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Great sailboat rentals near Captiva, Florida.

4.9(Average of 4,807 reviews in this area)
View our Captiva sailing boating guide
1 - 24 of 240 listings
Saturn SD470 RIB Boat Rental in Cape Coral, FloridaPowerboats in Sanibel Island6 guests

Saturn SD470 RIB Boat Rental in Cape Coral, Florida

New
$60hour
64' Horizon Sport Power Mega Yacht Rental in Fort Myers Beach, FloridaEvents in Sanibel Island12 guests

64' Horizon Sport Power Mega Yacht Rental in Fort Myers Beach, Florida

New
$850hour
"Tropic Whisper" Beneteau 473Sailing in Punta Gorda6 guests

"Tropic Whisper" Beneteau 473

New
Superowner
$448hour
Luxury Sailing yacht on Charlotte Harbor for short or long sailing expeditions!Events in Punta Gorda6 guests

Luxury Sailing yacht on Charlotte Harbor for short or long sailing expeditions!

New
$249hour
34' Island Packet Sailboat in NaplesSailing in Naples4 guests

34' Island Packet Sailboat in Naples

5.0
$120hour
Alligator 20ft Airboat Tours..... This one is worth the money!  4 hours!!!Powerboats in Naples6 guests

Alligator 20ft Airboat Tours..... This one is worth the money! 4 hours!!!

New
$100person
10 Hours on the Sailing Catamaran 44ft Fountaine Pajot in Naples and Marco IslandSailing in Marco Island10 guests

10 Hours on the Sailing Catamaran 44ft Fountaine Pajot in Naples and Marco Island

New
$219hour
6 Hours on the Cruising Catamaran 44ft Fountaine Pajot in Naples and Marco IslandSailing in Marco Island10 guests

6 Hours on the Cruising Catamaran 44ft Fountaine Pajot in Naples and Marco Island

New
$249hour
4 Hours on the Foutaine Pajot 44ft Luxury Sailing Catamaran in Naples and Marco IslandSailing in Marco Island10 guests

4 Hours on the Foutaine Pajot 44ft Luxury Sailing Catamaran in Naples and Marco Island

5.0
$300hour
Sailboat Nauticat 321 Sloop for charter with captain in Apollo Beach, FLSailing in Apollo Beach6 guests

Sailboat Nauticat 321 Sloop for charter with captain in Apollo Beach, FL

5.0
$94hour
2 hours Dolphin Watch Sailing Excursion on Boca Ciega Bay and the Greater Tampa BayTours in Gulfport18 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 BeachSailing in Gulfport12 guests

2 Hour Private Sunset Sailing Trips in St. Pete Beach

New
$908hour
2 to 2 1/2 hr. Public Sunset Sailing Excursions from St. Pete Beach, Florida!Sailing in Gulfport15 guests

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

5.0
$59person
Enjoy the the wonderful and famous Florida sunset on our Beneteau 40 Sailboat for Rent in Tierra VerdeSailing in Gulfport6 guests

Enjoy the the wonderful and famous Florida sunset on our Beneteau 40 Sailboat for Rent in Tierra Verde

New
$150hour
Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' YachtSailing in Saint Petersburg6 guests

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

5.0
$181hour
Cruising Monohull Rental in St. Petersburg, FloridaSailing in Saint Petersburg6 guests

Cruising Monohull Rental in St. Petersburg, Florida

New
$150hour
Sea Ray 270 SDX Luxury Deck Boat Rental in Riverview, FloridaPowerboats in Riverview10 guests

Sea Ray 270 SDX Luxury Deck Boat Rental in Riverview, Florida

New
$160hour
Godfrey Sweetwater 22ft Party Pontoon for 12 people in Riverview!Powerboats in Riverview12 guests

Godfrey Sweetwater 22ft Party Pontoon for 12 people in Riverview!

New
$100hour
Treasure Island, Madeira and St. Pete Beach: Sailing, dolphins, sightseeing and sandbar time!Sailing in Treasure Island6 guests

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

New
$200hour
9425 US Hwy 41 S, Riverview, FL 33578Tampa3 guests

9425 US Hwy 41 S, Riverview, FL 33578

New
$60day
BRAND NEW - Yamaha AR250 Jet boat in Tampa Bay, FLPowerboats in Tampa10 guests

BRAND NEW - Yamaha AR250 Jet boat in Tampa Bay, FL

5.0
$120hour
BRAND NEW - Yamaha AR250 Jet boat in Clearwater, FLPowerboats in Clearwater10 guests

BRAND NEW - Yamaha AR250 Jet boat in Clearwater, FL

5.0
$120hour
Offshore / Inshore Fishing or Visit Sandbar in Anclote Key with 21' Bayliner TrophyFishing in Holiday8 guests

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

5.0
$100hour
Spa Austin Whaler Sailboat Rental in MiamiSailing in Everglades2 guests

Spa Austin Whaler Sailboat Rental in Miami

New
$10hour

Sailing Reviews in Captiva

  1. TT
    Tom
    34' Island Packet Sailboat in Naples

    Safe and clean boat. The captain was very knowledgeable about sailing as he has spent a better part of his life sailing in different locations around the world. He is a great communicator and is enjoyable to spend a morning or afternoon with visiting while sailing around the gulf. We had drinks, saw dolphins and had some technical discussions about sailing. The entire time our captain kept our safety and enjoyment his priority. I will repeat this experience next time we’re in Naples.

  2. NP
    Natalie
    4 Hours on the Foutaine Pajot 44ft Luxury Sailing Catamaran in Naples and Marco Island

    We had an amazing half-day out on the water with Paradise Coast Sailing, celebrating a bachelorette party! Kailani is a gorgeous catamaran. Even though it was windy, we sailed smoothly. It was a relaxing, luxurious experience. Capts. Josh and Campbell were fun and took such great care of us. They had a fridge full of snacks and beverages, made us a delicious guac and little sandwiches, and kept the boat clean as the day went on. They are knowledgable naturalists/marine biologists, so we learned so much! They also played great music, and we felt safe the whole time. Thank you!!!

  3. Leticia
    Leticia
    Sailboat Nauticat 321 Sloop for charter with captain in Apollo Beach, FL

    Captains Patti and Bob are just amazing. Friendly, polite, cheerful and communicative. I wanted to make a birthday surprise for my husband who loves sailing. Captain Patti was very solicitous. The boat impeccable, beautiful inside and out, clean. Everything's good. Nice tour and they are great guides. Congratulations!! We highly recommend.

  4. FM
    Fred
    Sailboat Nauticat 321 Sloop for charter with captain in Apollo Beach, FL

    What an amazing day with Captian Patti and Bob! From the booking to the sailing everything was outstanding. We could not have asked for anything better. Please do yourselves a favor and book a day on the water with these two. We will absolutely be back. The boat is beautiful!

  5. 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!

  6. 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

Boating Guide - Captiva Sailing

Step onboard a sailboat for an unforgettable experience in Captiva, Florida.

Get ready for a fun adventure when you hit the open water onboard a sailboat in Captiva, Florida. Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Captiva, Florida is a wonderful sailboat rental destination.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat has 240 listings for Sailing experiences in Captiva with 4,807 reviews.

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