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.
“Excellent cruise! Don’t hesitate, book this one! Plenty of different wines with hors d’oeuvres. We had a great time! Beautiful scenery. Crew was awesome!”
Adults-only Key West sunset champagne cruise on a 14-passenger catamaran: unlimited wine, gourmet cheese, and Moët upgrades.
“This is one of the best experiences of any of our recent trips. JP and Sara made us feel like first class guests! They offered to take our pictures, kept our drinks full, and were engaging and fun. JP frequently changed the ship direction to help us capture the light perfectly. This is a memory…”
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.
“Great boat, very nice Captain, seen Dolphins, sunset, snorkling - all as promised. Worth every dollar !”
Private 2-hour Key West sunset sail on a 65-ft schooner with global wines, craft beer, snacks, and a calm private-group vibe.
“This was our third sunset, wine tasting, cruise with Danger in the last two years. Comfortable boat, fun and accommodating staff, good wine, tasty food, beautiful sunset.”
Private Key West sunset cruise on a thatched tiki bar boat. BYOB with blender and Bluetooth sound, photo stops, harbor views, 2 hours.
“It was a Beautiful day to take a TIKI Sunset cruise. My husband and I truly enjoyed it. We were able to see the entire island.”
Private Key West half-day fishing with live bait for tarpon, sharks, snappers, jacks, and more. Up to 4, 4 hours from Stock Island.
“Captain Jaggar was amazing. We had an epic day fishing and really enjoyed his laid back style. Thanks for great fishing and and incredible day.”
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!! We saw so many parts to the island and surrounding area, he was funny, professional and overall just a great night!! We will certainly book with him again when we visit! This is a must book!!”
Private fishing charter from Ramrod Key: 4-hour Florida Keys backcountry flats with Captain Jim. Gear, bait, and shallow-water action.
“The fishing was great. My son and I caught about 12 fish each. Jim was on time, got us on the fish, his boat is nice and he is very personable. I highly recommend this to anyone looking to go fishing in the Keys.”
Private Key West sandbar cruise with Captain Donnie: mangrove backcountry, Snipe Keys swimming, snorkel gear, and time to relax.
“Very relaxing trip. Beautiful sandbar and a great captain!!! The boat ride was nice getting to the sandbar. Captain Don informed us of all the great places on the way out to the sandbar. This is the perfect way to enjoy a different side of Key West.”
