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HomeCruiseMay 2024 Inspiring Itinerary: The Perfect Disney Besties Cruise to Alaska

May 2024 Inspiring Itinerary: The Perfect Disney Besties Cruise to Alaska

Why a Disney Besties Cruise?

As many of you know, Love of the Magic Vacations has been specializing in group travel experiences for a while (and we’ve even won awards for them! We were given Travel Weekly’s Magellan Award for Group Travel Experiences in 2023)! Over the years, we’ve evolved and refined the Group Travel we offer to include the very best vendors in the Travel Industry. 

We’ve even evolved in name: what you may remember as the BRB Going to Disney Group, has now morphed into the Disney Besties Group, because, not only do we all become Besties after traveling with each other, but we (Jamie and all the advisors who make the Magic happen) also work incredibly hard to create the very “Best” Disney Group experiences out there. 

Disney Besties

As any “Bestie” will tell you, a Disney Besties Trip is unique because within the Group, there are familiar faces who keep returning trip after trip, whether by land or by sea, and also, there are always newcomers, too, who are not just warmly welcomed, but who are also celebrated for joining our fabulous Disney Bestie Group! When you think about it, whenever and wherever you travel, you’re always going to encounter a good amount of people throughout your trip, especially on cruises, so why not choose a trip on which many of the people you come into contact with are either already friends, or at the very least, are people with whom you share similar interests. Trust me, by the end of the Bestie Trip, you’ll have some new Besties for sure!


Why Alaska?

Vacations to Alaska have been on the rise for years, decades even, and it’s not hard to see why: known as The Last Frontier, Alaska offers unparalleled amounts of untouched wilderness and epic adventure. Alaska is, by far, the largest state in America, and it’s actually roughly one fifth of the size of the entire continental United States. 

With that much space (365 million acres, to be specific), and with only 160,000 acres occupied by civilization, a visit to Alaska can make you feel like a true explorer, traversing land (or ice!) that may have only been walked on by a handful of other humans. As the saying goes, though, tread lightly, because Alaska prides itself on its connection to, and preservation of, the land. 

Whale Alaska

If you’ve been following along on the blog for a while, you’ll know that Alaska has been featured a number of times: in the Dozen National Parks You Need on Your Travel Bucket List (not just one, but two of Alaska’s Parks made the list), in the Top Ten Journeys of a Lifetime (as a suggestion for an Arctic Adventure), with mentions in a bunch of other Blogs, and with two other trips to Alaska already on the list of Inspiring Itineraries (an Inside Passage Cruise and a Land Adventure), it’s a testament to JUST how much Alaska has to offer that this Itinerary is, again, completely different, with hardly any of the same cities and ports as those featured on the other blogs. It’s almost unbelievable that Alaska can be featured so many times for so many different experiences; guess you have to see it to believe it!

This time, we’ll be exploring Alaska through the lens of Disney, on Disney Cruise Line. For those who have never been, Disney Cruise Line is the PERFECT family vacation when you want to change things up from trips to the Parks. If you’re already a seasoned DCL cruiser, you know that Disney Cruise Line truly offers the perfect mix of Disney Magic on the ship, and real world discoveries and adventures off the ship! 

Eagle Alaska

The ships on Disney Cruise Line are full of the Characters we all know and love, with plenty of opportunities to interact and take pictures, plus themed dining experiences with even more Characters, absolutely incredible kids’ clubs for different age groups, Broadway-caliber shows and entertainment, just like you find in the Disney Parks. In addition, there are dozens of areas for relaxing, taking in the gorgeous Alaskan views, and spotting wildlife along the way, plus tons of other Disney details that take your cruise experience to the next level (think hidden Mickeys, friendly door decorations, and specialty Disney treats, just to name a few). 

And on top of everything, you’ll be with your Disney Besties Group the whole time! What could be better? So what are we waiting for…

Let’s Go!


Day 1 

Although your adventure begins in the Canadian city of Vancouver, as soon as you arrive, you’ll begin to understand why this corner of the world has garnered so many visitors. As is always the case with cruises, it’s best to arrive at least a day in advance of your embarkation date to prevent any flight delays from causing you to quite literally, miss the boat. Depending how much in advance you arrive, you’ll have at least some time to explore the city of Vancouver.


