Christopher Penland, Travel Agent in Winter Haven, FL

Christopher Penland

Winter Haven, FL Travel Agent
Super Agent

Christopher Penland

Winter Haven, FL · 16 Years of Experience

Your Best Life Vacations, LLC, an independent agent with Cruises & Tours, Unlimited, a Travel Leaders Network Affiliate Agency
4.8
(16)
100% Recommended
I can’t say enough great things about Chris and his incredible travel planning skills! He did a phenomenal job organizing my dream trip to Spain to... Read More >
About
My Travel Specialties
Reviews
Certificates & Awards
My Places
Travel Stories & Media
Itineraries
Client Testimonials

Areas of expertise

Destinations:

Alaska, Cozumel, Aruba, Ocean Cay, Inside Passage

Interests:

Bucket List, Cruises, Family Vacations, LGBTQ+ Travel, Beach Vacations

Suppliers:

Celebrity Cruises, MSC Cruises, Princess Cruises®, Virgin Voyages, Holland America Line

About Me

Family Cruise Planning Specialist

For over 20 years, my husband and I have enjoyed sailing on various cruise lines, sometimes as a couple and often with our two daughters and now our grandchildren, creating memories across generations. Cruising is a truly multi-generational way to travel. It offers the perfect balance of family time and individual activities, ensuring that everyone—from grandparents to kids—has something to enjoy. As a parent, guardian, or loved one, you may have questions about bringing children onboard. Concerns like: Documentation requirements Onboard activities and kids' clubs Food allergies and dining options Medical care availability Excursions and age restrictions These are just a few of the many topics I’m here to help with. My goal is to provide you with peace of mind and expert guidance as we plan a special vacation tailored to your family’s needs. Let’s work together to create a cruise experience that will leave you with cherished memories to last a lifetime!

My Travel Specialties

Discover the Unparalleled Beauty of Alaska Through

Discover the Unparalleled Beauty of Alaska Through
Alaska Cruising: A Journey Through Nature's Majesty As a passionate travel agent specializing in Alaska cruises, I find endless joy in curating unforgettable journeys through this awe-inspiring wilderness. Alaska is a land where rugged natural beauty meets rich history and vibrant cultures...Read More ▶

LGBTQ+ Vacations

LGBTQ+ Vacations
LGBTQ+ Travel Advisor: Crafting Inclusive Cruise Vacations Hello and welcome! I’m Chris, your dedicated travel advisor specializing in unforgettable cruise vacations tailored to LGBTQ+ travelers. With extensive experience and in-depth knowledge of cruise lines, destination...Read More ▶

Family Cruise Planning Specialist

Family Cruise Planning Specialist
No matter how big or small your family is, there is always a desire to take that relaxing vacation.  My family’s journey began in 2004 when my husband and I decided to take our 2 girls on a 4-day cruise out of LA to Catalina and Ensenada where we have never experienced such full service before. <...Read More ▶

Cruise Vacation Destination Specialist

Cruise Vacation Destination Specialist
Meet Christopher Penland: Your Trusted Travel Advisor With over 20 years of experience in the travel industry, I specialize in creating customized travel experiences that bring your unique dreams to life. Whether you’re planning a luxury ocean cruise, a family-friendly vac...Read More ▶

REVIEWS

Rating: 4.8
16 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.
Search reviews:

