14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii visit planner

Plan created by another user. Make it yours
1
Honolulu, Oahu
— 5 nights
2
Lahaina, Maui
— 4 nights
3
Hilo, Island of Hawaii
— 2 nights
4
Kailua-Kona, Island of Hawaii
— 1 night

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5
nights
Honolulu, Oahu

Honolulu ©

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.
Venture out of the city with trips to Kailua Beach Park (in Kailua) and Haleiwa (Waimea Bay, Sunset Beach Park, &more). And it doesn't end there: tour the pleasant surroundings at Diamond Head State Monument, explore the different monuments and memorials at National Memorial Cemetery of the Pacific, take in the dramatic scenery at Manoa Falls, and steep yourself in history at Battleship Missouri Memorial.

For where to stay, traveler tips, photos, and tourist information, use the Honolulu road trip planner.

San Juan, Puerto Rico to Honolulu is an approximately 17-hour flight. The time zone difference when traveling from San Juan to Honolulu is minus 6 hours. Plan for little chillier nights when traveling from San Juan in January since evenings lows in Honolulu dip to 22°C. Cap off your sightseeing on the 6th (Wed) early enough to travel to Lahaina.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trips

Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach

4
nights
Lahaina, Maui

Lahaina ©

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.
You'll find plenty of places to visit near Lahaina: Kalepolepo Beach Park (in Kihei), Wisdom Flow Yoga (in Makawao) and Haleakala Crater (in Haleakala National Park). Spend the 8th (Fri) exploring the striking scenery along Hana Highway - Road to Hana. Next up on the itinerary: get interesting insight from Tours, kick back and relax at Ka'anapali Beach, test your problem-solving skills at Maui Escape Rooms, and admire nature's wide array of creatures at Maui Ocean Center.

Use Inspirock's suggestions to plan your Lahaina trip and find the best activities and attractions for your vacation.

Traveling by flight from Honolulu to Lahaina takes 3.5 hours. In January, plan for daily highs up to 30°C, and evening lows to 22°C. Wrap up your sightseeing on the 10th (Sun) to allow time to travel to Hilo.

Things to do in Lahaina

Parks · Outdoors · Scenic Drive · Nature

Side Trips

Highlights from your plan
Haleakala Crater ©
Haleakala Crater
Scuba & Snorkeling
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana

2
nights
Hilo, Island of Hawaii

Hilo ©

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.
Kick off your visit on the 11th (Mon): get impressive views of Kīlauea, examine the collection at Jagger Museum, then trek along Kipuka Puaulu (Bird Park) Trail, and finally take in the dramatic natural features at Thurston Lava Tube (Nahuku). Here are some ideas for day two: take in nature's colorful creations at Liliuokalani Gardens, then admire the sheer force of Rainbow Falls, then whizz through the canopy at Skyline Hawaii - Big Island Zipline Tours, and finally take in the dramatic scenery at Akaka Falls State Park.

To see where to stay, photos, ratings, and tourist information, use the Hilo trip planner.

Traveling by flight from Lahaina to Hilo takes 3.5 hours. In January in Hilo, expect temperatures between 32°C during the day and 20°C at night. Wrap up your sightseeing on the 12th (Tue) early enough to drive to Kailua-Kona.

Things to do in Hilo

Parks · Nature · Outdoors · Tours

Side Trips

Highlights from your plan
Thurston Lava Tube (Nahuku) ©
Thurston Lava Tube (Nahuku)
Skyline Hawaii - Big Island Zipline Tours ©
Skyline Hawaii - Big Island Zipline Tours
Kipuka Puaulu (Bird Park) Trail ©
Kipuka Puaulu (Bird Park) Trail

1
night
Kailua-Kona, Island of Hawaii

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.
On the 13th (Wed), experience rural life at Kona Coffee Living History Farm, take a stroll through Holualoa Village, then get a new perspective on things with Boat Tours & Water Sports, and finally kick your exploration up a notch at Hawaii Forest and Trail.

For other places to visit, more things to do, where to stay, and other tourist information, refer to the Kailua-Kona trip planner.

Getting from Hilo to Kailua-Kona by car takes about 2 hours. Other options: take a bus. In January in Kailua-Kona, expect temperatures between 31°C during the day and 22°C at night. Cap off your sightseeing on the 13th (Wed) early enough to travel back home.

Things to do in Kailua-Kona

Side Trip

Highlights from your plan
Swim with Dolphins
Hawaii Forest and Trail ©
Hawaii Forest and Trail
Kona Coffee Living History Farm ©
Kona Coffee Living History Farm

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