Cayman Islands 2022 Trip Report
Travel party of 14!! Myself and husband, 44, our younger kids, 8 and 12, known as “the lils,” our older kids, 24 and 21 and thier bf/gf, my mom, and my sister's family, similar in makeup to ours.
Travel mood: Willing to combine a points stash with lots of cash to have quality food and entertainment experiences.
Transportation
Flew out of Chicago's Midway on Southwest. Booked when schedules opened for 30k RT each (one stop) and two companion passes. The mask mandate was struck down the day before our return flight, meaning our U.S. airport experience and flights were mask optional. I would say probably 90% of travelers were mask free.
Lodging
I really sort of don't even want to share this trip report because we love the resort so much and it sort of flies under the radar (likely because there are significant costs associated with a points stay). This is our third visit to the Kimpton Seafire Resort & Spa in Grand Cayman and it has yet to disappoint. What we love about it:
- Amazing ocean views of crystal blue water on Seven Mile Beach with huge balconies
- Luxury service, but with a relaxed attitude
- Boutique resort size with lots of nooks for lounging and playing
- Great amenities included in the resort fee
- Always room at the pool or beach without playing silly towel games
- Quality food and a legendary Sunday Brunch (common in the Cayman Islands)
We booked
standard rooms, 2 queen oceanview rooms, available on points, at 70k IHG points/nt, but if you have an IHG credit card, you receive the fourth night free, bringing the points down to 52.5k/nt. Unlike many resorts in Europe and other places, the standard room sleeps four and is ocean view. With our platinum IHG status through the IHG premier card, we received an upgrade on nights 2-4 to a
King One Bedroom Ocean View Suite (though this took a bit of back and forth to make happen, so I wouldn’t go in expecting an upgrade, AT ALL). Our suite had two balconies and a wet bar with two fridge drawers, so it was super helpful as a gathering place for our group of 14.
The cash rate for the standard room was ~$6500 for four nights, including taxes and fees. Our group had four rooms and most are not travel hackers. Travel hack: You can buy points during a 100% points bonus promotion (run several times annually) for $1050, combined with the fourth night free cc benefit. Tack on the $80/nt resort fee and your all in lodging cost for 5 days = $1370
The resort fee is a whopping $80/nt and I don’t mind it one bit, honestly. Here’s what it includes:
- Morning coffee and tea in the lobby for 3 hours (in the past this included iced coffees with a variety of syrups, etc, but has been slimmed down due to COVID)
- afternoon social hour (now grab n go hard seltzer due to COVID, but previously glasses of wine)
- sunscreen and aloe stations, and bottled water
- water rentals: ocean rafts, snorkeling gear, go-pro cameras, kayaks, stand-up paddle boards, water tricycle, small sailboat, fitness classes and gym, other resort activities
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Entertainment
Most of our days were spent at the pool or beach. We booked Cayman Island’s largest catamaran,
Catch the Cat, arranged through the resort concierge. We chartered the cat for half a day (4 hours) and snorkeled, went to Stingray City, Starfish point and used the onboard jet ski. We don’t have a ton of experience with boats and while we’ve done private boat tours, we’ve never chartered a boat before. We LOVED this experience. The size of the catamaran was ideal for our group and we loved the freedom to comfortably walk about the cat while in motion, lounging on the trampoline nets and customizing our day and time at each stop.
Stingray City is a sandbar in the middle of the ocean which apparently used to be where fisherman would come to clean their catch in calm waters. This became a gathering place for stingrays as an easy source of food. It has now become a tourist destination where the stingray have become very accustomed to swimming and interacting with humans. You can stand in water about 4-5 feet and the HUGE stingray (up to 5 feet) come and swim alongside you. Your guide will help you kiss a stingray for seven years of luck and pose with one, if you desire. I personally prefer a more observational approach and I really enjoy just standing in the water as these huge, majestic creatures allow you into their playground.
Weather was 84 (RealFeel 90-92) and sunny every day.
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Food
If you are familiar with the Kimpton brand, you know they have exquisite food offerings. Every dish we had was delightful, from poolside service to their beachfront restaurant, to the luxury Easter Brunch. We spent nearly 3 hours at Easter Brunch, which can include their hand-crafted cocktails, if desired. While not inexpensive ($122-156 w/ or w/o alcohol + gratuity), it includes carving stations, fresh seafood, crab legs, oysters, sushi, salads, Mediterranean cuisine and typical breakfast offerings. Sunday Brunch is offered every week, at perhaps a more palatable pricepoint of $84-96 USD.
*While Kimpton’s are part of the IHG family, you won’t earn loyalty points on food and beverage spend, even if charged to your room.
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Key Takeaways
It seems few vacations are actually relaxing these days. This one IS, Every. Single. Time. The Kimpton resort is a real contender with Ritz Carlton service and is actually attainable on points. You’ll need to prepare to bring plenty of cash if you want to enjoy the foodie experience of the Kimpton. Stingray City/Starfish point tours can be booked with points through portals like Chase Travel.
We really, really enjoy traveling in large groups (usually 7-16) and I sort of feel like it’s my niche, putting together travel for our large family. We love being able to treat our family to experiences they otherwise wouldn’t pay for themselves and help them travel hack to get to some amazing destinations. This is a trip we will definitely repeat, not so much because we love the Cayman Islands themselves, but because this resort fits us so perfectly. The Kimpton Seafire was the ideal multi-generational resort for us, for it’s boutique size, service-level and foodie options.
Detailed Pricing
I always struggle trying to convey this because we are a big family, so I've tried to break it down into either individual costs or costs per night to be more helpful to try to apply it to your group size. For some things, that's just not possible.
Lodging | | | |
Kimpton Seafire IHG 4 nts, per room (52.5k/nt) | 210,000 | IHG points | $ 320 |
Kimpton Seafire IHG 4 nts, per room (52.5k/nt) | 210,000 | IHG points | $ 320 |
Transportation | | | |
Flights- Southwest (4) | 30,000 | RRs/pp/round-trip | $ 96 |
Flights- Companion pass tickets (2) | 0 | RRs/pp/round-trip | $ 96 |
Chicago Midway Airport Economy Parking | | | $ 75 |
Majestic Tours Airport Transport (total for 14 pax) | | $ 270 | |
Entertainment | | | |
Catch the Cat half day catamaran w/jet ski | | | $ 2,000 |
Easter Brunch at Kimpton Seafire pp (14) | | | $ 181 |
Miscellaneous | | | |
Insure my trip policy | | | $ 90 |
eMed Covid tests (4) | | | $ 117 |
Totals | 540,000 | IHG/RR points | $ 5,841 |