Nestled on a lush peninsula in southwestern British Columbia, Vancouver boasts an unparalleled setting, enveloped by the glistening waters of the Pacific Ocean and embraced by a majestic, snow-capped mountain range. While here, you can choose to wander through over 200 verdant parks, traverse the iconic Capilano Suspension Bridge (a century-old marvel spanning the Capilano), or indulge your inner shopper in Granville Island, a cultural hotspot teeming with artisanal treasures, delectable cuisine, and captivating art galleries. 

If you’re looking for more specifics about Vancouver, we just featured it on the Blog in our new City Guide series, specifically designed for cruise travelers who arrive early to their port (as everyone should!). Find the Vancouver City Guide here!

After a day of traveling and exploring the city a bit, you’ll surely be looking forward to a good night’s sleep before the big day tomorrow!

Disney Cruise Alaska

Day 2 

Embarkation Day! Hooray! There’s nothing quite like the excitement of boarding a cruise ship, especially while enthusiastic Cast Members wave you Bon Voyage, and then as soon as you get on the ship, Cruise Cast Members greet you by name! 

Disney Cruise Sunrise

Once everyone is settled on board, you’ll be invited to meet up with anyone sailing with your Disney Besties Cruise Group. At this point, you’ll find out details about when and where the Disney Besties Group Party will be, and you’ll also have a chance to plan as many, or as few, group meet-ups as you’d like to participate in throughout the cruise. 

Then you’ll have some time to begin exploring the ship before heading down to your first cruise dinner experience! Since all Disney Cruise Line dining is on a rotating schedule, you’ll have something exciting to look forward to each night!

Mickey on Deck

Day 3 

Your first day on board will be spent at sea, sailing from the Canadian waters outside Vancouver to the American waters of your main destination: Alaska! Days at Sea with your favorite characters for company are never long enough! Between the Broadway-style shows, the clubs for kids of every age, the character meet-and-greets, and the endless activities to do around the ship, your first day at sea will fly by faster than the glistening waters of the Pacific Ocean below your stateroom balcony! Not to mention, you’ll have a full day of high-end dining experiences as well, which will be capped off with one of the ship’s fabulous rotating dinner restaurants. 

Glacier Iceberg

Day 4 

Although today will be another day onboard The Wonder, unlike your first Day at Sea, today, you’ll immerse yourself in the untamed beauty of a place where glaciers reign supreme, mountains stand tall, and wildlife roams free. The day’s highlight will be sailing through the breathtaking Stikine Icecap, nestled approximately 45 miles south of Juneau, Alaska, within the majestic embrace of the Tongass National Forest. From the comfort of your ship, you’ll get an up close and personal view of the remote wilderness as it offers a portrait of serenity that will leave you speechless.

As you glide along the waterway, where ice bobs like cubes in a drink, prepare to be captivated by a world untouched by time. Behold towering rock formations, steep valleys, and cascading waterfalls that converge with sapphire waters and shimmering blue ice, creating a scene of unparalleled grandeur.


The highlight of today’s journey will be seeing the Stikine Icecap, with its legendary granite spires and formidable peaks, standing as a testament to nature’s awe-inspiring power. Spanning the Alaska-British Columbia border, this vast icefield is a sight to behold, with its glaciers feeding into the Taku River and the Stikine River. Keep a watchful eye for the mesmerizing spectacle of calving, where massive ice chunks break off and plunge into the sea below, a reminder of the ever-changing landscape.

But the allure of the Stikine Icecap extends beyond its geological marvels. Here, amidst the pristine wilderness, a diverse array of wildlife thrives, from majestic bald eagles soaring overhead to elusive brown bears, agile mountain goats, and graceful whales dancing in the distant waves. Capture these fleeting moments with your camera, and let the majesty of nature unfold before your eyes.

Once you’ve passed through the fjord, you’ll have the chance to rejoin some of the ship’s activities until it’s time for your nightly dinner rotation. Then, you can delight in some classic Disney entertainment for the evening before resting up for your Port Adventures tomorrow!


