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All listings in Clearwater

Great sailboat rentals near Clearwater, Florida.

5.0(Average of 17 reviews in this area)
11 listings
BRAND NEW - Yamaha AR250 Jet boat in Clearwater, FL
Powerboats in Clearwater · 10 guests

BRAND NEW - Yamaha AR250 Jet boat in Clearwater, FL

5.0
$120hour
Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

5.0
$196hour
38ft Sailing Catamaran in Clearwater Beach Day Sails and Sunset Cruises, Events, Celebrations!
Sailing in Clearwater · 12 guests

38ft Sailing Catamaran in Clearwater Beach Day Sails and Sunset Cruises, Events, Celebrations!

New
$250hour
Cruising Monohull Rental in St. Petersburg, Florida
Sailing in Saint Petersburg · 6 guests

Cruising Monohull Rental in St. Petersburg, Florida

5.0
$150hour
Enjoy the the wonderful and famous Florida sunset on our Beneteau 40 Sailboat for Rent in Golfport FL
Sailing in Gulfport · 6 guests

Enjoy the the wonderful and famous Florida sunset on our Beneteau 40 Sailboat for Rent in Golfport FL

5.0
$150hour
Offshore / Inshore Fishing or Visit Sandbar in Anclote Key with 21' Bayliner Trophy
Fishing in Holiday · 8 guests

Offshore / Inshore Fishing or Visit Sandbar in Anclote Key with 21' Bayliner Trophy

5.0
$100hour
2 to 2 1/2 hr. Public Sunset Sailing Excursions from St. Pete Beach, Florida!
Sailing in Saint Pete Beach · 15 guests

2 to 2 1/2 hr. Public Sunset Sailing Excursions from St. Pete Beach, Florida!

5.0
$59person
Treasure Island, Madeira and St. Pete Beach: Sailing, dolphins, sightseeing
Sailing in Madeira Beach · 6 guests

Treasure Island, Madeira and St. Pete Beach: Sailing, dolphins, sightseeing

New
$200hour
2 hours Dolphin Watch Sailing Excursion on Boca Ciega Bay and the Greater Tampa Bay
Tours in Saint Pete Beach · 18 guests

2 hours Dolphin Watch Sailing Excursion on Boca Ciega Bay and the Greater Tampa Bay

5.0
$54person
2 Hour Private Sunset Sailing Trips in St. Pete Beach
Sailing in Gulfport · 12 guests

2 Hour Private Sunset Sailing Trips in St. Pete Beach

New
$908hour
2006 Sea Doo Sportster Bowrider near Palm Harbor, Florida
Powerboats in Dunedin · 4 guests

2006 Sea Doo Sportster Bowrider near Palm Harbor, Florida

New
$100hour

Sailing Reviews in Clearwater

  1. KM
    Kirk
    Enjoy the the wonderful and famous Florida sunset on our Beneteau 40 Sailboat for Rent in Golfport FL

    Beautiful boat. Incredible sunset and cruise. Cpt and crew were excellent. Highly recommend to anyone.

  2. Robert
    Robert
    Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

    If you're looking for a professional to take you sailing but you don't want it to feel like a tour boat, take a ride on Nick's personal boat. Bring along something cold to drink and enjoy the peace and quiet of being out on the water. My only regret is I should have made it a full day

  3. GM
    Gary
    Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

    Nick was a very experienced and knowledgeable skipper who truly welcomed us aboard. This is a beautiful sailing vessel that provides a fun, safe and comfortable ride for everyone aboard. We had a super trip with Nick and would love to book a whole day with him next time we are in town.

  4. AK
    Atta
    2 to 2 1/2 hr. Public Sunset Sailing Excursions from St. Pete Beach, Florida!

    Wonderful experience! Boats are beautiful and the captains are very knowledgeable and fun. The sunset is amazing, even though it was cloudy, we were able to get some great colors. We also had a pod of dolphins following the boats and jumping next to us. Great experience, good value, they offer water/sodas on the boat for free. Good overall experience and will def. do it again! Thank you!

  5. Santiago
    Santiago
    Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

    Sailing with Satori was an experience out of this world! Nick is an amazing captain who goes above and beyond. Clear communication, humble man and excellent sailing. Thank you and we'll be back for round 2! Cheers!

  6. Michelle
    Michelle
    Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

    Nick was a wonderful captain and was especially considerate to my friend that was worried about getting sea sick. We enjoyed a beautiful sunset sail, and we all left smiling and relaxed!