29 days in Hawaii Itinerary

29 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary planner

Make it your trip
Fly
1
Lihue
— 4 nights
Fly
2
Honolulu
— 8 nights
Fly
3
Lahaina
— 8 nights
Fly
4
Kailua-Kona
— 4 nights
Drive
5
Hilo
— 2 nights
Fly

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Lihue

— 4 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. You'll get in some beach time at Pali Ke Kua Beach (Hideaway s Beach) and Kalapaki Beach. Kilohana and Ninini Point Lighthouse Cache Site will appeal to history buffs. Step out of Lihue to go to Kilauea and see Boat Tours & Water Sports, which is approximately 44 minutes away. Next up on the itinerary: hike along Kauai Path, tour the pleasant surroundings at Maha'ulepu Heritage Trail, enjoy the sand and surf at Hanalei Bay, and indulge in some personalized pampering at some of the best spas.

To find traveler tips, where to stay, maps, and other tourist information, use the Lihue online vacation planner.

Milan, Italy to Lihue is an approximately 23.5-hour flight. The time zone changes from Central European Standard Time (CET) to Hawaii-Aleutian Standard Time (HST), which is usually a -11 hour difference. Expect somewhat warmer evenings in Lihue when traveling from Milan in July, with lows around 27°C. Wrap up your sightseeing on the 5th (Mon) to allow time to travel to Honolulu.

Things to do in Lihue

Outdoors · Parks · Beaches · Trails

Side Trips

Honolulu

— 8 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Get outdoors at Diamond Head State Monument and Waikiki Beach. Your inner history buff will appreciate Makapuu Lighthouse Trail and Byodo-In Temple. Venture out of the city with trips to Ko Olina Lagoons (in Kapolei), Kailua (Lanikai Beach & Kailua Beach Park) and Waimanalo Beach (in Waimanalo). Next up on the itinerary: enjoy the sand and surf at Sharks Cove, get a dose of the wild on a nature and wildlife tour, explore the activities along Hanauma Bay Nature Preserve, and admire the sheer force of Manoa Falls.

For where to stay, ratings, other places to visit, and other tourist information, refer to the Honolulu trip maker app.

You can fly from Lihue to Honolulu in 2.5 hours. Alternatively, you can fly. July in Honolulu sees daily highs of 36°C and lows of 28°C at night. Finish your sightseeing early on the 13th (Tue) so you can travel to Lahaina.

Things to do in Honolulu

Outdoors · Parks · Beaches · Wildlife

Side Trips

Lahaina

— 8 nights

Crown Jewel of Maui

Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
Step off the beaten path and head to Zipline and Napili Beach. Get in touch with nature at Wailea Beach and Kapalua Coastal Trail. Explore Lahaina's surroundings by going to Wailuku (Maui Tropical Plantation & Iao Valley), Wailea (Wailea Beach Path, Keawakapu Beach, &more) and Kihei (Kamaole Beach Park II & Kamaole Beach Park III). There's still lots to do: kick back and relax at Kapalua Beach, glide through the air with a parasailing or paragliding tour, tour the pleasant surroundings at Ho'okipa Beach Park, and steep yourself in history at Old Lahaina Courthouse.

For other places to visit, maps, reviews, and other tourist information, you can read our Lahaina sightseeing planner.

Traveling by flight from Honolulu to Lahaina takes 3.5 hours. Alternatively, you can fly. In July, daytime highs in Lahaina are 35°C, while nighttime lows are 26°C. Finish your sightseeing early on the 21st (Wed) so you can travel to Kailua-Kona.

Things to do in Lahaina

Parks · Outdoors · Beaches · Nature

Side Trips

Kailua-Kona

— 4 nights

Heart of the Kona Coast

Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Take a break from the city and head to Swim with Dolphins and Hapuna Beach State Recreation Area. You'll enjoy a bit of beach vacationing at Manini'owali Beach (Kua Bay) and Honaunau Bay. Explore the numerous day-trip ideas around Kailua-Kona: Pu'uhonua O Honaunau National Historical Park (in Honaunau), The Painted Church (in Captain Cook) and Queen's Bath (in Princeville). There's lots more to do: take in the awesome beauty at Mauna Kea, indulge your thirst for a good beer at Kona Brewing Company, look for all kinds of wild species at Kanaloa Octopus Farm, and cruise along Saddle Road.

To find more things to do, photos, and tourist information, use the Kailua-Kona trip planner.

Fly from Lahaina to Kailua-Kona in 4.5 hours. Expect a daytime high around 35°C in July, and nighttime lows around 28°C. Wrap up your sightseeing on the 25th (Sun) early enough to drive to Hilo.

Things to do in Kailua-Kona

Parks · Outdoors · Nature · Beaches

Side Trips

Hilo

— 2 nights

America's Wettest City

One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
On the 26th (Mon), stroll through Richardson Beach Park, kick back and relax at Carlsmith Beach Park, then take in nature's colorful creations at Liliuokalani Gardens, and finally discover the deep blue sea with a scuba or snorkeling tour. Get ready for a full day of sightseeing on the next day: take a memorable drive along Chain of Craters Rd, stroll through Sulphur Banks, and then explore the fascinating underground world of Kazumura Cave Tours.

Plan my trip to Hilo with suggested itineraries provided by Inspirock.

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. Expect a bit cooler evenings in Hilo when traveling from Kailua-Kona in July, with lows around 25°C. Finish your sightseeing early on the 27th (Tue) so you can travel back home.

Things to do in Hilo

Outdoors · Parks · Beaches · Tours

Side Trips

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.

Maui travel guide

4.5
Scuba & Snorkeling · Beaches · Luaus
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.