Showing 16 reviews

Bucket List Trip to Spain
Reviewed By Reide - Fort Meade FL | Traveled to Spain | Europe
I can’t say enough great things about Chris and his incredible travel planning skills! He did a phenomenal job organizing my dream trip to Spain to celebrate my graduation from the University of Florida. From the very beginning, Chris listened carefully to what I wanted and made sure every detail—from flights and accommodations to excursions and local experiences—was perfectly planned. His attention to detail, responsiveness, and deep knowledge of travel made the entire process stress-free and exciting. Thanks to Chris, this trip will be an unforgettable milestone in my life. I highly recommend his services to anyone looking to plan a special getaway!
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
Best Summer Vacation
Reviewed By Olson Family - San Antonio, TX | Traveled to Inside Passage | Alaska | USA
Thanks to Chris, our annual summer cruise to Alaska was unforgettable. He found us the perfect family cabin with bunk beds for the kids and booked us on excursions where we got the opportunity to see whales and eagles up close and take a scenic train ride. My kids are still talking about the ice cream station on the ship!
I would recommend this agent to my family and friends.
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Traveling with Kids
Reviewed By Nikki2 - Orlando, FL | Traveled to Cozumel | Quintana Roo | Mexico
Trying to book a cruise with a toddler and a teenager is not something I was looking forward to, but Chris made it look easy. From proper documentation needed, to reviewing the kids' clubs on board and what they include really got my Teen excited about the activities onboard and knowing there was Pizza. Chris helped me find a cabin that was in a great location and as for the food, even my picky eater loved the options onboard!
I would recommend this agent to my family and friends.
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Once in a Lifetime Alaska
Reviewed By Nikole R. - Las Vegas, NV | Traveled to Alaska | USA
My bucket list cruise to Alaska exceeded every expectation! Chris booked me on a 7 day inside passage cruise on Princess that was perfect. He took the time to go over the different excursions at each port and booked the ones I wanted based off my requests. Whale watching was breathtaking, Dog Sledding unforgettable, let not forget meeting the sled dog puppies onboard the ship, absolutely adorable. I couldn’t have planned it better if I tried. Five stars aren’t enough!
I would recommend this agent to my family and friends.
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Generational Cruise
Reviewed By Counterman Family - Asheville, NC | Traveled to Mexico
I was nervous planning a family cruise, but Your Best Life Vacations thought of everything on the cruise portion. From securing adjoining cabins for my grand-children to helping scheduling kid-friendly excursions, it was seamless. I was hoping he could help book my air, yet he explained in a way I understood that this may be something better for me to do.
I would recommend this agent to my family and friends.
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Certifications & Awards

A Honeymoon Wishes Agent provides the only full service honeymoon registry for couples that expect a higher standard for their wedding.
Holland America Line Academy Specialist
Holland America Line Academy Specialist
MSC Masters
MSC Masters
NCL University - Associate Degree
NCL University - Associate Degree
NCL University - Bachelor's Degree
NCL University - Bachelor's Degree
NCL University - Master's Degree
NCL University - Master's Degree
NCL University - PHD Degree
NCL University - PHD Degree
Royal Caribbean University - Bachelor of Adventure
Royal Caribbean University - Bachelor of Adventure
Seabourn Academy Graduate
Seabourn Academy Graduate
Seacademy - Gold Certification
Seacademy - Gold Certification
Seacademy - Scarlet Certification
Seacademy - Scarlet Certification
Seacademy - Silver Certification
Seacademy - Silver Certification
Seacademy - Violet Certification
Seacademy - Violet Certification
TRACKS (Rocky Mountaineer Specialist)
TRACKS (Rocky Mountaineer Specialist)
Celebrity Learning Certification
Celebrity Learning Certification
CLIA - Certified Cruise Counselor

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.

My Photo Albums and Videos

MSC Ocean Cay Marine Reserve
View Album
Mazatlan Highlights

My Travel Stories

Granddaughter Snorkeling for the First Time

How we found value in cruising vs land vacations

No matter how big or small your family is, there is always a desire to take that relaxing vacation.  My family’s journey began in 2004 when my husband and I decided to take our 2 girls on a 4-day cruise out of LA to Catalina and Ensenada. We have never experienced such full service before.  Our girls tried food they never would have before, enjo...
Read more

Client Testimonials

Bucket List Spain Trip
I can’t say enough great things about Chris and his incredible travel planning skills! He did a phenomenal job organizing my dream trip to Spain to celebrate my graduation from the University of Florida. From the very beginning, Chris listened carefully to what I wanted and made sure every detail—from flights and accommodations to excursions and local experiences—was perfectly planned. His attention to detail, responsiveness, and deep knowledge of travel made the entire process stress-free and exciting. Thanks to Chris, this trip will be an unforgettable milestone in my life. I highly recommend his services to anyone looking to plan a special getaway!
Reide V. Fort Meade, FL
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