AI Travel Planner LogoaiplannerBrowse All

Maui 16-Day Trip Itinerary

Maui Trip - Jan 6, 2026 to Jan 21, 2026

Jan 6 - Jan 21

This 16-day multi-generational family trip to Maui, based in Kihei, promises a relaxed pace with diverse activities for everyone. From beach relaxation and nature exploration to cultural experiences and local food, this moderate to luxury Hawaiian escape caters to all ages, from active grandparents to young children.

Maui view
1

Arrival in Maui & Kihei Welcome

Tuesday, January 6
1.1
Afternoon

Arrive at Maui Airport (OGG)

Land at Kahului Airport (OGG), collect your luggage, and pick up your rental vehicle (highly recommended for Maui exploration) or arrange a shuttle/taxi to Kihei.

Pre-book your rental car well in advance, especially for a larger group and with car seats if needed. OGG is about a 25-minute drive from Kihei.

1.2
16:00

Check-in to Maui Coast Hotel

Settle into your accommodation in Kihei.

Take some time to unpack, relax, and explore the hotel's amenities.

Familiarize yourselves with the hotel layout, pool area, and any on-site dining options.

1.3
17:30
USD 0 for 6 people

Sunset Beach Stroll

Enjoy a leisurely walk along one of Kihei's beautiful beaches (e.

g., Kamaole Beach Park III, directly opposite the hotel). Let the kids play in the sand and the grandparents enjoy the ocean breeze as the sun sets.

Kihei beaches are known for their gentle waves, perfect for families. Don't forget sunscreen and hats!

1.4
19:00
USD 150-250 for 6 people

Casual Family Dinner

Dine at a family-friendly restaurant in Kihei.

There are many options ranging from casual Hawaiian plates to Italian or American cuisine.

Many restaurants in Kihei offer outdoor seating, which can be pleasant in the evening. Consider 'Da Kitchen Cafe' for local Hawaiian comfort food.

2

Kihei Beach Day & Relaxation

Wednesday, January 7
2.1
09:00 - 12:00
USD 0 for 6 people

Morning Beach Fun

Spend the morning at Kamaole Beach Park I or II, known for gentle waves and soft sand, perfect for swimming, building sandcastles, and wading for the younger ones.

Grandparents can relax under shaded areas.

These beaches have restrooms, showers, and picnic areas. Pack snacks, water, and plenty of sun protection.

2.2
12:30
USD 100-180 for 6 people

Lunch at a Local Eatery

Grab lunch at a casual spot in Kihei, perhaps a food truck or a local cafe.

Check out 'Maui Brewing Co.' for craft beer and pub fare (with a family-friendly vibe) or 'South Maui Fish Company' for fresh poke bowls.

2.3
14:00 - 17:00

Hotel Pool & Downtime

Enjoy the hotel pool, let the kids splash around, and allow everyone some relaxed downtime after the morning beach activities.

This is a great opportunity for naps or quiet play.

Take advantage of your hotel's amenities. Bring pool toys or floaties for the children.

2.4
18:30
USD 200-350 for 6 people

Fresh Seafood Dinner

Indulge in a fresh seafood dinner.

Maui offers fantastic options for locally sourced fish.

Consider 'Sansei Seafood Restaurant & Sushi Bar' for a lively atmosphere and delicious sushi/seafood or 'Coconuts Fish Cafe' for fish tacos.

3

Turtle Town Snorkel & Wailea Serenity

Thursday, January 8
3.1
09:00 - 11:00
USD 714 for 6 people

Marine Biologist Guided Snorkel

Embark on a unique shore snorkel tour at Turtle Town with a Marine Biologist.

Learn about Hawaii's vibrant marine life while observing sea turtles, coral, and colorful fish. Suitable for all ages and skill levels, with personalized guidance.

Booking is required. Wetsuits, snorkel gear, and photos included. This is a great educational and gentle activity for the whole family.

3.2
12:00
USD 150-280 for 6 people

Lunch in Wailea

After your snorkel adventure, drive a short distance to Wailea for lunch.

This area offers beautiful resorts and upscale dining options.

Consider 'Monkeypod Kitchen' for farm-to-table cuisine and famous pies, or 'Tommy Bahama Restaurant & Bar' for a relaxed atmosphere.

3.3
15:00
USD 49 for 6 people (base package)

Family Beach Photoshoot

Capture beautiful family memories with a professional photoshoot at a scenic beach in Wailea.

This activity is perfect for all ages and creates lasting souvenirs.

