14 days in Hawaii Itinerary

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Honolulu, Oahu
— 4 nights
Lahaina, Maui
— 5 nights
Volcano, Island of Hawaii
— 2 nights
Kailua-Kona, Island of Hawaii
— 2 nights


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.
Let the collections at USS Arizona Memorial and Iolani Palace capture your imagination. Battleship Missouri Memorial and USS Bowfin Submarine Museum & Park are good opportunities to explore the local culture. You'll find plenty of places to visit near Honolulu: Haleiwa (Sunset Beach Park & Waimea Bay), Pu’u O Mahuka Heiau State Monument (in Pupukea) and Kailua Beach Park (in Kailua). There's much more to do: enjoy the sand and surf at Waikiki Beach, take in the pleasant sights at Diamond Head State Monument, contemplate the waterfront views at Hanauma Bay Nature Preserve, and see some colorful creatures with a scuba or snorkeling tour.

To find ratings, more things to do, other places to visit, and other tourist information, you can read our Honolulu road trip planner.

Boston to Honolulu is an approximately 11-hour flight. The time zone changes from Eastern Standard Time to Hawaii-Aleutian Standard Time, which is usually a -5 hour difference. Traveling from Boston in July, expect a bit warmer with lows of 75°F in Honolulu. Finish your sightseeing early on the 20th (Thu) so you can fly to Lahaina.
Side Trips
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Lahaina, Maui — 5 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.
Take a break from the city and head to Scuba & Snorkeling and Hana Highway - Road to Hana. Your itinerary includes some good beach time at Wailea Beach and Ka'anapali Beach. Change things up with a short trip to Haleakala Crater in Haleakala National Park (about 1h 50 min away). There's still lots to do: enjoy the sand and surf at D.T. Fleming Park, stroll through Kapalua Beach, view the masterpieces at Maui Hands, and get up close and personal with brilliant marine life at Maui Ocean Center.

Discover how to plan a Lahaina trip in just a few steps with Klarna Trips's itinerary builder.

Traveling by flight from Honolulu to Lahaina takes 2.5 hours. In July, plan for daily highs up to 86°F, and evening lows to 73°F. Cap off your sightseeing on the 25th (Tue) early enough to catch the flight to Volcano.
Outdoors · Parks · Beaches · Scenic Drive
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Volcano, Island of Hawaii — 2 nights

Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
On the 26th (Wed), wander the streets of Kalapana, explore and take pictures at Pu'u Loa Petroglyphs, and then tour the pleasant surroundings at Pu'u Huluhulu trail. On the 27th (Thu), you'll have a packed day of sightseeing: hike along Sulphur Banks, get a taste of the local shopping with Volcano Art Center Gallery, then take a memorable drive along Devastation Trail, and finally trek along Kilauea Iki Trailhead.

To see where to stay, reviews, traveler tips, and more tourist information, use the Volcano online road trip planner.

Fly from Lahaina to Volcano in 2.5 hours. In July, daily temperatures in Volcano can reach 85°F, while at night they dip to 71°F. Wrap up your sightseeing on the 27th (Thu) early enough to drive to Kailua-Kona.
Parks · Outdoors · Trails · Historic Sites
Side Trip
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Kailua-Kona, Island of Hawaii — 2 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.
Start off your visit on the 28th (Fri): identify plant and animal life at Kona Cloud Forest Sanctuary, fulfill a lifelong dream with a swim-with-the-dolphins experience, and then take in the exciting artwork at Kona Henna.

To see where to stay, ratings, traveler tips, and other tourist information, refer to the Kailua-Kona day trip planning tool.

You can drive from Volcano to Kailua-Kona in 2.5 hours. Alternatively, you can take a bus. July in Kailua-Kona sees daily highs of 86°F and lows of 76°F at night. Finish up your sightseeing early on the 29th (Sat) so you can catch the flight back home.
Wildlife · Tours · Outdoors · Parks
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Hawaii travel guide

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.