Crystal Shores vs. Ocean Pointe for 20+ family reunion vacation

[Seaport104]

Hello Again,

So Europe is now out (thanks to all who replied to my previous post) and family has settled on FL. The trip will be end of June for 20+ people (all adults except for 2 tweens) who are not huge beach goers.

Maybe one day we will have a beach and/or pool day but otherwise, my family likes to do things. I know Crystal Shores is nicer as far as units/resort amenities are concerned but the availability of things to do are more important for us. Haven't been to CS but I've been to OP about 20 times and love it. However, I'm a huge beach person so I spend most of my time on the beach. So I'm not really familiar with other things to do by Ocean Pointe.

With that in mind, which do you think is better - Crystal Shores or Ocean Pointe? What tours/activities can we do at either location? Below is what I've come up with so far. Note: zoos and waterparks are not an interest for anyone in the family.


By Ocean Pointe:

Jungle Queen Dinner Cruise out of Fort Lauderdale
City Place for dinner and walking around

By Crystal Shores:

Jetski Dolphin Tour


By either locations -

Everglades airboat tour

 

[Hindsite]

Crystal shores is generally regarded is one of the best in the system. It is, however, a difficult trade in II so you'd need to use club points for the reservation of be very lucky.

 

[Seaport104]

Crystal shores is generally regarded is one of the best in the system. It is, however, a difficult trade in II so you'd need to use club points for the reservation of be very lucky.

Agree for CS, I would points to book and have rented points transferred to my account if I don’t have enough.

 

[Superchief]

We prefer Marco Island over Singer Island. but enjoy beach and pool and watching dolphins. The area around Marco Island is a lot less congested than West Palm Beach area and people are friendlier. Naples and Ft Myers are within an hour drive for shopping and sightseeing. Everglades national park is definitely worth a visit. If you enjoy more city activities, then OP would be better,

If you are using Abound points, Crystal Shore has more view options and would likely require fewer points for the island view and poolside lower floor view, but both still have better views than Ocean View at Ocean Point. You really can't go wrong with either resort.

 

[Dean]

Hello Again,

So Europe is now out (thanks to all who replied to my previous post) and family has settled on FL. The trip will be end of June for 20+ people (all adults except for 2 tweens) who are not huge beach goers.

Maybe one day we will have a beach and/or pool day but otherwise, my family likes to do things. I know Crystal Shores is nicer as far as units/resort amenities are concerned but the availability of things to do are more important for us. Haven't been to CS but I've been to OP about 20 times and love it. However, I'm a huge beach person so I spend most of my time on the beach. So I'm not really familiar with other things to do by Ocean Pointe.

With that in mind, which do you think is better - Crystal Shores or Ocean Pointe? What tours/activities can we do at either location? Below is what I've come up with so far. Note: zoos and waterparks are not an interest for anyone in the family.


By Ocean Pointe:

Jungle Queen Dinner Cruise out of Fort Lauderdale
City Place for dinner and walking around

By Crystal Shores:

Jetski Dolphin Tour


By either locations -

Everglades airboat tour

OP. It's easier to get that time of year and will be much cheaper than CS even if you could get CS in sufficient volume. It's also easier to get to than CS if flying or driving. About 10 years ago we had to pivot for our larger family trip which we normally do week 25 or 26. Kim and I had planned a trip that would have precluded our family trip but by the time our plans changed, getting MGO for our trip was impossible. OP was easy to book at about 11 months out. We had our choice of OF or OS including 3BR options. From a resort standpoint I'd chose CS but I think you'll have difficulty booking what you need and even if you get sufficient volume, it's unlikely you'll be able to get the rooms in close proximity. Currently CS and South Beach are the only resorts in FL without 7 day availability for a group of 6. For 20, I'd book ONE 3BR OF if you can get it, ONE 2BR OF and the rest OS. There are only one 3 BR and one 2 BR OF in each of the 4 buildings that are together, not sure about the separate 5th building 3BR setup.

 

[Seaport104]

Good point about the flights. Half are coming from west coast and theres probably a lot more available flights to FLL or PBI rather than RSM.

