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Hawaii: Oahu, the Big Island and Maui for three generations

9 days from Honolulu to Maui for grandparents, parents and children 6 and up: Pearl Harbor and the North Shore on Oahu, Hawaii Volcanoes National Park from Hilo, and Haleakala, turtles and beach afternoons on Maui.

9 days · Honolulu to Kahului · up to 12 guests

The facts

At a glance

Length
9 days, 8 nights
Start and end
Honolulu to Kahului
Group size
7 to 12 guests
Longest drive
4 h on day 3No drive day is longer than 4 hours.
Activity level

Easy

Walks of 0.5 to 3 km a day on paved paths, boardwalks and some uneven lava, with plenty of benches and the van close by. The one real climb is Diamond Head, about 1.3 km each way and 170 m up with stairs; the crater floor is the easy alternative. The Kilauea Iki crater trail (about 5 km) is an option only. Haleakala's summit is at 3,055 m by daylight, cold and windy, and anyone can stay lower. Snorkelling is optional, with float vests. Drives are in legs of 45 minutes or less except the 1 hour 45 minute climb up Haleakala, with a stop halfway.

Meals included
8 breakfasts, 7 lunches, 1 dinner
Room of your own
+ CAD 1,430 (estimated price)
Season
All year; school holidays in July, August and late December are the busiest, and December to April adds humpback whales off Maui

Highlights

Why this trip

  • The boat out to the USS Arizona Memorial at Pearl Harbor on one of the first programs of the morning
  • Shave ice in Haleiwa and green sea turtles resting on a North Shore beach
  • A planetarium show at Imiloa in Hilo, then a swim off Coconut Island
  • Junior Ranger badges at Hawaii Volcanoes National Park, after walking through a lava tube
  • The summit of Haleakala at 3,055 m by daylight, with the clouds below and silverswords at your feet
  • Snorkelling a calm Maui reef with turtles, then sharks overhead in the Maui Ocean Center tunnel
  • Three nights in Waikiki, two in Hilo and three on Maui's south shore, with pool or beach afternoons on five days

What makes this trip different

  • Short drives, all published

    Every drive is listed day by day, and none is longer than 4 hours.

  • Free time is part of the plan

    Free time and choices are marked on the days they fall.

  • Solo without the penalty

    A room of your own is + CAD 1,430 (estimated price).

Day by day

Itinerary

The longest drive is 4 h, on day 3.

KAUAIOAHUMOLOKAILANAIMAUIBIG ISLANDPacific Ocean123WaikikiDays 1 to 4Pearl HarborDay 2HaleiwaDay 3KualoaDay 3HiloDays 4 to 6KilaueaDay 5Iao ValleyDay 6MaalaeaDay 8KiheiDays 6 to 9HaleakalaDay 7

Tap any stop on the map to open that day

Arrive in Honolulu

Honolulu airport (HNL) to Waikiki

  • Welcome dinner at 5:30 pm
  • Stay in Honolulu
  • Drive about 30 min
Apartment and hotel towers of Honolulu lit up at night under a black sky, with a dark glass high-rise in the centre
Photo: Daniel Ramirez, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Close-up_of_Azure_at_night,_Honolulu,_Hawaii.jpg)

Fly into Daniel K. Inouye International Airport (HNL) in Honolulu, ideally landing by about 2 pm. Our driver meets each family at arrivals, with booster seats ready for the children who need them, and takes you about 30 to 40 minutes to your hotel in central Waikiki, where we have asked for family or connecting rooms. If you arrive early, the calmest water for children is inside the Kuhio Beach breakwater, a shallow walled pool off the main beach with lifeguards nearby, and grandparents can sit in the shade of the banyan tree on Kalakaua Avenue. At about 4:30 pm your See Sight Tours guide meets the group in the hotel lobby: introductions for every generation, the plan for the week, the two inter-island flights and what to pack for a day at 3,000 m.

Evening

The welcome dinner starts at 5:30 pm, a short walk away, so the youngest are in bed early. Most guests from Canada and the mainland wake early on their first morning, which suits tomorrow.

Included

  • Arrival transfer from Honolulu airport (HNL) to your Waikiki hotel
  • Welcome meeting with your guide at 4:30 pm
  • Welcome dinner in Waikiki at 5:30 pm

Free time: Afternoon free on Waikiki Beach before the welcome meeting

Activity: Landing after 5 pm? Your guide catches you up at breakfast.

