Plan your trip with a Hawaii travel expert!

Personalized Hawaii Vacation Planning

We help travelers cut through the noise and plan Hawaii vacations that fit their travel style, priorities, and budget.

Whether you're dreaming of a romantic Maui getaway, an adventure-filled Kauai itinerary, or a multi-island family vacation, we'll help you make confident decisions from day one.

With four major islands, hundreds of resorts, and an endless list of activities, planning a Hawaii vacation can quickly become overwhelming. Should you spend your entire trip on one island or visit several? Is a luxury resort worth the splurge? Which experiences are truly worth your time?

That's where we come in.

There are countless ways to experience Hawaii. We'll help you find the one that's right for you.

We help you choose the right island (or islands)
Oahu, Maui, Kauai, Lanai, and the Big Island are completely different trips. We match you to the island that fits your family, and if you're hopping more than one, we plan the order and timing so it flows.

We take care of you the whole trip.
We don't just book your resort. We handle flights, inter-island travel, rental cars, and the tours and activities worth your time.

We make sure the trip itself is magical.
This starts before you go. We send you island guides, keep you on top of anything that needs booking ahead, and pass along the insider stuff (the luau actually worth your evening, the beaches worth the drive, where to watch the sunset, and the spots most visitors never find).

What exactly do we do?

01/04

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K. Ditta

from

"Rose was fantastic to work with and made our vacation to Oahu, Hawaii amazing. She found the perfect hotel with breathtaking views and the trip was worry free. My husband said it was the best vacation of his life, and this was his 5th time to Hawaii."

What our Clients Say

02/04

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M. Hendricksen

from

"Rose was absolutely delightful to work with. She planned a a 10 night trip to the Hawaiian Islands for my 60th birthday that was amazing. From air travel, car rentals, hotels, and excursions the trip was planned perfectly. My husband and I will definitely have Rose plan our future Hawaiian vacations.”

What our Clients Say

03/04

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E. Parker

from

"My sons and I had an amazing vacation to Maui thanks to Rose. Going to Hawaii was a once in a lifetime trip for us and she made every one of our wishlist items come true! Her attention to detail made this the most perfect trip I have ever experienced!”

What Our Clients Say

04/04

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M. Matzke

from

"Rose with Where to Go Travel designed our "once in a lifetime" trip to Hawaii for our 45th anniversary. She took the stress out of travel which is what you need for a vacation. I recommend this service highly!"

What Our Clients Say

No. Our planning comes at no additional cost to you, and you'll never pay more than booking on your own.

Is there a fee to work with you?

Frequently Asked Questions

We specialize in 4 and 5-star resort experiences, and the properties we work with typically start around $650 per night. If that's the kind of trip you're after, we'd love to help.

Do you have a minimum trip budget?

Frequently Asked Questions

The earlier the better. The best resorts and rooms book up far ahead, especially over school breaks, and more lead time means more options.

When should I start planning?

Frequently Asked Questions

Yes! We'll give you a day-by-day itinerary with the personalized recommendations for your family. We like to include a few scheduled activities, but also build in free time, so you have a plan without feeling overscheduled.

Can you help us plan our day-to-day itinerary?

Frequently Asked Questions

We do, as long as you're not using points to book your flights.We want to support you from the moment you leave home until you return.

Do you book airfare too?

Frequently Asked Questions

That's exactly what we're here for. We'll match you to the right island based on how your family likes to travel, then build the trip around it.

Which island(s) should we go to?

Frequently Asked Questions

Start Planning

If you want a trip that feels smooth, well thought out, and genuinely enjoyable from beginning to end…

You’re in the right place.

Start with our planning form and let’s design your trip together.