Any suggestions re tours or things to do?

 

[Dean]

Good point about the flights. Half are coming from west coast and theres probably a lot more available flights to FLL or PBI rather than RSM.

Any suggestions re tours or things to do?

We didn't do anything specific such as organized tours other than we explored Palm Beach including the Breakers hotel plus some of the party did a sightseeing boat tour of Palm Beach. There was a water taxi but we didn't take it.

As for flights, OP will give you more options with PLI, FLL, MIA & MCO all viable plus Brightline gets you close from Orlando or Miami direction. That's not to say that flying to MIA, F. Myers or FLL then renting a car isn't viable for CS, it is, but will be more expensive for Ft. Myers. IF you can work it out for CS with all rooms that can be assigned in the same building AND the group just wants to hang out at the pool and beach, I'd chose CS. The reason I said OP is that I doubt you can get the reservations in a way that would fill those requirements. Plus it locks in the group to car rental but I'd want sufficient cars to get around regardless. It will also be cheaper by far if using points and should be fairly easy to exchange to through II though you may have missed your best chances for 2025 if using II for 2BR for this size group.

 

[Seaport104]

IF you can work it out for CS with all rooms that can be assigned in the same building AND the group just wants to hang out at the pool and beach, I'd chose CS.

The latter is exactly the reason why I don't think CS is better for the group, putting aside the ability to get units. Worst case, I can rent some to supplement.

My family (not me) would be bored just to hang out at the pool and beach. They need 2-3 activities to do during the week.

 

[Superchief]

OP. It's easier to get that time of year and will be much cheaper than CS even if you could get CS in sufficient volume. It's also easier to get to than CS if flying or driving. About 10 years ago we had to pivot for our larger family trip which we normally do week 25 or 26. Kim and I had planned a trip that would have precluded our family trip but by the time our plans changed, getting MGO for our trip was impossible. OP was easy to book at about 11 months out. We had our choice of OF or OS including 3BR options. From a resort standpoint I'd chose CS but I think you'll have difficulty booking what you need and even if you get sufficient volume, it's unlikely you'll be able to get the rooms in close proximity. Currently CS and South Beach are the only resorts in FL without 7 day availability for a group of 6. For 20, I'd book ONE 3BR OF if you can get it, ONE 2BR OF and the rest OS. There are only one 3 BR and one 2 BR OF in each of the 4 buildings that are together, not sure about the separate 5th building 3BR setup.

I think the flight costs and availability will vary based on where you are flying from. Flights from CVG were actually less expensive to RSW (Ft Myers) than FLL or PBI, especially on Sundays. Keep in mind that FLL is a primary cruise airport so flights are often more expensive and more crowded. Ft Myers is a great airport and rental cars are attached rather than offsite (FLL).

Orlando airport is another option for OP because there are Brightline trains from MCO to Palm Beach and it is only a 2h train ride.

 

[Superchief]

The latter is exactly the reason why I don't think CS is better for the group, putting aside the ability to get units. Worst case, I can rent some to supplement.

My family (not me) would be bored just to hang out at the pool and beach. They need 2-3 activities to do during the week.

I checked all three (added Oceana Palms) using points for next June for 7 nights and CS doesn't show any availability in June. Since you have such a large group, Singer Island offers more options. Ocean Point has lockoffs, so one bedroom or studios could be used if there are any smaller parties in your group. If there isn't sufficient availability at Ocean Pointe, Oceana Palms is close and is a very nice resort. 2BR point requirements are similar across all three resorts.

 

[jmhpsu93]

The latter is exactly the reason why I don't think CS is better for the group, putting aside the ability to get units. Worst case, I can rent some to supplement.

My family (not me) would be bored just to hang out at the pool and beach. They need 2-3 activities to do during the week.

Then why a beach resort, if no one likes the beach? You'd be better off at Park City or even Branson.

 

[dioxide45]

Then why a beach resort, if no one likes the beach? You'd be better off at Park City or even Branson.

Or Orlando!

