KEY WEST
Ranked by traveller popularity
The 10 most popular private & small-group tours in Key West. Here's what they actually deliver, who runs them, and what they cost.
Small-group Key West sunset sail with a wine tasting, unlimited beer, and hors d’oeuvres, plus crew stories and a smoother pace for two hours.
“What an amazing experience! The wine was plentiful, the snacks were delicious, and the view of the water and sunset were unbeatable. Mary, James, and Connor were professional and friendly. All around absolutely worth doing this!”
Adults-only Key West sunset champagne cruise on a 14-passenger catamaran: unlimited wine, gourmet cheese, and Moët upgrades.
“This was such a wonderful experience. Having a small group made it even more special. The sunset was beautiful. The captain and crew were knowledgeable and hospitable. If you’re wondering if you should book this trip- you definitely should!”
Walk Key West’s southern edge with a small group: shipwreck stories, Mel Fisher, Audubon House, a moved lighthouse, Hemingway tales, and a buoy photo.
“This was a great tour. Our guide was very knowledgeable and personable and we had a wonderful morning exploring Key West. I highly recommend this tour.”
Small-group Key West dolphin spotting and snorkeling on a 25-foot boat. Max six, gear included, sandbar time, great for all abilities.
“Because of our change in travel schedule, we were unable to make the experience work. However, this company was extremely accommodating and trying to get us out on the tour with the best weather at the best time. They were extremely nice on the phone and much more accommodating than other companies we have worked…”
Private 2-hour Key West sunset sail on a 65-ft schooner with global wines, craft beer, snacks, and a calm private-group vibe.
“The crew was friendly and there was a good variety of wine. The atmosphere was reserved without the obnoxious crowds. One thing to improve upon was the food. There was not many choices and one can only have so many cheeses. Read more”
Private Key West sunset cruise on a thatched tiki bar boat. BYOB with blender and Bluetooth sound, photo stops, harbor views, 2 hours.
“Very great family experience. We had a chance to experience a very nice sunset on a tiki bar. Many thanks to you, we live it ❤️ and recommend the tour.”
Private Key West half-day fishing with live bait for tarpon, sharks, snappers, jacks, and more. Up to 4, 4 hours from Stock Island.
“My husband, 13 and 10 year old sons had a fabulous time out with Justin! They caught a huge variety of fish and came home with enough fish for dinner. They would highly recommend this charter to others!”
A private Key West sunset cruise for up to 6, timed by a local captain. See Sunset Key, Mallory Square, and more in ~2 hours.
“Don was amazing! He adjusted the cruise to account for the cooler than normal temperatures, spending more time hunting wildlife in little inlets than offshore waiting for the sunset. We were able to see a manatee and many other animals while learning a lot about what brought him to the Keys. By the end of…”
Private fishing charter from Ramrod Key: 4-hour Florida Keys backcountry flats with Captain Jim. Gear, bait, and shallow-water action.
“(HUSBAND/WIFE TRIP)”
Private Key West sandbar cruise with Captain Donnie: mangrove backcountry, Snipe Keys swimming, snorkel gear, and time to relax.
“Great communication from Don as soon as we booked and a great morning on the water having to work around some weather early on. Boat is perfect for a small group and the stops he took us too were great to get a feel for the back country weaving through mangroves and stopping at 2…”
