31 days in Hawaii & Jamaica Itinerary

Make it your trip
Fly
1
Kailua-Kona, United States
— 3 nights
Drive
2
Hilo, United States
— 2 nights
Fly
3
Lahaina, United States
— 5 nights
Fly
4
Waimea, United States
— 2 nights
Fly
5
Honolulu, United States
— 10 nights
Fly
6
Montego Bay, Jamaica
— 7 nights
Fly

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Kailua-Kona, United States — 3 nights

Heart of the Kona Coast

Explore the numerous day-trip ideas around Kailua-Kona: Hapuna Beach State Recreation Area (in Puako), Puukohola National Historic Park (in Kawaihae) and Pu'uhonua O Honaunau National Historical Park (in Honaunau). Next up on the itinerary: fulfill a lifelong dream with a swim-with-the-dolphins experience, tour the pleasant surroundings at Mauna Kea Beach, kick back and relax at Kahaluu Beach, and experience rural life at The Vanillerie.

To see traveler tips, photos, ratings, and more tourist information, use the Kailua-Kona trip maker app.

Brisbane, Australia to Kailua-Kona is an approximately 14.5-hour flight. The time zone difference moving from Australian Eastern Standard Time (AEST) to Hawaii-Aleutian Standard Time (HST) is minus 20 hours. Prepare for a bit warmer weather when traveling from Brisbane in May: high temperatures in Kailua-Kona hover around 33°C and lows are around 26°C. Cap off your sightseeing on the 3rd (Sat) early enough to go by car to Hilo.
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Outdoors · Parks · Beaches · Nature
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Find places to stay May 31 — Jun 3:

Hilo, United States — 2 nights

America's Wettest City

Start off your visit on the 4th (Sun): trek along Kipuka Puaulu (Bird Park) Trail, then trek along Kilauea Iki Trailhead, then cruise along Devastation Trail, and finally take in the dramatic scenery at Rainbow Falls. On your second day here, browse the fresh offerings at Hilo Farmers Market, then admire the sheer force of Akaka Falls State Park, then admire the natural beauty at Hawaii Tropical Bioreserve and Garden, and finally admire the natural beauty at Liliuokalani Gardens.

Find out how to plan Hilo trip without stress by asking Klarna Trips to help create an itinerary.

Getting from Kailua-Kona to Hilo by car takes about 2 hours. Other options: drive; or take a bus. Traveling from Kailua-Kona in June, plan for slightly colder nights in Hilo, with lows around 24°C. Finish your sightseeing early on the 5th (Mon) so you can fly to Lahaina.
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Parks · Outdoors · Trails · Nature
Side Trips
Find places to stay Jun 3 — 5:

Lahaina, United States — 5 nights

Crown Jewel of Maui

You'll find plenty of places to visit near Lahaina: Iao Valley (in Wailuku), Surfing Goat Dairy (in Kula) and Ho'omana Spa Maui (in Makawao). Spend the 6th (Tue) exploring the striking scenery along Hana Highway - Road to Hana. And it doesn't end there: see some colorful creatures with a scuba or snorkeling tour, stroll around Lahaina Banyan Court, tour the pleasant surroundings at Kalepolepo Beach Park, and kick your exploration up a notch at some of the top local zipline courses and adventure parks.

To see where to stay, ratings, photos, and other tourist information, use the Lahaina online trip maker.

You can fly from Hilo to Lahaina in 2.5 hours. In June, plan for daily highs up to 34°C, and evening lows to 26°C. Wrap up your sightseeing on the 10th (Sat) early enough to fly to Waimea.
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Outdoors · Parks · Beaches · Scenic Drive
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Find places to stay Jun 5 — 10:

Waimea, United States — 2 nights

On the 11th (Sun), stroll through Salt Pond Beach Park, then trek along Canyon Trail, and then get a new perspective on things with Boat Tours & Water Sports. On the next day, take in breathtaking views at Waimea Canyon State Park, take your sightseeing to a higher altitude at Koke'e Mountains, and then appreciate the extensive heritage of Kalalau Lookout.

To see reviews, where to stay, photos, and other tourist information, refer to the Waimea route planner.

Fly from Lahaina to Waimea in 2.5 hours. Expect a daytime high around 34°C in June, and nighttime lows around 26°C. Wrap up your sightseeing on the 12th (Mon) to allow time to fly to Honolulu.
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Parks · Outdoors · Nature · Tours
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Find places to stay Jun 10 — 12:

Honolulu, United States — 10 nights

Big Pineapple

Explore Honolulu's surroundings by going to Haleiwa (Waimea Bay, Sunset Beach Park, &more) and Pu’u O Mahuka Heiau State Monument (in Pupukea). There's much more to do: take in the pleasant sights at Diamond Head State Monument, kick back and relax at Kailua Beach Park, pause for some photo ops at USS Arizona Memorial, and get a tailor-made plan with Private Tours.

Plan my trip to Honolulu with suggested itineraries provided by Klarna Trips.

Getting from Waimea to Honolulu by flight takes about 2.5 hours. In June, plan for daily highs up to 35°C, and evening lows to 27°C. Finish your sightseeing early on the 22nd (Thu) to allow enough time to travel to Montego Bay.
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Outdoors · Parks · Beaches · Museums
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Find places to stay Jun 12 — 22:

Montego Bay, Jamaica — 7 nights

Change things up with these side-trips from Montego Bay: Firewater Mineral Healing Spring (in St. Ann's Bay), YS Falls (in Saint Elizabeth Parish) and Ocho Rios (Jewels & Time Duty Free Jewelers & Dunn's River Falls and Park). Next up on the itinerary: kick back and relax at Seven Mile Beach, admire the sheer force of Original Mayfield Falls Jamaica, relax and rejuvenate at Fern Tree SPA, and steep yourself in history at Rose Hall Great House.

For other places to visit, ratings, reviews, and more tourist information, use the Montego Bay trip planner.

Use the Route module to find suitable travel options from Honolulu to Montego Bay. Due to the time zone difference, you'll lose 5 hours traveling from Honolulu to Montego Bay. In June, daytime highs in Montego Bay are 38°C, while nighttime lows are 29°C. Finish up your sightseeing early on the 29th (Thu) so you can catch the flight back home.
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Outdoors · Parks · Tours · Wildlife
Side Trips
Find places to stay Jun 22 — 29:

Hawaii travel guide

4.4
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.
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Jamaica travel guide

4.2
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.
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