60 days in Hawaii & Maine Itinerary

60 days in Hawaii & Maine Itinerary

Created using Inspirock United States attractions planner

Make it your trip
Fly
1
Kailua-Kona, Island of Hawaii
— 6 nights
Drive
2
Hilo, Island of Hawaii
— 7 nights
Fly
3
Lahaina, Maui
— 7 nights
Fly
4
Lihue, Kauai
— 6 nights
Fly
5
Honolulu, Oahu
— 9 nights
Fly to Boston, Bus to Portland
6
Portland
— 8 nights
Drive
7
Camden
— 8 nights
Drive
8
Bar Harbor, Mount Desert Island
— 8 nights
Fly

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Kailua-Kona, Island of Hawaii

— 6 nights

Heart of the Kona Coast

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.
Kids will appreciate attractions like Swim with Dolphins and Pololu Valley Lookout. Change things up with these side-trips from Kailua-Kona: Statue "King Kamehameha" (in Kapaau), Waikoloa (Waikoloa Beach Resort, Anaehoomalu, &more) and Papakōlea Green Sand Beach (in Naalehu). There's still lots to do: enjoy the sand and surf at Hapuna Beach State Recreation Area, explore the wealth of natural beauty at Puukohola National Historic Park, head outdoors with Kona Cloud Forest, and hike along The 1871 Trail.

To see where to stay, more things to do, and more tourist information, you can read our Kailua-Kona trip itinerary planner.

San Francisco to Kailua-Kona is an approximately 7-hour flight. The time zone difference when traveling from San Francisco to Kailua-Kona is minus 2 hours. Expect a bit warmer temperatures when traveling from San Francisco in August; daily highs in Kailua-Kona reach 87°F and lows reach 77°F. Finish your sightseeing early on the 6th (Mon) to allow enough time to drive to Hilo.

Things to do in Kailua-Kona

Parks · Outdoors · Beaches · Nature

Side Trips

Hilo, Island of Hawaii

— 7 nights

America's Wettest City

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.
Bring the kids along to Akaka Falls State Park and Imiloa Astronomy Center. Get out of town with these interesting Hilo side-trips: Hawaii Volcanoes National Park (Kīlauea, Kipuka Puaulu (Bird Park) Trail, &more), Laupahoehoe Beach Park (in Laupahoehoe) and Waipiʻo Valley Lookout (in Honokaa). There's still lots to do: take in the dramatic scenery at Rainbow Falls, take in nature's colorful creations at Hawaii Tropical Bioreserve and Garden, learn about wildlife with up-close encounters at Panaewa Rainforest Zoo and Gardens, and examine the collection at Lyman Museum.

To see where to stay, traveler tips, ratings, and other tourist information, use the Hilo driving holiday planner.

Getting from Kailua-Kona to Hilo by car takes about 2 hours. Other options: take a bus. Traveling from Kailua-Kona in September, expect little chillier with lows of 71°F in Hilo. Finish your sightseeing early on the 13th (Mon) to allow enough time to fly to Lahaina.

Things to do in Hilo

Parks · Outdoors · Museums · Trails

Side Trips

Lahaina, Maui

— 7 nights

Crown Jewel of Maui

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.
Kids will appreciate attractions like Scuba & Snorkeling and Hana Highway - Road to Hana. Venture out of the city with trips to Wailuku (Maui Tropical Plantation & Iao Valley), Wailea (Wailea Beach & Makena Beach) and Haleakala Crater (in Haleakala National Park). There's lots more to do: kick back and relax at Ka'anapali Beach, get impressive views of Molokini Crater, get outside with Maui Mobility Systems, and examine the collection at Whalers Village Museum.

For ratings, other places to visit, and other tourist information, you can read our Lahaina sightseeing planning tool.

Traveling by flight from Hilo to Lahaina takes 2.5 hours. In September in Lahaina, expect temperatures between 86°F during the day and 74°F at night. Finish up your sightseeing early on the 20th (Mon) so you can catch the flight to Lihue.

Things to do in Lahaina

Outdoors · Parks · Beaches · Nature

Side Trips

Lihue, Kauai

— 6 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Family-friendly places like Zipline and Tunnels Beach will thrill your kids. Change things up with these side-trips from Lihue: Waimea Canyon State Park (in Waimea), Na Aina Kai Botanical Gardens (in Kilauea) and Hanalei (Hanalei Beach, Hanalei Valley Lookout, &more). There's still lots to do: enjoy the sand and surf at Poipu Beach Park, admire the sheer force of Opaekaa Falls, stroll through Hanalei Bay, and immerse yourself in nature at Wailua River State Park.