Booking required. Bold colors are recommended for clothing. The photographer will guide you to the best spots for lighting and scenery.

3.4
18:30
USD 150-250 for 6 people

Relaxed Dinner in Kihei

Head back to Kihei for a relaxed dinner at a local establishment, perhaps trying a different cuisine or revisit a favorite spot.

Consider '808 Deli' for gourmet sandwiches or 'Nalu's South Shore Grill' for Hawaiian-inspired dishes and live music.

4

Maui Marine Life Exploration

Friday, January 9
4.1
09:30 - 13:00
USD 200-250 for 6 people

Maui Ocean Center Aquarium

Explore the Maui Ocean Center, a world-class aquarium showcasing Hawaii's diverse marine life.

It features large exhibits of live Pacific corals, sharks, rays, and interactive displays, perfect for all ages.

Allow plenty of time to enjoy all the exhibits, especially the 750,000-gallon Open Ocean exhibit with a 54-foot walk-through tunnel. Pre-book tickets online to save time.

4.2
13:30
USD 100-180 for 6 people

Lunch near Ma'alaea Harbor

Dine at one of the casual eateries around Ma'alaea Harbor, conveniently located next to the Maui Ocean Center.

Try 'Ma'alaea General Store & Cafe' for local favorites or 'Beach Bums BBQ & Grill' for relaxed dining with harbor views.

4.3
15:00 - 18:00

Afternoon Relaxation at Hotel

Return to the hotel for some rest and relaxation.

Enjoy the pool, read a book, or let the children have some quiet time.

A relaxed afternoon ensures everyone stays refreshed and happy, especially the younger children and grandparents.

4.4
18:30
USD 80-150 for 6 people

Casual Pizza Night

Enjoy an easy and family-favorite dinner with pizza.

Kihei has several great pizza places offering various styles.

Check out 'Dollie's Pub & Cafe' for New York-style pizza and a casual atmosphere, or 'Fabiani's Italian Restaurant' for gourmet pizzas.

5

Local Market & Beach Day

Saturday, January 10
5.1
07:00 - 10:00
USD 10-50 for 6 people

Maui Swap Meet (Saturday)

Experience the vibrant local culture at the Maui Swap Meet, the island's largest open-air flea market.

Browse for local crafts, souvenirs, fresh produce, and delicious snacks. This is a Saturday-only event.

Arrive early for the best selection and to avoid the biggest crowds. It's a great spot for unique gifts and local food trucks.

5.2
10:30
USD 60-100 for 6 people

Brunch at the Swap Meet

Enjoy a casual brunch from one of the many food vendors at the Maui Swap Meet.

You'll find a variety of local treats and international flavors.

Sample different dishes from various vendors – it's a great way to try local specialties.

5.3
12:30 - 16:00
USD 0 for 6 people

Afternoon at Sugar Beach

Head back towards Kihei and spend the afternoon at Ma'alaea Beach, also known as Sugar Beach, one of Maui's longest sandy beaches.

It's great for long walks, shell collecting, and gentle swimming.

This beach is generally less crowded than Kihei's Kamaole beaches. It's also known for whale sightings from shore during whale season (Dec-May).

5.4
18:00
USD 300-600 for 6 people

Dinner with Ocean Views

Enjoy a lovely dinner at a restaurant with ocean views in Kihei or nearby Wailea, celebrating your first few days on Maui.

Consider 'Morimoto Maui' for exquisite Japanese-influenced cuisine at Andaz Maui in Wailea, or 'Mama's Fish House' in Paia for an unforgettable, albeit expensive, meal (book far in advance!). For a more relaxed option, try 'Sarento's on the Beach'.

6

Beach Day & Marine Life Discovery

Sunday, January 11
6.1
09:00 - 12:00

Morning at Kihei Beach

Enjoy a leisurely morning on one of Kihei's beautiful beaches, perfect for swimming, sunbathing, and building sandcastles with the kids.

The calm waters are ideal for young children and provide a relaxing start to the day.

Kihei boasts several fantastic beaches. Kamaole Beach Park I, II, or III are popular family choices with restrooms and lifeguards.

6.2
13:30 - 16:30
USD 200 for 6 people

Maui Ocean Center

Explore the wonders of Hawaii's underwater world at the Maui Ocean Center, home to one of the largest displays of live Pacific corals.

A fantastic educational and engaging experience for all ages, from the 4-year-old to the grandparents.

6.3
18:30 - 20:00

Dinner in Kihei

Dine at a family-friendly restaurant in Kihei, offering fresh local cuisine.