 

[dgf15215]

Or Orlando!

Reading the messages, I agree with dioxide45 - Orlando has huge housing capabilities, many attractions even apart from Disney, and countless restaurants. If you're not in or near the water, there's not much to do at Ocean Pointe or Beachplace Towers (both my favorite spots).

 

[Seaport104]

Then why a beach resort, if no one likes the beach? You'd be better off at Park City or even Branson.

They like the beach but not as much as me. I'm happy being on the beach every day and going out for dinner.

My family on the other hand, need things to do for the week. Usually we have one beach/pool day of the trip where we hang out all the beach/pool all day and BBQ. The rest of the time, maybe beach or pool in the morning but then they want things to do off the resort.

I brought up Orlando, Branson and Park City and they were all shot down. For reference, the prior reunion destinations were:

Marriott Timber Lodge -
HGVC Hilton Hawaiin Village Lagoon Tower - Waikiki, HI -
Marriott Koolina -
HGVC Oceans Enclave - Myrtle Beach
Garza Blanca (PV Mexico)
Marriott Aruba Ocean Club
HGVC Elara - Las Vegas

Open to suggestions for a destination within the US. I own Marriott (weeks and points) and HGVC

We don't mind driving within 1.5 hours max for things to do.

 

[Hindsite]

Open to suggestions for a destination within the US. I own Marriott (weeks and points) and HGVC

We don't mind driving within 1.5 hours max for things to do.

MVC St Thomas should be achievable and has a decent mix.
MVC St Kitts (Sorry not in US but worth a mention) is also another good one with a great selection of things to do an beaches. You'll have to be OK with it being hot and the logistics of getting there from some parts of the US can be too difficult for some.

 

[Dean]

They like the beach but not as much as me. I'm happy being on the beach every day and going out for dinner.

My family on the other hand, need things to do for the week. Usually we have one beach/pool day of the trip where we hang out all the beach/pool all day and BBQ. The rest of the time, maybe beach or pool in the morning but then they want things to do off the resort.

I brought up Orlando, Branson and Park City and they were all shot down. For reference, the prior reunion destinations were:

Marriott Timber Lodge -
HGVC Hilton Hawaiin Village Lagoon Tower - Waikiki, HI -
Marriott Koolina -
HGVC Oceans Enclave - Myrtle Beach
Garza Blanca (PV Mexico)
Marriott Aruba Ocean Club
HGVC Elara - Las Vegas

Open to suggestions for a destination within the US. I own Marriott (weeks and points) and HGVC

We don't mind driving within 1.5 hours max for things to do.

While probably not workable for 2025, in future years you might consider the higher end resorts on Hilton Head or Myrtle Beach. I suspect the only beach front resort of th ones mentioned that will be available to scale will be OP.

 

[Pamplemousse]

When you say the family likes to do things- what kind of things?

We take beachfront vacations often because it is beautiful and we love to beach walk, but we rarley spend more than a few hrs a day on the beach and 2 members of my family get rashes from pools so that’s out.

We found much more to do while staying at crystal shores- we enjoyed the mini golf and restaurants across the street, we love the Naples Botanical gardens, we did 2 boat tours at the everglades, we visited the Edison & Ford winter estates in Fort Myers and stopped at the outlets on the way back (spring training baseball too if you are there then), plus really liked the restaurants across the street.

We found less to do on Singer island. We did go to the Mounts gardens and Four Arts gardens in Palm Beach as well as wander around downtown for awhile and up to Jupiter to the lighthouse.

Have you tried Hilton Head? That gives you the option to go to Savannah in less than an hour with so much to do (we recently did a riverboat cruise) plus Bluffton just over the bridge. There’s mini golf, zip line, horseback riding, shopping, Pinckney Island nature preserve, boat tours.

Another suggestion is Phoenix. No beach but tons to do there and a trip to the Grand Canyon is feasible (we made it an overnight but you could do it as a day trip especially if you use a tour). Taliesin west, Phoenix Botanical Gardens and old town Scottsdale are great.

