14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

Make it your trip
Fly
1
Kailua-Kona, Island of Hawaii
— 3 nights
Fly
2
Poipu, Kauai
— 2 nights
Drive
3
Haena, Kauai
— 1 night
Drive to Lihue Airport, Fly to Daniel K Inouye International Airport
4
Honolulu, Oahu
— 4 nights
Fly
5
Lahaina, Maui
— 3 nights
Fly

S M T W T F S
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Kailua-Kona, Island of Hawaii

— 3 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.
Get in touch with nature at Hapuna Beach State Recreation Area and Swim with Dolphins. Discover out-of-the-way places like Pu'uhonua O Honaunau National Historical Park and Mauna Kea. There's still lots to do: identify plant and animal life at Kanaloa Octopus Farm, tour the pleasant surroundings at Manini'owali Beach (Kua Bay), contemplate the long history of Puako Petroglyph Archaeological Preserve, and get engrossed in the history at H.N. Greenwell Store Museum.

To see reviews, other places to visit, maps, and other tourist information, read Kailua-Kona trip itinerary website.

Cleveland to Kailua-Kona is an approximately 13.5-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Cleveland to Kailua-Kona. Prepare for much warmer weather when traveling from Cleveland in February: high temperatures in Kailua-Kona hover around 81°F and lows are around 69°F. Finish your sightseeing early on the 24th (Wed) to allow enough time to travel to Poipu.

Things to do in Kailua-Kona

Outdoors · Parks · Nature · Beaches

Side Trips

Poipu, Kauai

— 2 nights
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. Kick off your visit on the 25th (Thu): admire the sheer force of Wailua Falls and then discover the deep blue sea with a scuba or snorkeling tour. Get ready for a full day of sightseeing on the 26th (Fri): stroll through Waimea Canyon State Park, kick back and relax at Polihale State Park, and then trek along Maha'ulepu Heritage Trail.

To see where to stay, other places to visit, reviews, and more tourist information, read our Poipu attractions planner.

You can fly from Kailua-Kona to Poipu in 3 hours. In February, daytime highs in Poipu are 78°F, while nighttime lows are 66°F. Finish up your sightseeing early on the 26th (Fri) so you can go by car to Haena.

Things to do in Poipu

Parks · Nature · Outdoors · Wildlife

Side Trips

Haena, Kauai

— 1 night
Hāena State Park is a state park located on the north shore of the Hawaiian island of Kauai. On the 27th (Sat), take some stellar pictures from Puu Hinahina Lookout, examine the collection at Kokee Natural History Museum, then identify plant and animal life at Kalalau Trail, and finally identify plant and animal life at Na Pali Coast State Park.

To find photos, maps, traveler tips, and other tourist information, you can read our Haena road trip planning site.

Traveling by car from Poipu to Haena takes 2 hours. Finish up your sightseeing early on the 27th (Sat) so you can travel to Honolulu.

Things to do in Haena

Wildlife · Parks · Trails · Outdoors

Side Trips

Honolulu, Oahu

— 4 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.
You'll explore the less-touristy side of things at Makapuu Lighthouse Trail and Koko Crater Railway Trail. Step out of the city life by going to Scuba & Snorkeling and Diamond Head State Monument. Venture out of the city with trips to Lanikai Beach (in Kailua) and Haleiwa (Waimea Valley & Sunset Beach Park). There's much more to do: get a dose of the wild on a nature and wildlife tour, explore the striking landscape at Halona Blowhole, examine the collection at USS Bowfin Submarine Museum & Park, and get great views at Puu Ualakaa State Park.

To see traveler tips, other places to visit, photos, and tourist information, you can read our Honolulu trip itinerary builder tool.

Use the Route module to find suitable travel options from Haena to Honolulu. In February, plan for daily highs up to 81°F, and evening lows to 69°F. Finish up your sightseeing early on the 3rd (Wed) so you can travel to Lahaina.

Things to do in Honolulu

Parks · Outdoors · Tours · Trails

Side Trips

Lahaina, Maui

— 3 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.
On the 4th (Thu), kick back and relax at Napili Beach, then tour the pleasant surroundings at Kapalua Coastal Trail, and then see some colorful creatures with a scuba or snorkeling tour. Get ready for a full day of sightseeing on the next day: kick back and relax at Ho'okipa Beach Park, whizz through the canopy at some of the top local zipline courses and adventure parks, and then stroll through Wailea Beach.

To find maps, where to stay, photos, and more tourist information, read Lahaina trip maker website.

Traveling by flight from Honolulu to Lahaina takes 4 hours. In March, daily temperatures in Lahaina can reach 78°F, while at night they dip to 67°F. Wrap up your sightseeing on the 6th (Sat) to allow time to travel back home.

Things to do in Lahaina

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.

Kauai travel guide

4.5
Scuba & Snorkeling · Zipline · Beaches
The Garden Isle
The northernmost of Hawaii's major islands, Kauai earned the nickname "Garden Island" because of its abundance of lush greenery and tropical plants, watered frequently with plentiful rainfall. Kauai's landscape continues to suffer from powerful erosion, resulting in natural attractions that include plunging canyons, tall mountain peaks, and the longest sandy coastline of all the Hawaiian islands. Offering a mild tropical climate and pristine wilderness areas largely unspoiled by mass tourism, Kauai is a great vacation destination for visitors eager to escape Hawaii's more crowded tourist resorts. For a genuine Kauai experience, join the locals for one of their famous traditional meat and vegetable feasts, prepared in underground pits lined with hot rocks.

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.