Needing to stretch my legs a little bit, my new friend Chaundra offered to drive to check out Point Udall and do a small hike. What I thought would just be a scenic view, the hike to Jack and Isaac’s Bay turned into my favorite adventure on St. Croix so far.



The trail is open year round, and is around a 3.5 mile out and back hike. A majestic part of the hike was the serene solitude we experienced. We passed a couple with a baby in a hiking carrier headed back to the trailhead, and then we never saw another hiker on our way out.
While we took a break at a covered pavilion to hide from the midday rainstorm, we saw a girl walking her two dogs. I found out dogs are welcome on the trail, as long as they’re on a leash. The dogs were loving the trek and cooled off in the ocean for a bit. On our venture back, we passed another couple with a baby before we realized it was the same family!


Total count of other hikers: 3 adults, 2 dogs, 1 baby
While there weren’t many hikers on our excursion, we were warned not to leave any valuables in the car at the trailhead. There are rumors cars are broken into. However, we had no disturbance to the car and felt incredibly safe on our voyage.


Chaundra, a Washington state native, is a hiking pro. I, from the flat state of Florida, am not. While I wore sneakers for the hike, she was able to do it comfortably in hiking sandals. The trail is described as moderate and I felt that was an appropriate description of the path. Compared to the hike to the Annaly Tide Pools, which was also described as moderate, this is on the easier end.

Things to Remember as you hike to Jack and Isaac’s Bay
Watch out for the turtle nesting areas, and be sure to leave nothing on the beaches. Many people snorkel and enjoy the pristine waters. While Isaac Bay doesn’t offer shade, if you hike to the end, Jack Bay has covered patio tables to enjoy a snack (pack your own) and take a break.


Just remember to bring sunscreen and plenty of water (no spots to refill) as it’s a much drier climate without much shade. It gets warm! Also try to use bathrooms before you arrive at the trailhead. I don’t remember seeing any facilities along the way.

The hills vary in elevation, but because of the diversity, you get the opportunity to hike both up and downhill. The trails are well established and leave plenty of room to move. As a novice hiker, I felt very comfortable on our journey. Also, the surrounding trails that split give you the chance to build your own adventure and travel all around the area. There’s so much to see as you walk, the aesthetic surrounding you makes the hike worth it. The ocean surrounds the hills and is one of the most picturesque spots I’ve seen in St. Croix.
Environment during hike to Jack and Isaac’s Bay

The most incredible part of the hike is how different the environment is on the east side of the island. It’s a much drier climate, with cacti bordering the hike. It gives a completely different aesthetic while moving along the trail. I sat enamored looking at all the surrounding flora & fauna. In an effort to catch my breath, I fawned over the cactus with the red top. After googling, I found out it’s referred to as a “Turk’s Cap” and they are abundant on the east end. They’re absolutely breathtaking and give so much character to the hike. I can’t say I’ve ever seen a cactus like it.

Additionally, it was my first time seeing the iguanas, peering over the bush up at Point Udall. After I noticed this one, I started seeing them all over the island. However, I haven’t seen wild iguanas since my time in the Galapagos, so it was such a sight here in St. Croix! They have a similar comfortability like in South America, as they’re not seen as prey. He remained close and at one point, I thought he was posing for the camera.
Information on your hike to Jack and Isaac’s
Find more information on Jack Bay and Isaac Bay, I found St. Croix Hiking had great information for how to get to the spot. While hiking, I used All Trails app. There’s not much service on that side of the island, so you can follow the map and route out your visit. UncommonCaribbean also had a great take on his experience on the hike.
If you’re looking for a great place to get some exercise and be surrounded by the beauty of St. Croix, make sure you add Jack and Isaac Bay Preserve Trail to your list! The beaches are serene and full of sights, so bring your snorkel gear and lunch and make a day out of it! Thank you to Chaundra for such a rewarding experience here in St. Croix!