Adding one more non beach- Palm Desert. Great for hiking, jeep trips in Joshua tree, Living Desert zoo & garden and Moorten botanical gardens, Air museum.

 

[Seaport104]

When you say the family likes to do things- what kind of things?

We take beachfront vacations often because it is beautiful and we love to beach walk, but we rarley spend more than a few hrs a day on the beach and 2 members of my family get rashes from pools so that’s out.

We found much more to do while staying at crystal shores- we enjoyed the mini golf and restaurants across the street, we love the Naples Botanical gardens, we did 2 boat tours at the everglades, we visited the Edison & Ford winter estates in Fort Myers and stopped at the outlets on the way back (spring training baseball too if you are there then), plus really liked the restaurants across the street.

We found less to do on Singer island. We did go to the Mounts gardens and Four Arts gardens in Palm Beach as well as wander around downtown for awhile and up to Jupiter to the lighthouse.

Have you tried Hilton Head? That gives you the option to go to Savannah in less than an hour with so much to do (we recently did a riverboat cruise) plus Bluffton just over the bridge. There’s mini golf, zip line, horseback riding, shopping, Pinckney Island nature preserve, boat tours.

Another suggestion is Phoenix. No beach but tons to do there and a trip to the Grand Canyon is feasible (we made it an overnight but you could do it as a day trip especially if you use a tour). Taliesin west, Phoenix Botanical Gardens and old town Scottsdale are great.

Adding one more non beach- Palm Desert. Great for hiking, jeep trips in Joshua tree, Living Desert zoo & garden and Moorten botanical gardens, Air museum.

In prior trips, we've done:

Marriott Timber Lodge - gondola ride and activities at Heavenly Mountain, white water rafting, casinos, lake beach day, Lake Tahoe sightseeing cruise
HGVC Hilton Hawaiin Village Lagoon Tower - Waikiki, HI - all day island tour, hiking up Diamond Head, Polynesian Cultural Center (included luau), snorkeling at Hanauma Bay
Marriott Koolina - snorkeling with wild dolphins, Paradise Cove luau, Dole plantation, Kualoa Ranch
HGVC Oceans Enclave - Myrtle Beach - mini golf, Broadway at the Beach (this included a wedding so that took up a few days)
Garza Blanca (PV Mexico) - Rhythms of the Night, Las Caletas, Sayulita and San Pancho, UTV tour to waterfalls, Swim with Sea Lions and Dolphins
Marriott Aruba Ocean Club - All day Aruba tour via bus, jeep tour to natural pool and caves/sites not accessible by bus tour, baby beach, catamaran snorkeling tour, casinos
HGVC Elara - Las Vegas - Grand Canyon, casino, comedy club (it was 118 degrees so it really limited what we can do outdoors!), mani/pedi spa day

Due to school schedules, the trip needs to be from end of June to end of July and no Hawaii this time just continental US. We just got back from Vegas where it was 118 degrees and no one wants to go back to any desert in the summer, so AZ and Palm Springs is definitely out. Also, the entire family has now done the Grand Canyon so that's off the list.

We did discuss HHI, but half the group is coming from California and Las Vegas, so the flights were not ideal, and they do not want to drive to HHI from Savannah for 1 hour after travelling 9-12 hours due to lack of nonstop flights.

Here's what I've come up with so far as activities/tours

By Ocean Pointe:

Jungle Queen Dinner Cruise out of Fort Lauderdale
Snorkeling/boat trip to Peanut Island


By Crystal Shores:

Jetski Dolphin Tour


By either locations -

Everglades airboat tour

 

[Pamplemousse]

In prior trips, we've done:

