After 6 trips to Hawaii from California and countless island-hopping adventures, I’ve developed an intimate understanding of each island’s distinct personality. From my first wide-eyed visit to Oahu after high school graduation to attending destination weddings in Maui, these islands have evolved from mere vacation spots into deeply familiar territories with their own rhythms and secrets.

best island to visit in hawaii: The Ultimate Guide to Choosing Your Perfect Hawaiian Island

Personal Take: Why Hawaii Keeps Drawing Me Back

Living in California means Hawaii is practically in our backyard—a mere 5-6 hour flight away. I’ve watched Maui transform through different seasons, discovered hidden corners of Oahu that tourists rarely see, and developed a deep appreciation for how each island offers something uniquely compelling. Hawaii isn’t just a collection of beaches strung across the Pacific—it’s a living, breathing network of distinct personalities. Each island pulses with its own energy, The food scene alone (particularly on Oahu) keeps drawing me back, not to mention those perfect beaches and the infectious spirit of aloha that permeates daily life.

Which of the Hawaiian Islands is the best to visit

Breaking Down best hawaii island to visit

Let me give you a guide with detailed pros and cons for each island, the best things to do , and where to stay. Starting with the most popular island.

Maui : The Versatile Charmer

After attending three destination weddings here, I can confidently say Maui masters the art of being all things to all people.

Join the newsletter

Don’t miss out on the latest travel intel &deals

Email*

Submit

Maui Island Character

• Diverse landscapes from rainforest to desert
• Perfect blend of luxury and local culture
• Consistently excellent weather on the leeward side
• Home to Hawaii’s most diverse beach collection
• West Maui offers the perfect blend of luxury and local charm
• Upcountry Maui holds the island’s authentic soul
• South Maui delivers consistently perfect weather
• Insider discovery: The food truck scene in North Kihei rivals Oahu’s best kept secrets

Maui is best island in Hawaii to go for 

• best island to visit in hawaii for first time
• best island to visit in Hawaii for couples
• Families seeking balance
• Beach enthusiasts

Where to Stay in Maui Hotels:

• Four Seasons Maui at Wailea (luxury perfected)
• Westin Ka’anapali Ocean Resort Villas (ideal for extended stays)
• Hyatt Regency Maui Resort & Spa

things to do in the hawaiian islands of Maui

• Road to Hana Tour (start by 7 AM to beat crowds)
• Maui Nui Luau at the Sheraton
• Molokini Crater Snorkeling
• West Maui and Molokai Helicopter Tour
• Haleakalā Sunrise Tour (book permits 60 days in advance)
• Ka’anapali Beach sunset sail
• Twin Falls early morning hike
• Hidden gem: Little Beach on Sunday evenings for drum circles

Maui Pros vs Cons: best Hawaiian island to visit

Pros:

• Most diverse selection of beaches I’ve encountered in Hawaii
• Perfect balance of development and natural beauty
• Spectacular whale watching (Dec-April)
• Diverse dining scene from food trucks to fine dining
• Consistently amazing weather on the leeward side
• Ideal mix of luxury resorts and local experiences
• Insider note: The food truck scene in Kihei rivals anything I’ve found on Oahu

Cons:

• Significant crowds at major attractions
• Car rental absolutely necessary (and expensive)
• Restaurant prices often shock even California natives
• Limited authentic local experiences in tourist areas
• Personal pain point: The Road to Hana gets more crowded each year

hawaiian islands oahu- The Dynamic Heart

My first Hawaiian love—where I discovered poke bowls before they were trendy. Having watched Oahu evolve from my post-graduation trip to now, I’ve seen it masterfully balance cosmopolitan energy with authentic Hawaiian tradition. The island somehow manages to feel both energetically modern and deeply rooted in history.

hawaiian islands oahu Character

• Most developed Hawaiian island
• Dramatic mountain ranges frame city views
• Perfect mix of urban and island experiences
• Cultural hub of the Hawaiian archipelago

Oahu best place to stay in Hawaii for

• Urban explorers
• Best places to visit in Hawaii for families 
• Food enthusiasts
• History buffs
• Shopping aficionados

Where to Stay in Oahu Hotels

• Luxury: Moana Surfrider (historic elegance meets bea ch access)
• Luury: The Ritz-Carlton O’ahu, Turtle Bay (North Shore escape)
• Boutique: The Laylow (boutique charm in Waikiki)
• Insider tip: The Laylow’s location in the heart of Waikiki is unbeatable for food exploration

things to do in the hawaiian islands of Oahu

• North Shore food truck circuit
• Pearl Harbor Tour (book first morning tour)
• Private Oahu Sunset Charter 
• Diamond Head sunrise hike
• Kualoa Ranch private tour

