60 days in Hawaii Itinerary

60 days in Hawaii Itinerary

Created using Inspirock Hawaii Trip Planner

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Route & dates

Start: Santo Domingo, Dominican Republic
Fly:  20 h
1
Honolulu, Oahu
— 13 nights
Fly:  2 h 30 min
2
Kapaa, Kauai
— 9 nights
Fly + Bus:  2 h
3
Lahaina, Maui
— 12 nights
Bus + Fly:  1 h 30 min
4
Hilo, Island of Hawaii
— 12 nights
Drive:  2 h
5
Kailua-Kona, Island of Hawaii
— 12 nights
Bus + Fly:  19 h 45 min
End: Santo Domingo, Dominican Republic

13
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.
Explore hidden gems such as Manoa Falls and Koko Crater Railway Trail. Get in touch with nature at Diamond Head State Monument and Waikiki Beach. Get out of town with these interesting Honolulu side-trips: Kailua (Lanikai Beach & Kailua Beach Park), Ko Olina Lagoons (in Kapolei) and Turtle Bay Beach (in Kahuku). There's lots more to do: enjoy the sand and surf at Kapiolani Regional Park, look for all kinds of wild species at Hanauma Bay Nature Preserve, tour the pleasant surroundings at Sunset Beach Park, and examine the collection at USS Bowfin Submarine Museum & Park.

To find reviews, where to stay, more things to do, and more tourist information, you can read our Honolulu holiday planner.

Santo Domingo, Dominican Republic to Honolulu is an approximately 23.5- hour flight. The time zone difference when traveling from Santo Domingo to Honolulu is minus 6 hours. In February, daily temperatures in Honolulu can reach 32°C, while at night they dip to 24°C. Wrap up your sightseeing on the 14th (Tue) early enough to travel to Kapaa.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Kailua, Oahu, Pupukea, Dole Plantation
Highlights from your plan
Manoa Falls ©
Manoa Falls
Kailua Beach Park ©
Kailua Beach Park
Lanikai Beach ©
Lanikai Beach

9
nights
Kapaa, Kauai

Kapaa ©
Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Give yourself a bit of retail therapy at Talk Story Bookstore and Hawaiian Trading Post. You'll enjoy a bit of beach vacationing at Hanalei Beach and Shipwreck Beach. Change things up with these side-trips from Kapaa: Poipu (Poipu Beach Park, Makawehi Bluff, &more), Waimea (Waimea Canyon State Park, Aunty Liliko'i, &more) and Scuba & Snorkeling (in Eleele). The adventure continues: stroll through Kalalau Trail, stop by Garden Isle Bath & Body LLC, visit a coastal fixture at Ninini Point Lighthouse Cache Site, and take in the dramatic scenery at Wailua Falls.

To find ratings, reviews, more things to do, and tourist information, read our Kapaa tour itinerary planning website.

You can fly from Honolulu to Kapaa in 2.5 hours. Expect a daytime high around 30°C in February, and nighttime lows around 22°C. Finish up your sightseeing early on the 23rd (Thu) so you can travel to Lahaina.

Things to do in Kapaa

Parks Outdoors Beaches

Side Trips

Lihue, Poipu, Kauai, Hanalei, Waimea
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Hanalei Beach ©
Hanalei Beach
Polihale State Park ©
Polihale State Park

12
nights
Lahaina, Maui

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.
Get outdoors at Scuba & Snorkeling and Wailea Beach. Your cultural itinerary includes sights like Village Galleries in Lahaina and Lahaina Front Street. Explore Lahaina's surroundings by going to Ho'okipa Beach Park (in Paia), Kihei (Kamaole Beach Park I, Kamaole Beach Park II, &more) and Maui Tropical Plantation (in Wailuku). There's lots more to do: let the river carry you with a rafting and tubing tour, kick back and relax at Ka'anapali Beach, look for gifts at Maui Mike's Beach House, and tour the pleasant surroundings at Kapalua Beach.

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

Traveling by combination of flight and bus from Kapaa to Lahaina takes 3.5 hours. In February, daily temperatures in Lahaina can reach 30°C, while at night they dip to 22°C. Finish up your sightseeing early on the 7th (Tue) so you can travel to Hilo.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Wailea, Kihei, Kapalua, La Perouse Bay, Ho'okipa Beach Park
Highlights from your plan
Ka'anapali Beach ©
Ka'anapali Beach
Keawakapu Beach ©
Keawakapu Beach
Ho'okipa Beach Park ©
Ho'okipa Beach Park

12
nights
Hilo, Island of Hawaii

Hilo ©
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.
Eschew the tourist crowds and head to Rainbow Falls and Kilauea Iki Trailhead. Waipio Valley and Jagger Museum are good opportunities to explore the local culture. Venture out of the city with trips to Volcano (Volcano Garden Arts, Volcano Winery, &more), Laupahoehoe (Hamakua Heritage Farm & Laupahoehoe Beach Park) and Hawaii Volcanoes National Park (Volcano Art Center Gallery, Thurston Lava Tube (Nahuku), &more). There's still lots to do: tour the pleasant surroundings at Richardson Beach Park, Head underground at Kazumura Cave Tours, browse the fresh offerings at Hilo Farmers Market, and kick back and relax at Kehena Black Sand Beach.

To find reviews, where to stay, ratings, and other tourist information, use the Hilo trip maker site.

Do a combination of bus and flight from Lahaina to Hilo in 3.5 hours. Alternatively, you can fly; or do a combination of bus and flight. March in Hilo sees daily highs of 31°C and lows of 22°C at night. Cap off your sightseeing on the 19th (Sun) early enough to go by car to Kailua-Kona.

Things to do in Hilo

Parks Nature Outdoors

Side Trips

Hawaii Volcanoes National Park, Volcano, Island of Hawaii, Laupahoehoe, Pahoa
Highlights from your plan
Rainbow Falls ©
Rainbow Falls
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Thurston Lava Tube (Nahuku) ©
Thurston Lava Tube (Nahuku)

12
nights
Kailua-Kona, Island of Hawaii

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.
Pu'uhonua O Honaunau National Historical Park and Puako Petroglyph Archaeological Preserve will appeal to history buffs. Visiting Swim with Dolphins and Mauna Kea will get you outdoors. You'll find plenty of places to visit near Kailua-Kona: Captain Cook (Kona Pacific Farmers Cooperative, Big Island Bees, &more), Naalehu (Paradise Meadows Orchard & Bee Farm Home of Hawaii's Local Buzz & Papakōlea Green Sand Beach) and Waimea (Waialea Beach & Samuel M. Spencer Beach Park). There's still lots to do: kick back and relax at Punalu‘U Beach, tour the pleasant surroundings at Manini Kapahukapu Beach, see some colorful creatures with a scuba or snorkeling tour, and experience rural life at Greenwell Farms.

For photos and more tourist information, use the Kailua-Kona day trip planning site.

Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. In March in Kailua-Kona, expect temperatures between 32°C during the day and 24°C at night. Cap off your sightseeing on the 31st (Fri) early enough to travel back home.

Things to do in Kailua-Kona

Outdoors Parks Beaches

Side Trips

Captain Cook, Island of Hawaii, Honaunau, Kealakekua, Pahala
Highlights from your plan
Mauna Kea ©
Mauna Kea
Punalu‘U Beach ©
Punalu‘U Beach
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area

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