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All listings near me

Find Sailing Charters Near You

4.9
(4,996 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
Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast
Sailing in Friendship · 6 guests

Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast

5.0
Snoozed - Active 19 Sep 2025
★Midcoast Maine aboard the Schooner Yacht Meteor ★
Sailing in Rockland · 4 guests

★Midcoast Maine aboard the Schooner Yacht Meteor ★

5.0
$175/hour
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 4 guests

★ 28' Classic Schooner in Rockland, Maine ★

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
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
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
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
Set Sail on a Suncoast Escapade!
Sailing in Treasure Island · 6 guests

Set Sail on a Suncoast Escapade!

New
$225/hour
St. Pete Sunset Sails - 34ft Sailboat
Sailing in Saint Petersburg · 4 guests

St. Pete Sunset Sails - 34ft Sailboat

New
$160/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
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Petersburg · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

New
$133/hour
Instant Book
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 - Sarasota
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

5.0
$499+/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

Local Sailing Reviews

  1. MV

    Michael

    ★ 28' Classic Schooner in Rockland, Maine ★

    Great experience. Captain Neal is a wealth of sailing knowledge and a lot of fun. My girls were thrilled for a chance to take the tiller! Would definitely book again.

  2. JA

    Jeremy

    Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast

    Ralph made bareboating a great experience end to end. His Morgan 36-5 Nelson Marek was just right, in working order and easy to sail for just my wife who does not sail and me. The equipment was all good, including a new and simple to use chart plotter mounted right at the helm. Beautiful location, conditions and waters made for great sailing. Convenient getting answers in advance, getting started and finished. All good. Highly recommendation. And there’s a super lobster place right nearby.

  3. Zach

    Zach

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    Could not recommend this vessel and crew more. We rented it for the 4th of July and it was an unforgettable experience for our group. Despite some shaky weather we still had a blast. The boat is incredible and such a fair rate compared to other similar listings. Captain Dave and Joe were AWESOME. Would book again in a heartbeat!

  4. Deja

    Deja

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    We can’t thank Captains Dave & Joe enough. From the communication with Bailey, to the overall experience.. everything went smooth and easy. I booked for my friend’s Bachelorette Party and they made our time worth while. I definitely recommend for any occasion. Both Captains Dave and Joes made sure we were equipped with everything and comfortable during our sailing. My favorite part was swimming and lounging on the floatable pools.. oh, and seeing dolphins! Overall 10/10 experience!

  5. NS

    Nicole

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    Perfect 16th birthday experience for our daughter and her friends!

  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!