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Christopher Penland
Winter Haven, FL Travel Agent· 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 >
Areas of expertise
Destinations:
Alaska, Cozumel, Aruba, Ocean Cay, Inside PassageInterests:
Bucket List, Cruises, Family Vacations, LGBTQ+ Travel, Beach VacationsSuppliers:
Celebrity Cruises, MSC Cruises, Princess Cruises®, Virgin Voyages, Holland America LineAbout 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!
Areas of expertise
Destinations:
Alaska, Cozumel, Aruba, Ocean Cay, Inside PassageInterests:
Bucket List, Cruises, Family Vacations, LGBTQ+ Travel, Beach VacationsSuppliers:
Celebrity Cruises, MSC Cruises, Princess Cruises®, Virgin Voyages, Holland America LineMy 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.
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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

Holland America Line Academy Specialist

MSC Masters

NCL University - Associate Degree

NCL University - Bachelor's Degree

NCL University - Master's Degree

NCL University - PHD Degree

Royal Caribbean University - Bachelor of Adventure
Seabourn Academy Graduate

Seacademy - Gold Certification

Seacademy - Scarlet Certification

Seacademy - Silver Certification

Seacademy - Violet Certification
TRACKS (Rocky Mountaineer Specialist)

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
MSC Ocean Cay Marine Reserve
Mazatlan Highlights
Cabo Highlights
My Travel Stories
My Itineraries
7 Days Exploring Alaskan Nature and Wildlife
Countries visited
Alaska, British Columbia
Suggested Duration
7 Days
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