Marriott Timber Lodge - gondola ride and activities at Heavenly Mountain, white water rafting, casinos, lake beach day, Lake Tahoe sightseeing cruise
HGVC Hilton Hawaiin Village Lagoon Tower - Waikiki, HI - all day island tour, hiking up Diamond Head, Polynesian Cultural Center (included luau), snorkeling at Hanauma Bay
Marriott Koolina - snorkeling with wild dolphins, Paradise Cove luau, Dole plantation, Kualoa Ranch
HGVC Oceans Enclave - Myrtle Beach - mini golf, Broadway at the Beach (this included a wedding so that took up a few days)
Garza Blanca (PV Mexico) - Rhythms of the Night, Las Caletas, Sayulita and San Pancho, UTV tour to waterfalls, Swim with Sea Lions and Dolphins
Marriott Aruba Ocean Club - All day Aruba tour via bus, jeep tour to natural pool and caves/sites not accessible by bus tour, baby beach, catamaran snorkeling tour, casinos
HGVC Elara - Las Vegas - Grand Canyon, casino, comedy club (it was 118 degrees so it really limited what we can do outdoors!), mani/pedi spa day

Due to school schedules, the trip needs to be from end of June to end of July and no Hawaii this time just continental US. We just got back from Vegas where it was 118 degrees and no one wants to go back to any desert in the summer, so AZ and Palm Springs is definitely out. Also, the entire family has now done the Grand Canyon so that's off the list.

We did discuss HHI, but half the group is coming from California and Las Vegas, so the flights were not ideal, and they do not want to drive to HHI from Savannah for 1 hour after travelling 9-12 hours due to lack of nonstop flights.

Here's what I've come up with so far as activities/toursj

By Ocean Pointe:

Jungle Queen Dinner Cruise out of Fort Lauderdale
Snorkeling/boat trip to Peanut Island


By Crystal Shores:

Jetski Dolphin Tour


By either locations -

Everglades airboat

FYI Crystal Shores is an hour drive from the Southwest Fl airport
If your group is happy with those 2 locations you might try looking on trip advisor or local area sites for activities.
It will likely be 90 at both locations in July.
Enjoy your trip.

 

[Dean]

In prior trips, we've done:

Marriott Timber Lodge - gondola ride and activities at Heavenly Mountain, white water rafting, casinos, lake beach day, Lake Tahoe sightseeing cruise
HGVC Hilton Hawaiin Village Lagoon Tower - Waikiki, HI - all day island tour, hiking up Diamond Head, Polynesian Cultural Center (included luau), snorkeling at Hanauma Bay
Marriott Koolina - snorkeling with wild dolphins, Paradise Cove luau, Dole plantation, Kualoa Ranch
HGVC Oceans Enclave - Myrtle Beach - mini golf, Broadway at the Beach (this included a wedding so that took up a few days)
Garza Blanca (PV Mexico) - Rhythms of the Night, Las Caletas, Sayulita and San Pancho, UTV tour to waterfalls, Swim with Sea Lions and Dolphins
Marriott Aruba Ocean Club - All day Aruba tour via bus, jeep tour to natural pool and caves/sites not accessible by bus tour, baby beach, catamaran snorkeling tour, casinos
HGVC Elara - Las Vegas - Grand Canyon, casino, comedy club (it was 118 degrees so it really limited what we can do outdoors!), mani/pedi spa day

Due to school schedules, the trip needs to be from end of June to end of July and no Hawaii this time just continental US. We just got back from Vegas where it was 118 degrees and no one wants to go back to any desert in the summer, so AZ and Palm Springs is definitely out. Also, the entire family has now done the Grand Canyon so that's off the list.

We did discuss HHI, but half the group is coming from California and Las Vegas, so the flights were not ideal, and they do not want to drive to HHI from Savannah for 1 hour after travelling 9-12 hours due to lack of nonstop flights.

Here's what I've come up with so far as activities/tours

By Ocean Pointe:

Jungle Queen Dinner Cruise out of Fort Lauderdale
Snorkeling/boat trip to Peanut Island


By Crystal Shores:

Jetski Dolphin Tour


By either locations -

Everglades airboat tour

I doubt you'd be able to reserve HHI, CS or MB for the time next year and certainly not for that volume. Given the choices you have given (continental US, on the beach, easy to get to by air, some mix of other activities), OP or Oceana Palms are likely the only choice available MVC but there might be a couple on the Vistana/Sheraton side. For 2025 I'd just make the reservations there and move on with planning the trip or move to a condo/house rental instead. I plan a group yearly much larger than yours, I don't try to get consensus on what everyone wants. I do ask for input big picture and take others circumstance into account but I make the reservations and let them know the dates and that they can come. But I'm covering the trip itself so that gives me leverage plus most are driving and that limits our reasonable choices. We also love HHI and specifically MGO. I'm actually in the planning process for summer 2026 right now, sent out the first wave of emails about 4 AM today since 7/4 is on a Sat and we usually go over the week of the 4th.