Many options provide outdoor seating with ocean views.

7

Molokini Snorkel Adventure

Monday, January 12
7.1
08:00 - 13:00
USD 1134 for 6 people

Molokini Snorkel & Turtle Tour

Embark on an exciting 5-hour boat tour to Molokini Crater, one of the best snorkeling spots in Hawaii, and then visit a turtle cleaning station.

The 'No Ka Oi' boat offers a comfortable and safe experience for the whole family.

Bring sunscreen, hats, and towels. Snorkel gear is typically provided. Early morning tours often have calmer waters. Product Code: 45339P2. Booking: https://www.viator.com/tours/Maui/4-Hour-Molokini-Snorkel-Tour-Adventure-in-Maui/d671-45339P2?mcid=42383&pid=P00266106&medium=api&api_version=2.0

7.2
14:00 - 17:00

Afternoon Relaxation

After your exhilarating morning on the water, enjoy a relaxed afternoon back at your hotel or on a nearby Kihei beach.

Perfect for napping, light reading, or playing by the pool.

7.3
18:30 - 20:00

Casual Family Dinner

Enjoy a relaxed dinner at one of Kihei's many family-friendly restaurants, perhaps trying some local Hawaiian comfort food.

8

Paddleboarding & Sunset Picnic

Tuesday, January 13
8.1
09:30 - 11:30
USD 954 for 6 people

Private Beginner Paddleboard Lesson

Take a private Stand Up Paddleboarding (SUP) lesson at Makena Landing.

This beginner-friendly session is perfect for your family group, ensuring everyone gets personalized attention and can enjoy floating above Maui's beautiful coastline.

Wear swimwear and bring water. The private setting is ideal for learning at your own pace. Makena Landing is known for its calm waters and turtle sightings. Product Code: 11724P2. Booking: https://www.viator.com/tours/Maui/Private-2-Hour-Beginner-Paddleboarding-101-from-Maui/d671-11724P2?mcid=42383&pid=P00266106&medium=api&api_version=2.0

8.2
12:00 - 17:00

Leisure & Lunch

Enjoy a relaxed afternoon after your paddleboarding adventure.

Grab lunch at a local eatery in Kihei and spend time relaxing at the hotel pool or a nearby beach, allowing for plenty of downtime.

8.3
17:30 - 19:00
USD 179 for 6 people

Romantic Sunset Picnic

Experience a memorable romantic sunset picnic at a pristine beach, complete with a charcuterie board and professional photos and video.

This intimate setting is perfect for couples or families to unwind and create beautiful memories as the sun sets over Maui.

Wear comfortable attire. This is a unique opportunity for family photos. Product Code: 408920P1. Booking: https://www.viator.com/tours/Maui/Charcuterie-Board-and-Sunset-at-a-Hidden-Beach-W-Photo/d671-408920P1?mcid=42383&pid=P00266106&medium=api&api_version=2.0

9

Whale Watching Excitement

Wednesday, January 14
9.1
10:00 - 12:00
USD 600 for 6 people

Prime Time Maui Whale Watching

Experience the magic of Maui's whale season on a 2-hour prime time whale watching tour.

With guaranteed whale sightings in January, this comfortable boat trip offers 360-degree views, perfect for photographers and families to witness these magnificent creatures.

January is peak whale watching season in Maui. Bring binoculars, a camera, and wear layers as it can be cooler on the water. Product Code: 5532808P2. Booking: https://www.viator.com/tours/Maui/2-Hour-Prime-Time-Maui-Whale-Watching/d671-5532808P2?mcid=42383&pid=P00266106&medium=api&api_version=2.0

9.2
12:30 - 17:00

Lunch & Poolside Afternoon

After your whale watching adventure, enjoy lunch at a casual spot and then spend a leisurely afternoon by the hotel pool.

Perfect for the kids to splash around and the adults to relax.

9.3
18:30 - 20:00

Family Games & Dinner

Enjoy a fun evening with board games or card games at the hotel, followed by a casual family dinner in Kihei.

10

Turtle Town Snorkel & Kihei Exploration

Thursday, January 15
10.1
09:00 - 11:00
USD 714 for 6 people

Marine Biologist Guided Snorkel

Discover Hawaii's vibrant marine life with a Marine Biologist Guided Snorkel Tour from shore at Turtle Town.

This easy and personalized experience is perfect for all skill levels, allowing your family to safely explore Maui's oldest and most colorful reef.

