Caileigh Cole-Gall, Travel Agent in Bend, OR

Caileigh Cole-Gall

Bend, OR Travel Agent

Caileigh Cole-Gall

Bend, OR · 4 Years of Experience

Olive and Sage Travel, an independent agent with Travel Group Collective, LLC, a Travel Leaders Network Affiliate Agency
5.0
(5)
100% Recommended
AM/FM Travel and specifically Caileigh Cole-Gall did an excellent job planning and coordinating my family's recent 2 week trip to Switzerland and Italy. I contacted Caileigh... Read More >
About
Reviews
Certificates & Awards
My Places

Areas of expertise

Destinations:

Worldwide, Tuscany, London, Bangkok, Kruger National Park

Interests:

Luxury, Wine Country Vacations, Historical Sites, Arts & Culture, Holiday Travel

About Me

Luxury Travel Consultant

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Travel is more than a getaway—it’s a deeply personal investment in memories, connection, and once-in-a-lifetime experiences. As a luxury travel advisor based in Bend, Oregon, I specialize in designing seamless, highly personalized journeys for retired luxury travelers, multi-generational families, honeymooners, wine enthusiasts, and history lovers seeking something truly extraordinary.

My path into travel began after a successful career in real estate. While I loved helping clients find homes, I longed for a career that allowed me to explore the world more than once a year. I took the leap into travel advising to align my profession with my passion—and now I help others experience the world in ways that are meaningful, effortless, and unforgettable.

I am especially passionate about Italy. My husband and I were married there and spent three weeks traveling throughout the country, and I have returned multiple times since. From the rich history of Rome to the vineyards of Tuscany and the charm of smaller regional towns, I know Italy intimately. I also curate immersive journeys throughout Europe, encourage multi-country itineraries, and design incredible experiences in Southeast Asia—particularly Thailand, which I have visited three times. After transformative visits to Egypt and Jordan in 2025, I am equally passionate about the Middle East and its extraordinary historical depth.

When I travel, I experience destinations exactly as my clients would—carefully evaluating every hotel, guide, and experience. I build strong supplier relationships to secure VIP treatment and monitor each trip in real time to resolve any issues seamlessly.

If you’re ready to elevate your travel experience and create unforgettable memories, I would be honored to design a journey tailored uniquely to you. Reach out to me today and let’s get started planning!  

REVIEWS

Rating: 5.0
5 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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Terrific trip to Switzerland and Italy
Reviewed By Jon & Family - Detroit, Michigan | Traveled to Europe
AM/FM Travel and specifically Caileigh Cole-Gall did an excellent job planning and coordinating my family's recent 2 week trip to Switzerland and Italy. I contacted Caileigh relatively last minute and she put together a great itinerary in less than 3 weeks. I appreciated the itinerary app and the connectivity back to Caileigh during the trip. She was very professional, responsive, and helpful when adjustments came up during the trip. Thank you for the wonderful service!
I would recommend this agent to my family and friends.
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Relaxing Trip in San Juan Cabin
Reviewed By Sisi - Spokane, WA | Traveled to Roche Harbor | Washington | USA
We recently had the pleasure of working with Caileigh for our trip to the San Juan Islands, and the experience was exceptional. Caileigh took all the planning off our shoulders, allowing us simply to show up and enjoy our vacation. This was a huge relief, especially for someone like me who usually handles all the family vacation planning. Her organization made my life feel 1000 times easier. Even when we had to reschedule a couple of times, Caileigh managed everything seamlessly, providing a stress-free experience. Her communication was outstanding, marked by quick responses and helpful knowledge. She even offered to plan activities while we were at our destination, showcasing her dedication to ensuring we had a memorable trip. I would recommend Caileigh to anyone looking for a reliable and knowledgeable travel agent.
I would recommend this agent to my family and friends.
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10 days in Ireland & 10 days in Scotland, amaz
Reviewed By Dave - Sisters Oregon | Traveled to Ireland ~ Europe
Caileigh did an amazing job, pre-trip planning was a breeze and she accommodated all of our trip plan wishes flawlessly, we will definitely be using her for our future trips overseas
I would recommend this agent to my family and friends.
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Fabulous time in Italy
Reviewed By Steve - Redmond, OR | Traveled to Florence ~ Italy ~ Europe
This was the first time my wife and I traveled to Europe and we were big time rookies. We had limited experience with airline travel as well. Caileigh arranged for airline tickets as well as 4 train trips in Italy. Aside from the time change, Caileigh was a huge help whenever we needed it. Especially arranging for last minute assistance at the airports on our return journey due to my wife's difficulty walking great distances.
I would recommend this agent to my family and friends.
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Very enjoyable trip!
Reviewed By Bailey John - Oregon | Traveled to Oahu Island ~ Hawaii ~ USA
Very good experience
I would recommend this agent to my family and friends.
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Certifications & Awards

ASTA is the leading global advocate for travel agents, the travel industry and the traveling public.It is the world's largest association of travel professionals.Our members include travel agents and the companies whose products they sell such as tours, cruises, hotels, car rentals, etc.Expand your world. Go with the pros.

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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