1. Island Tales Charters

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Key West, FL

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Island Tales Charters

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

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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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1 year ago

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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

Linda D Sportfishing - Seven foot nurse shark caught and released

Linda D Sportfishing

(66 reviews)

We had an excellent time fishing with captain Billy and first mate Jesse! I already was happy when…read moreBilly contacted me before we left regarding a cold front coming in and it would be advantageous to change our first scheduled day since conditions would be favorable. I'm so glad we did! The boat was equipped with everything we needed - had a bathroom, mini fridge for your lunch, they provided a cooler with plenty of water for the day which was very nice. We had fun catching a variety of fish, including mahi mahi, Bonita, one little tuna and the biggie: a white marlin, which was an unexpected surprise for us all and the highlight of our outing. Jesse worked tirelessly the entire time and it was an overall fantastic day. Once we returned back to the dock, he filleted our mahi for us and we took it over to Kaya Island eats per his recommendation which was the perfect end to a fun, tiring but successful day on the water. If you want a great day with nice, knowledgeable folks who will work hard to make your day memorable, I highly recommend booking with Linda D. UPDATE: Went out again on Wednesday and had an equally fantastic time w/captain Billy & Jesse. We caught several mackerel, king fish (including one very large one) and a few barracuda - the weather was beautiful and it was fun to catch such a different variety of fish over our couple of outings - our dinner was again delicious :) We will for sure be back!

My daughter and I boarded the Linda D V on time with Capt. Wicker and mate Jessie for am trip at…read moreKey West. Caught more than enough fish, various species with the expert trolling and multiple lines, excellent gear. Jessie was everywhere keeping fresh bait on lines, giving assistance where needed and Capt Wicker maneuvered to find and catch fish. Fish were filleted and iced once we returned. Both Captain and mate were very friendly, helpful, and competent. Boat was very. comfortable. Highly recommend this boat and crew.

Gulfstream Fishing

Gulfstream Fishing

(86 reviews)

Our group of 5 had an amazing day on the water fishing and sightseeing. The captain and crew were…read morehelpful with instruction, oversight, guidance, and assistance. We were on the water for about 1/2 day and plenty long enough to get some sun and catch enough to have a mess of fish for dinner later. We fished and moved to at least 4 spots. Be sure to bring plenty of sunscreen. We also packed a small cooler with drinks and snacks. Don't forget the hand sanitizer -- you'll be glad you did after handling bait and (hopefully) any fish you catch! When we returned to the dock, the crew prepped and filleted our catch for a nominal fee. Tips are appreciated and should definitely be considered a standard practice by patrons and not just a courtesy. Well earned after the hard work of a day on the water. The boat charter can accommodate about 40 passengers; however, on the day we went, we were at about 2/3 capacity. Customers were a wide skill range from rookies to regulars. We took our fresh prepped fish home and sautéd it later for an impromptu house party for 7 diners. Great experience to be able to eat something we'd caught earlier that day!

Staff was helpful, knowledgeable, and friendly. Boat was clean and spacing/position on boat was…read morefair... meaning we asked "if" a position on the stern is available we would like to be considered. Captain was more than accommodating and we truly enjoyed ourselves. We ended up giving our fish to some other folks who hadn't been as lucky. We highly recommended Gulfstream Fishing

Island Tales Charters - boatcharters - Updated October 2026

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