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All listings near me

Find Sailing Charters Near You

4.9
(4,823 Reviews)

Page 7 of 10240 listings

Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$450/hour
Newport Private Day Sail onboard 28' Sabre Yacht Serenity
Sailing in Newport · 4 guests

Newport Private Day Sail onboard 28' Sabre Yacht Serenity

New
$150/hour
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
Sailing in Newport · 6 guests

Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

5.0
$200/hour
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

5.0
$159+/hour
Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht
Sailing in New Bedford · 6 guests

Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht

5.0
$180/hour
Mattapoisett Sailboat Cruise - 42ft "Our Passion"
Sailing in Mattapoisett · 6 guests

Mattapoisett Sailboat Cruise - 42ft "Our Passion"

New
Superowner
$315/hour
Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts
Sailing in Salem · 6 guests

Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts

5.0
$550/hour
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/hour
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
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
Superowner
$315/hour
Private Sailing Charter on Martha's Vineyard
Sailing in Tisbury · 6 guests

Private Sailing Charter on Martha's Vineyard

5.0
Snoozed - Active 02 Jul 2026
Martha's Vineyard Best Sailing Charters on 60' Luxury Ketch
Sailing in Tisbury · 6 guests

Martha's Vineyard Best Sailing Charters on 60' Luxury Ketch

New
$300/hour
Sail Gloucester Harbor and Beyond on a Private 43ft Sailing Catamarant!!
Sailing in Gloucester · 6 guests

Sail Gloucester Harbor and Beyond on a Private 43ft Sailing Catamarant!!

5.0
$225+/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
Sail & Stay in Nantucket – Private Charters + Overnight Aboard a Beneteau 36.7
Sailing in Nantucket · 6 guests

Sail & Stay in Nantucket – Private Charters + Overnight Aboard a Beneteau 36.7

New
$320+/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
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/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
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

Local Sailing Reviews

  1. SB

    Sarah

    Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

    Our sail with David was wonderful! He’s so nice and had some great ideas for pictures for our engagement shoot!

  2. ST

    Samantha

    Custom Sailing Charter - Newport/ Block Island

    We really enjoyed our sail with Candace, Stephanie and Matt - and we can't forget Eddie Spaghetti the daschaund! They told us a lot about the history of the area and made sure we were comfortable and well-taken care of on this sail. Many thanks to Stephanie too for the wonderful photos on the trip.

  3. sk

    sarah

    Custom Sailing Charter - Newport/ Block Island

    Captain Candace, Captain Don and Stephanie were an absolute delight to work with from start to finish. Capt. Candace was very easy to communicate with and worked to accommodate our age diverse group. Great directions and instructions as to how to find the boat, the boat was in pristine condition and VERY comfortable accommodations for our sail. Captain Don and Stephanie were very clear about safety first at all times, very knowledgable sailers and wonderful tour guides and historians when the wind was not working with us. We could not have asked for anything more - the boat and the crew are top notch. We hope to have the opportunity to sail with Candace and crew again. Our sailing experience was the highlight of our trip to Newport.

  4. Madison

    Madison

    Custom Sailing Charter - Newport/ Block Island

    Candace is an amazing host & captain and her boat is absolutely beautiful! The space in the back was more than enough room for our bachelorette party of 6. She lets us BYOB, food, and connect to her bluetooth to play our own music. Not to mention her crew mate Stephanie was also more than happy to be our personal photographer the whole time lol!! 100% recommend sailing with Serendipity Sailing we had SO much fun!

  5. MS

    Megan

    Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

    Captain Dave is awesome. He’s knowledgeable, accommodating, friendly and down to earth. My 5 friends and I had an amazing time sailing in Newport as part of a Bachelorette party, but we all agreed we would do it again any time because it was so fun! I’d highly recommend this experience to anyone!

  6. MB

    Mark

    Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

    Our sail with David was great! Even though we had light winds, we still covered a lot of ground. David is very capable and knowledgeable, and he also knows a lot about the area and the maritime region. The boat is in very good condition and very roomy. We ended up with 4 guests and were very comfortable. We expect to sail again with David in the future.