Living the Dream Charters and Watersports

Living the Dream Charters and Watersports Helping make your dreams come true in the lower keys since 2012 Let us help you Live YOUR Dream for the day!! Let's go FISHING!!!!! Weeks? A month?

Whether its a relaxing visit to a remote beach for some sunning and lunch or an offshore fishing excursion we can make your dreams come true. We offer full and half day excursions to some of the most beautiful places in the keys. Overnight camping trips with kayaks, sand bar BBQ's, birdwatching, porpoise watching, booze cruise, lobstering are just a few of the things we have done. Yellowtailing is

great here all year round and passes the time as you hope to pull a grouper or mutton snapper up from the reef. Yellow tail snapper are a clean delicious fish served in the majority of seafood restaurants in the keys. Offshore we target Mahi-Mahi and blackfin tuna. They are both excellent fighters and at times elusive, but well worth the adventure! Our boats are kept clean and safe for you and your family. We provide continual preventative maintenance on all of our boats to ensure you have an enjoyable day on the water. Great Rates- Located 30 minutes north of Key West and south of Marathon, Living the Dream Watersports offers lower rates and better boating. Summerland Key is in the heart of the nature keys. We proudly serve Sugarloaf, Cudjoe, Summerland, Ramrod, the Torch Keys and Big Pine Key. Multi-day Discounts- Planning to be in the area for a few days? We’ll take care of you with discounts on multiple trips during your extended stay. Enjoy the Nature Keys!

Cuban chugs. It’s amazing how desperate people are to get away from Cuba to come here. Little do they know 
03/15/2026

Cuban chugs. It’s amazing how desperate people are to get away from Cuba to come here. Little do they know 

This new chapter is already shaping up to be even more amazing than the last.
03/15/2026

This new chapter is already shaping up to be even more amazing than the last.

Late photo dumps
01/14/2026

Late photo dumps

12/11/2025

DOLPHIN FOR LIVING THE DREAM!
Lance from Baltimore, Maryland caught this dolphin in 600' with Captain Chet from Living the Dream Charters out of Cudjoe Key.

Something about a fall sunrise
11/06/2025

Something about a fall sunrise

https://www.facebook.com/share/p/1B8wSfeFys/?mibextid=wwXIfrWho wants to have dinner with me at one of my faves!!!???
08/16/2025

https://www.facebook.com/share/p/1B8wSfeFys/?mibextid=wwXIfr

Who wants to have dinner with me at one of my faves!!!???

Happy Summer Key West! For our beloved locals starting today until October 15th, 30% off all food (brunch, appetizers, lunch, dinner), wines & sangrias. Discount valid up to Key Largo, please bring your id! Not valid during Happy Hour (3-6). Live music daily 7-10pm. Greetings from Alfredo & Gaston, and Diego Peretti in the middle 😁, a very famous actor from Argentina.

08/10/2025
08/05/2025

Walk into the No Name Pub on Big Pine Key, Florida and you’re instantly surrounded by thousands of signed dollar bills covering the walls and ceiling...locals claim there’s over $90,000 taped up inside! This quirky Florida Keys spot started in the 1930s as a general store and bait shop, but it’s the offbeat charm (and great food) that keeps people coming back. Try the shrimp pizza, smoked fish dip, or a piled-high grouper sandwich. You’ll find cold beer, low ceilings, and a tiki patio out back. And don’t be surprised if a Key deer strolls past your car while you’re parked.

08/01/2025

Coming to Key West and want to catch some fish without sacrificing an entire day? Want to have fun on the water without breaking the bank? Can’t find a split charter?

This is who WE RECOMMEND

https://www.facebook.com/share/1BuneUVPse/?mibextid=wwXIfr!

The Salty Goat is a 50ft Coast Guard Inspected Party Fishing Vessel located at the Galleon Marina in Key West Florida. She is equipped with a 400hp turbo diesel to get her on the reef quickly and make the most of your fishing trip. Make some memories!

Address

Summerland Key, FL
33042

Opening Hours

Monday 7am - 5pm
Tuesday 7am - 5pm
Wednesday 7am - 5pm
Thursday 7am - 5pm
Friday 7am - 5pm
Saturday 7am - 5pm
Sunday 7am - 5pm

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