For traveler tips, reviews, more things to do, and more tourist information, refer to the Lihue tour itinerary website.

You can fly from Lahaina to Lihue in 2.5 hours. In September, daily temperatures in Lihue can reach 86°F, while at night they dip to 76°F. Cap off your sightseeing on the 26th (Sun) early enough to catch the flight to Honolulu.

Things to do in Lihue

Parks · Outdoors · Beaches · Nature

Side Trips

Honolulu, Oahu

— 9 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Kids will enjoy Waikiki Beach and USS Arizona Memorial. Explore the numerous day-trip ideas around Honolulu: Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua (Kailua Beach Park, Lanikai Beach, &more) and Haleiwa (Sunset Beach Park & Waimea Bay). Next up on the itinerary: go for a walk through Diamond Head State Monument, get engrossed in the history at Iolani Palace, take in the dramatic scenery at Manoa Falls, and kick back and relax at Ala Moana Beach Park.

To find reviews, traveler tips, ratings, and other tourist information, go to the Honolulu trip itinerary planner.

You can fly from Lihue to Honolulu in 2.5 hours. In September, daytime highs in Honolulu are 88°F, while nighttime lows are 76°F. Wrap up your sightseeing on the 5th (Tue) to allow time to travel to Portland.

Things to do in Honolulu

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Portland

— 8 nights

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Kids will enjoy Marginal Way Walkway and Funtown Splashtown USA. Get out of town with these interesting Portland side-trips: Ogunquit (Footbridge Beach & Ogunquit Beach), Gooch's Kennebunk Beach (in Kennebunk) and Moody Beach (in Wells). The adventure continues: tour the pleasant surroundings at Popham Beach State Park, enjoy the sand and surf at Short Sands Beach, enjoy the sea views from Nubble Lighthouse, and savor the flavors at Food & Drink.

For traveler tips, photos, and tourist information, go to the Portland travel route app.

Getting from Honolulu to Portland by combination of flight and bus takes about 13.5 hours. Due to the time zone difference, you'll lose 5 hours traveling from Honolulu to Portland. Prepare for colder weather when traveling from Honolulu in October: high temperatures in Portland hover around 62°F and lows are around 43°F. Finish up your sightseeing early on the 13th (Wed) so you can go by car to Camden.

Things to do in Portland

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Camden

— 8 nights
Bring the kids along to Morning In Maine Boat Tour and Pitcher Pond. Explore the numerous day-trip ideas around Camden: Todd Audubon Sanctuary at Hog Island (in Bremen), Bristol (Pemaquid Point Lighthouse, The Swimming Hole At Bristol Dam, &more) and Dodge Point Public Reserved Land (in Newcastle).

To see reviews, ratings, photos, and tourist information, go to the Camden vacation planner.

Traveling by car from Portland to Camden takes 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. In October, daily temperatures in Camden can reach 58°F, while at night they dip to 42°F. Wrap up your sightseeing on the 21st (Thu) to allow time to drive to Bar Harbor.

Things to do in Camden

Parks · Wildlife · Outdoors · Nature

Side Trips

Bar Harbor, Mount Desert Island

— 8 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kids will appreciate attractions like Schoodic Peninsula and Boat Tours & Water Sports. Explore Bar Harbor's surroundings by going to Schoodic Point (in Winter Harbor), Chipman's Wharf (in Milbridge) and Jasper Beach (in Machiasport). The adventure continues: contemplate the waterfront views at Frenchman Bay, get outside with Osprey, see the interesting displays at The Seal Cove Auto Museum, and stroll through Great Head Trail.

To find maps, photos, reviews, and other tourist information, use the Bar Harbor trip itinerary maker.

Traveling by car from Camden to Bar Harbor takes 2 hours. Alternatively, you can take a bus. In October, daily temperatures in Bar Harbor can reach 59°F, while at night they dip to 42°F. Finish your sightseeing early on the 29th (Fri) so you can fly back home.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trips

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
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.

Maine travel guide

4.6
Beaches · Lighthouses · Mountains
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.