Top 10 luxury & private things to do in Islamorada

1. Half Day Private Tour to Islamorada Alligator Reef and Sandbar

One of Islamorada’s best treasures, the sandbar and Alligator Reef Light House accessible by water Transportation is by boats you will see lounge chairs, barbecue grills, picnic table, umbrellas, all submersed in the water. The sandbar is a great spot for all ages, and even welcomes our four legged friends.

2. Four-hour private snorkel charter to Islamorada Sandbar

Four hours from Angler House Marina — a leisurely trip to Islamorada Sandbar with opportunities to spot dolphins and manatees en route.

3. Half-day private boat tour in Islamorada

Three hours guided by a USCG licensed captain — explore mangrove islands while searching for dolphins, manatees, and nesting birds.

“We’ve been on a boat tour with Keyz Charters annually since 2020 and have always had great experiences. This year, we enjoyed a 3-hour snorkeling tour in stunning Islamorada. Our captain, Henry, was fantastic—his knowledge about the Keys and the engaging stories he shared made the experience even better. We had such a wonderful time with him last year that we specifically requested him again.”— markkX4292BV

4. Half-day private boat charter in Islamorada

Half-day charter to a scenic lighthouse with a licensed captain — crystal-clear waters, floating devices, and a cooler with ice and water provided.

“Ryan was a fantastic captain, and we thoroughly enjoyed our time. We encountered a sea turtle, had a blast at the sandbags, and even had dolphins swimming alongside our boat, playing in the wake. It truly was a wonderful afternoon.”— L6210CCjilll

5. Private sunset cruise in Islamorada

Two hours on a Tiki-style pontoon boat — cruise through Islamorada, watch for dolphins, and enjoy music under the stars after sunset.

“The Captain was remarkably thoughtful, playing excellent country music on the boat and taking us to witness a breathtaking sunset.”— Lei_W

6. Private sunset cruise in Islamorada by tiki boat

Two hours on a private tiki boat — enjoy the Florida Keys sunset, with beverages and marine life sightings along the way.

“It was an enjoyable experience. Despite the windy conditions, Captain Merv proved to be very skilled. We encountered dolphins and witnessed a beautiful sunset. The conversations were also delightful. Overall, it was a fantastic time.”— Theresa_S

7. Private Sandbar cruise in Islamorada — 4-hour charter

Four hours on the water — a private charter to Islamorada Sandbar, with a scenic cruise through Whale Harbor Channel and a stop for swimming and relaxation.

“The weather could have been better.”— jeromesU5795YD

8. Private 2-hour tiki boat charter in Islamorada

Two hours on a private catamaran-style tiki boat — cruise the Florida Keys, watch for dolphins, and enjoy refreshing drinks.

“We had an incredible time on a sunset cruise with Captain Vern. The ride was incredibly smooth, and the sunset over the water was stunning. We brought along wine and snacks, and enjoyed some lively conversation. Our group appreciated learning about the area's history and picking up tips on restaurants and activities. Vern truly excelled as our captain and host.”— cindykW6280OT

9. Three-hour private charter to Islamorada Sandbar

Three hours cruising from Angler House Marina to Islamorada Sandbar, ideal for swimming and soaking up the sun.

“Merv was fantastic. He served as an excellent guide, making for a truly wonderful experience. We really enjoyed the area, and he provided us with an outstanding tour.”— Robert_C

10. Private ecotour and snorkeling boat trip in Islamorada

Four hours, private boat, knowledgeable captain — explore mangroves for wildlife like dolphins and manatees, plus snorkeling opportunities.

“This was a fantastic experience. Our guide was both friendly and well-informed. She even managed to keep the rain at bay.”— patrickfP9720XW