Expert Advice

The Ultimate Hawaiian Island Hopping Itinerary — Things To Do, Where To Eat And Where To Stay With Hilton Grand Vacations

See Oahu, Kauai, Maui and the Big Island in just 11 days

Raeanne V
A Hilton Grand Vacations Member surfs in Oahu, Hawaii

Aloha. Welcome to Hawaii, a string of eight major islands in the vast expanse of the Pacific Ocean. While I’ve spent a month in Oahu, island hopping is a great way to maximize your vacation and see several islands in one trip.

Dive into my island-hopping highlights and see how you can embark on an adventure to Oahu, Maui, Kauai and the Big Island — plus my recommendations of things to do and restaurants to visit.

A Hilton Grand Vacations Member on China Walls in Oahu, Hawaii, at sunset 


Day 1: Wander Waikiki Beach

Morning: Start your day with a hearty breakfast at Island Vintage Coffee, ALOH Health Bar & Cafe or Kono’s. Then soak in the sun as you watch surfers catch party waves at Kuhio Beach, or try your hand at surfing with a board rental or lesson from Moku Surf Shop.

Afternoon: A trip to Hawaii isn’t complete without poke, and Maguro Spot is the place to go. After enjoying this Hawaiian staple, take a trip to the Honolulu Zoo or shop until you drop at Kalakaua Avenue.

Evening: Make a dinner reservation at Eating House 1849 or Roy’s to celebrate the start of your vacation. Then dance the night away at Buho or enjoy artsy cocktails and live music at The Gallery Waikiki.

Day 2: Tour The North Shore

Morning: Begin with breakfast at Farm to Barn or Coffee Gallery. Head to the historic surf town of Haleiwa, where you can explore surf shops, art galleries and clothing stores.

A Hilton Grand Vacations Member scuba dives in Oahu, Hawaii 

Afternoon: Savor a meal from North Shore’s food trucks. Giovanni’s Shrimp Truck is famous across Oahu.

After grabbing a bite, head to Laniakea Beach to see sea turtles, relax at Sunset Beach or schedule a dive with Banzai Divers at Shark’s Cove.

Evening: Return to Waikiki and stop at Oahu’s “it” community Kaka’ako for dinner. Try traditional Hawaiian plates at Highway Inn, or explore other hip cafes and restaurants in this up-and-coming area.

Day 3: Explore East Side

Morning: Start your day with a sunrise hike to Lanikai Pillbox. After your hike, relax on the powdery white sand and swim in Lanikai Beach's calm waters.

Afternoon: Enjoy Korean-style fried chicken on loco moco — a Hawaiian dish with rice, a hamburger patty and a fried egg topped with gravy — at The Food Company. Or try a Hawaiian plate and haupia ice cream at Waiahole Poi Factory.

Finish the afternoon with a thrilling UTV adventure or horseback riding tour at Kualoa Ranch  — and feel like you’re in Jurassic Park.

A Hilton Grand Vacations Member's photo of Hilton Hawaiian Village® Waikiki Beach Resort from their room in Oahu, Hawaii 

Evening: End your day with an epic sunset at China Walls for stunning views as the sun sets behind Diamond Head. If you’re adventurous, you can join surfers and cliff-jumpers and take advantage of the waves crashing against the rock platforms. Top off the night at Kona Brewing Company or Marugame Udon in Waikiki.

Where To Stay In Oahu

Hilton Hawaiian Village® Waikiki Beach Resort offers incredible views along Honolulu’s pristine beaches. Stay at one of these Hilton Grand Vacations timeshares within this slice of paradise and access resort amenities like sparkling pools and luaus:


Day 4: Pause In Poipu

Morning: Arrive in Kauai and settle into your Suite. Head to Spouting Horn blowhole to witness this dramatic natural wonder.

Afternoon: Just a short drive from Spouting Horn are The Shops at Kukui’ula. Savor delicious bites and peruse a variety of stores at your leisure. After lunch, head to Lawa'i Beach to discover coral, fish and other marine life.

A Hilton Grand Vacations Member on the Awa'awa'puhi Trail in Kauai, Hawaii 

Evening: Enjoy the sunset at Poipu Beach or from the poolside of the resort. Go for a nice dinner at Merriman’s, or stay in and have a relaxing game night while making kalbi or burgers at the resort’s grills.

Day 5: Choose Your Adventure On Kauai

Morning: Looking for a cute cafe this morning? Little Fish Coffee offers organic, fair-trade coffees, smoothies, fresh acai bowls, and tasty breakfast sandwiches.

Afternoon: Choose whether you’d rather spend the day in the ocean or the mountains.

If you prefer to stick to the seas, sail away on a catamaran journey along the majestic Na Pali Coast. My all-time favorite activity in Hawaii was a sunset snorkel tour with Kauai Sea Tours. This catamaran tour offers captivating views of the coast and surprise visits from spinner dolphins, turtles and whales. The all-star crew truly makes this an unforgettable experience.

A Hilton Grand Vacations Member takes a selfie while on a catamaran on Kauai's Na Pali Coast in Hawaii 

If a day at sea isn’t your thing, discover the breathtaking canyons and awe-inspiring landscapes of Kauai on foot. First, stop by Waimea Canyon State Park for a scenic lookout point. Then, head to Koke’e State Park for breathtaking views of the coast. The Awa’awa’puhi Trail tops my hiking list. This trail is a 6.2-mile round trip and boasts stunning panoramic views of the green coasts contrasted against the bright blue hues of the Pacific Ocean. Be prepared for the challenging uphill return hike.

If you’re on a crunch for time or would rather catch these picturesque views by car, drive to the Kalalau Valley Lookout for similar views.

