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All listings near me

Find Sailing Charters Near You

4.9
(4,502 Reviews)

Page 8 of 10240 listings

Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$150/hour
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Sailing in Tisbury · 6 guests

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

5.0
$200/hour
Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!
Sailing in Gloucester · 6 guests

Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

New
$175+/hour
Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!
Sailing in Gloucester · 60 guests

Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!

New
$1,200+/hour
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
Sailing in Gloucester · 6 guests

Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

5.0
$250/hour
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
Take a Sunset Sail, or Sailing Lesson with Capt. Jack!
Sailing in Jacksonville · 4 guests

Take a Sunset Sail, or Sailing Lesson with Capt. Jack!

New
$300/hour
Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin
Sailing in Shalimar · 6 guests

Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

5.0
$150/hour
Private Sunset Cruise (2-Hours) in Destin, Florida
Sailing in Fort Walton Beach · 6 guests

Private Sunset Cruise (2-Hours) in Destin, Florida

5.0
$175/hour
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/hour
Instant Book
4 Hour Private Charter in Destin, FL! Crab Island, Snorkeling, Dolphins & More!
Sailing in Fort Walton Beach · 6 guests

4 Hour Private Charter in Destin, FL! Crab Island, Snorkeling, Dolphins & More!

5.0
$150/hour
3-Hour Daytime Cruise in Destin, Florida
Sailing in Fort Walton Beach · 6 guests

3-Hour Daytime Cruise in Destin, Florida

5.0
$150/hour
 LOVELY 40FT SAILING CATAMARAN
Sailing in Pensacola · 6 guests

LOVELY 40FT SAILING CATAMARAN

New
$250/hour
Morgan 382 Sailboat for charter in Pensacola, Florida
Sailing in Pensacola · 6 guests

Morgan 382 Sailboat for charter in Pensacola, Florida

5.0
$75/hour
Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.
Sailing in Portland · 6 guests

Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.

New
$850/day
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
$125/hour
★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
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
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
Herreshoff 12 1/2 Sailboat Charter
Sailing in North Haven · 3 guests

Herreshoff 12 1/2 Sailboat Charter

New
Snoozed - Active 28 Sep 2025
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

Local Sailing Reviews

  1. AB

    Amanda

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    My family and I had a spectacular sailing adventure. Mason and Lynn are friendly and professional and really made us feel welcome. They gave us an experience that we will never forget. The boat had plenty of room for all of us to enjoy sightseeing and even allowed some on board fishing. We had never sailed before and after our time with Mason and Lynn, we can’t wait to sail with them again. If you’re looking for an unforgettable time on the water, I recommend sailing with them. ⭐️⭐️⭐️⭐️

  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. AN

    Alexis

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    My husband and I booked this excursion with Mason and Lynn for the 4th of July weekend, and it was the best part of the entire weekend! Mason and Lynn were incredibly hospitable and caring, communicative, and thoughtful. Mason suggested taking the day to go to Cuttyhunk and it was worth it. We had the best lobster rolls of our lives and walked around the town. It was a magical day. The boat was beautiful and Mason and Lynn went out of their way to make sure we had a great day. Highly highly recommend!

  4. AP

    Albalia

    Morgan 382 Sailboat for charter in Pensacola, Florida

    We shared our 24th wedding anniversary with Robert and Carly in their beautiful boat. The only thing we regret is not doing this sooner because they are amazing and it is an experience to cherish. You guys are the best and we will definitely be back! Looking forward for that paella next time! Thank you!!!

  5. AM

    Andrew

    ★ 28' Classic Schooner in Rockland, Maine ★

    Captain Neal was a top tier captain, super communicative and friendly. We had a great sail on the Meteor and would recommend it to everyone!

  6. MH

    Madeline

    Experience Maine on 65ft Classic Schooner Yacht

    It was an absolutely beautiful sail! The captain and crew were so personable, sweet and accommodating! Gorgeous day and a BREATHTAKING boat! 10000/10 would recommend