Hawaiian Islands in Winter: 10 Day Tropical Getaway

As I leaned over the boat railing on a crisp Maui morning, a gentle hush fell over the group—our guide pointed to a ripple on the horizon. Suddenly, a massive humpback whale breached, its glistening body catching the sunlight before crashing back into the turquoise waves. The awe-inspiring sight was accompanied by a thunderous splash and echoed by excited gasps. That moment, surrounded by the raw power and beauty of nature, reminded me why Hawaii in winter is nothing short of magical.

@camillalxy, Your AAdventure Guide

Essential Information

Sample Itinerary

Day 1 - Arrival in Honolulu (HNL) -> Waikiki Beach

Arrive at Daniel K. Inouye International Airport (HNL) in the afternoon, pick up your rental car, and check into your accommodation in Waikiki. Spend the evening exploring the vibrant Waikiki area, relaxing on the famous beach, and enjoying the lively atmosphere.

Day 2 - Hike Diamond Head -> Snorkeling at Hanauma Bay

Start your day with a morning hike up Diamond Head, one of Oahu's most iconic landmarks, offering panoramic views of Honolulu and the Pacific Ocean. In the afternoon, head to Hanauma Bay for an unforgettable snorkeling experience in crystal-clear waters teeming with colorful marine life.

Day 3 - Shark Diving at Haleiwa -> Kualoa Ranch

Begin the day with an exhilarating shark dive at Haleiwa, where you can safely encounter these majestic creatures up close. In the afternoon, explore Kualoa Ranch, known for its lush landscapes and as a filming location for numerous movies and TV shows. Enjoy a guided tour to discover the natural beauty and cinematic history of the ranch.

Day 4 - Hilo -> Hawai'i Volcanoes National Park

Return your rental car and catch a morning flight to Hilo International Airport (ITO) on the Big Island. Pick up a new rental car and check into your accommodation in Hilo. Spend the afternoon and evening exploring Hawai'i Volcanoes National Park, witnessing the awe-inspiring power of active volcanoes and otherworldly landscapes.

Day 5 - Punalu'u Beach -> Kona -> Manta Ray Night Snorkel

Drive from Hilo to Kona, stopping along the way at the striking black sands of Punalu'u Beach and the historic site of Ka Lae, the southernmost point in the United States. In the evening, arrive in Kona, check into your accommodation, and embark on a Manta Ray Night Snorkel Tour for an unforgettable underwater experience.

Day 6 - Kona Coffee Tour -> Mauna Kea Sunset and Stargazing

Start your day with a visit to a Kona coffee farm, where you can learn about the cultivation and processing of world-renowned Kona coffee and enjoy some tastings. Spend the afternoon and evening on the Mauna Kea Summit Adventure, witnessing breathtaking celestial views from one of the best stargazing spots on the planet.

Day 7 - Kahului -> Kapalua Coastal Trail -> Nakalele Blowhole

Catch a morning flight to the Kahului Airport (OGG) and check into your lodging in Kahului. Begin your Maui adventure with a scenic drive to Kapalua, where you'll hike the picturesque Kapalua Coastal Trail. After lunch, continue along the stunning coastline and conclude your afternoon at the dramatic Nakalele Blowhole before heading back to Kahului for a relaxing evening.

Day 8 - Sunrise at Haleakalā Summit -> Road to Hana -> Pīpīwai Trail

Start your day before dawn with a drive to Haleakalā Visitor Center to witness the unforgettable sunrise from Maui's highest peak. Afterward, embark on the Road to Hana, hike the Pīpīwai Trail to see lush rainforests and breathtaking waterfalls and explore the charming town of Hana. End your adventurous day with a drive back to Kahului.

Day 9 - Whale-watching Tour -> Old Lahaina Luau

Head to Lahaina in the morning for an unforgettable whale-watching tour, where you can see majestic humpback whales in their winter breeding grounds. Spend the afternoon strolling through Lahaina's historic streets and browsing local shops. Cap off your Maui journey with an evening at the Old Lahaina Luau, enjoying traditional Hawaiian cuisine, music, and dance.

Day 10 - Departure from OGG

Return your rental car and fly out of OGG, carrying with you unforgettable memories from your Hawaiian adventure. Don't forget to share your photos and experiences with us to be featured on Voyagers' social media. We'd love to hear your stories!

This Trip Is Best For

Hawaii first-timers: "I want to experience the full spectrum of Hawaiian winter activities."

Easygoing voyagers: "I appreciate a mix of relaxed schedules with moments of adventure."

Travel photographers: "I love capturing beautiful landscapes and taking stylish travel photos."

Outdoor adventurers: "I prioritize unique outdoor experiences over food and lodging conditions."

Independent explorers: "I enjoy a mix of guided tours and self-guided trips in a small group."

How To Autopilot

1. Pay a deposit to receive the full itinerary and secure your spot if you'd like to join a group.

2. Answer a few questions from us to be matched with compatible group members. 

3. Pay the balance to meet your group and get ready for your self-guided adventure together.

• Once you've met your group, no refunds will be issued for cancellations.
  
• Each additional participant you bring gets 10% off the balance for everyone in the same party, until your party size reaches the max group size of the trip.

For just $20 or less, you'll be ready to go with an actionable itinerary AND travel buddies you'll get along with.

That's like HOURS ⏰ of trip planning and HUNDREDS OF DOLLARS 💰 on travel agency SAVED ✅

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