Maui Vacation 10 Day Travel Itinerary

Maui Vacation 10 Day Travel Itinerary

  • Maggie Salerno
  • 11/5/22

Where to Stay:


For the first part of the vacation I suggest staying in Kihei/Wailea and then for the last few days stay in Lahaina/Kaanapali. Kihei/Wailea are on the south side of Maui and the area is home to some of the best hotels, restaurants, and beaches on the island and it is relatively close to all that Maui has to offer. The west side of Maui also has great restaurants, shopping, hotels, and beaches as well and has so much to do you will never have to leave the west side for any amenities. 


Day 1: Adjusting to Island Time


After hours of travel, I would suggest taking your first day to get acclimated to the serene Maui  lifestyle. First stop from the airport would be Costco and Target to pick up the essentials such as your favorite snacks, easy meals to bring to the beach, reef safe sunscreen, and much more! Then check in to your hotel/airbnb, change into your bathing suit and spend the rest of the day relaxing by the beach or the pool. And lastly enjoy an early dinner at one of the south side favorites like Monkeypod, Paia Fish Market SouthSide, or Lineage. 


Day 2: Beach Day on South Side and Dinner at The Shops of Wailea


Take the first full day to relax on the beach. The tides in the morning are typically smoother than in the afternoon, and the beaches are less crowded. At noon, the sun is at the highest point of the day so be sure to wear reef safe sunscreen, and reapply after cooling off in the ocean. On the south side of Maui are some of the best beaches on the island. Some of my favorites include Makena Beach (also known as Big Beach), Keawakapu, Po’olenalena, and La Perouse Bay. Keawakapu and La Perouse bay have some of the best snorkeling on the island, in both of these spots I have seen turtles, eels, and plenty of fish while snorkeling! After spending the day on the beach, I would recommend stopping at the Shops of Wailea for a delicious dinner at some of the top restaurants on the island such as Tommy Bahama’s, Lineage, or Ruth Chris’ Steak House. There’s also world-class shopping at the Shops of Wailea with smaller island boutiques as well as luxury brands like Gucci, Louis Vouitton, Lululemon, and much more! 


Day 3: Paia Town and Ho'okipa Lookout 


On the north shore of the island is a quaint surfer town called Paia, that has eclectic boutiques and delicious restaurants with healthy choices. Some of my favorite stores for souvenirs include Alice in Hulaland, Jammin’ on Maui, and By the Bay. My favorite restaurants in Paia are Cafe Des Amis which serves crepes, curries, and cocktails and the original Paia Fish Market that always has a line out the door for their affordable and delicious entrees. I would advise you to call ahead and order a to-go order for Paia fish market to skip the line and enjoy your meal on the beach. There’s great beaches nearby such as Baldwin Beach, Paia Bay and Kuau Cove. When venturing out to Paia town, I would also suggest making a stop at Ho’okipa Lookout, where you can watch windsurfers and turtles resting on the beach. You have to really look at first because the turtles blend in with the rocks, but there’s always tons of turtles relaxing on the beach at Ho’okipa. When exploring the beach and taking pictures of the turtles please be mindful and keep your distance from these magical sea creatures. 


Day 4: Road to Hana 


The Road to Hana is a must when visiting the island of Maui. Rich with greenery, waterfalls, and wildlife there is so much to explore on the drive. Some of my favorite stops along the way are Waianapanapa State Park, Garden of Eden Arboretum, Hana Farms Roadside Stand, and Seven Sacred Pools. Prior to your travels, be sure to make a reservation to go to Waianapanapa State Park. When you are there you can explore the black rock beach, venture into the cave on the ocean, and hike up the rock path to discover blow holes. The Garden of Eden is absolutely breathtaking! The admission fee is $20, but you will not be disappointed! There’s so much to do when you are through the gates, take pictures by the botanical gardens, get some drinks and snacks at the cafe, perouse the art gallery to support local artists, and you can even schedule a rappel tour where you can cruise down jungle cliffs and waterfalls. Hana Farms Roadside Stand is a must for any Hana trip. I am originally from New York and can confidently say that they have the best pizza on the island! Also, the Hana Farms offers a gorgeous, lush environment that transports you to a Bali inspired oasis. Seven Sacred Pools is one of the most popular stops on the road to Hana for a reason! The spectacular waterfalls that are out of a fantastical storybook, the streams cascade over the rocks creating breathtaking waterfalls that stream into plunge pools until the stream empties into the deep blue Hawaiian ocean. 


Day 5:  Ali’i Kula Lavender Farms and Kula Winery 


After adventuring the Road to Hana, it is crucial to take the next day to relax and unwind. Ali’i Kula Lavender Farms is a fantastic place to wander and breathe in the fresh Kula air with hints of lavender. The garden is extensive and the gift shop has so many wonderful goodies that are infused with fresh lavender from the farm. Last time I was there I discovered my favorite daily moisturizer and partook in freshly baked lavender scones that were out of this world! The lavender farm is a wonderful oasis with panoramic views of the island of Maui – a very enjoyable and relaxing destination to explore the best Maui has to offer. Any excuse I get when I am upcountry, I always take the chance to go to MauiWine which is a scenic vineyard and commercial winery. Their selection of handcrafted pineapple wines are unparalleled local favorites across the Hawaiian islands. Each wine reflects the richness of the island’s landscape and culture. The grounds of the winery transport you to the old Kingdom of Hawaii where the King’s cottage tasting room sits near ancient trees that have greeted guests for over 150 years. Sip on pineapple wine, take in the crisp Kula air, and feel the warm aloha. 


