you find in Europe or Asia. You can comfortably navigate most resort areas.
The Reality: Nature is still nature. Beaches have deep sand, and hiking trails (like on the Road to Hana) are often rugged, muddy, and rooted.
Our Recommendation: Stick to the "Wailea Beach Path" or the "Kaanapali Beach Walk" for oceanfront rolling. These are paved, flat, and offer incredible views. Many beaches also offer complimentary "beach wheelchairs" with thick tires. Ask the hotel concierge or lifeguards about them.
Our Favorite Discovery: Leoda's Kitchen and Pie Shop You will drive past this plantation-style building in Olowalu a dozen times, but you must stop. Leoda's became our obsession. It is casual and bustling, but the pies are Michelin-level good. They are personal-sized (so you do not have to share!) and perfect for taking back to your hotel lanai. We tried almost every flavor and while the Olowalu Lime is super popular, we loved the Coconut and Banana Cream pies the best. The crust is buttery perfection. It is the sweetest "pit stop" on the island. And their savory pies are amazing as well!
Island time. Maui resorts are lush and incredibly well-maintained, many feeling like a tropical garden that happens to have a few pools in it.
The TudorTravels Perspective
Maui is more than just a tropical backdrop. It is a place with a deep soul. We want you to feel that connection rather than just see the sights.
The Connection: We encourage our clients to go beyond the resort gates. We can arrange experiences that connect you with the culture. Think of a private ukulele lesson with a local master or a volunteer morning helping to restore a taro patch. These are the moments that stick with you long after the tan fades.
The Logistics of Leisure: We know that "island time" can sometimes mean "slow service." We manage expectations and bookings so you are never left hungry or frustrated. We know which luaus have the best seating. We know which snorkel boats have the most stable decks.
Supporting Recovery: By traveling with us, you are traveling responsibly. We prioritize vendors and businesses that are locally owned and directly support the recovery of Lahaina. You can enjoy your vacation knowing your presence is making a positive impact on the community we love so much.
Ready to find your Aloha? Contact us to start planning your tropical escape!