Cruise Vacation Destination 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
Reviews
Certificates & Awards
My Places
Itineraries
Client Testimonials

Areas of expertise

Destinations:

Alaska, Caribbean, Ocean Cay, Mexico, Central America

Interests:

Cruises, Family Vacations, Beach Vacations, Celebration Travel, LGBTQ+ Travel

Suppliers:

Celebrity Cruises, Holland America Line, Princess Cruises®, MSC Cruises, Royal Caribbean

About Me

Cruising the Inside Passage
Cruising the Inside Passage

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 vacation, or an adventurous expedition, I have the knowledge and expertise to make it seamless and unforgettable.

Why Choose Me?

Extensive Experience:

  • Former travel advisor for Expedia’s vacation and cruise departments
  • Sales agent for Carnival Cruise Lines in Miramar, FL
  • Corporate travel planner for top law firms in Las Vegas and Los Angeles
  • Personally sailed on 50+ cruises and visited 70+ destinations worldwide, including Europe, Alaska, Mexico, and the Caribbean

Certified Expertise:

  • Certified Cruise Counselor (CLIA)
  • Certified Alaska Travel Expert
  • Specialist in luxury cruises, river cruises, and expedition travel with renowned lines like Silversea, Windstar, and more
  • Disney & Universal Studios Theme Park Certifications

A Personal Touch

As part of a diverse and inclusive family, my husband and I have been passionate cruisers for over 20 years, joined by our children and grandchildren. We love how cruising offers the perfect blend of adventure, connection, and acceptance.

I bring that same passion to my work, helping clients discover the joys of cruise vacations, family getaways, and luxury travel experiences. My insider knowledge and attention to detail ensure every journey is stress-free and filled with lifelong memories.

Let’s Make Your Travel Dreams a Reality

Whether you’re looking for a tailored luxury cruise, a family-friendly adventure, or a transformational escape, I’m here to guide you every step of the way.Contact me today to start planning your next unforgettable vacation!

Testimonials I have received

* Booking with Chris is an extremely easy process. As an avid cruiser himself, he is very knowledgeable about ships and ports. Great communication, he answers questions very quickly. Chris goes above and beyond helping select the perfect ship, cabin, and itinerary. He listens to your wants and requirements and makes recommendations based off exactly what you’re looking for. Highly professional but so comfortable to talk to—you’ll have a friend for life. 

* Chris at Vacation with Pride has been extremely helpful with all my vacation needs.  Chris is an excellent communicator, explaining the entire process in great detail. He’s always been quick to respond to any of my questions. I’ve already recommended their services to one of my co workers.

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.
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.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
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.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO

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
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.
Cozumel, Quintana Roo, Mexico
Booked It
Been There
Trying to book a cruise with a toddler and a teena...
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Ocean Cay, Bahamas, Caribbean
Booked It
Been There
My husband and I had the pleasure of booking our r...
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Inside Passage, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Skagway, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
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Amber Cove, Dominican Republic, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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Sitka, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
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Ketchikan, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
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Beach Club at Bimini, Bahamas, Caribbean
Booked It
Been There
My husband and I had the pleasure of booking our r...
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Freeport, Bahamas, Caribbean
Booked It
Been There
My husband and I had the pleasure of booking our r...
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Half Moon Cay, Bahamas, Caribbean
Booked It
Been There
My husband and I had the pleasure of booking our r...
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Nassau, Bahamas, Caribbean
Booked It
Been There
My husband and I had the pleasure of booking our r...
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Paradise Island, Bahamas, Caribbean
Booked It
Been There
My husband and I had the pleasure of booking our r...
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Grand Cayman, Cayman Islands, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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Jamaica, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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Aruba, Netherlands Antilles, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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Bonaire, Netherlands Antilles, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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Curacao, Netherlands Antilles, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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Princess Cays, Princess Cays, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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San Juan, Puerto Rico, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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St. Maarten, St. Martin, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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St. Martin, St. Martin, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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Grand Turk, Turks and Caicos Islands, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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St. Thomas, Virgin Islands, Caribbean
Booked It
Been There
I didn’t think a Caribbean cruise could get any be...
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Belize City, Belize, Central America
Booked It
Been There
My husband and I had the pleasure of booking our r...
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Mahogany Bay, Honduras, Central America
Booked It
Been There
My husband and I have always wanted to see Alaska,...
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Roatan, Honduras, Central America
Booked It
Been There
Working with Chris was an absolute pleasure! As an...
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Ensenada, Baja California Norte, Mexico
Booked It
Been There
Trying to book a cruise with a toddler and a teena...
Read more
Cabo San Lucas, Baja California Sur, Mexico
Booked It
Been There
Trying to book a cruise with a toddler and a teena...
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Acapulco, Guerrero, Mexico
Booked It
Been There
Trying to book a cruise with a toddler and a teena...
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Ixtapa, Guerrero, Mexico
Booked It
Been There
Trying to book a cruise with a toddler and a teena...
Read more
Zihuatanejo, Guerrero, Mexico
Booked It
Been There
Trying to book a cruise with a toddler and a teena...
Read more
Puerto Vallarta, Jalisco, Mexico
Booked It
Been There
Trying to book a cruise with a toddler and a teena...
Read more
Costa Maya, Quintana Roo, Mexico
Booked It
Been There
Trying to book a cruise with a toddler and a teena...
Read more
Progreso, Yucatan, Mexico
Booked It
Been There
Trying to book a cruise with a toddler and a teena...
Read more
Anchorage, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
College Fjord, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Glacier Bay, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Hubbard Glacier, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Icy Strait, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Juneau, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Sawyer Glacier, Alaska, USA
Booked It
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Grand Canyon, Arizona, USA
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Yosemite National Park, California, USA
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Las Vegas, Nevada, USA
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Bryce Canyon, Utah, USA
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Lake Powell, Utah, USA
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Zion National Park, Utah, USA
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
Jackson Hole, Wyoming, USA
Been There
Thanks to Chris, our annual summer cruise to Alask...
Read more
West Yellowstone, Wyoming, USA
Been There
Thanks to Chris, our annual summer cruise to Alask...
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Yellowstone National Park, Wyoming, USA
Been There
Thanks to Chris, our annual summer cruise to Alask...
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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