All snorkel gear is provided. Listen to your guide for an enriching educational experience about the local ecosystem and marine species. Product Code: 339602P1. Booking: https://www.viator.com/tours/Maui/Snorkel-with-a-Marine-Biologist/d671-339602P1?mcid=42383&pid=P00266106&medium=api&api_version=2.0

10.2
12:00 - 16:00

Kihei Shopping & Lunch

Spend a relaxed afternoon browsing the local shops and boutiques in Kihei for souvenirs or local crafts.

Enjoy a casual lunch at one of the many cafes or food trucks in the area.

10.3
18:30 - 20:30

Sunset Dinner in Kihei

Enjoy a special sunset dinner in Kihei, celebrating the wonderful coastal adventures and family memories made during this segment of your trip.

Consider a restaurant with ocean views.

11

Private Road to Hana Adventure

Friday, January 16
11.1
08:30 - 16:30
USD 2274 for 6 people

Private Road to Hana Tour

Embark on Maui's most popular private tour, the Road to Hana.

Your exceptional guide will provide a backstage pass experience, customized for your family's pace and interests, including stops at waterfalls and scenic viewpoints. This tour is renowned for its personalized approach.

Being a private tour, you can adjust the pace and stops to suit both the children and grandparents. Bring snacks, water, swimwear, and towels. Wear comfortable shoes for light walking.

11.2
18:00 - 19:30
USD 180-300 for 6 people

Relaxed Kihei Dinner

Enjoy a casual, family-friendly dinner at a local restaurant in Kihei after your day of exploration.

Many options offer beautiful sunset views.

Consider dining at a restaurant with outdoor seating to enjoy the evening breeze. Reservations are recommended for larger groups.

12

Pineapples & Whale Watching

Saturday, January 17
12.1
09:30 - 11:30
USD 210-300 for 6 people

Maui Pineapple Tour

Discover the history and cultivation of Hawaii's iconic pineapple with a guided tour.

Learn about the hard work that goes into producing this tropical fruit and enjoy fresh samples.

This educational and tasty tour is suitable for all ages. Pre-booking is highly recommended. Wear comfortable shoes.

12.2
12:00 - 13:00

Upcountry Lunch

Enjoy lunch in the charming Upcountry Maui area, perhaps in Makawao or Paia, before heading back towards the coast.

Explore local eateries offering fresh, farm-to-table options.

12.3
14:00 - 16:00
USD 600 for 6 people

Prime Time Whale Watching

Experience a guaranteed whale sighting tour.

Our newly remodeled boat offers comfort, 360-degree views, and plenty of space, making it a photographer's dream during whale season.

Whale watching is a fantastic experience for all ages in January. Bring sunscreen, a hat, and a light jacket. Motion sickness medication might be advised for those prone to seasickness.

12.4
16:30 - 18:00
Price varies

Browse Maui Swap Meet

Visit Maui's largest open-air flea market, offering local food, crafts, and unique souvenirs.

A great place to find bargains and local flavor.

Open every Saturday morning, so this afternoon slot might be less crowded towards closing. Cash is often preferred by vendors. Great for a casual browse.

13

Turtle Town Snorkel & Beach Day

Sunday, January 18
13.1
09:00 - 11:00
USD 714 for 6 people

Marine Biologist Guided Snorkel Tour

Snorkel from shore at Turtle Town with a marine biologist as your guide.

Discover sea turtles, vibrant coral, and colorful fish on Maui's oldest reef during this easy and personalized experience.

This guided tour is perfect for all skill levels, including beginners and children. All gear is provided. Listen to your guide for insights into the marine ecosystem. Remember to apply reef-safe sunscreen.

13.2
11:30 - 16:00

Relax at Kamaole Beach Park

Spend a relaxed afternoon enjoying one of Kihei's beautiful Kamaole Beach Parks.

These beaches offer calm waters for swimming, shaded areas for relaxation, and playgrounds for the kids.

The Kamaole beaches have lifeguards, restrooms, and picnic tables. Perfect for swimming, building sandcastles, or simply unwinding.

13.3
18:00 - 19:30
USD 180-300 for 6 people

Casual Kihei Dinner

Enjoy a relaxed dinner at one of Kihei's many family-friendly restaurants, perhaps trying some local Hawaiian fare.

Consider fresh seafood options, or places offering live music for an enjoyable evening.

14

Ocean Center & Sunset Memories

Monday, January 19
14.1
10:00 - 13:00
USD 180-240 for 6 people

Maui Ocean Center Aquarium

Explore Hawaii's marine life at the Maui Ocean Center, home to one of the world's largest displays of live Pacific corals.

