Things to do over Labor Day weekend in Islamorada (Updated 2026)

Islamorada, USA
Private 3-Hour Islamorada Sandbar Tour
Special Offer
Special Offer

Conch City Charters One-of-a-kind Tiki boat is the most fun and comfortable way to experience Islamorada from the water. Our A+ Captain is always ready...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (60)
$500
$499

4 Hour Private Ecotour and Snorkeling Boat Tour
Likely to Sell Out
Likely to Sell Out

Our private tours are guided by knowledgable USCG licensed captains who have background in Marine biology and environmental science. We take you through some of...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (56)
$900
$899

Islamorada Sandbar Escape Sightseeing Paddleboarding and Swimming
Likely to Sell Out
Likely to Sell Out

Explore the vibrant beauty of the Florida Keys with the Islamorada Sandbar Escape. Enjoy a scenic sightseeing cruise around the island, followed by a relaxing...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (13)
$80.55
$79.55

Private Islamorada Sunset Cruise
Likely to Sell Out
Likely to Sell Out

Look no further for the greatest sunset experience the Keys can give to you! Conch City Charters Tiki-style pontoon boat provides the most comfortable seating...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (17)
$350
$349

Private 2 hour Mangrove Ecotour
Likely to Sell Out
Likely to Sell Out

Our private tours are guided by knowledgable USCG licensed captains who have background in Marine biology and environmental science. We take you through some of...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (37)
$525
$524

Half Day Private Boat Tour
Likely to Sell Out
Likely to Sell Out

Our private tours are guided by knowledgable USCG licensed captains. We take you through some of the most unique mangrove islands and channels in search...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (21)
$900
$899

Snorkel and Sandbar Combo Adventure in Islamorada
Likely to Sell Out
Likely to Sell Out

A captivating 4-hour journey awaits in the stunning waters of the Florida Keys, where snorkeling and relaxation meet. Begin your adventure at Alligator Reef, a...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (13)
$111.45
$110.45

2 Hour Sunset Eco-Cruise
Likely to Sell Out
Likely to Sell Out

Explore the last hours of daylight in nature by exploring the mangroves of Islamorada by boat with our expert guides in search for all the...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (11)
$525
$524

1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar
Special Offer
Special Offer

Our tours start with an open ocean ride where you have a 15 minutes “FREEDOM RIDE” in a big open area. From there, we start...

1 hour 30 minutes
1 hour 30 minutes
1 hour 30 minutes
4.7 (84)
$259
$258

Golden Glare Fishing Charter with Experienced Captain
Likely to Sell Out
Likely to Sell Out

Intently focused on the spring Tarpon migration in the upper Florida Keys and Everglades National Park. We still enjoy all the other outstanding fishing opportunities...

8 hoursFree Cancellation
8 hoursFree Cancellation
8 hours • Free Cancellation
5.0 (6)
$650
$649

38' Private Boat Charter Rental - Islamorada W/Capt up to 13ppl
Likely to Sell Out
Likely to Sell Out

Our captains, boats, and fact we customize every trip to every clients dream day is what sets us apart and why we dominate other charter...

2 to 8 hoursFree Cancellation
2 to 8 hoursFree Cancellation
2 to 8 hours • Free Cancellation
5.0 (3)
$899
$898

Half Day Private Charter
Special Offer
Special Offer

Our all inclusive package comes with a Unites States Coast Guard licensed captain with many years of experience, these captains have been hand picked by...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (20)
$650
$649

2 Hour Private Sandbar Day Charter In Islamorada
Special Offer
Special Offer

This charter is 2hour long in Islamorada Florida. Our authentic catamaran-style tiki boats are the perfect combination of fun and relaxation. Enjoy a cool beverage...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (2)
$450
$449

2 Hour Private Sandbar and Sunset Charter Islamorada Florida
Special Offer
Special Offer

Come aboard and take in the famous Florida Keys sunset! Our authentic catamaran-style tiki boats are the perfect combination of fun and relaxation. Come aboard...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (7)
$499
$498

Private 3 hour Charter and Sandbar in Islamorada
Special Offer
Special Offer

Cruise to the Famous Islamorada Sandbar Come aboard for a fantastic cruise to the world-famous Islamorada Sandbar — the ultimate island escape! We depart from...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (2)
$599
$598

Private 4 Hours Islamorada Sandbar Charter
Special Offer
Special Offer

Cruise to the Famous Islamorada Sandbar Come aboard for a fantastic cruise to the world-famous Islamorada Sandbar — the ultimate island escape! We depart from...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
4.0 (4)
$749
$748

Islamorada Whale Harbor Snorkeling Activity
Special Offer
Special Offer

We are the original Snorkel and Sandbar Combo trip in the Florida Keys In business since 2010 and serving Islamorada since 2016...

3 hours 30 minutesFree Cancellation
3 hours 30 minutesFree Cancellation
3 hours 30 minutes • Free Cancellation
5.0 (2)
$151
$150

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