16 days in Cuba & Hawaii Itinerary

16 days in Cuba & Hawaii Itinerary

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Route & dates

16 days in Cuba & Hawaii Itinerary

Start: Orlando
Fly:  8​h 45​min
1
Cuba
— 1 night
Fly:  14​h
2
Volcano, Island of Hawaii
— 1 night
Drive:  2​h 15​min
3
Kailua-Kona, Island of Hawaii
— 2 nights
taxi + Fly:  3​h 15​min
4
Kula, Maui
— 3 nights
Fly + taxi:  3​h 15​min
5
Hanalei, Kauai
— 2 nights
taxi + Fly:  3​h
6
Honolulu, Oahu
— 4 nights
Fly:  15​h
End: Orlando

1
night
Cuba

Cuba ©
Cuba is a city in Crawford County, Missouri, United States. Kick off your visit on the 18th (Sat): don't miss a visit to Fanning 66 Outpost.

To find traveler tips, photos, other places to visit, and more tourist information, read Cuba road trip planner .

Orlando to Cuba is an approximately 9-hour flight. You can also drive. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. Traveling from Orlando in May, things will get slightly colder in Cuba: highs are around 74°F and lows about 53°F. Wrap up your sightseeing on the 19th (Sun) to allow time to travel to Volcano.

Things to do in Cuba

Nature Parks

Side Trip

Leasburg
Highlights from your plan
Onondaga Cave State Park ©
Onondaga Cave State Park
The Murals of Cuba ©
The Murals of Cuba
Fanning 66 Outpost ©
Fanning 66 Outpost

1
night
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.
On the 20th (Mon), take in nature's colorful creations at Liliuokalani Gardens, trek along Kilauea Iki Trailhead, then examine the collection at Jagger Museum, then get a taste of the local shopping with Volcano Art Center, and finally hike along Kipuka Puaulu (Bird Park) Trail. Get ready for a full day of sightseeing on the 21st (Tue): take in nature's colorful creations at Akatsuka Orchid Gardens, take in the dramatic natural features at Thurston Lava Tube (Nahuku), then stroll through Devastation Trail, and finally head outdoors with Keanakakoi Crater Overlook.

For where to stay, ratings, and tourist information, read Volcano day trip app .

The Route module can help you plan travel from Cuba to Volcano. Traveling from Cuba to Volcano, you'll gain 4 hours due to the time zone difference. Plan for somewhat warmer temperatures traveling from Cuba in May, with highs in Volcano at 82°F and lows at 67°F. Wrap up your sightseeing on the 21st (Tue) to allow time to drive to Kailua-Kona.

Things to do in Volcano

Outdoors Parks Trails

Side Trips

Hawaii Volcanoes National Park, Liliuokalani Gardens
Highlights from your plan
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Liliuokalani Gardens ©
Liliuokalani Gardens
Kipuka Puaulu (Bird Park) Trail ©
Kipuka Puaulu (Bird Park) Trail

2
nights
Kailua-Kona, Island of Hawaii

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 22nd (Wed): fulfill a lifelong dream with a swim-with-the-dolphins experience and then see majestic marine mammals with a dolphin and whale watching tour. Here are some ideas for day two: enjoy the sand and surf at Mauna Kea Beach and then stroll through Hapuna Beach State Recreation Area.

For other places to visit, ratings, more things to do, and more tourist information, you can read our Kailua-Kona journey tool .

Traveling by car from Volcano to Kailua-Kona takes 2.5 hours. Alternatively, you can take a bus. Traveling from Volcano in May, plan for somewhat warmer nights in Kailua-Kona, with lows around 73°F. Cap off your sightseeing on the 23rd (Thu) early enough to travel to Kula.

Things to do in Kailua-Kona

Outdoors Wildlife Tours

Side Trips

Hapuna Beach State Recreation Area, Mauna Kea Beach
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©
Dolphin & Whale Watching

3
nights
Kula, Maui

Kula is a district of Maui, Hawaii, that stretches across the "up-country", the western-facing slopes of Haleakalā, from Makawao to Ulupalakua. Explore the numerous day-trip ideas around Kula: Wailuku (Maui Ocean Center & Iao Valley), Haleakala Crater (in Haleakala National Park) and Lahaina (Lahaina Banyan Court, Ka'anapali Beach, & more). It doesn't end there: stop by Proteas of Hawaii and enjoy the sand and surf at Kalepolepo Beach Park.

For other places to visit, more things to do, where to stay, and more tourist information, refer to the Kula trip builder tool .

Traveling by combination of taxi and flight from Kailua-Kona to Kula takes 3.5 hours. Alternatively, you can fly; or do a combination of flight and taxi. Plan for slightly colder nights when traveling from Kailua-Kona in May since evenings lows in Kula dip to 68°F. Wrap up your sightseeing on the 26th (Sun) early enough to travel to Hanalei.

Things to do in Kula

Parks Outdoors Nature

Side Trips

Lahaina, Wailuku, Kalepolepo Beach Park, Haleakala Crater
Highlights from your plan
Zipline
Haleakala Crater ©
Haleakala Crater
Ka'anapali Beach ©
Ka'anapali Beach

2
nights
Hanalei, Kauai

Hanalei ©
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Start off your visit on the 27th (Mon): identify plant and animal life at Na Pali Coast State Park, then explore the stunning scenery at Waimea Canyon State Park, and then admire the sheer force of Hanakapiai Falls. On the 28th (Tue), you'll have a packed day of sightseeing: hit the best photo ops around with an inspiring photography tour and then see the world from above with a helicopter tour.

To find ratings, traveler tips, maps, and other tourist information, read Hanalei vacation planning site .

Traveling by combination of flight and taxi from Kula to Hanalei takes 3.5 hours. In May, plan for daily highs up to 82°F, and evening lows to 71°F. Finish up your sightseeing early on the 28th (Tue) so you can travel to Honolulu.

Things to do in Hanalei

Nature Parks Tours

Side Trips

Waimea Canyon State Park, Hanakapiai Falls, Na Pali Coast State Park, Photography Tours, Helicopter Tours
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Waimea Canyon State Park ©
Waimea Canyon State Park
Helicopter Tours

4
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.
When in Honolulu, make a side trip to see Kailua Beach Park in Kailua, approximately 32 minutes away. And it doesn't end there: take an in-depth tour of USS Arizona Memorial, contemplate the waterfront views at Hanauma Bay Nature Preserve, see the interesting displays at USS Bowfin Submarine Museum & Park, and browse the different shops at Ala Moana Center.

To see traveler tips, maps, reviews, and more tourist information, you can read our Honolulu online vacation builder .

Getting from Hanalei to Honolulu by combination of taxi and flight takes about 3 hours. In May, daytime highs in Honolulu are 84°F, while nighttime lows are 71°F. Wrap up your sightseeing on the 1st (Sat) early enough to travel back home.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trip

Kailua Beach Park
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach
Diamond Head State Monument ©
Diamond Head State Monument

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