An engaging and educational experience for all ages.

Perfect for a family outing, especially if you need a break from the sun. The exhibits are fascinating for both children and adults. Check for feeding times or special presentations.

14.2
13:30 - 14:30

Lunch near Ma'alaea Harbor

Enjoy a leisurely lunch at one of the restaurants around Ma'alaea Harbor after your aquarium visit.

Several casual dining options are available with harbor views.

14.3
16:30 - 17:30
USD 294 for 6 people

Maui Beach Photoshoot in Wailea

Capture beautiful family memories with a private beach photoshoot in Wailea.

The professional photographer will help you look your best against Maui's stunning scenery.

Bold colors photograph best for sunset; avoid wearing all white. Book early in your trip to avoid sunburn. This is a lovely way to create lasting souvenirs.

14.4
18:00 - 19:30
USD 1074 for 6 people

Romantic Sunset Picnic with Photo/Video

Indulge in a beautiful sunset picnic at a pristine beach, complete with a charcuterie board and professional photo and video capture.

A perfect way for the family to unwind and connect.

Enjoy the stunning natural beauty and delectable bites. This unique experience offers a relaxed atmosphere and beautiful photo opportunities for your family.

15

Beach Fun & Farewell

Tuesday, January 20
15.1
09:00 - 12:00

Morning at Kihei Beach

Enjoy a final leisurely morning at one of Kihei's beautiful beaches.

Swim, play in the sand, or simply relax under the sun. It's a perfect way to soak in the last moments of Maui's tranquility.

Choose a favorite beach from your stay or explore a new one nearby. Don't forget reef-safe sunscreen and plenty of water.

15.2
12:30 - 13:30
USD 150-240 for 6 people

Casual Farewell Lunch

Have a casual farewell lunch at a favorite Kihei eatery, perhaps trying a dish you haven't yet experienced.

Many restaurants offer quick and delicious options for lunch, from local Hawaiian plates to international cuisine.

15.3
14:00 - 16:00

Souvenir Shopping

Spend the afternoon browsing for last-minute souvenirs and gifts in Kihei or nearby towns to bring a piece of Maui home with you.

Look for local artisan crafts, Hawaiian-themed clothing, or unique food items. Lahaina offers a historic Front Street with many shops.

15.4
18:00 - 19:30
USD 240-450 for 6 people

Special Farewell Dinner

Enjoy a special farewell dinner to celebrate your memorable family trip to Maui.

Choose a restaurant with a pleasant ambiance and perhaps ocean views.

Reservations are highly recommended for a special dinner, especially for a group of 6. Consider a restaurant that offers a taste of authentic Hawaiian cuisine.

16

Last Aloha & Departure

Wednesday, January 21
16.1
08:30 - 10:00

Leisurely Morning & Beach Stroll

Enjoy a relaxed final breakfast at your accommodation or a local cafe, followed by a gentle stroll along one of Kihei's beautiful beaches, soaking in the last moments of your Hawaiian vacation.

Look for shells, enjoy the calm morning waters, and take in the panoramic views.

16.2
10:00 - 12:00

Last-Minute Souvenir Shopping

Explore the local shops in Kihei for any last-minute gifts or keepsakes to remember your Maui trip.

You'll find a variety of Hawaiian crafts, apparel, and local treats.

Many shops offer unique Hawaiian-made products. Consider visiting the 'Maui Crafts Guild' for artisan goods.

16.3
12:00 - 13:30
USD 120-180 for 6 people

Farewell Lunch in Kihei

Enjoy a final lunch at one of Kihei's family-friendly restaurants, savoring local flavors before heading to the airport.

Options range from casual eateries to those with ocean views.

Consider 'Coconuts Fish Cafe' for delicious fish tacos or 'Fork & Salad' for fresh, healthy options.

16.4
13:30 - 16:30

Hotel Check-out & Transfer to Kahului Airport

Complete your check-out procedures from the Maui Coast Hotel.

Allow ample time for the transfer to Kahului Airport (OGG), which is approximately a 25-30 minute drive from Kihei.

Ensure all luggage is packed and accounted for. Consider pre-booking a taxi or a larger shuttle service for your group and luggage.

This 16-day itinerary for Maui can be customized using our AI travel planner. Chat with our AI assistant to modify activities, adjust timings, add personal preferences, and get recommendations for restaurants, hotels, and transportation.