Sherry Holiday

Greenwood, IN

Destination Wedding and Honeymoon Specialist

I’ve been traveling for most of my life, and I’m always searching for the next beautiful destination to visit. After many years of creating my own itineraries, I realized that I wanted to help everyone experience their dream vacation. Tod...
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I know how to help couples create their dream wedding in any destination, and I’ll simplify the process to make everything stress-free. I’ll listen to you and help you create the perfect wedding while also taking care of all logistics like venue booking, flights, transfers, catering, and everything else you need for an unforgettable day.

For honeymoons, I’ll make sure you have a relaxing and amazing time with scenic views, great meals, and all the activities you desire. I’ll customize everything about your vacation so you can have the time of your life anywhere you go.

I book vacations and cruises to countless destinations, and some of my recent bookings were to:

The Bahamas
Jamaica
Dominican Republic
Mexico
Canada
St. Lucia
And more!

I’m also certified with many top cruise lines and resorts, and I have a deep understanding of their best offerings and routes. I’ll work with you to find the perfect option that fits your interests, and I’ll research your destination to provide great local recommendations. I’ve also been to most destinations in the Caribbean so I can share firsthand tips as well.

I’m aware that sometimes the weather changes or you may want to change part of your itinerary along the way, and that’s why I’m always available to assist you with anything you need. Simply contact me and I'll be ready to help immediately! I’ll simplify the booking process and ensure that your travels are as relaxing as possible. I always go above and beyond for my clients, and I'll do everything I can to make your trip the best it can be.

Whether you want to enjoy a luxury cruise, a romantic honeymoon in Cancun, or a destination wedding on the beach, I’m excited to book for you today!

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Custom Road Trips

Hi there! There's nothing I love more than hitting the open road for an epic adventure. If you’re dreaming of the ultimate road trip, you’ve come to the right place!

From the vast landscapes of the American West to the charming coastal routes of New England, I’ve planned and experienced road trips that are as unique as the travelers taking them. Whether it’s a solo journey, a couple’s getaway, or a family vacation, I’ve got the insider tips and detailed itineraries to make your road trip absolutely unforgettable.

What I bring to the table is an abundance of firsthand knowledge. I've scouted out the best scenic routes, quirky roadside attractions, amazing eateries, and cozy accommodations. Plus, with Caldwell Travel's great relationships with hotels and service providers, I can snag you some fantastic deals and perks along the way.

Planning a road trip can be overwhelming, but that’s where I come in. I'll handle all the nitty-gritty details so you can focus on enjoying the journey—because a great road trip is about the memories you make along the way.

So, pack your bags, fill up the tank, and let’s get ready for a road trip you’ll never forget!

Happy travels with Sherry Holiday and Caldwell Travel!

My Travel Albums

Badlands National Park

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My Reviews

32 of 47 people found this review helpful

Aloha!

Sherry is thorough, friendly and easily accessible. She not only plans and books what you request, she offers suggestions for the tours and activities for the area you are visiting. She made sure we had tour tickets to Pearl Harbor, the Lahaina Luau and that a rental car was booked for our time on Maui. She made sure we had transfers from the Honolulu airport and hotels/condos that were exceptional but reasonably priced. We were very pleased with our trip and when we decide to return to Maui, we will be sure to call Sherry.

By Happy Traveler from Indianapolis, Indiana
Traveled to Hawaii ~ USA

I would recommend this agent to my family and friends

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26 of 37 people found this review helpful

Always Helpful!

Sherry always tries to get the best price and flights based on the (sometimes difficult!) parameters we set. I work for a not for profit company and she understands and honors our limitations. Sherry has booked tickets for our members all over the US to destinations all over the US.

By Kelly from Indianapolis, IN
Traveled to Des Moines ~ Iowa ~ USA

I would recommend this agent to my family and friends

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23 of 33 people found this review helpful

West Coast

Sherry is the best travel agent as evidenced by planning several vacations for myself and my family. She really listens to what I want do, then gets the best deals within the time frame I have available. I am planning on visiting her in the next week to plan my next trip.

By Michele from Indianapolis, Indiana
Traveled to California ~ USA

I would recommend this agent to my family and friends

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23 of 36 people found this review helpful

Honeymoon!

Sherry helped us plan our honeymoon, and it was the best vacation we have been on. She took all the stress out of planning a vacation. I especially appreciat that she did not try to "upsell". She helped us find a trip based on our price range and seemed quite knowledgeable about the different locations we were thinking about going to.

By Honeymooners from Indianapolis
Traveled to Jamaica ~ Caribbean

I would recommend this agent to my family and friends

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20 of 31 people found this review helpful