1. Island Tales Charters

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Key West, FL

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Island Tales Charters

4.9 (18 reviews)
Closed • 9:00 am - 5:00 pm

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perfect
Mark R.

This was the second time in the last 12 months that we (3 buddies) booked Captain Andy. Always a pleasure, I will continue to charter with him when visiting Key West. Our mission this time was simple: tour the island's coast to see the shores we normally stand on, looking out at the water; do some light fishing to catch dinner for that night; and relax on a sandbank for a cookout, some swimming, and, of course, cigars & whiskey. All this while enjoying perfect weather under the Florida sun in the Gulf of America! Mission accomplished! His boat, "Kiss Aweigh" is solid, spacious, safe, and very comfortable. His skills as a retired military helicopter pilot gave us confidence that we were in good hands the entire journey. Andy is very personable, which makes the whole day so much more enjoyable. His people and customer skills are excellent (not always the case when hiring a captain), which is key to everyone relaxing together while spending good money for a day on the water. Looking forward to bringing my wife and family in the future!

As a young family its difficult to make sure all 5 people find something they enjoy in each outing. Well Captain Andy @ Island Tales Charters did checked every box. Sandbars, great fishing, a shipwreck in the mangroves, and a private beach!!! What else could you ask for?!?! Andy is knowledgeable, professional, and an all around really nice guy! We were very lucky to have found him and will certainly be back! Thanks again Andy!

Key West water
Missy M.

Today was a Wonderful Water Wednesday! We took a trip on the waters of the Keys with Captain Andy & Mate Lily for the day! Started off with fishing, MY FAVORITE! We caught Yellowtail Tuna, Red Snapper & Grunt! They really do grunt too, it's quite hilarious! Then to a small island with; you guessed it "the swing". Loved this! Very cool! We saw a nurse shark, sting ray & lots of different fish. This stop included Capt. Andy's special tacos! AMAZING!!! So so good! He is famous not only for his special fishing holes but his Tacos! Last stop was one more sandbar, to hunt for the 300 lb grouper. No luck but had a little time with some puppies and clear water! Wonderful Day! If you make it to the Keys and love unique tours, take this one! You will love it and Lily! Island Tales Charters

Patricia V.

The best experience ever! My son planned this as a birthday trip present to me, lucky me was captain Andrew's birthday as well!! Enjoyed the trip with his wife Cathy, his two beautiful doggy pets was a plus Sophie and Lily, also the delicious fajita tacos cooked right at the sand bar by Captain Andrew, I just can't describe the memories I made on this trip, other charters just dont do it because of the business, but this particular one made it memorable, I 100% recommend this

Alison L.

Thanks for an amazing adventure! We had the best time (repeat customers) and captain Andy went above and beyond to give us great memories. Highly recommend for your next key west adventure.

Erica D.

Island Tales - Captain Andy Baldwin BOOK THIS TRIP WITH CAPTAIN ANDY: We had such a great day with Captain Andy. He took us out on a beautiful day to explore the Keys. Our first stop was dropping lines out to do a little fishing with the kids. It got hot quick so after fishing we took a trip to a sandbar with a swing to cool off. Our next stop was to power out to another island/sandbar where he cooked us amazing tacos and let us relax. Next Andy surprised the kids by taking us to a rope swing to entertain the husband and the kids and then he drove us around to show us the multimillion dollar houses on the island. It was such a fantastic day and our kids absolutely loved the adventure. We saw sharks, barracuda, a sea turtle and a ton of tropical fish. We got pictures galore and memories that will last a lifetime. I'm pretty sure this is what heaven is like.

Brandy, Uncle Andy and Dave
Brandy M.

If you are looking for a charter that will exceed your expectations then Captain Andy is your ticket! His knowledge of the Keys is amazing! He will forever be apart of our annual Key West trip. He is so down to earth and personable. He went the extra mile and even got a birthday cake for me and my Husband. For us Captain Andy tuned in to Uncle Andy as he really makes you feel like family. An added bonus was his four legged fur baby Lily joined us on the trip as well.

Hubby before taking off on the swing lol
Roxanne I.

Ok so we called him based on a referral from a friendly staff on base. Within ONE hour and on Easter Sunday we were off to a Sandbar full day excursion. Thank you so much Captain Andy and sidekick water dog Lily!!! You have no idea how much of a vacation you made for our family of 6! Truly the best , friendliest and most hospitable. You've made us consider moving to Florida hahaha!

Hanging out
Doug A.

Had a terrific time with Andy! Great tour of the back country of Key West. We even stopped on a small local sand bar where he made chicken tacos! Very knowledgeable and a great story teller!

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Andrew B.

Thanks Michael

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4 years ago

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Andrew B.

My pleasure MISSY, Lily enjoyed you folks as well.

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Andrew B.

Thank you so much

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Ask the Community - Island Tales Charters

Review Highlights - Island Tales Charters

“Captain Andy was incredible--friendly, knowledgeable, and made the entire trip fun and relaxing for our whole family.”

Mentioned in 16 reviews

Read more highlights

Lost Reef Adventures

Lost Reef Adventures

(166 reviews)

My fiancé and I booked online with Lost Reef Adventures for our first ocean dives. We were…read morecertified back in October in a fresh water quarry. The day we went, the waves were pretty choppy. I got in the water and panicked. Kelly, our guide, expertly made sure I got back to the boat. Spencer, our dive master, helped me up and reassured me the whole time. I got to spend the next couple hours hanging out with Spencer and robin (the captain), which honestly, was a great time. What I loved is how committed they were to safety, and also making me feel valid in my decision to abort the dives. My partner successfully completed two dives and had a fantastic experience with Kelly guiding him. If/when we're back in key west again for diving, we will definitely book with Lost Reef again!!

Lost Reef Adventures...the worst dive shop that I have encountered in 30 years of scuba diving…read more The negatives: The owner, Nick, was extremely unfriendly to the point of being hostile. He had a serious attitude problem and had no idea what the concept of "customer service" meant. He just stares at you, waiting for you to say something...it's really creepy. After telling us to show up at 7:00 for the morning dives, no one from the shop bothered to show up until 7:45. The crew was only okay. The dive master acted like this was an annoyance to be taking us out on a dive...like he just wanted to get this over and done with. He just swam around for 45 minutes until it was time to re-board. The boat pilot told us, "We're not leaving the dock until you get your gear ready." There was one guy (with a mullet and ear rings) that was pretty cool and very helpful. The equipment was fair, but had some issues. The first tank that I hooked up to only had 1200 psi, turns out that 1/4 of the tanks onboard had previously been used and not removed or refilled. The fact that they all had the rubber covers on the valve (indicating a fresh tank) made it very confusing as to which tank to use. My dive buddy's regulator was inoperable. The dives were fair at best. I guess Key West really isn't that great for sea life when compared to the USVI or Belize, buy the dive master didn't even bother to point out sea life. EVERY dive I've been on in 30 years had a dive master that took pride in his/her job and did their best to point out - things to see - during the dive. I told the travel office on the base at Sigsbee not to recommend them. There are vastly superior shops like Southpoint Divers and Captain's Corner that will give you a much more pleasant experience. I dove with Southpoint on all of my subsequent dives in Key West. The positives: The boat was great - lotsa space for everyone, safety equipment was plentiful, and the safety briefing was well done. As I mentioned before, one of the crew (lives in Roatan, Honduras and was visiting his daughter) was very helpful but unfortunately, he was the exception. The BCDs, masks, and fins were fine. There's not really anything else positive that came out of my experiences. Do yourself a favor and use one of the other dive shops in Key West.

Island Tales Charters - boatcharters - Updated October 2026

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