Evening: End the day with traditional curries, salads and other vegetarian dishes at Anatta's Thai Street Food Truck.

Where To Stay In Kauai

Spend your nights at The Point at Poipu, a Hilton Vacation Club at the southernmost tip of Kauai. Unwind at the property’s pool, beach, hot tub, sauna or gardens after exploring the island.


Day 6: Check Out Kihei

Morning: Fly to Maui and check into your resort of choice.

Afternoon: Start your Maui adventure in Kihei. Explore tropical foliage at South Maui Gardens and discover food truck delights like Roll it Up. Afterward, head to The Shops at Wailea to browse high-end boutiques and galleries. Treat yourself to the sweet flavors of Hawaii at Lappert’s Ice Cream.

Evening: Indulge in a blend of local and international flavors at Humble Market Kitchin.

A Hilton Grand Vacations Member at  Haleakala National Park at sunset in Maui, Hawaii 

Day 7: Hit Up Haleakala, Makawao And Paia

Morning: Wake up early for a breathtaking sunrise at the dormant volcano of Haleakala National Park. I recommend arriving about an hour before sunrise. Be sure to layer up since the weather can be chilly at higher elevations.

After sunrise, explore the park’s otherworldly landscape and hiking trails.

Afternoon: Visit Makawao to explore the upcountry town’s quaint boutiques, galleries and local shops. Stop for lunch at Freshies Maui or Makawao Garden Cafe.

Evening: Make your way towards Paia to watch the sunset at Ho’okipa Beach. Walk through Paia’s local shops and end your night with dinner at the renowned Paia Fish Market.

Day 8: Ride The Road To Hana

Embark on the 64.4-mile winding Road to Hana. Start early to maximize your day and finish the drive before sunset since the roads can be tricky in the dark. I highly recommend Dramamine if you get motion sick. Also, pack your meals to go — there are limited dining options along the road but plenty of lookouts for a scenic picnic. The one exception is Aunty Sandy’s Banana Bread, a must-visit.

A Hilton Grand Vacations Member at lava flows on Maui, Hawaii 

Feel free to go at your own pace and discover stops off the beaten path. Some notable stops include Twin Falls, Garden of Eden Arboretum & Botanical Garden, Wai'anapanapa State ParkHamoa Beach, HanaKaihalulu Beach, Seven Sacred Pools and the bamboo forest along the Pipiwai Trail.

Where To Stay In Maui

Choose from two Hilton Grand Vacations resorts in Maui: the iconic, pastel-pink exterior of Hilton Vacation Club Ka’anapali Beach or Maui Bay Villas, a Hilton Grand Vacations Club, loved for its spacious Suites and unforgettable amenities.

Big Island

Day 9: Beaches And Bites At Kona

Morning: Stop for brunch at Island Vintage Coffee at Kings’ Shops.

Afternoon: Head to Pololu Valley and hike to the black sand beach.

Evening: Drive towards Kailua-Kona for dinner at Broke Da Mouth Grindz. Wander the shops along Ali’i Drive before heading to a night snorkel, or dive with Big Island Divers to experience Kona’s majestic manta rays.

A Hilton Grand Vacations Member at Hawaii Volcanoes National Park 

Day 10: Hike Volcanoes National Park

Morning: Enjoy pancakes at the famous Ken’s House of Pancakes in Hilo. Stop for a detour at Akaka Falls and Rainbow Falls.

Afternoon: Explore Hawaii Volcanoes National Park and its incredible hikes. Some highlights are the Kilauea Iki Trail, Sulphur Banks Trail, Thurston Lava Tube and the Holei Sea Arch.

Hungry after all that hiking? Grab a late lunch at either Aloha Mix Food Truck or Cafe Ono.

Evening: If you’re lucky enough to visit the Big Island during a volcanic eruption, stay at the park until dark to truly experience the bright red hues of the lava. Stick to the guided trails and follow the park rangers’ instructions.

Day 11: Relax At The Hilton Waikoloa Village

Morning & Afternoon: Wind down from your adventures by taking advantage of the resort amenities.

If you’re looking for something to do not too far from Hilton Waikoloa Village, plan a day of golfing at the Francis H. I’i Brown Golf Courses. Or go on a walk to see the historic Waikoloa Petroglyphs.

Evening: End your trip with dinner at Foster’s Kitchen in Kailua-Kona.

A Hilton Grand Vacations Member surfs in the lagoon at Hilton Waikoloa Village on the Big Island of Hawaii 

Where To Stay On The Big Island

Hilton Waikoloa Village is an expansive resort. It features multiple swimming pools, a koi pond and spa services. On-site activities include an on-site luau, swimming with dolphins, paddle boarding or kayaking.

Book a Suite at one of Hilton Grand Vacations’ properties within Hilton Waikoloa Village to access all resort amenities. Take your pick from:

From the towering peaks of Haleakala to the mesmerizing cascades of waterfalls like Akaka, Hawaii captivates all with its diverse landscapes. Island-hopping is a great way to experience all the aspects of Hawaii in a single trip. Head to the Rainbow State to discover its breathtaking beauty, crystal-clear waters and a harmonizing balance of adventure and relaxation.

Read “A Hilton Grand Vacations Owner Review: Must-See Hawaii Resorts And Amenities” for another Member’s perspective on this tropical paradise.

HGV Newsletter Sign Up
Hilton Grand Vacations Owner Raeanne surfing while on vacation in Hawaii

Raeanne V

Raeanne’s been an Owner since 2019. One of her highlights of ownership was using her ClubPoints to WFH (work from Hawaii) for three nonconsecutive months. Follow Raeanne to satiate your travel bug for adventurous vacations.

Popular Articles