Oahu Pros vs Cons: best places to visit in hawaii islands

Pros:

• Best food scene in Hawaii (particularly Asian fusion)
• Excellent flight connections and typically best fares
• Incredible hiking options within city limits
• Rich cultural and historical sites
• Most diverse accommodation options
• Hidden gem: The north shore still feels authentically Hawaiian

Cons:

• Waikiki can feel overwhelmingly commercial
• Traffic rivals Los Angeles (no joke)
• Popular beaches get extremely crowded
• Higher crime rate than other islands
• Reality check: Finding authentic local experiences requires effort

Transportation

• TheBus: Extensive public transit network ($3 per ride)
• Rental car: Essential for exploring beyond Waikiki. Book on Discovery Cars
• Waikiki Trolley: Convenient tourist loops
• I suggest renting a car for at least two days

Best places to visit hawaiian islands

Kauai – Nature’s Masterpiece

My go-to recommendation for friends seeking the Hawaii of their imagination—raw, beautiful, and slightly wild.

Kauai  Island Character

• Most lush Hawaiian island
• Dramatic Na Pali coastline
• Small-town atmosphere prevails
• Limited development by law (no building taller than a coconut tree)

Kauai best places to stay in Hawaii for

• Nature photographers
• Hiking enthusiasts
• Peace seekers
• Adventure couples

Where to Stay in Kauai Hotels

• Luxury: Grand Hyatt Kauai
• Mid-Range: Koa Kea Hotel
• Boutique: Koloa Landing Resort at Po’ipu
• Personal discovery: The north shore properties offer the most dramatic mountain-meets-ocean views I’ve encountered in Hawaii

things to do in the hawaiian islands of Kauai

• Nā Pali Coast (boat tour in summer, helicopter tour in winter)
• Waimea Canyon at sunrise
• Hanalei Bay snorkeling
• Insider tip: The Kalalau Trail requires permits months in advance—book the second they’re released

Kauia Pros vs Cons: best hawaiian island to visit

Pros:

• Most dramatic natural scenery
• Least developed major island
• Best hiking trails (personal opinion)
• Most peaceful atmosphere
• Authentic Hawaiian vibe still intact
• Secret plus: Best sunsets I’ve seen in Hawaii

Cons:

• Frequent rain (it’s called the Garden Isle for a reason)
• Limited dining and shopping options
• Fewer direct flights
• Activities often weather-dependent
• Worth noting: Some of the best beaches require serious hiking

Best place in Hawaii to visit

Kona Big Island – The Adventure Laboratory

This island continuously surprises me—where else can you experience snow-capped mountains and active volcanoes–– where else can you experience 8 climate zones in one day?

IKona Big Island sland Character

• Twice the size of all other Hawaiian islands combined
• Home to active volcanoes and 11 climate zones
• Rich agricultural heritage (coffee, chocolate, vanilla)
• Newest and still-growing Hawaiian island

Kona Big Island best place to stay in Hawaii for

• Geology enthusiasts
• Coffee aficionados
• Astronomy buffs
• Adventure seekers

Where to Stay in Big Island Kona Hotels

• Luxury: Fairmont Orchid (Kohala Coast luxury)
• Mid-Range: Holualoa Inn (coffee country elegance)
• Unique Experience: Volcano House (within the national park)
• Pro tip: Split your stay between Kona and Volcano Village for the full experience

things to do in the hawaiian islands of Kona Big Island

• Manta ray night dive
• Early morning coffee farm tours (Greenwell Farms opens at 8:30)
• Sunrise at Mauna Kea summit
• Fair Wind morning snorkel cruise
• Hidden gem: Kahalu’u Beach Park for turtle watching

Big Island Kona Pros vs Cons

Pros:

• Only active volcanoes in Hawaii
• Most diverse landscapes
• Best stargazing in the Northern Hemisphere
• Lowest tourist density per square mile
• Most affordable accommodation options
• Unexpected bonus: Best coffee culture in Hawaii

Cons:

• Requires extensive driving
• Fewer white sand beaches
• Variable volcanic activity
• Different sides of island have dramatically different weather
• Reality check: The size can be overwhelming for short trips

Transportation Essentials

• Rental car mandatory—choose 4WD for summit access
• Plan for long drives between attractions
• Two major airports: Kona (KOA) and Hilo (ITO)

best places to see in hawaii

Lānai: The Refined Escape

An island that taught me luxury and authenticity aren’t mutually exclusive.

