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All listings near me

Find Sailing Charters Near You

4.9
(4,671 Reviews)

Page 9 of 10240 listings

Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!
Powerboats in Nobleboro · 8 guests

Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!

New
$260+/day
Instant Book
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 6 guests

★ 28' Classic Schooner in Rockland, Maine ★

5.0
$175/hour
★Midcoast Maine aboard the Schooner Yacht Meteor ★
Sailing in Rockland · 4 guests

★Midcoast Maine aboard the Schooner Yacht Meteor ★

5.0
$175/hour
Experience Maine on 65ft Classic Schooner Yacht
Sailing in Rockport · 30 guests

Experience Maine on 65ft Classic Schooner Yacht

5.0
$500/hour
52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

5.0
$110/hour
Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!
Sailing in New Orleans · 6 guests

Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!

5.0
$110/hour
Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

5.0
$110/hour
Herreshoff 12 1/2 Sailboat Charter
Sailing in North Haven · 3 guests

Herreshoff 12 1/2 Sailboat Charter

New
$50/hour
Tampa Bay - Clearwater Area with a perfect & elegant Carver Mariner 38 x 190$/h
Powerboats in Tampa · 12 guests

Tampa Bay - Clearwater Area with a perfect & elegant Carver Mariner 38 x 190$/h

New
$250/hour
Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch
Sailing in Southwest Harbor · 6 guests

Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch

New
$290/hour
''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl
Events in Cape Canaveral · 11 guests

''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl

5.0
$382/hour
38ft Leopard Catamaran in Cape Canaveral
Sailing in Cape Canaveral · 6 guests

38ft Leopard Catamaran in Cape Canaveral

5.0
$250/hour
Sunset Sails: Explore the Open Waters of Tampa, Florida
Sailing in Tampa · 6 guests

Sunset Sails: Explore the Open Waters of Tampa, Florida

5.0
$225/hour
Instant Book
55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida
Events in Tampa · 13 guests

55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida

New
$801/hour
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

4.7
Superowner
Snoozed - Active 02 Jan 2026
Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!
Sailing in Treasure Island · 28 guests

Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!

New
$695/hour
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
$205+/hour
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Saint Petersburg · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
Superowner
Best of 2025
$300+/hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
Best of 2025
$315+/hour
44ft Aquila "A Lil Bit Nauti" Yacht Charter in Palmetto, FL
Sailing in Palmetto · 13 guests

44ft Aquila "A Lil Bit Nauti" Yacht Charter in Palmetto, FL

New
$590/hour
2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Powerboats in Holmes Beach · 8 guests

2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!

4.9
$372+/day
42' Wanderlust - The Best Sailing Cat in the Market
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market

New
$449+/hour
Instant Book
''Aloan at Last''r Mega Yacht Rental in Sarasota, Florida
Events in Sarasota · 13 guests

''Aloan at Last''r Mega Yacht Rental in Sarasota, Florida

New
$1,690/hour
Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul
Sailing in Stuart · 6 guests

Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul

5.0
$225/hour

Local Sailing Reviews

  1. Kieron

    Kieron

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    Bailey's luxury catamaran was gorgeous and the sunset cruise we took for my husband's 40th birthday with family was a very special experience. Captain Dave and Emma were so nice and accommodating for our group of 12. They provided us with ice and beverages as well as utensils and napkins for the catered platters we brought. We were also able to connect to the sound system to play our music for the entire trip. We had perfect weather and got to see dolphins frolicking prior to heading out into the Gulf for a gorgeous sail and stunning sunset!

  2. TM

    Tyrone

    Sunset Sails: Explore the Open Waters of Tampa, Florida

    Arlo was fantastic! Wanted to propose to my girlfriend on the charter and Arlo was super accommodating to make sure everything went perfect. Great Captain/host! 5/5 Stars!!

  3. MG

    Matt

    38ft Leopard Catamaran in Cape Canaveral

    Thank you for a great day on the water. We weren't sure what to expect, but the up and down of the the xalm waters of the canal and river provided a relaxing and pleasant experience.

  4. LO

    Lauren

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    My group of 12 had such a fun time! Absolutely no complaints.

  5. AS

    Anna

    52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

    Captain Jim is the best! He knows the sails, and goes above and beyond to ensure you enjoy your time on Lake Pontchartrain. The boat is very nice and a perfect size for a group of 6. Highly recommend!!

  6. AD

    Andrew

    ★Midcoast Maine aboard the Schooner Yacht Meteor ★

    We just got back from a wonderful day on the water :) We bareboat chartered the Meteor. Captain Neal was able to be flexible on our timing since our original day was bad weather and he did not have many bookings around the same time. He made perfect suggestions regarding weather, currents, tides and routes to help us learn the area quickly and be able to navigate a beautiful day on Penobscot Bay. 100% we will be back again! Treat his boat well and Capt Neal will treat you well in return! Thanks so much for a wonderful day!