Day 6: Hike Haleakala Crater and Sunset on top of Haleakala 


There is no better way to explore Haleakala Crater than on your two feet! With over 30 miles of hiking trails that range from 10 minute walks to multiple day excursions. You can hike in the native shrubland, looking for native forest birds, endemic plants, or in the Aeolian cinder desert, exploring the geologic history of the volcano. The hike to the Haleakala crater is 2.2 miles round trip with a 400 ft change in elevation. When hiking to the summit it is crucial to be prepared, you will want to bring a backpack, jacket, water, snacks and an app for navigation, we love using the app AllTrails. If you plan ahead far enough, there is also a cabin nestled within the crater, where you can book the Historic Wilderness Cabins in Haleakalā National Park. I recommend going to the sunset on the top of Haleakala rather than the sunrise because you do not have to make a reservation, usually there is less people, and you can also stay up there at night and stargaze after the sun goes down. Both the sunrise and sunset on the top of Haleakala are magical and pictures do not do it justice. Make sure to check the weather before your trip and bring tons of jackets and blankets with you since it is very cold at the top of the crater. 


Day 7: Snorkeling Excursion to Molokini Crater 


Whether you are on the south side or west side, most molokini crater snorkeling excursions leave conveniently from Maalaea Harbor which is very central on the island. You can explore the crater year round, however it is optimal to go early in the morning before the tradewinds pick up. My favorite catamaran company for snorkeling excursions is The Trilogy. For breakfast on the spacious catamaran they serve fresh cinnamon rolls and Kona coffee.On The Trilogy excursion they make multiple stops – first at Molokini crater and then Turtle Town. After snorkeling, lunch is served like a sit down meal with a delicious plate lunch with proper silverware. The whole excursion is around 5 hours, so be sure to wear reef safe sunscreen! Molokini crater is an iconic snorkel destination of Hawaii with incredibly clear water off of Maui’s Southern coast. The reef visibility on most days is very clear. When I went on the excursion last I saw a diverse selection of marine wildlife, including sea turtles, various fish species, and manta rays! A snorkel tour is a MUST when exploring Maui!


Day 8: Beach Day at Black Rock Beach and Dinner at Whalers Village 


Black Rock beach on the west side of Maui is a family favorite for so many reasons! It is located in the resort area of Ka’anapali by the Sheraton. It is a public beach with things for everyone– whether you like sunbathing on the beach, dining at the hotel cabanas, cliff jumping into the ocean, snorkeling, boogie boarding, and much more! You can rent/buy beach gear from the concession stands, find a central spot on the beach for all family members, and enjoy the day doing various beach activities. After spending the day on the beach, I would recommend stopping at the infamous Whalers Village – an oceanfront mall with plenty of shops and restaurants to choose from. Some of my favorite restaurants at Whalers Village are Monkeypod, Hula Grill, and Leilani’s – perfect restaurants to go to for dinner after a joyous beach day. 


Day 9: Restaurants and Shopping on Front Street 


Front Street in the iconic Lahaina Town is a must-see when traveling to Maui. This quaint plantation-style port town has so many shops, restaurants, and art galleries to choose from. It is a great place to find souvenirs for friends and family. You can easily roam the streets for hours stopping into local boutiques and talking to artisans. The shopping is very diverse with lots of cost effective options as well as one-of-a-kind high end finds. On Front Street there are also historical buildings and parks surrounded by the notorious Banyan trees. Typically you can also find street vendors and musicians performing on the sidewalk. There is so much character and charm to the town hub of Lahaina – Front Street is a must-see!


Day 10: Relaxing Beach Day and Luau Dinner


For the last full day on Maui, it is important to take the necessary time to unwind before hopping back on a long flight to your busy everyday life. Enjoy the last day on the beach of your choice, appreciating the clear waters, soft sand, and sunkissed skin. For one last hoorah - head to a luau after your last beach day. Some lovely luaus I would recommend are Old Lahaina Luau and the Grand Wailea luau. The Old Lahaina Luau is one of the oldest luaus on the island and it is also the most authentic one I have been to. The luau is huge and can serve 500 people on any given night. The menu offers the traditional Polynesian feast – Kulua pork, lau lau, taro leaf stew and much more! The Grand Wailea luau is much more luxurious and well worth the price! The performance was absolutely spectacular and the food was Polynesian inspired with an elegant-flare the Grand Wailea is known for. My favorites on the menu include the Ahi Poke, Kulua pork, and flank steak. The food and entertainment at the Grand Wailea is top-notch – you will not be disappointed!


Get In Touch

We're a top-rated team, with a wealth of knowledge in the area. Fill out your information below and one of our team members will get back to you.

Work with Mick and Maggie

We offer the highest level of expertise, service, and integrity. Specializing in Luxury Homes & Investment Sales, Mick & Maggie has amassed a Rolodex of clientele that reaches far internationally. They pride themselves on ensuring their clients the highest level of success in all of their real estate ventures. Whether it’s your next investment condo, your first property, or your retirement villa, Mick & Maggie are here to serve.

Follow Us on Instagram