Lanai Hawaii Island Character

• No traffic lights—just pure island rhythm
• Only 30 miles of paved roads
• Former pineapple plantation turned luxury escape
• Population under 3,500
• Home to Hawaii’s most pristine beach (Hulopoʻe)
• Perfect for digital detox getaways
• Personal observation: The morning light in Lānaʻi City is pure magic

Where to Stay in Lanai Hotels

• Four Seasons Lanai (unparalleled luxury)

things to do in the hawaiian islands of Lanai

• Hulopoe Beach snorkeling (morning for spinner dolphins)
• Garden of the Gods at sunset
• Lanai Cat Sanctuary visits
• Four Seasons cultural programs
• Polihua Beach 4×4 expedition
• Kaiolohia (Shipwreck Beach) exploration
• Saturday market in Dole Park

Lanai Pros vs Cons

Pros

• Uncrowded beaches
• World-class golf
• Exceptional snorkeling
• True escape from crowds
• Unique red rock landscapes

Cons

• Limited dining options
• Expensive accommodations
• Minimal nightlife
• Limited direct flights

Transportation Notes:

• Limited rental car availability—book months ahead
• Most resorts offer shuttle services
• Consider scheduling a 4×4 tour
• Strategy: Combine with Maui for a perfect luxury duo

Best places in Hawaii to go

Molokai: The Untouched Hawaii

Where I go when I need to remember what Hawaii felt like decades ago.

Molokai Island Character

• Most traditional Hawaiian culture
• World’s highest sea cliffs
• Limited tourist infrastructure
• Authentic local lifestyle
• Reality check: This isn’t for everyone—and that’s its charm

Where to Stay in Molokai Hotels

• Hotel Molokai remains the primary option
• Vacation rentals require deep research
• Limited but authentic choices
• Insight: Book through local connections when possible

things to do in the hawaiian islands of Molokai

• Kalaupapa National Historical Park (mule ride or hike)
• Halawa Valley cultural hike
• Papohaku Beach sunset

Molokai Pros vs Cons

Pros

• Genuine Hawaiian experiences
• Uncrowded everything
• Outstanding photography opportunities
• Rich cultural heritage
• Hawaii’s longest white sand beach

Cons

• Very limited amenities
• Few tourist facilities
• Minimal dining options
• Limited accommodations

Getting Around:

• Rental car mandatory book on Discovery Cars for best rates
• Limited taxi services
• No ride-share options

Choosing Your Perfect Island Match

Choose Maui If You:

• Want the perfect balance of activities and relaxation
• Seek excellent resorts and dining options
• Love diverse beach experiences
• Enjoy road trips (Road to Hana)
• Value consistent weather

Choose Oahu If You:

• Appreciate urban conveniences
• Want extensive dining options
• Love mixing history with beach time
• Need excellent shopping
• Enjoy nightlife options

Choose Kauai If You:

• Prioritize natural beauty
• Love hiking and outdoor activities
• Prefer smaller crowds
• Don’t mind some rain
• Seek authentic Hawaiian culture

Choose The Big Island If You:

• Want to see active volcanoes
• Enjoy coffee culture
• Seek astronomical experiences
• Like road trips and exploring
• Appreciate diverse climates

Choose Lanai If You:

• Want ultimate luxury
• Seek complete privacy
• Love golf
• Don’t mind limited dining options
• Appreciate exclusive experiences

Choose Molokai If You:

• Want the most authentic Hawaiian experience
• Don’t need luxury amenities
• Appreciate slow-paced life
• Seek true solitude
• Value cultural immersion

Helpful Tip: First-time visitors often try to pack too many islands into one trip. I’d recommend spending at least 5-7 days on one island rather than island-hopping – you’ll get a much deeper experience of the place and its unique rhythm.

Best Time to Visit Hawaii

My years of strategic trip planning have taught me this: each season in Hawaii offers distinct advantages.

When to Visit Hawaii

High Season in Hawaii ( Hawaii in December – April)

• Peak whale watching season (especially in Maui)
• Perfect escape from mainland winter
• Higher prices and larger crowds
• Personal tip: I’ve found mid-January to be the sweet spot—just after the holiday crowds disperse

Shoulder Season in Hawaii ( Hawaii in  May & September-November)

• My favorite time to visit
• More reasonable prices on accommodations
• Excellent weather conditions
• Ideal swimming conditions
• Insider tip: October brings perfect beach weather without peak season crowds

Low Season / Summer in Hawaii ( Hawaii in June – August)

• Counter-intuitive but true: summer is actually low season
• Warmest temperatures
• Consistent, dry weather
• Ideal for water activities
• Pro tip: Book August trips for best deals while maintaining perfect weather

How Many Days to Spend in hawaii

Ideal Trip Lengths:

• Single Island:
  • Maui: 7-10 days
  • Oahu: 5-7 days
  • Kauai: 6-8 days
  • Big Island: 8-10 days
• Multi-Island:
  • Two Islands: Minimum 10 days
  • Three Islands: 14+ days
  • From experience: Anything less than 5 days per island creates more stress than enjoyment