Since it sounds like you plan this group trip repeatedly, I'd suggest you move your planning to 1.5 to 2 yrs out so that you can make reservation when the 13 months window opens, make arrangement for points if you need to rent some and put in any exchange request needed such that when people start depositing, you're already in the cue. Maybe try for CS for 2026 Trying to get consensus prior to booking sounds like nightmare that I would want to avoid. There will be things to do both locations, I always find things even is smaller out of the way locations. But you'll have more overall options for OP over CS with some overlap.

I'd also point out that you're looking at an hour drive or more for any of your options for most flights. Personally I wouldn't want to drive from the Miami area to Marco at night. OP will give you more options if people are arriving at different times or airports or want to avoid a car rental.

 

[Superchief]

When our children were still in school, we switched our summer vacations to mountain locations due to the cooler temperatures and lower humidity. It is also not high season so costs are lower and outdoor activities are more comfortable. We now prefer Park City or Vail, but Park City offers more MVC availability at Mountainside or Summit Watch. Salt Lake City provides easy access by plane or train and is only 40 minute drive. There are several national parks in the area that are seldom crowded and have great hiking trails. Mountainside can get crowded in late June-July due to a lot of owners bringing families from SLC, but Summit Watch is in the middle of town and usually less crowded. There are also several good restaurants in the area and free bus service in and around town.

 

[vacation dreaming]

When our children were still in school, we switched our summer vacations to mountain locations due to the cooler temperatures and lower humidity. It is also not high season so costs are lower and outdoor activities are more comfortable. We now prefer Park City or Vail, but Park City offers more MVC availability at Mountainside or Summit Watch. Salt Lake City provides easy access by plane or train and is only 40 minute drive. There are several national parks in the area that are seldom crowded and have great hiking trails. Mountainside can get crowded in late June-July due to a lot of owners bringing families from SLC, but Summit Watch is in the middle of town and usually less crowded. There are also several good restaurants in the area and free bus service in and around town.

What National Parks are in the Park City area?

 

[jwalk03]

What National Parks are in the Park City area?

There are none in the Park City area directly. But some that are a drive away from there.

Closest are:
Timpanogos Cave National Monument- 1.25 hour one way
Golden Spike National Historical Park- 2 hours one way
City of Rocks National Reserve- 3 hours one way
Dinosaur National Monument- 3 hours one way
Capitol Reef National Park- 4 hours one way
Canyonlands & Arches National Parks- 4 hours one way

I drove to City of Rocks and Golden Spike from Summit Watch one day when my legs need a break from the deep powder the day before! It was a long day of driving but doable.

 

[Seaport104]

I doubt you'd be able to reserve HHI, CS or MB for the time next year and certainly not for that volume. Given the choices you have given (continental US, on the beach, easy to get to by air, some mix of other activities), OP or Oceana Palms are likely the only choice available MVC but there might be a couple on the Vistana/Sheraton side. For 2025 I'd just make the reservations there and move on with planning the trip or move to a condo/house rental instead. I plan a group yearly much larger than yours, I don't try to get consensus on what everyone wants. I do ask for input big picture and take others circumstance into account but I make the reservations and let them know the dates and that they can come. But I'm covering the trip itself so that gives me leverage plus most are driving and that limits our reasonable choices. We also love HHI and specifically MGO. I'm actually in the planning process for summer 2026 right now, sent out the first wave of emails about 4 AM today since 7/4 is on a Sat and we usually go over the week of the 4th.

