14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii travel route maker

Make it your trip
Fly
1
Honolulu, Oahu
— 5 nights
Fly
2
Lahaina, Maui
— 4 nights
Fly
3
Hilo, Island of Hawaii
— 2 nights
Drive
4
Kailua-Kona, Island of Hawaii
— 1 night
Fly

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Honolulu, Oahu

— 5 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.
Change things up with these side-trips from Honolulu: Haleiwa (Waimea Bay, Sunset Beach Park, &more) and Kailua Beach Park (in Kailua). There's lots more to do: take an in-depth tour of USS Arizona Memorial, see the interesting displays at Bishop Museum, admire the sheer force of Manoa Falls, and contemplate the long history of Battleship Missouri Memorial.

To see other places to visit, ratings, photos, and more tourist information, read Honolulu trip planner.

San Juan, Puerto Rico to Honolulu is an approximately 17-hour flight. Traveling from San Juan to Honolulu, you'll gain 6 hours due to the time zone difference. Expect slightly colder evenings in Honolulu when traveling from San Juan in December, with lows around 24°C. Cap off your sightseeing on the 31st (Fri) early enough to catch the flight to Lahaina.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trips

Lahaina, Maui

— 4 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.
Get out of town with these interesting Lahaina side-trips: Kalepolepo Beach Park (in Kihei), Wisdom Flow Yoga (in Makawao) and Haleakala Crater (in Haleakala National Park). Spend the 2nd (Sun) exploring the striking scenery along Hana Highway - Road to Hana. There's still lots to do: see some colorful creatures with a scuba or snorkeling tour, walk around Lahaina Banyan Court, observe the fascinating underwater world at Maui Ocean Center, and test your problem-solving skills at Maui Escape Rooms.

For ratings, reviews, traveler tips, and more tourist information, use the Lahaina travel itinerary planner.

Getting from Honolulu to Lahaina by flight takes about 2.5 hours. In December, daytime highs in Lahaina are 30°C, while nighttime lows are 23°C. Wrap up your sightseeing on the 4th (Tue) to allow time to fly to Hilo.

Things to do in Lahaina

Parks · Outdoors · Scenic Drive · Nature

Side Trips

Hilo, Island of Hawaii

— 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.
Kick off your visit on the 5th (Wed): contemplate the geological forces at KÄ«lauea, see the interesting displays at Jagger Museum, then trek along Kipuka Puaulu (Bird Park) Trail, and finally explore the striking landscape at Thurston Lava Tube (Nahuku). On the next day, take in nature's colorful creations at Liliuokalani Gardens, take in the dramatic scenery at Rainbow Falls, then whizz through the canopy at Hawaii Zipline Tours, and finally admire the sheer force of Akaka Falls State Park.

To find where to stay, maps, traveler tips, and more tourist information, you can read our Hilo online journey planner.

Traveling by flight from Lahaina to Hilo takes 2.5 hours. In January, daily temperatures in Hilo can reach 32°C, while at night they dip to 20°C. Wrap up your sightseeing on the 6th (Thu) to allow time to drive to Kailua-Kona.

Things to do in Hilo

Parks · Nature · Outdoors · Adventure

Side Trips

Kailua-Kona, Island of Hawaii

— 1 night

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.
Start off your visit on the 7th (Fri): relax in the rural setting at Kona Coffee Living History Farm, then wander the streets of Holualoa Village, then head outdoors with Outdoor Activities, and finally gain interesting insight with Hawaii Forest and Trail.

For other places to visit, photos, more things to do, and more tourist information, go to the Kailua-Kona trip planner.

Getting from Hilo to Kailua-Kona by car takes about 2 hours. Other options: take a bus. January in Kailua-Kona sees daily highs of 31°C and lows of 22°C at night. Finish up your sightseeing early on the 7th (Fri) so you can catch the flight back home.

Things to do in Kailua-Kona

Tours · Wildlife · Outdoors · Adventure

Side Trip

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.