We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Tails2Sails

Features Animals
5130 US Highway 1, Key West, FL 33040-4324
+1 305-923-9305
Website
Share
Save
Review Highlights
EPIC FISHING!

Went out on Aug 11 and we limited out on red snapper in an hour, crushed fish the rest of the day... read more

Reviewed 4 days ago
Thomas O
Very Professional, highly recommended

We took a half day charter with Captain Chuck and mate Jenna on July 24th. The boat and crew were... read more

Reviewed 2 weeks ago
kenmissy
,
Smithtown, New York
Read all 10 reviews
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
More
Tails2Sails Charters out of Key West, FL offers you the ultimate in light tackle sport fishing. The Boat is a 31Ft Yellowfin Center Console with Twin Suzuki Outboards and excellent sea comfort. All Equipment and Bait provided. Key West waters provide best fishing in the US. Regardless of your fishing skill level, adults families,regardless your age. We Catch Fish.
  • Excellent100%
  • Very good0%
  • Average0%
  • Poor0%
  • Terrible0%
4 days ago
“EPIC FISHING!”
2 weeks ago
“Very Professional, highly recommended”
Suggested Duration: More than 3 hours
LOCATION
5130 US Highway 1, Key West, FL 33040-4324
CONTACT
Website
+1 305-923-9305
Write a ReviewReviews (10)
Traveller rating
Traveller type
Time of year
Language
Filter

1 - 10 of 10 reviews

Reviewed 4 days ago

Went out on Aug 11 and we limited out on red snapper in an hour, crushed fish the rest of the day. Capt Chuck and Jenna worked hard, kept us on fish, dodged a couple of storms, and had us laughing all day too. We...More

Thank Thomas O
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 2 weeks ago

We took a half day charter with Captain Chuck and mate Jenna on July 24th. The boat and crew were very organized and they took the time to teach some not so experienced fisherman the way to catch fish. The were especially good with two...More

Thank kenmissy
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 2 weeks ago via mobile

I went out w capt. Chuch and mate Jenna. We had a great time,and a lot of laughs. We limited out in our half day trip. 2 adults and a 12 y/o on his 2nd fishing trip. If your in Key West look him up.

Thank mikelarmony
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
See more reviews
Reviewed 2 weeks ago via mobile

We did our shopping around and went with our gut feeling based on Captain Chuck knowledge on the fish and experiences he and Jenna have been through. We HIGHLY RECOMMEND Tails 2 Sales fast boat, great service and a guarantee you’re going home with a...More

Thank James D
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 3 weeks ago

My friends,family and I have charted many fishing trips and every time we are in the keys it will always be with Captain Chuck!!!!!!! When you charter a fishing trip with Capt. Chuck, you realize at the end of the trip that you actually charted...More

Thank Joey R
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 3 weeks ago

I have been fishing around the world for 25 years and always return to fish with Captain Chuck. He is a knowledgeable Captain and angler and knows how to get fish in the boat. More importantly he makes the adventure a learning experience and enjoyable...More

Thank mjaargentina
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 4 weeks ago via mobile

Do not usually post anything, but my wife & I have been fishing with Capt Chuck for 10+ years and have been out at least 25 times. Obviously he a great Capt, knows where the fish are and gets them to the boat. Truly an...More

Thank David B
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 29 June 2018 via mobile

Captain Chuck definitely delivers fish! He is an experienced captain with a great attitude and has a perfect fishing boat. We did an all day trip and filled the boat with red snapper, amberjack, yellowtail and tuna. Can’t wait till we get out there again!

1  Thank kwtwinsmom
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 29 June 2018

I’ve spent forty years fishing the Florida Keys. I’ve had the privilege of fishing with dozens of captains over the years. Some are good and some not so good. However that all changed in one trip with Chuck. Most captains only want to know your...More

3  Thank 593troy
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 28 June 2018 via mobile

My family and I recently stayed in Key West. I have been booking Tails2Sails for the last 8 years. Captain Chuck is a true Captain and not just a guide. This guy put us on multiple species on the last trip. Mutton Snappers, Yellowtail Snappers...More

2  Thank Osgeese
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Nearby
Nearby HotelsSee all 51 hotels in Key West
Hyatt Residence Club Key West, Beach House
639 reviews
.21 miles away
Key West Marriott Beachside Hotel
3,010 reviews
.30 miles away
Fairfield Inn & Suites by Marriott Key West at The Keys Collection
667 reviews
.32 miles away
Hilton Garden Inn Key West - The Keys Collection
848 reviews
.34 miles away
Nearby Restaurants
El Siboney Restaurant Stock Island
11 reviews
.58 miles away
Tavern N Town
1,793 reviews
.31 miles away
Matt's Stock Island Kitchen & Bar
173 reviews
.67 miles away
Roostica Wood-Fire Pizzeria
783 reviews
.66 miles away
Nearby Attractions
Mermaid Therapy Charters
10 reviews
.07 miles away
Key West Tropical Forest and Botanical Garden
257 reviews
.27 miles away
Key West Pro Guides
1,450 reviews
.03 miles away
Laid Back Key West
109 reviews
.04 miles away
Questions & Answers
Get quick answers from Tails2Sails staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines
Submit