Hawaii Travel Agent FAQ

Certified Hawaii Destination Expert

Hawaii Travel Agent FAQ

Hawaii travel agent FAQ-Frequently Asked Questions about planning a trip to Hawaii.


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Vacation Planning & Budget

Arrange a package that fits my budget. Will you help me decide which island to visit?


Can I book a multi-island package, arriving on one island, and departing from another?

Yes, I can book your package to take advantage of the best flights for inbound and outbound from any island.

hawaii-multi-island-vacation-packages
Guided Tours on All Islands

Include tours and activities for each island that I want to visit.

Once we get the itinerary plan with travel dates, names and birthdates, the activities can be added to your itinerary.

Book with a dedicated activity specialists.

How to Choose Which Island to Visit

Yes, we will work together to create an itinerary that fits your dream vacation.

Whatever your budget, there are good deals available.


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Oahu is the best island to visit for free entertainment and you won’t need a car.

Oahu, Honolulu, and Waikiki Beach are ideal for families with teens and it is budget-friendly.

Enjoy the free music and hula pop-ups of the Hawaiian families that live on the island.

Which Island has the Most Beaches?


Discover Maui waterfalls and mountains

Maui has the best island for vacation rentals and resorts on amazing beaches.

Maui is the first choice for beachfront vacation rental condos and white sand beaches. Embark from the ports in South Maui for cruising the calm waters to snorkel or go whale watching in the channel.

Lahaina Town remains closed due to the fire in 2023, however, Kaanapali Beach and the resorts north of Lahaina Town are operating as usual.

Why is Kauai Called the Garden Island? Rainforests & Waterfalls

The quiet lifestyle of Kauai invites visitors to slow down and take it easy. Visit a rainforest and desert in one location at Kokee State Park.


Kauai Destination Specialist

Kauai is the best island for rainforest tours and quaint village lifestyles.

Poipu Beach is a favorite for families that prefer a vacation rental condo, or for a romantic getaway in an oceanfront suite.


Kona Coffee Farms

Where Can I See the Active Volcano?

Book a trip to the Big Island Hawaii

Hilo Volcanoes Park

The Big Island is the youngest island in the Hawaiian Islands chain and it likes to show off, a visit to Volcanoes Park is a must-see adventure.

Don’t miss out, visit Kona’s famous coffee farms and the farmer’s market for fresh fruit and “talk story” with the locals during your stay in Kona on the Big Island.


During Travel Customer Service

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Official Pleasant Holidays Website

Rose Royse, Hawaii Vacation Expert

Pleasant Holidays Elite Advisor 2024

24-hour customer phone number to assist you while traveling.

Weather and Flight Schedule Changes

What if I need help at the airport?

The call center is there to assist you with missed connections and delayed flights.

Trip Cancellation

Does the package include travel insurance in case we have to cancel or change our trip?

Yes, cancel for any reason insurance can be added to your package.

Choose either a cash back refund or a future travel credit.


A large cruise ship sailing in the ocean.
A large cruise ship sailing in the ocean.
A large cruise ship sailing in the ocean.
A large cruise ship sailing in the ocean.
A large cruise ship sailing in the ocean.
A large cruise ship sailing in the ocean.
A large cruise ship sailing in the ocean.
A large cruise ship sailing in the ocean.

Payments & Insurance

Do packages include a payment option?

Yes, a partial payment will confirm the entire package.

The deposit with booking includes full payment for the flights and insurance at the time of booking.

Final payment is due 60 days prior to departure for island packages and 120 day for cruise packages.


Tours and Activities All Islands

Oahu Tours and Activities

Maui Tours and Activities

Kauai Tours and Activities

Big Island Tours and Activities


Hawaii Vacation Specialty Travel


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