Day 5 

Today, you’ll experience the first port on your cruise: Skagway, the captivating town that inspired Jack London’s timeless tale, The Call of the Wild. Tucked away on the south coast of the Alaskan Panhandle, near the northern edge of the Lynn Canal, lies the charming enclave of Skagway—a place where history and adventure converge in a mesmerizing tapestry of past and present.

As you stroll along Broadway Street, the heartbeat of Skagway, prepare to be transported back in time. Imposing landmark buildings adorned with late 19th-century flair line the historic thoroughfare, offering a glimpse into the town’s illustrious past. Here, you’ll encounter locals donning period attire, bringing to life the era when Skagway thrived amidst the Klondike Gold Rush—a time when dreams of fortune lured treasure-seekers from far and wide.


Originally inhabited by the Chilkoots and Chilkats Native Americans, Skagway rose to prominence in 1896 with the discovery of gold along the Klondike River. The ensuing gold rush frenzy transformed the town into a bustling hub of activity, attracting hordes of prospectors in search of riches. Today, Skagway remains a testament to its storied past, welcoming visitors to explore its rich heritage against the backdrop of breathtaking mountain vistas and pristine river views.

As with most Ports, there are a variety of excursions available. Here are some options available in Skagway: 

A visit to The Klondike Gold Rush National Historic Park, where more than 15 meticulously preserved buildings offer a window into the town’s golden era. Browse through quaint boutiques brimming with Gold Rush-inspired treasures, from gleaming gold nuggets to exquisite jewelry and vintage train memorabilia.

Gold Rush

Take a scenic journey aboard the White Pass & Yukon Route Railroad, tracing the footsteps of Klondike prospectors as you ascend 2,865 feet to the summit of White Pass. Along the way, marvel at iconic landmarks such as Bridal Veil Falls and Dead Horse Gulch, each steeped in the lore of the Gold Rush Era.

For a deeper dive into Skagway’s fascinating past, wander through the Skagway Museum and Archives, housed within the historic McCabe College Building. Here, a treasure trove of relics, photographs, and mementos await, offering a glimpse into the town’s colorful history.


Nature enthusiasts will delight in a visit to Jewell Gardens, where vibrant flowers, aromatic herbs, and lush berries flourish amidst a picturesque landscape. Unleash your creativity at the glassblowing studio or hop aboard the miniature railroad train for a whimsical adventure through the gardens.

Step back in time along the Chilkoot Trail, where echoes of the past resonate amidst scenic vistas and historic relics. From weathered pickaxes to abandoned wagon wheels, each artifact tells a tale of the intrepid souls who once sought their fortune in Skagway’s rugged wilderness.

Once you’re back onboard The Wonder after your excursion, you’ll head to your dinner rotation for the evening, and depending how much energy you have left, you can seek out some onboard entertainment or retire to your cabin.


Day 6 

An Alaskan cruise wouldn’t be complete without a stop at the Port of Juneau. Nestled at the base of Mount Juneau amidst lush forests, Juneau is the largest capital in the United States (by area), and the city itself boasts a rich array of history, culture, and natural wonders waiting to be explored.

Here, the diverse blend of industries, from government to fishing, mining, and tourism, create a dynamic landscape shaped by tradition and innovation. Trace the footsteps of the Tlingit Native Americans and early prospectors as you uncover Juneau’s fascinating past. Founded in 1880 amidst the frenzy of the Klondike Gold Rush, Juneau emerged as a bustling hub of activity, drawing fortune-seekers from far and wide. Today, remnants of this storied era blend seamlessly with modern-day marvels, offering visitors a glimpse into the town’s rich heritage.


With a plethora of excursions to choose from, your day in Juneau is sure to be full of adventure. Here are some of the excursions available in Alaska’s capital city:

Explore the charming boutiques of South Franklin Street, where treasures from Alaskan artisans await. 

Ascend to new heights aboard the Mount Roberts Tramway and marvel at panoramic views of the city from 2,000 feet above sea level.


Journey to the awe-inspiring Mendenhall Glacier, a breathtaking spectacle of nature’s grandeur located just 13 miles from Juneau’s city center. 

