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!

Who is ready for their next adventure of a lifetime???
08/11/2026

Who is ready for their next adventure of a lifetime???

Lots of Blues around this year!! Who likes smoked fish dip?
08/09/2026

Lots of Blues around this year!!
Who likes smoked fish dip?

Have you ever wanted to go on a sailing adventure?
08/07/2026

Have you ever wanted to go on a sailing adventure?

A few from the morning trip last week. Nothing beats spring harvests from mother ocean.
05/18/2026

A few from the morning trip last week. Nothing beats spring harvests from mother ocean.

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

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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