Happy’s Watersports for Hyatt at Regatta Bay Guests in Destin, FL

Whether you’re planning a laid-back family outing, a romantic sunset on the water, or a fun group adventure, Happy’s Watersports offers some of the best on-the-water experiences in Destin. Our team has been serving Crab Island and Destin visitors for years, helping guests create memorable vacation moments with easy booking, great service, and exciting options for every age.

Featured Experiences for Hyatt Guests

Choose from our most popular Destin adventures — ideal for couples, families, and vacation groups looking to make the most of their stay.

MOST POPULAR!

All Ages
4 Hours, 8 Hours
Up to 13 People

Pontoon Boat Rentals in Destin, FL

Experience the Best Pontoon Rental in Destin, FL. Be the captain as you take the whole family out for a day of fun on Happy’s Watersports Brand New 2025 Trifecta Pontoon Boats. We offer half day and full day rentals!

All Ages
4 Hours, 8 Hours
Up to 14 People

Double-Decker Pontoon Rental

Explore Destin, Florida’s waters with the newest and largest Double-Decker Pontoon with two Water Slides. Half-day and full-day rentals available. Upgrade your regular pontoons into this massive play boat. More space, more fun!

All Ages
1.5 Hours

Sunset/Dolphin Cruise

Join us for a gorgeous Sunset Cruise in the majestic waters of Destin, FL! What better way to spend time with your family and friends than to go on a memorable sunset cruise with Happy’s Watersports. Make sure you bring a waterproof camera!

All Ages

3-Hour Crab Island Adventure Tour in Destin, FL

Crab Island is known for it’s majestic waters and not to mention the biggest day party every day! Tourists flock from places just to have a fun day out in the sea. We now offer a 3 hour tour at Destin’s most captivating – Crab Island!

All Ages

4 Hour Crab Island Adventure Tour

Your favorite tour, now made even longer and better! We now offer a 4 hour longer tour at Destin’s most captivating – Crab Island! With our extended 4 hour Crab Island Adventure Tour you’ll surely make the most of a fun day out in Destin!

18+ to Operate
1 Hour, 2 Hours, 4 Hours
Up to 3 People

Waverunner Rentals in Destin Florida

Have a fun day with your friends and family on Happy’s Watersports’ Yamaha Waverunners! Enjoy a slow sightseeing cruise along the Emerald Coast and mosey into the Choctawhatchee Bay to Crab Island or go on a high-intensity thrill-seeking ride that will definitely make you want more!

All Ages

4 Hour Crab Island Adventure Tour (Duplicate)

Your favorite tour, now made even longer and better! We now offer a 4 hour longer tour at Destin’s most captivating – Crab Island! With our extended 4 hour Crab Island Adventure Tour you’ll surely make the most of a fun day out in Destin!

All Ages
1.5 Hours

Dolphin Cruise in Destin, FL

Join us for a gorgeous Dolphin cruise!

18+ to Operate
2 Hours

Dolphin Excursion on Waverunners

Enjoy a a beautiful guided dolphin excursion on one of our waverunners!

Karaoke on the Water

Get ready to rock the boat with Happy Life Cruises’ Karaoke on the Water, the most entertaining Destin cruise experience for music lovers and partygoers alike! Hosted by Hysteria’s Entertainment, this lively karaoke cruise Destin FL brings together music, laughter, and breathtaking sunset views for a night you’ll never forget. Sing your favorite songs, enjoy a full-service bar, and snack on delicious finger foods as you perform under the stars on our open-air Sky Deck. Whether you’re a karaoke star or just love cheering friends on, this Destin nightlife cruise promises good vibes, great music, and endless fun for everyone on board.

Destin Dunset Dolphin Cruise

Join Happy Life Cruises every Saturday from 6–8 PM for an unforgettable Destin sunset dolphin cruise experience. Set out on the beautiful emerald waters of the Gulf Coast and enjoy breathtaking sunset views while spotting dolphins in their natural habitat.

Standup Comedy Destin

Set sail for a hilarious 2-hour comedy cruise featuring stand-up comedians Dan Hall and Eugene Bassham . Enjoy an unforgettable night on the water in beautiful Destin Harbor while taking in a live comedy performance that will keep the laughs rolling all evening.

Live Music in Destin

Wind down your weekend with a laid-back Sunday evening cruise aboard the Happy Life Paddle Boat, featuring live acoustic music from the Shack N Up Duo (drum & guitar) and beautiful sunset views over Destin Harbor.

Murder Mystery Cruise Destin

Step aboard Happy Life Cruises for a night of food, fun, and mystery on our Destin Dinner Cruise! Dinner To Die For combines a three-course meal, hilarious improv, and an interactive whodunit that keeps you guessing until dessert.

Mother's Day Dinner Cruise

Celebrate Mother’s Day evening in elegant style aboard a scenic dinner cruise in Destin, where a refined dining experience meets breathtaking sunset views over the harbor. Perfect for couples, families, and groups, this experience offers a relaxed yet sophisticated way to honor the occasion. Enjoy fine dining crafted by celebrity Chef Tim Creehan.

Mother's Day Brunch Cruise

Join us aboard a scenic brunch cruise in Destin, where a refined daytime dining experience meets breathtaking harbor views.

Destin Sunset Cruise Concert

Introducing the very first event in the Behind the Waves VIP Unplugged Concert Series aboard Happy Life Cruises.