21 days in Maui, Oahu & Kailua-Kona Itinerary

21 days in Maui, Oahu & Kailua-Kona Itinerary

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Route & dates

21 days in Maui, Oahu & Kailua-Kona Itinerary

Start: Gaborone
Fly + Drive:  35​h
1
Maalaea
— 3 nights
Fly:  4​h 15​min
2
Honolulu
— 4 nights
Fly:  3​h 45​min
3
Kailua-Kona
— 7 nights
Fly:  4​h
4
Lahaina
— 3 nights
Drive + Fly:  36​h
End: Gaborone


Learn more about your trip

3
nights
Maalaea

Maalaea ©
Māalaea is a census-designated place (CDP) in Maui County, Hawaii, United States. Get outdoors at Ke‘anae Point and Baby Beach, Sprecklesville Area. Step off the beaten path and head to Kamaole Beach Park I and Haleakala Highway (Crater Road). Change things up with these side-trips from Maalaea: Waihee Ridge Trail (in Waihee) and Haiku (Haiku Mill & Leilani Farm Sanctuary). There's still lots to do: get outside with Maui Diamond Sea Sports, pause for some serene contemplation at The Awakening Church, and take in the waterfront activity at Maalaea Harbor.

Discover how to plan a Maalaea trip in just a few steps with Inspirock's itinerary builder.

Gaborone, Botswana to Maalaea is an approximately 35-hour combination of flight and car. The time zone difference when traveling from Gaborone to Maalaea is minus 12 hours. Expect slightly colder weather when traveling from Gaborone in December: highs in Maalaea hover around 32°C, while lows dip to 22°C. Finish your sightseeing early on the 13th (Fri) to allow enough time to travel to Honolulu.

Things to do in Maalaea

Outdoors Parks Beaches

Side Trips

Kihei, Maui, Haiku, Waihee Ridge Trail, Baby Beach, Sprecklesville Area
Highlights from your plan
Kamaole Beach Park I ©
Kamaole Beach Park I
Baby Beach, Sprecklesville Area ©
Baby Beach, Sprecklesville Area
Waihee Ridge Trail ©
Waihee Ridge Trail

4
nights
Honolulu

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Head to Royal Hawaiian Center and Saturday Farmer's Market KCCfor some retail therapy. Step off the beaten path and head to Lanikai Beach and Koko Crater Railway Trail. Explore Honolulu's surroundings by going to Haleiwa (Shark Diving & Haleiwa Town Center), Swim with Dolphins (in Waianae) and Sharks Cove (in Pupukea). Next up on the itinerary: hike along Makapuu Lighthouse Trail, browse the eclectic array of goods at Aloha Stadium Swap Meet & Marketplace, admire the verdant scenery at Nu’uanu Pali, and examine the collection at USS Bowfin Submarine Museum & Park.

For photos, where to stay, reviews, and other tourist information, read Honolulu trip itinerary tool .

Getting from Maalaea to Honolulu by flight takes about 4.5 hours. Other options: do a combination of bus and flight; or do a combination of car and flight. In December, plan for daily highs up to 32°C, and evening lows to 24°C. Wrap up your sightseeing on the 18th (Wed) early enough to travel to Kailua-Kona.

Things to do in Honolulu

Outdoors Parks Shopping

Side Trips

Haleiwa, Swim with Dolphins, Lanikai Beach, Nu’uanu Pali, Sharks Cove
Highlights from your plan
Swim with Dolphins
Lanikai Beach ©
Lanikai Beach
Koko Crater Railway Trail ©
Koko Crater Railway Trail

7
nights
Kailua-Kona

Kailua-Kona ©
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.
Escape the urban bustle at Waipio Valley and Kaloko-Honokohau National Historical Park. Discover out-of-the-way places like Kona Joe Coffee and Scuba & Snorkeling. Explore the numerous day-trip ideas around Kailua-Kona: Hilo (Carlsmith Beach Park & Richardson Beach Park), Waialea Beach (in Waimea) and Hawaiian Vanilla Company (in Paauilo). There's lots more to do: kick back and relax at Honaunau Bay, pause for some photo ops at The Captain Cook Monument, admire the majestic nature at Kahalu'u Beach Park, and tour the pleasant surroundings at White Sand Beach.

For more things to do, other places to visit, photos, and tourist information, read our Kailua-Kona travel planner .

Getting from Honolulu to Kailua-Kona by flight takes about 4 hours. Expect a daytime high around 32°C in December, and nighttime lows around 24°C. Finish your sightseeing early on the 25th (Wed) so you can travel to Lahaina.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Hilo, Kahalu'u Beach Park, Waipio Valley, Kona Joe Coffee, The Captain Cook Monument
Highlights from your plan
Waipio Valley ©
Waipio Valley
Honaunau Bay ©
Honaunau Bay
Scuba & Snorkeling

3
nights
Lahaina

Lahaina ©
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.
Start off your visit on the 26th (Thu): get engrossed in the history at Baldwin Home Museum, then view the masterpieces at Village Galleries in Lahaina, then stroll through Acid War Zone Trail, and finally admire all the interesting features of Ohai Loop Trail and Overlook. On the 27th (Fri), you'll have a packed day of sightseeing: enjoy the sand and surf at Hanakao'o Beach Park, then tour the pleasant surroundings at Village Walking Trails, and then kick back and relax at Honokeana Bay.

To find ratings and more tourist information, use the Lahaina trip planner.

Getting from Kailua-Kona to Lahaina by flight takes about 4 hours. Other options: do a combination of taxi, flight, and bus; or do a combination of flight and bus. In December in Lahaina, expect temperatures between 30°C during the day and 23°C at night. On the 28th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Lahaina

Outdoors Parks Trails

Side Trips

Honokeana Bay, Village Walking Trails
Highlights from your plan
Acid War Zone Trail ©
Acid War Zone Trail
Honokeana Bay ©
Honokeana Bay
Tamura's Fine Wine & Liquors ©
Tamura's Fine Wine & Liquors

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