14 days in Hawaii, Maui & Kauai Itinerary

14 days in Hawaii, Maui & Kauai Itinerary

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Route & dates

14 days in Hawaii, Maui & Kauai Itinerary

Start: Boston
Fly:  12​h
1
Honolulu, Oahu
— 3 nights
Fly:  3​h 30​min
2
Lahaina
— 3 nights
Bus + Fly:  5​h
3
Volcano, Island of Hawaii
— 2 nights
Fly:  5​h
4
Poipu
— 2 nights
Fly:  2​h 30​min
5
Honolulu, Oahu
— 2 nights
Fly:  12​h
End: Boston

3
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Your day-by-day itinerary now includes The Big Kahuna Luau. Step off the beaten path and head to Shark Diving and Byodo-In Temple. USS Arizona Memorial and Makapuu Lighthouse Trail are good opportunities to explore the local culture. And it doesn't end there: trek along Koko Crater Railway Trail, explore the different monuments and memorials at National Memorial Cemetery of the Pacific, and get great views at Puu Ualakaa State Park.

For reviews, where to stay, maps, and more tourist information, you can read our Honolulu visit planner.

Boston to Honolulu is an approximately 12-hour flight. You can also do a combination of bus and flight; or do a combination of ferry and flight. Due to the time zone difference, you'll gain 5 hours traveling from Boston to Honolulu. Expect warmer temperatures when traveling from Boston in January; daily highs in Honolulu reach 81°F and lows reach 67°F. Cap off your sightseeing on the 20th (Mon) early enough to travel to Lahaina.

Things to do in Honolulu

Historic Sites Outdoors Parks

Side Trips

Shark Diving, Byodo-In Temple
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Makapuu Lighthouse Trail ©
Makapuu Lighthouse Trail
Koko Crater Railway Trail ©
Koko Crater Railway Trail

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.
Step out of the city life by going to Ho'okipa Beach Park and Scuba & Snorkeling. You'll discover tucked-away gems like Wailea Beach and River Rafting & Tubing. When in Lahaina, make a side trip to see Kamaole Beach Park III in Kihei, approximately 44 minutes away. There's more to do: stroll through Kapalua Beach and get a taste of the local shopping with Surf Ripper Shave Ice Co.

To find where to stay, ratings, photos, and other tourist information, you can read our Lahaina day trip tool .

You can fly from Honolulu to Lahaina in 3.5 hours. Alternatively, you can do a combination of flight and ferry; or do a combination of flight and bus. January in Lahaina sees daily highs of 78°F and lows of 67°F at night. Finish your sightseeing early on the 23rd (Thu) to allow enough time to travel to Volcano.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Kapalua Beach, Ho'okipa Beach Park, Kamaole Beach Park III, Wailea Beach
Highlights from your plan
Wailea Beach ©
Wailea Beach
Ho'okipa Beach Park ©
Ho'okipa Beach Park
Kapalua Beach ©
Kapalua Beach

2
nights
Volcano, Island of Hawaii

Volcano ©
Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
Start off your visit on the 24th (Fri): stop by Hilo Coffee Mill, take in nature's colorful creations at Liliuokalani Gardens, take in the dramatic natural features at Holei Sea Arch, then take in the natural beauty of Steam Vents, then get impressive views of Kīlauea, and finally examine the collection at Jagger Museum. Here are some ideas for day two: take in nature's colorful creations at Akatsuka Orchid Gardens, then do a tasting at Volcano Winery, and then trek along Sulphur Banks.

For photos, other places to visit, maps, and tourist information, use the Volcano tour planner .

Traveling by combination of bus and flight from Lahaina to Volcano takes 5 hours. Alternatively, you can fly. In January, daytime highs in Volcano are 81°F, while nighttime lows are 64°F. Finish your sightseeing early on the 25th (Sat) to allow enough time to travel to Poipu.

Things to do in Volcano

Parks Nature Outdoors

Side Trips

Hawaii Volcanoes National Park, Liliuokalani Gardens, Steam Vents, Hilo Coffee Mill
Highlights from your plan
Holei Sea Arch ©
Holei Sea Arch
Kīlauea ©
Kīlauea
Sulphur Banks ©
Sulphur Banks

2
nights
Poipu

Poipu ©
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. On the 26th (Sun), enjoy the sea views from Ninini Point Lighthouse Cache Site, view the masterpieces at Tabora Gallery, trek along Maha'ulepu Heritage Trail, then enjoy the sand and surf at Shipwreck Beach, and finally take in the dramatic natural features at Spouting Horn.

To find photos, more things to do, where to stay, and more tourist information, go to the Poipu vacation planner .

Fly from Volcano to Poipu in 5 hours. Alternatively, you can do a combination of bus and flight. January in Poipu sees daily highs of 79°F and lows of 65°F at night. Wrap up your sightseeing on the 27th (Mon) early enough to travel to Honolulu.

Things to do in Poipu

Parks Outdoors Beaches

Side Trip

Lihue
Highlights from your plan
Shipwreck Beach ©
Shipwreck Beach
Ninini Point Lighthouse Cache Site ©
Ninini Point Lighthouse Cache Site
Spouting Horn ©
Spouting Horn

2
nights
Honolulu, Oahu

Honolulu ©
Explore hidden gems such as Scuba & Snorkeling and Banzai Pipeline. Take a break from the city and head to Waikiki Beach and Lanikai Beach. Change things up with a short trip to Ka'ena Point State Park in Waianae (about 58 minutes away). See even more of Honolulu: steep yourself in history at Queen Emma Summer Palace.

To see where to stay, maps, photos, and more tourist information, go to the Honolulu travel route planning app .

You can fly from Poipu to Honolulu in 2.5 hours. Wrap up your sightseeing by early afternoon on the 29th (Wed) to allow enough time to travel back home.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Ka'ena Point State Park, Lanikai Beach, Banzai Pipeline, Scuba & Snorkeling
Highlights from your plan
Waikiki Beach ©
Waikiki Beach
Lanikai Beach ©
Lanikai Beach
Scuba & Snorkeling

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