The biggest question we heard after announcing our inaugural Keyholder Vacations Group Cruise was not about the ship, the itinerary, or what we had planned onboard.
It was simple: “When’s the next one?”
That question opened the door to a much bigger conversation. Rather than planning only one more cruise, we started thinking about how we could create more opportunities for this community to travel together. That could mean a weekend at Walt Disney World, a sailing to an unforgettable destination, or a completely different kind of vacation beyond the parks and cruise ships.
Today, we are excited to share the next chapter for DVC Fan and Keyholder Vacations, with six new events and travel opportunities on the horizon for 2027 and 2028.
These plans include the return of our popular community weekends, the introduction of Keyholder Getaways, and confirmation that planning has officially begun for our next full Keyholder Vacations Group Cruise.
From One BoardWalk Meetup to a Growing Travel Community
It is honestly a little difficult to believe how much these events have grown.
I can still remember our first meetup at Disney’s BoardWalk Villas more than two years ago. We did not know exactly who would show up or what the event might become. We simply knew that we wanted an opportunity to spend time face-to-face with a community that had already become incredibly important to us.
What followed was an amazing weekend filled with conversations, laughter, new friendships, and the kind of spontaneous Disney moments that are difficult to recreate through a screen. That first gathering helped lead to SummerFest, OktoberFest, our inaugural group cruise aboard Utopia of the Seas, and now an entire calendar of future opportunities to travel together.
Every step of this has happened because you kept asking for more.
You asked for another community weekend. You asked when we would cruise again. You asked whether we might explore destinations outside Walt Disney World. Most importantly, you trusted our team with your vacations, your time, and the memories you create with the people you love.
We do not take any of that lightly.
Watch the Announcements From Aboard Utopia of the Seas
We officially revealed these new events during a live recording of The DVC Show aboard Utopia of the Seas.
The episode captures the excitement in the room as each new event was introduced, along with the stories and conversations that led us to this moment. To watch the announcements and experience the reveals along with everyone onboard, check out the complete episode below.
What You Need to Know
The next chapter currently includes:
| Event | Dates | Location |
|---|---|---|
| DVC Fan WinterFest | January 29–31, 2027 | Disney’s Animal Kingdom Lodge |
| Keyholder Getaway: Alaska | May 21–28, 2027 | Alaska cruise |
| Keyholder Getaway: Massanutten Resort | Summer 2027 | Virginia |
| Keyholder Getaway: Hero of the Seas | September 25–October 2, 2027 | Western Caribbean |
| DVC Fan FallFest | October 22–24, 2027 | Disney’s BoardWalk Villas |
| 2nd Keyholder Vacations Group Cruise | Summer 2028 | To be announced |
Here is a closer look at everything currently in the works.
DVC Fan WinterFest Returns in January 2027
January 29–31, 2027
Disney’s Animal Kingdom Lodge
We are heading back to Walt Disney World for DVC Fan WinterFest, taking place January 29 through January 31, 2027.
WinterFest will follow a format similar to our previous SummerFest and OktoberFest weekends. These gatherings are designed to give Members and Disney fans a chance to spend time together without turning every minute into a rigidly scheduled activity. There will be opportunities to meet fellow members of the community, enjoy group activities, and experience Walt Disney World during one of our favorite times of year.
Animal Kingdom Lodge will serve as our home base for the weekend, placing us at one of the most recently refurbished Disney Vacation Club resorts while the EPCOT International Festival of the Arts is underway.
Festival of the Arts brings a very different energy to EPCOT than the fall festivals. Between the visual art, live performances, creative food studios, and Disney on Broadway concert series, it gives everyone plenty to explore before, after, and between our community activities.
More WinterFest details will be announced as plans are finalized. For now, be sure to save the dates and begin considering your resort reservation.
WINTERFEST EVENT INFORMATION
January 29–31, 2027
Disney’s Animal Kingdom Lodge
RSVP To DVC Fan WINTERFEST!
DVC Fan FallFest Comes to BoardWalk Villas
October 22–24, 2027
Disney’s BoardWalk Villas
Later in the year, we will return to the place where so much of this began.
DVC Fan FallFest will take place October 22 through October 24, 2027, at Disney’s BoardWalk Villas.
There is something special about gathering at the BoardWalk during the fall. The EPCOT International Food & Wine Festival is typically in full swing, Halloween season has arrived across Walt Disney World, and the entire Crescent Lake area becomes an ideal setting for a DVC Fan community weekend.
Like WinterFest, FallFest will build on the relaxed, community-focused style of SummerFest and OktoberFest. The goal is to create opportunities to get together while still leaving everyone room to enjoy their own vacation.
Specific activities and event details will be shared closer to the weekend. Because October can be a popular time for Disney Vacation Club reservations, we strongly recommend putting the dates on your calendar and booking your accommodations as soon as your booking window allows.