Since it sounds like you plan this group trip repeatedly, I'd suggest you move your planning to 1.5 to 2 yrs out so that you can make reservation when the 13 months window opens, make arrangement for points if you need to rent some and put in any exchange request needed such that when people start depositing, you're already in the cue. Maybe try for CS for 2026 Trying to get consensus prior to booking sounds like nightmare that I would want to avoid. There will be things to do both locations, I always find things even is smaller out of the way locations. But you'll have more overall options for OP over CS with some overlap.

I'd also point out that you're looking at an hour drive or more for any of your options for most flights. Personally I wouldn't want to drive from the Miami area to Marco at night. OP will give you more options if people are arriving at different times or airports or want to avoid a car rental.

Agree, the more replies and thinking about it further, looks like OP is the way to go for us in 2025. Also have the option of FLL or PBI for flights and if flying into PBI very easy for airport pickups and drop offs (MIA on paper doesn't seem to far but the traffic is horrendous). I will be arriving a day prior to set things up for arrival day.

@Dean your group is 3x bigger but since everyone chips in, I don't have the same leverage as you . Trying to start 2026 discussions already planning 11-12 months lead time is already mind baffling for them LOL!

 

[Dean]

Agree, the more replies and thinking about it further, looks like OP is the way to go for us in 2025. Also have the option of FLL or PBI for flights and if flying into PBI very easy for airport pickups and drop offs (MIA on paper doesn't seem to far but the traffic is horrendous). I will be arriving a day prior to set things up for arrival day.

@Dean your group is 3x bigger but since everyone chips in, I don't have the same leverage as you . Trying to start 2026 discussions already planning 11-12 months lead time is already mind baffling for them LOL!

IMO it'll drive you crazy if you have to go through these mental gymnastics every year. I'd suggest you consider letting everyone know how difficult this is for you, get their input then YOU make the decision. If they decide they can't or won't go, that's on them. If they know waiting isn't an option, they'll plan if they can and make do if they can't. You can always reserve for the group then pivot if you need to later AND the preferred option is available but you'll have something locked in. Or if someone can't go you can cancel and bank points, rent reservations, etc. That's far easier and less stressful than what you're doing now it would appear to me. Or else just go the non timeshare route with a home or other private rental and let someone else take the lead. There will be some adjustment the first year or 2 but either they'll come around or they won't. And the ones where it'll still be a problem will probably be a problem at 6 months out as well as 10-11 months out. I have my rules for the trip, you could do the same but would add in a line item or 2 to cover this situation. My rules are simple. Let me know if you are or are not going, don't leave charges on the room, one family meal and a family photo AND the biggest one, NO DRAMA. At this point we do the same week and same resort every year with rare exception at MY discretion though I do take the input of various people if we're thinking of something different which has been rare over the last 20 years or so.

Hopefully everyone is acting in good faith and just having trouble planning that they don't have control over, that we can all understand. What I would not let control this situation is people who simply can't make a decision when they have the opportunity to do so. I often see that non timeshare people have no clue the effort and commitment (financially and otherwise) required for such a trip. My process and personality make it fairly easy but if I weren't a planner and didn't have the means to do this, it'd be a real problem that does not sound like fun to me. The one thing that I have that it doesn't sound like you do is that many of them would not have the means to fly or do activities that require $$$. So I've tried to boil it down to the least commitment possible that we really like such as a driving location, controlling the cost of the family meal, etc. Until covid our family meal was out but even then we either did lunch with a lunch menu or an early dinner with an early bird. I know some have the means to do this on their own if they wanted but many of the group do not and even getting away with little commitments hanging out at the pool and beach could be taxing for them so I make every effort NOT to put people in a position to spend more than the basics.

Rarely we have someone who can't go but I'm actually amazed at how few that's been over the years and for some I'm surprised they haven't missed due to their work and personal situations.

I suggest you plan CS for 2026 and reserve at 12-13 months out if available since you won't have that that option for that time of year if you miss those reservations windows. Put in any exchange requests that you have access to as well. Or possibly do the same for Aruba. I'd take Aruba over St. Kitts due to the need for more going on.