Everybody in Islamorada stops for the sunset. Restaurants fill up on the bay side, people pull over on the bridges, and somebody always tries to photograph the green flash and misses it.
Watching it from a boat is better. You’re out where nothing blocks the horizon, the water goes orange around you, and you don’t have to fight anyone for a table. We run two trips that catch the sunset, and they’re pretty different, so here’s how to pick.
Option 1: The bayside sunset cruise
This is the calm one. The bayside and sunset cruise leaves in the late afternoon and spends about two hours on the Florida Bay side of the islands, where the water stays flat even when the ocean side is choppy.
On the way out we look for bottlenose dolphins and manatees, and cruise along the mangroves where wading birds and iguanas hang out. Then we catch the sunset on the way home. Islamorada faces west across the bay, so the sun drops right into the water in front of you.
It’s $50 for anyone 5 and up, and kids under 5 ride free. If someone in your group worries about getting seasick, this is the trip to book.
Option 2: Sunset at the reef, then the reef after dark
The night reef tour also starts with the sunset, but from the ocean side, out by Alligator Reef Lighthouse. We leave 15 to 30 minutes before sunset, watch the sun go down from the open deck, and wait for dark. Then we switch on the underwater lights.
A guest on our October 6 trip took these, and they show how fast the sky changes out there. The sun went down a little after 7, the lighthouse turned into a silhouette, and by blue hour the boat’s lights had the water glowing turquoise.
Once it’s dark, you watch the reef’s night shift come out through the glass: moray eels, octopus, lobster, squid, and sometimes nurse sharks and sea turtles. As far as we know, it’s the only night glass-bottom tour in Islamorada. Adults are $75, kids 5 to 17 are $60, and kids 4 and under ride free.
The catch is that it needs the reef. If it’s too windy to go out, the night tour doesn’t run, and we’ll contact you ahead of time.
Sunset and lighthouse photos: a guest on our October 6, 2026 night tour, shared with their permission.
Which sunset cruise should you pick?
Pick the bayside cruise if you want calm water, a cheaper ticket, dolphins and manatees, and you’ll be back around dark.
Pick the night tour if you want the lighthouse sunset and then the reef after dark, which most visitors to the Keys never see. It runs later, so think about bedtime if you have little ones.
Either way, you’re welcome to bring your own snacks and drinks, there’s a restroom on board, and the boat has a Seakeeper gyro stabilizer, so it rocks a lot less than most boats at anchor.
What time does the Islamorada sunset cruise leave?
It moves with the season, because the sunset does. In June the sun sets after 8 pm, and in early winter it’s down before 6. The booking calendar shows the exact departure for your date. Check in at World Wide Sportsman Bayside Marina 30 minutes before you leave.
Can you bring drinks on the sunset cruise?
Yes. Bring your own snacks and drinks. We also sell soda and bottled water on board.
Is the sunset cruise good for kids?
Yes. Nobody gets in the water, the deck is shaded, and kids under 5 ride free on both trips. The bayside cruise ends earlier, which makes it the easier choice for small kids.