This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.
Update: Some offers mentioned below are no longer available. View the current offers here.
This year my parents both turned 60 so I wanted to get the family together for a long weekend, and decided what better place to do it than Grand Cayman? As I’ve mentioned before, my introduction to the points and miles world was when I was eleven years old and figured out how to use my dad’s points to get my family of six to the Cayman Islands for relatively cheap. Being able to bring them back at my expense almost twenty years later meant a lot to me and would allow us to get some quality time together.
I found fares on JetBlue for my parents, brother, sister-in-law and seven-month-old niece to fly out of JFK nonstop to Grand Cayman for $370 roundtrip per person. Here’s a tip for parents traveling with a lap child: nicely ask the agent at check-in if there are any open seats so you can keep your baby in the car seat (instead of having to check the seat). It worked out for my brother Dan and his wife Sue both ways and made for much more enjoyable 5-hour flights!
I ended up flying from Miami, which was just a quick 90-minute flight, though it was quite a bit more expensive than the flights from New York. Economy fares on American from Miami are normally $536 round trip or $874 in business class. The cheaper airline for me would have been to fly on Cayman Airways Limited for $397 roundtrip, but I wanted to match up arrival times with my family so that option didn’t pan out.
In order to use miles to fly American into GCM you can sometimes find availability on BritishAirways.com. Now that you can book US Airways awards using Avios, this can be a great option if you can find nonstop flights from Charlotte or Philadelphia. Using Avios to fly from Miami would cost 9,000 Avios and $119 in economy and 18,000 Avios + $119 for business class roundtrip. If there had been award availability on the dates I was traveling, I definitely would have chosen to do that instead. To see a full listing of airlines that fly to the Cayman Islands and which days of the week flights operate on, visit this link.
Since I started planning this a few months in advance in order to match up work schedules among my family, I was able to find a great rental in Rum Point from GrandCaymanVillas.net. The villa was named Ecstasea, which we got a kick out of, and was comprised of 5 bedrooms and 5 full baths. The bedrooms were all really spacious and four of them had their own private bathrooms. One of the rooms even had its own den area with a crib so Dan, Sue and Juliette took that room and had more than enough room.
The back of the house had a nice stone patio with lounge chairs and right behind that were steps down to a picture-perfect private beach. There was also a pool on the opposite side of the house which could use some updating, but it was still nice to hang out around. We were warned to wear water shoes in the ocean because there is coral in the surrounding area, but when we attempted to snorkel we didn’t see much except for an old creepy doll that I found laying in the sand! A bit further down the beach towards Rum Point was a little better for snorkeling, but it still wasn’t anything amazing.
Rates for this house vary throughout the year, but for the weekend of February 6th I paid $4,467 for four nights, coming out to $1,116 per night . Since I was able to accommodate several adults in five bedrooms, have a private beach and pool, and a fully functional kitchen it was well worth it in my opinion. Unfortunately when booking with Grand Cayman Villas, the credit card charge gets categorized as “Business Services – other services” so I wouldn’t have been able to earn double points using my Sapphire Preferred. Instead I opted to use my Starwood Amex and bank 4,467 points there.
Tortuga Divers with Red Sail Sports
Unfortunately, no one else in my family is scuba certified so I ended up going by myself one morning and loved it so much that I booked another dive for the following morning. I wanted to book a dive charter that went out of Rum Point but we were in town from Thursday to Monday and Tortuga Divers with Red Sail Sports only offers dives from that location on Wednesdays. I booked the 2-Tank AM Wall Dive from Morritts Resort, (only about a 15-minute drive from the villa) for $130 and it included the tank, weights and fruits. My diving experience was incredible and the crew was professional, friendly and helpful.
Dining on Grand Cayman
The villa was about a 30-minute drive from the airport and we had rented two cars to get around, one SUV from Andy’s Car Rental and a standard car from Budget that was upgraded to a Jeep Wrangler since they didn’t have any standard cars available. Rum Point beach was just a few minutes further down the road from the house so there were some restaurants and shops close by.
One of the things I like most about staying in a rental house rather than a hotel is that you can go grocery shopping and cook some meals instead of having to go out to eat multiple times a day. On Friday night, my brother went out and found a local fish shop and cooked us all a delicious (and healthy!) Cajun-spiced salmon dinner with mixed greens and a homemade strawberry and pineapple salsa. Well done, Dan!
Saturday night we made a reservation at the Lighthouse Restaurant and had a table outside at the end of a pier that made it feel like we were sitting out in the middle of the ocean. We ordered a couple different appetizers like conch ceviche, sausage on portobello mushroom and Caesar salad – all were fantastic. For the main course, some of the highlights were the lobster on ravioli, and the seafood curry. Overall the service was great and everyone enjoyed their meal.
On our final night we went to the upstairs restaurant at Kaibo. They had an impressive whiskey collection and offer a five-course tasting menu with an option for wine pairing. We decided to forgo the five courses and ordered from the regular a la carte menu, but first started off with some tasty drinks. My mom tried The Porthole (pictured above) which was some kind of rum, lime and peppercorn mixture – A+ for presentation! As for meals, the grouper entree was the fan favorite of the night.
For lunch we went to Rum Point beach twice and sat at picnic tables at the outdoor restaurant that had amazing fresh fish sandwiches and tropical drinks like the Rum Runner and frozen Pink Lady. We also tried the Beach Bar and Grill that is downstairs at Kaibo, another great spot for salads and fish sandwiches.
Grand Cayman will always be a special place for me since that was my first international trip as a kid and I will definitely be returning in the future. It’s a perfect place to get away, avoid a ton of crowds and tourists and soak up some Caribbean sun. We had a really great weekend and with such a crazy travel schedule I always appreciate any time I get to spend with my family, especially my adorable niece! Next time I’d like to head over to Little Cayman and Cayman Brac, sister islands of Grand Cayman that are less inhibited and are reported to have incredible dive locations.
With some great bonus categories, the American Express Gold Card has a lot going for it. The card offers 4x points at US restaurants, at US supermarkets (up to $25,000; then 1x), and 3x points on flights booked directly with airlines or through amextravel.com. It is currently offering a welcome bonus of 35,000 bonus points after you spend $2,000 in the first three months.
- Earn 35,000 Membership Rewards® Points after you spend $2,000 on eligible purchases with your new Card within the first 3 months.
- Earn 4X Membership Rewards® points at U.S. restaurants. Earn 4X Membership Rewards® points at U.S. supermarkets (on up to $25,000 per year in purchases, then 1X).
- Earn 3X Membership Rewards® points on flights booked directly with airlines or on amextravel.com.
- Earn up to $10 in statement credits monthly when you pay with The Gold Card at Grubhub, Seamless, The Cheesecake Factory, Shake Shack, and Ruth's Chris Steak House. This is an annual savings of up to $120. Enrollment required.
- $100 Airline Fee Credit: up to $100 in statement credits per calendar year for incidental fees at one selected qualifying airline.
- Choose to carry a balance with interest on eligible charges of $100 or more.
- No Foreign Transaction Fees.
- Annual Fee is $250.
- Terms apply.
- See Rates & Fees