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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
Client Testimonials

Areas of expertise

Destinations:

Alaska, Inside Passage, Skagway, Sitka, Ketchikan

Interests:

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

Suppliers:

Princess Cruises®, Holland America Line, Seabourn, Viking

About Me

Zip Lining in Icy Strait Point
Zip Lining in Icy Strait Point

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, and cruising is the perfect way to immerse yourself in its splendor. Whether you're a seasoned traveler or embarking on your first adventure, exploring Alaska’s iconic destinations such as Ketchikan, Skagway, Sitka, Juneau, Icy Strait Point, and the majestic Inside Passage glaciers offers experiences that leave a lasting impression.

Ketchikan: The Gateway to the Last Frontier Nestled in the Tongass National Forest, Ketchikan is often your first glimpse of Alaska’s untamed charm. Known as the "Salmon Capital of the World," this quaint town boasts a blend of cultural heritage and natural beauty. Stroll along Creek Street, a historic boardwalk perched on stilts over the water, or marvel at the world’s largest collection of totem poles at Saxman Native Village. Adventure seekers will relish kayaking in the Misty Fjords, a pristine wilderness with dramatic fjords, waterfalls, and wildlife.

Skagway: Step Back in Time to the Klondike Gold Rush Skagway transports you to the days of the 1898 Klondike Gold Rush. The town's historic charm is preserved in its wooden boardwalks, vintage storefronts, and the renowned White Pass & Yukon Route Railway. This narrow-gauge railroad offers breathtaking views of mountain peaks, cascading waterfalls, and deep gorges. Whether you choose to pan for gold, hike the scenic trails, or explore the ghostly remnants of old mining camps, Skagway captures the adventurous spirit of Alaska's past.

Sitka: A Tapestry of Cultures and Natural Wonders Situated on Baranof Island, Sitka is a harmonious blend of Tlingit, Russian, and American cultures. Visit the iconic St. Michael’s Cathedral, a symbol of Russian influence, or admire the intricate artistry at the Sitka National Historical Park, home to totem poles that tell the stories of the Tlingit people. Nature enthusiasts can explore the rich marine life at the Alaska Raptor Center or embark on a whale-watching tour. Surrounded by snow-capped mountains and serene waters, Sitka’s beauty is both dramatic and tranquil.

Juneau: Alaska’s Capital of Adventure Juneau, Alaska’s picturesque capital, is accessible only by air or sea, making it a unique and intimate destination. Here, the Mendenhall Glacier beckons with its icy blue hues, inviting visitors to hike or paddle for an up-close view. Don’t miss a ride on the Mount Roberts Tramway for panoramic vistas of the city and Gastineau Channel. Juneau is also a culinary delight, offering fresh seafood like Dungeness crab and salmon at charming local eateries. From glacier tours to wildlife spotting, the possibilities are endless.

Icy Strait Point: Authentic Alaska Awaits Located near the Tlingit village of Hoonah, Icy Strait Point offers a truly Alaskan experience. This private destination is renowned for its sustainable tourism practices and connection to indigenous culture. Thrill-seekers can soar on the world’s largest zip line, while nature lovers can enjoy bear-watching excursions or whale-watching tours. The village atmosphere, with its artisan shops and cultural performances, provides a glimpse into the traditional Alaskan way of life.

Inside Passage Glaciers: Nature’s Sculptures in Motion Cruising through the Inside Passage is like stepping into a postcard. Towering glaciers, shimmering fjords, and abundant wildlife set the stage for an unforgettable journey. Witness the power of calving glaciers at Glacier Bay National Park, where massive chunks of ice crash into the water below, or marvel at the serenity of the Tracy Arm Fjord. Keep your binoculars handy for sightings of orcas, humpback whales, sea otters, and bald eagles. These icy giants and serene waterways epitomize Alaska’s raw and untamed beauty.

The Joy of Alaska Cruising An Alaska cruise is more than just a vacation—it’s a chance to reconnect with nature, immerse yourself in history, and experience cultures that have thrived for centuries in this rugged landscape. Every destination along the way offers its own unique charm and adventures, from glacier treks to gold rush reenactments, and from cultural performances to wildlife encounters.As a dedicated travel agent, I take pride in crafting itineraries that capture the magic of Alaska. Whether you’re dreaming of a luxurious voyage with fine dining and entertainment or a more adventurous expedition focused on outdoor exploration, I’m here to ensure every detail is perfect.

Let me guide you through Alaska’s wonders and help create memories that will last a lifetime.Your Alaska adventure awaits—let’s make it extraordinary together!

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

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
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)

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.

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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