A Relaxing and Adventurous Vacation to Maui

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Curated By

Danielle Di Maio

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  • USA

  • Hawai'i

  • Maui

  • Adventure Travel

  • Beaches

  • Domestic Travel

  • Tropical Vacations

  • Relaxation

  • Wineries

Footprints on a tan sand beach with white waves and green palm trees in Maui, Hawaii.
Curator’s statement

Maui is truly the ultimate paradise: tropical weather, breathtaking sunsets, magnificent landscapes, pristine beaches, an incredible food and drink scene and so much more. Whether you want relaxation, adventure or something in between, this beloved Hawaiian island has a little piece of paradise for everyone.

The Fora Difference

Book with Danielle to access exclusive perks and experiences on your trip.

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Killer perks

Free upgrades, spa credits and more—we got you

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Personalized recs

Customized travel planning for your style

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Insider knowledge

Expert advice from people who’ve actually been there

Where to stay

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Andaz Maui At Wailea Resort - a Concept by Hyatt

Guests come to Andaz Maui for its luxe accomodations, but stay for its vibrant cuisine and cascading infinity pools overlooking the ocean.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Four Seasons Resort Maui at Wailea

Expect spot-on service, a mix of upscale restaurants and a prime location overlooking famed Wailea Beach.

Fora Perks
  • When you book Four Seasons through Fora, you will enjoy exclusive Four Seasons Preferred Partner benefits. Your advisor will be pleased to give you more details.

Montage Kapalua Bay

On Maui’s northwest coast, this all-suite resort incorporates Hawaiian culture into everything from its architecture and restaurants, to kids’ club and spa.

Fora Perks
  • $150 spa credit.

  • $60 breakfast credit daily.

  • Upgrade & extended check-in/out whenever possible.

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Unlock perks by contacting Danielle to book your trip.

Day 1: Arrive in Maui

A large brown banyan tree with green leaves in Maui, Hawaii.

Upon arrival, take the first day to explore the historic town of Lahaina at your leisure. Some must do's and must see's are:

  • Banyan Tree Park

  • Lahaina Front Street (for shopping!)

  • The rooftop at Fleetwood's on Front Street for a drink

Enjoy your first dinner at the five star Lahaina Grill – considered one of the top dining restaurants in the United States.

Day 2: Wine and luau

A paved road with a white truck driving into green mountains into the distance in Maui, Hawaii.

Take the scenic drive to Maui's best known winery, Maui Wine, and take in the beautiful views of Maui's south coast with a wine glass in hand. On your way there (or back) stop at The Mill House for lunch.

At night, attend an authentic Hawaiian Luau known as the Old Lahaina Luau, complete with traditional Hawaiian cuisine, culture and music. Afterwards, enjoy drinks on the harbor at Kimo's Maui.

Day 3: Beach it up

A yellow sunset over the water with four boats floating in Maui, Hawaii.

Today, you have options! Snorkel at some of Maui's most pristine reefs and take in views of Lana'i's stunning sea cliffs on a luxury catamaran. Tropical fruits, drinks and lunch all included on this five hour, relaxing cruise.

Or you can explore Maui's beaches at your own leisure. Some great options are Ka'anapali Beach, Black Rock Beach (both close to your hotel and great for snorkeling!) and Big Beach. 

For lunch, if you are near Lahaina, stop at Down The Hatch. If you're near Big Beach,  Jazzy's Kitchen Mexican Food Truck is a classic for some tacos.

Head to Maui's north shore for a dinner at Mama's Fish House, a local landmark complete with a seafood-driven Hawaiian menu, Polynesian decor and epic ocean views – considered a must visit when you are on Maui.

Day 4: Road to Hana

A pavement road with a red car driving up in the middle of lush greenery on The Road to Hana in Maui, Hawaii.

Begin your drive to Hana town (you'll want to leave early!), which will take roughly six to ten hours, depending on how long you stop at each spot. It is worth noting that you can turn around whenever you want! Most people drive to Hana and back instead of doing a full loop for the sake of time.

Must-sees on the Road to Hana: 

  • Ho'okipa Beach Park

  • Twin Falls

  • Maui Garden of Eden

  • Wailea State Wayside Park

  • Hanawi Falls

  • Nahiku Marketplace

  • Wai’anapanapa State Park

  • Hana Town

  • Hamoa Beach

  • Seven Sacred Pools

While in Hana, try Koki's Famous Huli Huli Chicken or Aunt Sandy's Banana Bread for a snack. For dinner, try some highly rated, delicious Italian food at Sale Pepe.

Day 5: Cruising and bites

Fish tacos and a green kale salad on white plates with a pink cocktail at Leilani's On The Beach in Maui, Hawaii.

Enjoy doing absolutely nothing today! Hang back at your beautiful resort and enjoy the pool or beach at your leisure.

Head to Honu Oceanside for lunch with beautiful ocean views.

Set sail on the number one sunset dinner cruise on Maui, known as the Pride of Maui. Dinner includes appetizers, locally grown salad, a choice of entrées, dessert and an array of drinks and cocktails. Island-style music and open sea views of Maui’s scenic coast add to the ambience of this memorable experience. 

Enjoy your last night with drinks at Leilani's On The Beach.

Need to Know

Hop on over to California and check out my '3-Day Guide to Food, Wine and Relaxation in Napa Valley, California'.

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Travel Advisor

Danielle Di Maio

Get in touch with Danielle

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