Sailing, Catamaran & Gulet Tours in Florida

21 boats available

The best out of 21 deals in Florida - enter dates to check availability

Top Sailing, Catamaran & Gulet Tours in Florida Destinations

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Top Sailing, Catamaran & Gulet Tours in Florida

Florida: 21 boats available

The Pink Dolphin Private Tiki to Crab Island
The Pink Dolphin Private Tiki to Crab Island
The Pink Dolphin Private Tiki to Crab Island

The Pink Dolphin Private Tiki to Crab Island

5.0
/5
(15 reviews)

Destin • 26 ft • 18 persons

4 Hr – Crab Island - Sun-Th (AM)
4 hour trip • starts at 09:00 AM
The Pink Dolphin is one of the coolest boats on the Destin Harbor.

"We had the absolute BEST time on our morning 4-hour tiki cruise with Destin Private Tiki!" —⁠ BoatBooker Member,
4 Hr – Crab Island - Sun-Th (AM)
Instant confirmation
2 adults • 0 children
US $350
Party Boat Rentals
Party Boat Rentals
Party Boat Rentals

Party Boat Rentals

Fort Myers • 50 ft • 18 persons

2 Hour – Dolphins & Sandbars
2 hour trip • starts at 08:00 AM
Step aboard Party Boat Rentals, a luxurious 2020 Africat 500 Motor Yacht based in Fort Myers, and enjoy the ultimate day on the water.
2 Hour – Dolphins & Sandbars
Instant confirmation
2 adults • 0 children
US $1,800
Charter this 42ft Exclusive Private Boat
Charter this 42ft Exclusive Private Boat
Charter this 42ft Exclusive Private Boat

Charter this 42ft Exclusive Private Boat

5.0
/5
(2 reviews)

Bradenton Beach • 42 ft • 13 persons

⚓️ 2 Hour – Island Hop, Explore ⚓️
2 hour trip • starts at 11:00 AM
We’re flexible with start times. Once you book, just let us know what time works best to kick off your cruise.

"Visiting from Kentucky celebrating our 32nd Anniversary. Captain Carlo was great!" —⁠ Joe,
⚓️ 2 Hour – Island Hop, Explore ⚓️
Instant confirmation
2 adults • 0 children
US $999
Always Somethin' Shallow water tours
Always Somethin' Shallow water tours
Always Somethin' Shallow water tours

Always Somethin' Shallow water tours

4.9
/5
(588 external reviews)

Key West • 23 ft • 6 persons

Always Somethin' Shallow water tours is a 2025 Panga Marine Panga Panga based out of Key West.
Instant confirmation
trips fromUS $199
Smooth Sailing Of Miami
Smooth Sailing Of Miami
Smooth Sailing Of Miami

Smooth Sailing Of Miami

5.0
/5
(2 reviews)

Miami • 42 ft • 6 persons

4 Hour – Sailing Charter
4 hour trip • starts at 10:00 AM
Step aboard Smooth Sailing of Miami, a luxurious 2018 Lagoon 42 Catamaran ready to make your Miami adventure unforgettable.

"We took our whole family on a half day trip and it was wonderful." —⁠ Jim,
4 Hour – Sailing Charter
Instant confirmation
2 adults • 0 children
US $1,200
Seas The Day Destiny
Seas The Day Destiny
Seas The Day Destiny

Seas The Day Destiny

5.0
/5
(2 reviews)

Shalimar • 21 ft • 6 persons

Experience the ultimate adventure aboard Seas The Day Destiny!

"We had the most wonderful day with Captain Shelly!  She took us to Crab Island where we saw many dolphins and then anchored us right in the most perfect spot." —⁠ Jennifer,
Instant confirmation
trips fromUS $425
Blue H2O Cruisers – Sonya
Blue H2O Cruisers – Sonya
Blue H2O Cruisers – Sonya

Blue H2O Cruisers – Sonya

4.3
/5
(1 review)

Fort Lauderdale • 60 ft • 12 persons

Blue H2O Cruisers operates a 2015 Fountaine Pajot Sonya Catamaran based out of Fort Lauderdale.

"The trip was good, the crew was great and the boat was beautiful!" —⁠ Colby,
Instant confirmation
trips fromUS $1,800
The Pink Pelican Tiki
The Pink Pelican Tiki
The Pink Pelican Tiki

The Pink Pelican Tiki

5.0
/5
(2 reviews)

St. Pete Beach • 26 ft • 18 persons

Welcome aboard The Pink Pelican Tiki, a thrilling and vibrant tiki boat experience nestled in the heart of St.

"Captain Chris and Lisa were fantastic! They took our crew of 15 (ages 6-73) on a perfect four hour tour of the St." —⁠ Brad,
Instant confirmation
trips fromUS $350
The Pink Flamingo Tiki Boat – Ft. Mcree
The Pink Flamingo Tiki Boat – Ft. Mcree
The Pink Flamingo Tiki Boat – Ft. Mcree

The Pink Flamingo Tiki Boat – Ft. Mcree

5.0
/5
(1 review)

Pensacola • 26 ft • 18 persons

3 Hour – Morning (Sun - Thur)
3 hour trip • starts at 09:00 AM
The Pink Flamingo Tiki Boat – Ft. McRee is a 2024 Beachcat Custom Tiki Catamaran based in Pensacola, perfect for groups of up to 18 guests.

"We had a great time and would recommend this to anyone!" —⁠ Jessica,
3 Hour – Morning (Sun - Thur)
Instant confirmation
2 adults • 0 children
US $299
Dolphin Landings Charter Boats – Phoenix
Dolphin Landings Charter Boats – Phoenix
Dolphin Landings Charter Boats – Phoenix

Dolphin Landings Charter Boats – Phoenix

5.0
/5
(2 reviews)

St. Pete Beach • 41 ft • 12 persons

2 Hour – Private Sailing C (copy)
2 hour trip • starts at 12:00 PM
Step aboard Sailing Yacht Phoenix, a classic 41ft Gulfstar Ketch built in 1975 and beautifully maintained for unforgettable adventures out of St.

"So much fun! Highly recommend for a relaxing cruise and sight seeing." —⁠ Laura,
2 Hour – Private Sailing C (copy)
Instant confirmation
2 adults • 0 children
US $908
Treasure Coast Sailing Adventures
Treasure Coast Sailing Adventures
Treasure Coast Sailing Adventures

Treasure Coast Sailing Adventures

Stuart • 42 ft • 12 persons

2 Hour – Afternoon Adventure Sail
2 hour trip • starts at 01:00 PM
Set sail with Treasure Coast Sailing Adventures aboard a beautifully restored 1976 Jarvis Newman Friendship Sloop, fully refurbished in 2023.
2 Hour – Afternoon Adventure Sail
Instant confirmation
2 adults • 0 children
US $650
Adrift Adventures
Adrift Adventures
Adrift Adventures

Adrift Adventures

4.9
/5
(5 reviews)

Shalimar • 26 ft • 6 persons

3 Hr – Snorkel,Dolphins,Crab Island
3 hour trip • starts at 09:00 AM
Step aboard Adrift Adventures, a spacious 2008 Glacier Bay 2640 SX Catamaran, and get ready for an unforgettable experience on the waters of the Emerald Coast!

"Our boat ride with Adrift Adventures and Corey was fantastic!" —⁠ Raina,
3 Hr – Snorkel,Dolphins,Crab Island
2 adults • 0 children
US $375
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Sailing, Catamaran & Gulet Tours in Florida

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