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Great sailboat rentals near Jacksonville, Florida.

4.9(Average of 4,836 reviews in this area)
View our Jacksonville sailing boating guide
1 - 24 of 240 listings
2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOATSailing in Jacksonville2 guests

2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT

New
$40hour
64' Roberts Sailing Ketch for Charter in Jacksonville AreaSailing in Fleming Island6 guests

64' Roberts Sailing Ketch for Charter in Jacksonville Area

5.0
$200hour
30' Kurt Hughes Cruising Catamaran rental in Fernandina Beach, FloridaSailing in Amelia Island6 guests

30' Kurt Hughes Cruising Catamaran rental in Fernandina Beach, Florida

4.8
$200hour
50' Chris White Design, Cruising Catamaran rental in beautiful Ponce Inlet Florida.Sailing in Ponce Inlet48 guests

50' Chris White Design, Cruising Catamaran rental in beautiful Ponce Inlet Florida.

5.0
$26person
Robalo 2440 Center Console Rental in Orange CityPowerboats in Lake Monroe12 guests

Robalo 2440 Center Console Rental in Orange City

New
$150hour
2021 22ft Avalon LS Entertainer for Rent in Clermont, FloridaPowerboats in Clermont10 guests

2021 22ft Avalon LS Entertainer for Rent in Clermont, Florida

New
$125hour
NEW! Rent the Splash n Chill Island Float in Central Florida | Great for Lakes & Ponds!Sailing in Orlando7 guests

NEW! Rent the Splash n Chill Island Float in Central Florida | Great for Lakes & Ponds!

New
$30hour
Neon Drift Seadoo Switch Cruise Boat Rental in Orlando, FloridaPowerboats in Orlando7 guests

Neon Drift Seadoo Switch Cruise Boat Rental in Orlando, Florida

New
$100hour
MaineCat Sailing Catamaran in Merritt IslandSailing in Merritt Island32 guests

MaineCat Sailing Catamaran in Merritt Island

5.0
$599hour
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
Sailing in MelbourneSailing in Melbourne4 guests

Sailing in Melbourne

New
$125hour
Sunset Cruises (2-Hours) from Alligator Point, Florida $350.00Sailing in Alligator Point6 guests

Sunset Cruises (2-Hours) from Alligator Point, Florida $350.00

New
$175hour
Sailing Sampler Adventure (2-hours)  at Alligator Point, Florida $350.00Sailing in Alligator Point6 guests

Sailing Sampler Adventure (2-hours) at Alligator Point, Florida $350.00

New
$175hour
Half-Day Sailing Adventure (4 hours) at Alligator Point, Florida! $480Sailing in Alligator Point6 guests

Half-Day Sailing Adventure (4 hours) at Alligator Point, Florida! $480

New
$120hour
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
9425 US Hwy 41 S, Riverview, FL 33578Tampa3 guests

9425 US Hwy 41 S, Riverview, FL 33578

New
$60day
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
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
BRAND NEW - Yamaha AR250 Jet boat in Clearwater, FLPowerboats in Clearwater10 guests

BRAND NEW - Yamaha AR250 Jet boat in Clearwater, FL

5.0
$120hour
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
Cruising Monohull Rental in St. Petersburg, FloridaSailing in Saint Petersburg6 guests

Cruising Monohull Rental in St. Petersburg, Florida

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
Water Music-Well Appointed Beneteau323, Folly Beach, SCSailing in Folly Beach6 guests

Water Music-Well Appointed Beneteau323, Folly Beach, SC

5.0
$175hour
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

Top Destinations Nearby

Sailing Reviews in Jacksonville

  1. Chrystelle
    Chrystelle
    64' Roberts Sailing Ketch for Charter in Jacksonville Area

    What a fun day we had! We chartered Tom’s magnificent sail boat for our daughter’s 18th birthday. She will definitely remember this special day forever! Tom, our captain was so easy going from the second we talked on the phone- great communication. We all had an amazing time especially our teenagers (from jumping off the boat to swinging off the boat like monkeys lol). I definitely recommend Nepenthe Sails and Tom (captain/owner). We have gained a new friend in the process! 😄

  2. TH
    Tim
    64' Roberts Sailing Ketch for Charter in Jacksonville Area

    Captain Tom was friendly, incredibly knowledgeable, and provided an amazing experience for our group. He was helpful and accommodating. It was clear his goal was to provide us with an exceptional experience, and he succeeded! The sailboat Nepenthe was beautiful and sailed well. We can't wait to get back on the water. See ya soon, Captain Tom!

  3. Chantal
    Chantal
    30' Kurt Hughes Cruising Catamaran rental in Fernandina Beach, Florida

    We loved this experience! Boat and Captain Terry were early and waiting on us when we got to the dock! The catamaran boat was a lot of fun, our first time on one and we loved laying out in the sun! Captain Terry gave lots of information about the area. Highly recommended!!

  4. SR
    Sheila
    30' Kurt Hughes Cruising Catamaran rental in Fernandina Beach, Florida

    We are extremely happy with our trip today. Just fun and relaxing and not having to worry about anything because Captain Terry aka The Care Taker from Cumberland Island took great care of us. I would highly recommend Jason and Terry for a great trip. We already planning our next one. Thank you so much taking time out of your day for us. Much appreciated.

  5. Marsha
    Marsha
    30' Kurt Hughes Cruising Catamaran rental in Fernandina Beach, Florida

    My best friends and I had the pleasure of spending the afternoon with Captain Jason and First Mate Chad, they were FANTASTIC!!! They were not only fun and accomadating but also attended to all of our requests while engaging with us in a friendly manner. I would love to come back for another trip in the future. Thank you for the excellent experience on the Intercoastal Waterway!

  6. MS
    Martin
    BRAND NEW - Yamaha AR250 Jet boat in Tampa Bay, FL

    After launching the boat from Davis Island I set out to see the sights around Harbor Island and explore going up the Hillsborough River. We went up to dock at Armature Works and got something to eat. We then left and went back out past downtown and into the bay. All in all it was an awesome time on the water and the boat was an absolute pleasure. I would highly recommend renting the same boat from Cailun because the whole experience from start to finish was wonderful!

Boating Guide - Jacksonville Sailing

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

Get ready for a fun adventure when you hit the open water onboard a sailboat in Jacksonville, 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. Jacksonville, 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 Jacksonville with 4,836 reviews.

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