Hawaii Travel Specialist

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Shelley Cuthbertson, Travel Agent in Calgary, AB

Shelley Cuthbertson

Calgary, AB Travel Agent

Shelley Cuthbertson

Calgary, AB

Shelley's Compass, an independent agent with Jubilee Tours & Travel LTD/DBA Travel Best Bets, a Travel Leaders Network Affiliate Agency
5.0
(2)
100% Recommended
Great place, beautiful grounds, view of the lake and golf course from the fire pits on the patio. Very good price! Read More >
About
Reviews
My Places

Areas of expertise

Destinations:

Hawaii, Pacific Ocean

Interests:

Bespoke Travel, Bucket List, Car Travel, Arts & Culture, Vacation Rentals

Suppliers:

Enterprise, Viator

About Me

Hi, I’m Shelley — a Hawaii travel specialist and experienced travel advisor who has spent the last 15 years exploring all four major Hawaiian islands firsthand: Oahu, Maui, the Big Island, and Kauai.

I don’t just sell Hawaii travel — I’ve lived it, explored it, and driven it. On every island, I’ve rented a car, travelled beyond the resorts, and discovered the beaches, lookouts, local spots, and hidden gems that make each island truly unique.

That firsthand experience allows me to design trips that go far beyond the typical tourist itinerary.

Each Hawaiian island offers something completely different, and I help you match the right island to the right type of trip:

  • Oahu – Extended Family & Multi-Generational trips perfect for families who want variety. From Waikiki’s energy to North Shore beaches and cultural experiences, I design Oahu itineraries that balance relaxation, activities, and family-friendly convenience.
  • Maui – Friends’ Getaways & Adventure trips ideal for groups looking for a mix of adventure and relaxation. Think scenic drives along the Road to Hana, snorkelling, sunset cruises, and boutique stays that make group travel unforgettable.
  • Big Island – Couples Who Love Nature & Exploration A perfect romantic escape for couples who want something more rugged and dramatic. From volcanoes to black sand beaches and stargazing on Mauna Kea, I create experiences that feel both adventurous and deeply personal.
  • Kauai – Romantic Couples’ Retreats known as the “Garden Isle,” Kauai is perfect for couples seeking quiet luxury, lush landscapes, waterfalls, and slow, meaningful travel.

I design peaceful itineraries that focus on connection and natural beauty.My approach is always customized travel planning based on your travel style, budget, and experience goals.

Whether you want resort luxury, boutique stays, or a mix of adventure and relaxation, I take care of the details so your Hawaii trip feels seamless and unforgettable.

I specialize in:

  • Hawaii vacation planning and island itineraries
  • Multi-island trip coordination
  • Family, group, and romantic getaway planning
  • Car rental-based exploration itineraries (so you truly experience each island)
  • Hidden gems, local experiences, and curated recommendations

Traveling Hawaii is more than just booking a resort — it’s about knowing where to go, when to go, and how to experience each island beyond the surface. That’s where I come in.

If you’re ready to plan your Hawaii trip — whether it’s a family adventure on Oahu, a friends’ getaway in Maui, a romantic escape on Kauai, or an exploration of the Big Island — I’ll help you create a trip that feels effortless, personal, and unforgettable.

REVIEWS

Rating: 5.0
2 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 2 reviews

Nice "resort" feel
Reviewed By Travel Bug - Alberta | Traveled to Las Vegas | Nevada | USA
Great place, beautiful grounds, view of the lake and golf course from the fire pits on the patio. Very good price!
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
A great overnight
Reviewed By Carol - Westin Lake Resort & Spa | Traveled to Las Vegas | Nevada | USA
The hotel Shelley picked for us was absolutely wonderful. A great price the grounds were great for a walk about. Rooms were very clean and the valet service and front desk very friendly. A great job all the way around.
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.
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