  1. Honolulu3 nights
  2. Hilo2 nights
  3. Kihei3 nights
  4. Kahuluiend
  • Overnight stop
  • Day trip
  • By boat or train
Print itinerary

Wildlife and weather: Hawaii is warm all year: about 27 to 31 C by day on the coast in summer and 25 to 28 C in winter, with sea temperatures of about 24 to 27 C. Hilo is wet in every month, so expect showers on the Big Island days; Waikiki and Kihei are much drier. Green sea turtles are seen in all seasons. From about December to April humpback whales winter off Maui, and from about November to March big North Shore swells close beaches there to swimmers, so the stop becomes a wave-watching one. The Haleakala summit can be near freezing even at midday.

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Get the day-by-day itinerary by email, or ask us anything about this trip. A trip planner replies the same or next business day.

Before you book

Right for you?

Good for you if you want

  • Grandparents, parents and children aged 6 and up travelling together
  • Families who want three islands without planning the flights, timed entries and driving
  • Grandparents who walk well on the flat but would rather skip long climbs
  • Children who like volcanoes, turtles, aquariums and a pool at the end of the day
  • A grandparent travelling with one grandchild who wants a fair room price

Not for you if you want

  • Families with children under 6
  • Travellers who want Haleakala at sunrise, Maunakea at night or Kauai: see our three-island and four-island Hawaii trips
  • Keen hikers looking for long daily trails
  • Families who want a luxury resort; our hotels are comfortable and central, not grand
  • Anyone who cannot manage a few hours at 3,000 m on Haleakala, though you can stay lower

Minimum age: 6

Most guests are 6 to 80

Book flights after we confirm your seat.

8 nights

Where you'll stay

Your hotels are named in your trip confirmation.

  • Honolulu3 nights
  • Hilo2 nights
  • Kihei3 nights

One price

What's in the price

Included

Accommodation

  • 8 nights: 3 in Waikiki (Honolulu), 2 in Hilo on the Big Island and 3 in Kihei on Maui
  • Central hotels of a 3-star-plus standard with a pool where the town has one, close to the beach or the town centre; we name each hotel when we confirm your dates
  • Family rooms or connecting rooms requested for each family
  • Hotel taxes and mandatory resort fees

Transport

  • Arrival transfer from Honolulu airport (HNL) and departure transfer to Kahului airport (OGG)
  • Two inter-island flights, Honolulu to Hilo and Hilo to Kahului (or via Honolulu), each with one checked bag
  • A vehicle and driver for the group on each island, from a local partner, with booster seats for children who need them
  • The Navy shuttle boat to the USS Arizona Memorial

Your guide

  • A See Sight Tours guide with the group from the welcome meeting on day 1 to the airport on day 9, including on the flights
  • Park rangers and licensed local guides where sites require them

Activities

  • Oahu: Pearl Harbor National Memorial and the USS Arizona Memorial, Diamond Head State Monument, the island loop with Kualoa, Haleiwa, a North Shore turtle beach and Waimea Bay, and the Dole Plantation garden maze
  • Big Island: Imiloa Astronomy Center with a planetarium show, Rainbow Falls, Liliuokalani Gardens and Coconut Island, Hawaii Volcanoes National Park with the steam vents, Nahuku lava tube and the Chain of Craters Road
  • Maui: Iao Valley State Monument, the summit of Haleakala National Park by daylight, a guided morning snorkel with gear and float vests, and the Maui Ocean Center at Maalaea
  • Junior Ranger booklets in both national parks, and all park, monument and state park entry fees and reservations for the visits above

Meals

  • 8 breakfasts
  • 7 lunches, including shave ice in Haleiwa
  • 2 dinners at 5:30 pm: a welcome dinner in Waikiki and a farewell dinner on Maui

Not included

  • International flights to Honolulu and home from Kahului
  • US entry documents: an ESTA or visa where needed
  • Travel insurance
  • Meals not listed above
  • Drinks
  • Tips for your guide, drivers and local guides
  • Optional activities, such as the Battleship Missouri tour or a whale watch on Maui
  • Extra checked bags on the inter-island flights
  • Personal expenses

Extras

Room of your own
CAD 1,430 (estimated price)

When you can go

Dates and prices

Pick your start date when you request to book. We check that date and confirm it in your quote.

Prefer to travel without a group or guide? Ask us about arranging hotels, transport and city tours for you to travel independently.

Before you book

Booking terms

Nothing is charged now. Full terms and the cancellation schedule come with your quote, before you accept.

