Your Guide to Hawaii

Beaches, volcanoes, surfing, and more – Hawaii has something for everybody. We partner with an incredible portfolio of hotels, resorts, and activities, and will work closely with you to design your perfect Hawaii itinerary. But before you go, use our essential guide to Hawaii to help plan your vacation to our 50th state.


How long to spend in Hawaii:

If you’re traveling from the East Coast plant to spend at least 7 nights in Hawaii; from the West Coast spend at least 5 nights.

Island Hopping:

There are regularly scheduled flights between the islands and they normally take about ½ hour to 1 hour. On average, plan on spending about $100 per person each flight.

Insider Tip:

Most islands have either a Costco or a Sam’s Club, so if you’re a member of one you can save money on gas and stock up on essentials.



Kauai is the northernmost and oldest tourist island and has been the setting for many movies, including Jurassic Park.

What to do:

  • Visit Waimea Canyon aka the “Grand Canyon of the Pacific”

  • View the Napali Coast by boat or by helicopter

  • Kayak or paddleboard on the state’s only navigable rivers

  • Tube the irrigation ditches of former sugar plantations

Where to stay:

  • Grand Hyatt Kauai Resort & Spa: fabulous lagoon-style pool (note the beaches are not swimmable)

  • Koloa Landing Resort: a condo-style property with A/C (not all condo properties have A/C!)

  • Koa Kea Hotel: great for couples

  • Princeville Resort


Oahu is home to Hawaii’s capital, Honolulu, and boasts an exciting mix of both history and adventure.

What to do:

  • Privately guided tour of Pearl Harbor

  • Surfing lessons

  • Helicopter tour

  • Hike Diamond Head and so many more!

  • Snorkel in Hanauma Bay

Where to stay:

  • The Kahala Hotel & Resort: Beachfront property in Waikiki

  • Aulani, a Disney Resort & Spa: Hawaiian feel with a touch of Disney — perfect for families

  • Turtle Bay Resort: get away from the city and experience authentic Oahu; location of Forgetting Sarah Marshall and Soul Surfer


One of the most popular islands, Maui is the valley isle and has great beaches.

What to do:

  • Sunrise at top of Haleakala

  • Whale watching in winter months

  • Snorkeling in Molokini Crater and Maluaka Beach

  • Power hang gliding in Hana

Where to stay:

  • Andaz Maui at Wailea: located in Wailea and has a gorgeous beach

  • Four Seasons Maui at Wailea: great beach and pools with some spectacular activities offered

  • Montage Kapalua Bay: beautiful property with fabulous Brownell amenities (like an upgrade at time of booking!)

  • Hana-Maui Resort: Decompress from your travels at one of the only hotels in Hana


A less commercialized island (we’re talking only one traffic light!), Lanai offers a more off-the-beaten path experience.

What to do:

  • Relax on the beach

  • Spot spinner dolphins or whale watch (when in season)

  • One of the many Lanai Adventures at the Four Seasons (like clay shooting or the adventure park).

Where to stay:

  • Four Seasons Resort Lanai: recently renovated and one of the most luxurious resorts in Hawaii

  • Sensei Lanai, A Four Seasons Resort: experience an adults-only, luxurious wellness enclave


The island of Hawaii, more commonly known as the Big Island, earned its nickname for a reason – all other islands can fit in it and it is still growing!

What to do:

  • Stargazing at the Mauna Kea observatory

  • Enjoy views from the many scenic overlooks

  • Explore waterfalls and black sand beaches

  • Nighttime manta ray snorkel trip

  • Visit Kona Coffee farms

Where to stay:

  • Mauna Lani, Auberge Resorts : Situated on 32 acres with 3 miles of walkable beach and recently renovated

  • Four Seasons Resort Hualalai: Villas and larger suites are great for families

Ready to book your Hawaiian adventure? Contact Red Letter Travel today!

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