Getting to Hawaii & Around

Flight Strategy

• Monitor prices 3-6 months out
• West Coast sweet spot: $300-400 roundtrip
• East Coast target: $600-700 roundtrip
• I use Hawaiian Airlines miles for inter-island flights
• Book Hawaiian Airlines for most reliable service
• Southwest offers competitive inter-island fares
• Morning flights face fewer delays

Airport in Hawaii

Honolulu International Airport (HNL)

• Most frequent mainland connections
• Primary hub for inter-island flights
• Pro tip: Terminal 2 houses most major carriers

Airport Transfer Options:

1. Hawaii Express Shuttle
   • Most cost-effective for Waikiki transfers
   • $17 to Waikiki
   • Advance booking essential
   • Services all major hotels
2. Private Car Services
   • Worth the splurge after long flights
   • $55-65 flat rate
   • Fixed rates eliminate surprises
   • [ BOOK HERE ]
3. Ride Share
   • Uber/Lyft pickup at designated area
   • Ride share: $25-35 depending on time
   • Surge pricing common during peak arrival times
   • Strategy: Walk to Terminal 2 for better pickup options

Rental Cars in Hawaii

• Essential on all islands except central Waikiki
• Book through Discover Cars for best rates
• Reserve months ahead for peak seasons
• Personal strategy: I always book a cancelable rate and keep checking for price drops

Hawai Island-Specific Transport Notes:

• Maui: Car essential, especially for Road to Hana
• Oahu: Optional in Waikiki, necessary elsewhere
• Kauai: Absolutely required
• Big Island: Non-negotiable due to size

Hawaii Island Hopping Guidelines

• Allow 4 hours between flights for connections
• Factor in rental car return time
• Consider weather patterns when planning
• My rule: minimum 3 nights per island

Hawaii Island Accommodation Strategy

Booking Windows:

• Peak Season (December-April): 6-8 months ahead
• Shoulder Season: 3-4 months ahead
• Low Season: 2-3 months ahead
• Inside track: Many properties offer “book early” rates 9+ months out

Property Types:

• Resorts: Best for first-timers and special occasions
• Condos: Ideal for families and longer stays
• Vacation Rentals: Perfect for authentic experiences
• Personal preference: I mix luxury resorts with local rentals for the full spectrum

Strategic Combinations for Hawaii Multi-Island Trips

Popular Pairings (Based on Personal Experience):

First-Timer’s Perfect Duo (10-12 days):

• Maui (6-7 days) + Oahu (4-5 days)
• Why it works: Combines classic Hawaiian beauty with urban convenience

Nature Lover’s Dream (12-14 days):

• Kauai (7 days) + Big Island (7 days)
• Personal favorite: Maximum natural diversity, minimum tourist crowds

Best of All Worlds (14+ days):

• Maui (5 days) + Big Island (5 days) + Oahu (4 days)
• Insider strategy: Start busy, end relaxed

Hawaii Money-Saving Tips

Flight Strategy:

• Book 3-6 months out
• Consider mainland airport alternatives
• Use Hawaiian Airlines miles for inter-island
• Score: Found $259 SFO-OGG fares booking 4 months ahead

Accommodation Hacks:

• VRBO often beats hotel rates
• Consider shoulder season travel
• Join hotel loyalty programs
• Insider move: Book cancelable rates and monitor price drops

Hawaii Packing Tips

Beach Essentials

• Reef-safe sunscreen (Hawaii law requirement)
• Multiple swimsuits (humidity affects drying time)
• UV protective rash guard
• Quick-dry beach towels
• I pack older suits—salt water and sand take their toll

Hiking Gear

• Sturdy water shoes (essential for waterfall hikes)
• Lightweight rain jacket
• Hiking sandals with grip
• Backpack with water bladder
• My must-have: microfiber towels for sudden showers

Hawaiian island Cultural Awareness & Etiquette

Essential Protocol

• Remove shoes when entering homes
• Respect sacred sites
• Learn basic Hawaiian words
• Accept hospitality graciously

Environmental Responsibility

• Use reef-safe sunscreen only
• Stay on marked trails
• Respect wildlife distance guidelines
• Follow local fishing regulations

Final Thoughts on best hawaii places to visit 

Hawaii isn’t just another beach destination—it’s a living, breathing cultural treasure that rewards those who approach it with respect and curiosity. After countless visits, I’m still discovering new corners and experiences that surprise me.

Remember: The perfect Hawaiian vacation isn’t about checking off every tourist spot—it’s about finding your own rhythm with these magnificent islands. Whether that means surfing at sunrise in Waikiki or finding a secret beach on Kauai’s north shore, Hawaii has a way of revealing exactly what you need, often in unexpected ways.