KEY WEST
Ranked by traveller popularity
The 10 most popular private in Key West. Here's what they actually deliver, who runs them, and what they cost.
Go private to Looe Key for a calmer snorkel with a captain, gear included, and big Florida Reef fish in about 3 hours.
“Loved spending time with Captain Brian and learning so much from him! He was patient with our girls wanting to dive out of the boat! Thank you :)”
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.
“Justin was an awesome guide. We caught a tarpon and nurse shark! Would 100% recommend him. Hope to be back and do it again.”
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 Key West sunset sail from the Historic Seaport. A 2-hour cruise with refreshments and BYOB cooler storage on your charter.
“It was Fantastic!!!! Our crew was just excellent and we did have an enjoyable, happy and relaxing evening. Erick and Harley are the best!!”
Nearly private Key West jet ski tour with free pickup, a sandbar swim stop, and guided views of the Southernmost Point and submarine pens.
“Family had so much fun, everybody enjoyed sailing , kayaking, snorkeling. Boat captain Luke with his crew: Sav and Frankie made the tour fun, safe and informative. First time in a sailboat, saw a lot of species of birds and fish, able to see a sea turtle while kayaking. Enjoyed the string rays, sharks and…”
Private fishing charter from Ramrod Key: 4-hour Florida Keys backcountry flats with Captain Jim. Gear, bait, and shallow-water action.
“We had a great day on the water. Capt. Jim did a great job finding the fish. He was attentive to our needs. I highly recommend Mile Marker 27 Fishing Charters. Thanks Capt. Jim!”
Private Key West sandbar cruise with Captain Donnie: mangrove backcountry, Snipe Keys swimming, snorkel gear, and time to relax.
“Captain Don was outstanding. He was extremely knowledgeable of the area and was willing to answer any question. I would recommend him as your guide. We look forward to utilizing his services again”
Private Key West sandbar and paddle trip by pontoon through calm mangrove creeks, with sandbar time, rafts, and a dog-friendly captain.
“Had a wonderful time! Lindsey our guide did a great job! Would definitely do it again! Thanks for a great trip!”
