Monroe County Boat Tours
The best out of 77 boat tours in Monroe County - enter dates to check availability
33 ft
Up to 6 people
Kilo Whiskey Charters
4.9
/5
(19 reviews)
Key West (3 min drive from Monroe County)
Welcome to Kilo Whiskey Charters, the premier destination for unforgettable aquatic adventures in the pristine waters of Key West, Florida.
"Captain Anthony and Kilo Whiskey charters made a concept of a private charter to Dry Tortugas with snorkeling and fishing come true for our family of 4." — Craig,
"Captain Anthony and Kilo Whiskey charters made a concept of a private charter to Dry Tortugas with snorkeling and fishing come true for our family of 4." — Craig,
+6
trips from
US $500
24 ft
Up to 6 people
Conch Republic Charters
4.9
/5
(25 reviews)
Key West
Set sail with Conch Republic Charters, a beautifully restored 1975 T Craft 24 Center Console (2025) in Key West.
"Captain Vaughn was absolutely outstanding! From the moment we stepped aboard, he made us feel welcome, safe, and relaxed." — Dennis,
"Captain Vaughn was absolutely outstanding! From the moment we stepped aboard, he made us feel welcome, safe, and relaxed." — Dennis,
+3
trips from
US $500
23 ft
Up to 5 people
Rising Tide Fishing Charters
Key West (2 min drive from Monroe County)
Experience the ultimate Key West adventure aboard Rising Tide Fishing Charters, a fully restored 2008 Pathfinder 2200 Bay boat (2025 upgrade).
trips from
US $450
26 ft
Up to 6 people
Conch Queen Charters
4.8
/5
(7 reviews)
Stock Island (2.4 miles from Monroe County)
Step aboard Conch Queen Charters, a comfortable 26 foot Twinvee Catamaran based in beautiful Key West. Perfect for small groups of up to six guests, this versatile vessel is powered by twin 175 HP Suzuki engines, cruising smoothly at 25 knots.
"My daughter and I had a great day cruising with Captain Jordan!" — Emily,
"My daughter and I had a great day cruising with Captain Jordan!" — Emily,
+3
trips from
US $550
20 ft
Up to 6 people
Tiki Boat Adventures - Key West
4.9
/5
(14 reviews)
Key West (3 min drive from Monroe County)
Ditch the ordinary and immerse yourself in a tropical escape with Tiki Boat Adventures in Key West! These custom-built tiki boats offer the ultimate setting for a fun and relaxing day on the water.
"tiki boat trip was amazing. so happy! we were a bit disappointed that we only went like 5 min out to one very small sandbar." — Missy,
"tiki boat trip was amazing. so happy! we were a bit disappointed that we only went like 5 min out to one very small sandbar." — Missy,
+3
trips from
US $375
18 ft
Up to 3 people
Always Somethin' Shallow Water Tours
5.0
/5
(3 reviews)
•
785 external reviews
Key West (2 min drive from Monroe County)
Always Somethin' Shallow Water Tours offers an intimate and unforgettable experience on the pristine waters surrounding Key West.
"Thank you so much! We had such a great experience!" — Michelle,
"Thank you so much! We had such a great experience!" — Michelle,
+3
trips from
US $289
31 ft
Up to 6 people
Tight Lines Charters of Key West
4.9
/5
(4 reviews)
Stock Island (2.5 miles from Monroe County)
Step aboard Tight Lines Charters of Key West, a fast and versatile 2001 Contender 31 Center Console based in Stock Island, perfect for private groups of up to 6 guests looking to explore the waters around Key West.
"We went on the sandbar and sunset trip and it was worth every penny!" — Ani, Pennsylvania
"We went on the sandbar and sunset trip and it was worth every penny!" — Ani, Pennsylvania
+2
trips from
US $550
25 ft
Up to 6 people
Something Fishy Charters
5.0
/5
(9 reviews)
Key West
Join Captain Billy Romano and Something Fishy Charters for an unforgettable adventure in the beautiful waters of Key West.
"We charted the boat to celebrate a birthday. Captain asked us what we wanted to do/see and customized the trip for us." — Kristin,
"We charted the boat to celebrate a birthday. Captain asked us what we wanted to do/see and customized the trip for us." — Kristin,
+2
trips from
US $390
24 ft
Up to 6 people
Danger Charters
4.7
/5
(1 review)
Key West (13 min drive from Monroe County)
Step aboard our sleek 24’ center console for an unforgettable private boat tour through Key West’s most breathtaking waters! Designed for up to six guests, this captain-guided experience takes you to pristine sandbars, secret beaches, and vibr
+1
trips from
US $700
25 ft
Up to 6 people
Reel Easy Charters
5.0
/5
(5 reviews)
Stock Island (3 min drive from Monroe County)
Reel Easy Charters, located in Stock Island, Florida, offers a wide range of exciting and customizable boating experiences, perfect for families, groups, or anyone looking to explore the beautiful waters around Key West.
"We had a great experience for my family of five (16,14 and 10) - we saw dolphins, sharks and an amazing sunset." — Eric,
"We had a great experience for my family of five (16,14 and 10) - we saw dolphins, sharks and an amazing sunset." — Eric,
trips from
US $700