FALLFEST EVENT INFORMATION
October 22–24, 2027
Disney’s BoardWalk Villas
RSVP To DVC Fan FALLFEST!
Information about both weekends will also be shared through dedicated event groups within the DVC Fan Facebook Group as it becomes available.
Introducing Keyholder Getaways
The next part of this announcement represents something entirely new: Keyholder Getaways.
Over the past few years, we have learned that not every community vacation needs to be a large, fully hosted event with a complete schedule of group programming. Sometimes people simply want access to a great trip, a strong value, and the opportunity to travel alongside others who share their love of Disney and travel.
That is the idea behind Keyholder Getaways.
These are thoughtfully selected vacations featuring benefits that may include exclusive group pricing, blocked inventory, onboard credits, and opportunities to connect with fellow Disney fans. Some members of our team may occasionally be traveling on a particular getaway, but these should not be confused with our fully hosted Keyholder Vacations Group Cruises.
Think of them as vacations we believe are worth taking, made even better by the chance to experience them with familiar faces!
Keyholder Getaway: Alaska
May 21–28, 2027
Travel With Paul and Amy
Alaska was the natural choice for our first Keyholder Getaway.
It is honestly one of Amy’s and my favorite places in the world. We have talked about Alaska so often, and with so much enthusiasm, that when the time came to choose the first destination for this new kind of community trip, it felt like the easiest decision we could make.
Then came the second decision: were we going too?
We could not help ourselves. The moment this getaway started coming together, Amy and I knew we wanted to be onboard. Alaska is simply too special to recommend from a distance, and the opportunity to experience it again alongside members of this community made the decision even easier.
It also appears that our enthusiasm may be contagious. After hearing us talk about Alaska so many times, Derek and Jeff may have been convinced to book rooms onboard as well. What originally began as a smaller, more intimate getaway is quickly starting to feel like quite the group cruise.
That is exactly what makes this new Keyholder Getaway concept so exciting. It may not have the full schedule of a hosted group cruise, but it still creates the opportunity to share an incredible destination with familiar faces, meet new friends, and enjoy the kind of spontaneous moments that happen when this community travels together.
Alaska is one of those destinations that can completely reset your expectations of what a vacation can be. The landscapes feel enormous, the scenery changes constantly, and there is a sense of adventure that begins almost as soon as the ship leaves port.
It is also an ideal destination to experience by cruise. Rather than packing and unpacking as you move between communities, glaciers, and coastal landscapes, the ship becomes your home base for the week.
Amy and I will be joining this May 21–28, 2027 sailing on Voyager of the Seas, and we would love to have even more members of the DVC Fan community travel with us!
Here is the funny part: I originally meant to publish this announcement four days ago.
At the time, we had an exclusive group rate and a block of staterooms ready to share. The problem was that you people managed to sell out every one of those rooms within a matter of hours!
That should probably tell you everything you need to know about the enthusiasm surrounding this trip.
Although our exclusive inventory has sold out, some excellent prevailing rates remained available as of this article’s publication. At that time, an Ocean View Balcony Stateroom for two guests could be booked for less than $3,000, making this an outstanding opportunity to experience Alaska.
Guests booking this getaway will also receive a $50 onboard credit.
Alaska Getaway Highlights
- May 21–28, 2027
- Seven-night Alaska itinerary
- Paul and Amy will be sailing
- Derek and Jeff may be joining the growing group?
- $50 onboard credit
- Limited stateroom availability
- Prevailing cruise-line rates apply now that the original group inventory has sold out
Cruise fares and availability can change at any time, so anyone considering the sailing should review the current options sooner rather than later.
A Massanutten Resort Getaway Is Coming in Summer 2027
Keyholder Getaways will not be limited to cruises.
We are also working on a summer 2027 getaway at Massanutten Resort in Virginia. This will give our community an opportunity to experience an entirely different style of vacation, with a mountain setting and resort activities outside the familiar worlds of Walt Disney World and cruising.
One of our goals with Keyholder Getaways is to introduce trips we genuinely think this community will enjoy, even when they fall outside the traditional Disney vacation calendar. Massanutten is an early example of how broad that idea can become.
We are not ready to share all the details quite yet, but more information will be coming soon.
Keyholder Getaway: Hero of the Seas
September 25–October 2, 2027
Seven-Night Western Caribbean Sailing
Our second cruise getaway for 2027 will place guests aboard one of Royal Caribbean’s newest ships during its inaugural season.
Hero of the Seas is part of Royal Caribbean’s Icon Class, and Amy and I have now sailed on an Icon Class ship four times. After those experiences, we genuinely believe this class of ship represents the apex of what is currently possible aboard a cruise ship.
The scale is remarkable, but what continues to impress us is how well everything works together. The neighborhoods, entertainment, dining, pools, family areas, and quieter spaces make the ship feel like far more than a floating resort. Even after multiple sailings, we still find new things to experience.
