Why I Needed This Trip
In early August, it hit me: I never took a real summer vacation. How was that possible? I had traveled for family, hosted visitors, worked long shifts, but I never carved out days just for me. My body and mind were feeling it.
I longed for braids, sunshine, and turquoise water. I craved a quick escape that wouldn’t blow up my budget. And because I live in South Florida, the Caribbean is right at my fingertips. I started looking.
Cruises were running $400–$500, but they didn’t feel worth it. I wanted something beautiful, simple, and cheap. Enter: the Cayman Islands.
How I Booked My Trip for Under $300
I was finishing up a late shift when I started searching. My secret weapon: Google Explore. I entered my home airport, the dates I needed, and scanned the map for the cheapest options.
Once I find a destination on Google Explore, I always check which airlines are flying and compare the best deals. Because I’m an American Airlines Gold member, I get perks like seat selection and free checked bags, so I often prefer to fly AA over cheaper carriers that tack on extra fees. For Cayman, AA had the best nonstop flight out of Miami for $336. But I wasn’t done yet. Could I make it cheaper?
Here’s the move: I compared points vs. cash. If the value of points is stronger than the cash ticket, I use miles. For Cayman, it was a win.
- Flight #1 (cash): $135
- Flight #2 (points): 13,000 American Airlines miles + $108 in taxes and fees
- Total Flight Cost: $243
Next up: the hotel. I love my Chase Sapphire Reserve card and all of the perks such as the Chase Sapphire Lounges (even though the rates are going up). It lets me use points to book luxury hotels, and this time it didn’t disappoint.
As soon as I logged in, I saw Hotel Indigo Grand Cayman listed for a discount: 22,000 points per night vs. $501.25 cash. Yes, I love luxury hotels, and this one looked like the restful vacation I was craving. My boyfriend also had Chase points, so it was an easy win.
- Hotel: 25,000 Chase Sapphire Reserve points
All in? Under $300 for flight + hotel.
That left extra money for food, cocktails, and little splurges once we arrived.
Hotel Indigo Blue: Boujee on a Budget
Upon arrival, the $40 cab ride reminded us quickly that Cayman is not cheap. The US dollar converts at a weaker rate, so everything costs more. But stepping into Hotel Indigo Blue took my breath away.
We were greeted with cool towels and glasses of sorrel and ginger cooler. As a Chase Sapphire Reserve member, I scored:
- Daily breakfast for two
- $100 resort credit
- A free upgrade to a junior ocean suite (#winning!)
Our room had a balcony, boho-chic vibes, a kitchen, and a bathroom so stylish I wanted to replicate it at home. We were welcomed with fruit, beers, and a handwritten note. Outside, a short walk (or a golf cart ride) took us to the beach club, where staff set up towels, brought ice water, and left us free to just… float.
Yes, a smoothie and cocktail were $50. But with so much saved on flights and hotel, I didn’t feel guilty. That’s part of the beauty of planning travel smart which is something I learned deeply during my sabbatical and wrote more about in How to Take a Sabbatical and Not Go Broke.
That first evening, we debated heading out to a local restaurant, Heritage Kitchen, but instead decided to enjoy the pool. We indulged in wings, salads, and cocktails, which were covered by our $100 resort credit. By the time we finally made our way out later that night, most restaurants were closed, and we ended up in a very local spot with plates of jerk chicken and festivals. Honestly, it felt perfectly in line with my travel style — a little boujee, a little local, and always an adventure.
Day 2: Bikes, Beaches, and Hidden Gems
The next morning, we enjoyed fluffy pancakes and fresh juice for breakfast. Normally $85, but free thanks to my Chase Sapphire upgrade.
We planned to ride out to Cemetery Beach, which is part of Seven Mile Beach. But when dark clouds rolled in, we hit pause. So what did we do? Jumped in the pool to wait it out. Once the skies cleared, we hopped on bikes (cute baskets included) and headed toward the beach.
Cemetery Beach was quiet, stunning, and crystal clear. Hardly any tourists — just locals and endless turquoise water. We swam for hours.
When hunger hit, we tried Heritage Kitchen, a well-known local spot, but to our disappointment it was closed. Instead, we found Foster’s Grocery, which had a surprisingly good buffet: burgers, fries, a salad bar, and local dishes at a fraction of the cost.
That night, we headed to Morgan’s Seafood Restaurant. I ordered the scallop, shrimp, and lobster paella — absolutely divine. They surprised us with a complimentary vegan appetizer and ended dinner with a small glass of port wine. Bonus: I’m pretty sure I spotted Jason Tatum there with his family (but I behaved — no photos).
Prior to calling it a night, we ventured up to the hotel’s rooftop lounge, Pom Pom, where the décor was a whole vibe. The space offered both indoor and outdoor seating, with a DJ spinning mellow tracks and layering in congo drum beats that amplified the energy. If I had realized how nice it was, I would have gone there the first night for sure.
Day 3: Poolside Until Takeoff
On our last morning, we squeezed in one last breakfast and headed for the beach. With a 2 p.m. flight, I wanted to soak up every second.
Of course, flights got delayed multiple times. But instead of stress, we turned it into bonus vacation time. Back to the pool, lounging until it was finally time to head to the airport.
Lessons Learned & Hacks for Cayman
- Get a rental car. Taxis are $40 a ride. Cars are $10 a day. Big difference.
- Budget for food. Meals add up quickly, so mix in grocery store finds with nicer restaurants.
- Stay for Sunday brunch. There are so many throughout the island. Our hotel had a buffet that was packed with people. It had about six food stations, seafood, and bottomless drinks for approximately $100.
- Use points strategically. My biggest win was combining airline miles + hotel points to slash costs.
Final Thoughts
This wasn’t a two-week European escape. It was a quick, intentional reset. Three days of sun, rest, and turquoise water.
Sometimes, that’s all you need.
Because I booked smart, I spent less than $300 on flights and hotel. That freedom let me enjoy good food, bike rides, cocktails, and pure Caribbean joy without guilt.
Cayman was worth every penny — and then some.
Take care, take breaks.