Family Cruise Planning Specialist

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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
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Client Testimonials

Areas of expertise

Destinations:

Cozumel, Ocean Cay, Bahamas, Amber Cove, Virgin Islands

Interests:

Family Vacations, Celebration Travel, Beach Vacations, Water Sports, LGBTQ+ Travel

Suppliers:

MSC Cruises, Princess Cruises®, Royal Caribbean, Shore Excursions Group, Viator

About Me

Our granddaughter holding a sloth
Our granddaughter holding a sloth

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. 

Our girls tried food they never would have before, enjoyed all the onboard entertainment, and they met new friends and had an amazing time on what we thought was a big ship being our first time. 

The trip set off a new annual family tradition that would carry over to our grandchildren. When people ask why we choose cruising over land packages, the one word I can use to define it all is value. 

What has value given to us as a family, that’s easy:  

1.    New family traditions - as a parent, when I think of all the money we spend on toys, games, parties, etc. while those inanimate objects may mean a lot in the beginning; however, they end up lost, broken, given away, not cared for, and in short, a waste of money.  We began an annual cruise in Feb – Mar time frame and used the money we were going to spend on those meaningless gifts and began cruising making a lifetime of memories and friendships. 

2.    The dining experiences were enriching - my oldest daughter tried lamb chops on a cruise, and it is now still one of her favorite dishes she looks forward to on cruises.  My husband absolutely loves all the various seafood options as we have tried caviar, sushi, and more.  My youngest daughter was known by name at the pizza station!! I personally enjoy the variety of cuisine that includes cultural dishes I would have never had on land.  There is always something for someone onboard to eat. 

3.    Onboard entertainment & activities were always in plenty.  The girls loves the available kids clubs, water features & pools, mini golf, one of a kind kids only experiences all while we as parents enjoyed soaking up the sun, playing trivia, attending shows, listening to live music and for family time, our favorite was always a Movie under the Stars with popcorn.  My granddaughters favorite was Bolt, the Roller Coaster at Sea. 

4.    Your new cruise family!! Our girls have made friends on cruises they have kept in contact with and speak to frequently over the past 15 years.  My husband and I have made new friends that we cruise often with, and now our oldest granddaughter is experiencing the same things her mother did. 

5.    Enriching experiences - our children have seen and have been immersed in historical, architectural, and natural significant locations in other countries.  From the ruins in Mexico, to cave tubing in Belize, riding a horse on the beach, experiencing the sights, sounds, smells, and flavors of different cultures.  Let us not forget the viewing and holding of the native wildlife such a monkeys, sloths, starfish, birds, and observing a variety of fish while snorkeling.

I know as parent(s), guardian(s), loved one(s) that there are questions when it comes to the children you are bringing onboard; questions such as:

Documentation Needed to travel

Activities onboard from sports decks to pools and more

Food Allergies / types of food available

Drink Packages for children

Medical Care

Kids Clubs / Age Groups

can my children go ashore / participate in an excursion

are there curfews onboard for children

are there video games / arcade onboard

are just to name a few.I am happy to answer all your questions and provide that peace of mind you seek as we plan that special vacation that will build memories to cherish for a lifetime.

 

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.
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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

A Honeymoon Wishes Agent provides the only full service honeymoon registry for couples that expect a higher standard for their wedding.
Celebrity Learning Certification
Celebrity Learning Certification
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
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)

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 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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