For anyone who joined us aboard Utopia of the Seas and loved that ship, the easiest way to describe Hero is this: imagine that experience on steroids.
Hero of the Seas brings the size, variety, and spectacle of Icon Class together with a strong seven-night Western Caribbean itinerary. Between everything happening onboard and stops throughout the Caribbean, there is a very real chance you will reach the end of the week wishing you had more than seven nights to experience it all.
The September 25th sailing is scheduled to visit Puerto Costa Maya, Roatán, Cozumel, and Perfect Day at CocoCay, along with two days at sea. That combination gives guests plenty of opportunities to explore ashore while still leaving meaningful time to enjoy the ship itself.
Being aboard one of Hero of the Seas’ inaugural-season sailings would already make this a memorable vacation. The group pricing secured by our Keyholder Getaway makes the opportunity even more compelling.
Our group rate for two guests is $3,921.86. At the time we compared pricing, Royal Caribbean’s best publicly available rate for the same room and two guests, including its advertised buy-one-get-one promotion, was $4,885.84.
That represents almost $1,000 in savings through the Keyholder Getaway group rate!
Guests booking within our available group inventory will also receive a $50 onboard credit.
Hero of the Seas Getaway Highlights
- September 25–October 2, 2027
- One of Hero of the Seas’ inaugural-season sailings
- Round-trip sailing from Miami
- Puerto Costa Maya, Roatán, Cozumel, Perfect Day at CocoCay
- Two days at sea
- Group rate of $3,921.86 for two guests
- Approximately $1,000 in estimated savings compared with the rate reviewed
- $50 onboard credit
- Limited stateroom availability
It is important to clarify that this is a Keyholder Getaway, not a fully hosted Keyholder Vacations Group Cruise. There will not be a complete private event schedule or the same level of organized programming planned for our inaugural Utopia sailing.
Instead, this is an opportunity to secure excellent group pricing, experience one of Royal Caribbean’s most ambitious ships, and share the week with other members of the community who may be traveling on the same sailing.
Rates, promotions, and availability are subject to change. The comparison above reflects the pricing available when this announcement was prepared.
How to Book the 2027 Keyholder Getaways
Reservations for the Alaska and Hero of the Seas getaways can be made through Keyholder Vacations.
Visit: KEYHOLDERVACATIONS.COM/GETAWAYS
Availability is limited, so don’t waste too much time deciding if you want to be a part of one of these amazing adventures!
The Keyholder Vacations team can assist with current pricing, stateroom options, deposits, and any questions about what is included with each getaway.
The Second Keyholder Vacations Group Cruise Is Coming
The response to our inaugural cruise immediately confirmed one thing: we have to do this again!
There is a difference between traveling on the same ship and truly sharing a vacation together. Throughout the inaugural cruise, we watched people who had previously known one another only through Facebook discussions, YouTube comments, or DVC Fan events become real-life friends.
We saw families sharing meals, groups gathering around the ship, and people making plans to travel together again before the first cruise was even over. Those moments were exactly what we hoped this event could create.
We are not ready to announce the ship or itinerary for our next hosted group cruise. Some of the itineraries we are considering are not yet available, and we want to make sure we have the right ship, dates, and overall experience before sharing the full details.
What we can officially announce is this:
Save the Date: Summer 2028
Planning has begun for the Second Keyholder Vacations Group Cruise, scheduled for summer 2028!
This will be the true follow-up to our inaugural hosted sailing, complete with the community atmosphere and special programming that made the first cruise so memorable.
More information will be announced as itineraries become available and plans are finalized. For now, save a place on your summer 2028 calendar and watch DVC Fan and Keyholder Vacations for updates!
This Next Chapter Belongs to the Community
When we organized that first BoardWalk meetup, we could not have predicted where it would lead.
We did not know that those early conversations would grow into recurring Walt Disney World weekends. We did not know that we would eventually gather aboard Utopia of the Seas for an entire cruise. We certainly did not know that we would one day be announcing six upcoming opportunities for this community to travel together.
All of it happened because you showed up.
Thank you for attending the meetups, joining the events, watching The DVC Show, sharing your feedback, and trusting our team to help plan your vacations. Most of all, thank you for making this community a place where genuine friendships can begin.
Whether you join us at WinterFest, spend a week exploring Alaska, try something new at Massanutten, sail aboard Hero of the Seas, return to the BoardWalk for FallFest, or wait for the full 2028 group cruise announcement, we hope you will find an opportunity that feels right for you.
This is not simply a longer list of events. It is the next chapter of a community that keeps finding new ways to spend time together.
We cannot wait to see where we go next!
Jennifer toto
August 6, 2026I love everything about this post!! I’m devastated I can’t join you all in Alaska:(