Delve into Alaska’s rich history at the Alaska State Museum, where artifacts and exhibits chronicle the state’s native heritage, mining legacy, and abundant wildlife.

Experience the rustic charm of the legendary Red Dog Saloon, where swinging saloon doors and live music transport you back to the city’s mining era. 

Discover the wonders of marine life at the Macaulay Salmon Hatchery, where you can witness salmon making their way upstream in a mesmerizing display of strength and determination.


Escape to the tranquil beauty of Glacier Gardens, a sprawling botanical oasis teeming with rare flowers, winding paths, and cascading waterfalls. 

Pay homage to the Shrine of St. Therese, a serene sanctuary dedicated to Alaska’s patron saint, nestled on a tiny island just a stone’s throw from Juneau’s bustling dock.

From cultural landmarks to natural wonders, Juneau offers endless opportunities for exploration and discovery, and will surely leave you wanting to come back for more! But for now, it’s back to your ship for dinner and a good night’s sleep!


Day 7 

Today’s Port brings you to the island community of Sitka, nestled within the breathtaking beauty of Alaska’s Inside Passage. Sitka’s rich tapestry of culture and flavor is woven from its awe-inspiring natural surroundings and its vibrant Tlingit and Russian heritage, earning it the illustrious nickname: “Paris of the Pacific.”


As the former capital of Russian America, Sitka’s past is steeped in history and adventure. From the ancient traditions of the Tlingit tribes, who inhabited the island for millennia, to the arrival of Russian settlers led by Aleksandr Baranov in 1799, Sitka’s story is one of resilience and rebirth. Explore the remnants of Old Sitka and the iconic Fortress of the Bear, where orphaned brown bear cubs find sanctuary amidst the rugged wilderness, and discover the historic landmarks of Sitka, from the storied grounds of Sitka National Historical Park to the iconic St. Michael’s Russian Orthodox Cathedral, a stunning example of Russian architecture that stands as a testament to the island’s enduring legacy.


Be sure to check out Sitka’s vibrant dining scene, where fresh seafood and Pacific Northwest cuisine reign supreme. From quaint waterfront eateries to charming cafes, you’ll find a feast for the senses that pays homage to the bounty of the sea.

Although Sitka is relatively small, it still offers a multitude of excursion options, including the following:

Immerse yourself in Sitka’s vibrant arts and culture scene, where the spirit of the past comes alive through traditional Russian and Tlingit dances performed by the renowned New Archangel Dancers. 

Marvel at the exquisite craftsmanship of Tlingit silverwork, carvings, and masks, or embark on a shopping adventure to discover unique treasures that capture the essence of this remarkable island.

Venture into the great outdoors and discover Sitka’s natural wonders, from towering mountain ridges to pristine ocean waters teeming with life. 


Take a kayak expedition along the rugged coastline, hike through ancient forests alive with the symphony of nature, or embark on a whale-watching adventure in search of majestic humpback whales frolicking in the seas.

Once you’ve completed your adventures on land, you’ll head back to your ship for your nightly adventures of dinner and spectacular entertainment before resting up for tomorrow’s last Port day. 


Day 8 

Today brings you to your final Port: Ketchikan, also known as the “Salmon Capital of the World,” where rich Native Alaskan traditions blend seamlessly with awe-inspiring natural wonders.

Nestled on Revillagigedo Island along the majestic Tongass Narrows, Ketchikan invites you to explore its fascinating culture and flavor. Discover the city’s proud Native roots as you wander amidst towering totem poles, the largest collection of original 19th-century totem poles in the world, each a masterpiece of Tlingit and Haida craftsmanship. Dive into the bustling fishing industry that has long been the lifeblood of Ketchikan, where the waters teem with five species of salmon, drawing professional and amateur fishermen from around the globe.


Journey back in time to Ketchikan’s humble beginnings, from the establishment of its first salmon saltery in 1883, to the bustling fishing trade that flourished by the turn of the century. Explore the town’s rich history as a mining supply center and a hub for the booming logging industry that shaped its identity throughout the 20th century.