Business addresses

See Sight Tours Trips (USA): 3172 N Rainbow Blvd, Las Vegas, NV 89108, United StatesSee Sight Tours Trips (Canada): 5305 50 Avenue, #1091, Red Deer, AB T4N 4B6, Canada+1-888-961-6584

Guest reviews

What guests say

Reviews from guests on our day tours.

Cornelius Amann
October 06, 2026
google

5/5

Parminder did a great job guiding us around, giving us tips & teaching us the history of the falls. A great experience!

Jane
October 06, 2026
gyg

5/5

Good views of the surrounding area of Halifax in a comfortable minivan

Susan
October 06, 2026
gyg

5/5

June was brilliant- made good contact beforehand and really attentive and knowledgeable. Made me feel like I was special- something only experience can do. Thank you June.

Tom L
October 05, 2026
tripadvisor

5/5

Our host was very knowledgeable, friendly and even provided some humor.

MandL83
October 05, 2026
tripadvisor

5/5

Peter was a very good guide, giving us insight into the various parts of the Park, including parking lot congestion details, trail and viewing location suggestions.

Darren O
October 05, 2026
tripadvisor

5/5

Excellent morning spent with my guide Nancy. Very knowledgeable and friendly. Thoroughly enjoyed my trip

4.7/5 from 38,601 guest reviews

Good to know

Questions

What does the Hawaii family trip include?

Eight nights in central hotels with taxes and resort fees, family or connecting rooms requested, 8 breakfasts, 7 lunches and 2 early dinners, both inter-island flights with a checked bag, a vehicle and driver on each island, your See Sight Tours guide throughout, and every visit in the day plan, including Pearl Harbor, Diamond Head, Hawaii Volcanoes, Haleakala, a guided snorkel and the Maui Ocean Center.

What age do children need to be?

Children must be 6 or older on the first day of the trip. The day plan is set so that a 9-year-old and a 70-year-old both enjoy every day: short walks, an easy option at each stop, pool or beach afternoons and dinners at 5:30 pm. Children under 18 travel with a parent, grandparent or guardian.

Is there a price for children?

The published price is per person sharing, for adults and children alike. Where a child shares a room with two adults, the hotel and some entries may cost less, and we quote a child price when you request to book. Tell us the ages of every child and how your family would like to share rooms.

How big is the group, and will we be with other families?

The small-group trip runs with 7 to 12 guests, counting children, so it fits one small vehicle and one table at dinner. Departures are marketed to three-generation families, so you will usually travel with one or two other families. A family of seven or more can fill a departure, or book the private version.

Who leads the trip?

A See Sight Tours guide travels with the group from the welcome dinner in Waikiki to the Maui airport, including on the two flights. Local partners provide the vehicle and driver on each island, and park rangers lead the Pearl Harbor and national park programs. Your guide also runs the snorkel and the Junior Ranger badges.

How much walking is there for grandparents?

Not much. Most days have 0.5 to 3 km on paved paths and boardwalks, with benches and the van close by. Diamond Head is the one climb, about 170 m up with stairs, and you can wait on the crater floor instead. The Haleakala summit at 3,055 m is reached by van, with viewpoints a few steps away.

I am a grandparent travelling with one grandchild. What is the single supplement?

A grandparent and grandchild sharing a room pay the normal per-person price and no supplement. A room of your own is CAD 1,430 on top of the small-group price, shown before you book. Solo adults take part in everything on the same terms as couples and families.

When is the best time to visit Hawaii with children?

The trip runs all year and the coast is warm in every month. Summer brings the calmest sea for snorkelling and North Shore swimming, and suits school holidays; December to April adds humpback whales off Maui and big surf to watch on Oahu. Hilo is showery in any season.

Why don't you go up Haleakala for sunrise?

Because a 3 am pickup and a freezing wait in the dark are hard on young children and grandparents. We go up by daylight, when the crater, the cinder cones and the silverswords are clearly visible and the cloud often still sits below you. Our three-island trip for adults includes the sunrise.

How does booking work?

Choose the small-group or private style and your start date, then send a request to book with the ages of your party. We check availability and provide the final quote, itinerary and booking terms before you accept. No payment is taken when you send the request.

Can our family travel privately or on our own dates?

Yes. The private version runs for your family only, on a date you choose, with your own guide and vehicle on every island. If you would rather travel independently without a guide, ask us from the dates section for a separate quote for the same hotels, flights and entries.

Do children need passports or visas for Hawaii?

Hawaii is part of the United States, so Canadian children need their own valid passport and no visa for a visit of this length. Many other visitors need an ESTA or a US visa. A child travelling without both parents should carry a signed consent letter from the parent or parents not travelling.

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