As expected, the opportunities for excursions here are plentiful. Here are some of the experiences you can choose from:

Indulge in a shopping spree steeped in Native American tradition, where jewelry and fur shops offer unique treasures alongside galleries brimming with totem carvings, masks, and hand-painted drums. 


Stroll along the historic boardwalk of Creek Street, where colorful houses now house museums, eclectic shops, and charming restaurants, offering a glimpse into Ketchikan’s storied past.

Visit the Totem Heritage Center, where salvaged totem poles and Native Alaskan relics paint a vivid picture of the region’s indigenous culture. 


Marvel at the majesty of the Deer Mountain Tribal Hatchery and Eagle Center, where thousands of salmon spawn amidst breathtaking natural beauty, while two magnificent bald eagles keep watch from their lofty perches.

Venture into the picturesque Saxman Totem Park and Totem Bight State Park, where beautifully sculpted totem poles stand as guardians of the land, offering a glimpse into authentic Native Alaskan heritage.

Journey to Misty Fjords National Monument, a pristine wilderness of towering mountaintops, rushing waterfalls, and majestic fjords accessible only by floatplane or boat. 

Whatever adventure you choose, by the end of the day, you’ll surely be ready for your nightly dinner rotation and the comfort of your cabin!


Day 9 

With one more full day onboard your ship to enjoy, you’ll have plenty of time to catch up with your fellow Disney Besties to recount your favorite moments from your adventures throughout the week.  Of course, you’ll also have time to relax and take in everything the ship has to offer, from Broadway shows to spa treatments. Or maybe you’d prefer sitting in the sun on the ship’s deck, stretched out on a lounge chair, scrolling through the hundreds (or maybe even thousands) of photos you took throughout the week, comparing selfies with your Besties. Whatever you choose for your last day onboard, the ship and the crew and characters who make it so special, plus your Disney Besties, will not disappoint! 


Day 10 

Disembarkation day brings you back to Vancouver, and although it always has that twinge of sadness to it, you’ll at least have all of your Disney Besties there with you going through the same thing! Plus, no doubt you’ll already be talking about your next Disney Bestie Meet-ups and Group Experiences. One of the best parts of traveling with a group of friends is being able to look forward to your next adventures together, and with Love of the Magic Vacations planning the Disney Bestie Experiences, you know whatever the next adventure is, it will be nothing short of Magical!


Ready to Plan?

If you are ready to experience a Disney Bestie Cruise through America’s Last Frontier for yourself, and would like to plan your Perfect Disney Besties Cruise to Alaska, contact your Love of the Magic Travel Agent today, or email  And of course, whether you want to journey with your Disney Besties to Alaska, or plan your next adventure somewhere totally different, your favorite LOTMV Travel Advisor will work with you to create the unique experience you’re looking for. 

Moose Alaska

Looking for more of our Inspiring Itinerary series?

You can find links to all of 2023’s Inspiring Itineraries in this Blog: 2023 Inspiring Itineraries Recap and even links to all of 2022’s Inspiring Itineraries here: A Year of Inspired Travel: 2022’s Inspiring Itineraries, Month by Month

So far in 2024, we have:

January 2024 Inspiring Itinerary: The Perfect Christmas River Market Cruise

February 2024 Inspiring Itinerary: The Perfect Myriad of Mexico Vacation

March 2024 Inspiring Itinerary: The Perfect Journey Through Japan

April 2024 Inspiring Itinerary: The Perfect Caribbean Escape to St. Lucia

Just like always, a new Inspiring Itinerary will come out each month!

And don’t forget to check out our Friday Blog Series: Jamie’s Destination “Do”s and “Don’t”s, where our favorite Travel Planning Aficionado shares her wealth of knowledge and experiences about traveling the world! You can find links to all of Jamie’s 2023 Travel Tips here: Jamie’s 2023 Destination “Do”s and “Don’t”s, A Recap, and to all of Jamie’s 2022 Travel Tips at this Blog: Jamie’s 2022 Destination “Do”s and “Don’t”s: A Recap

Ready to plan The Perfect Disney Besties Cruise to Alaska? Contact your Love of the Magic Vacations Travel Advisor today or email 



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