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All listings near me

Find Sailing Charters Near You

4.9
(4,925 Reviews)

Page 7 of 10240 listings

Narragansett Bay Sailing Onboard Classic 36' Hunter Yacht
Sailing in Warwick · 6 guests

Narragansett Bay Sailing Onboard Classic 36' Hunter Yacht

New
$150/hour
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
$180/hour
Providence Private Day Sail Onboard Classic 28' Sabre Yacht Serenity
Sailing in Providence · 6 guests

Providence Private Day Sail Onboard Classic 28' Sabre Yacht Serenity

New
$150/hour
High Demand
63' Catamaran - Newport, RI - Luxury sailing for large groups!
Sailing in Newport · 40 guests

63' Catamaran - Newport, RI - Luxury sailing for large groups!

New
$833/hour
42ft J Boat Sailing Yacht in Newport, Rhode Island
Sailing in Newport · 4 guests

42ft J Boat Sailing Yacht in Newport, Rhode Island

5.0
$260/hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$450/hour
Luxury Sailing Catamaran for up to 12
Sailing in Newport · 12 guests

Luxury Sailing Catamaran for up to 12

5.0
$350/hour
Instant Book
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
Explore Newport Harbor and Narragansett Bay Aboard Beneteau Sense 55 Sailboat
Sailing in Newport · 6 guests

Explore Newport Harbor and Narragansett Bay Aboard Beneteau Sense 55 Sailboat

New
$400/hour
Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Endeavor Sailboat
Sailing in Newport · 6 guests

Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Endeavor Sailboat

5.0
$300/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
Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston
Sailing in Boston · 8 guests

Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston

New
$550/hour
Instant Book
Mattapoisett Sailboat Cruise - 42ft "Our Passion"
Sailing in Mattapoisett · 6 guests

Mattapoisett Sailboat Cruise - 42ft "Our Passion"

New
Superowner
$355/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
$355/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 36ft Sailing Catamarant!!
Sailing in Gloucester · 6 guests

Sail Gloucester Harbor and Beyond on a Private 36ft 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

Local Sailing Reviews

  1. BA

    Bridget

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    Our sail with Captain Perrin was an absolute dream. We were lucky enough to have gorgeous weather for our sunset sail and Perrin could not have been more accommodating. Our bachelorette party of five loved his historic tidbits and great vibes. Would definitely book again when back in the area!

  2. SC

    Steven

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    This wasn’t just a sail—it was an adventure filled with stories, laughter, and the kind of peaceful moments you only find out on the water. I can’t recommend Kenneth highly enough if you’re looking for a memorable and truly enjoyable sailing experience. Highly recommend! 🚤⛵️

  3. MH

    Melissa

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    We had a great trip with Kenny - highly recommend. Very prompt, communicative, and clear in departure directions. We had a great sail with beautiful conditions and Kenny is personable and knowledgeable. Highly recommend for a great time on the water, we’ll definitely go sailing with him again next time!

  4. GM

    Gwen

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    Kenneth and his boat exceeded all expectations and we had a fabulous day. He was very engaging and informative, and made our day alternating between sailing and listening to music in front of the folk fest an amazing experience. He even anchored us right up next to the stage with expertly navigating between a ton of other boats. Can’t wait for next year and highly recommend.

  5. WI

    Whitney

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    Capt Ken was fantastic - highly recommended for small groups especially with kids. Ken was super communicative leading up to the trip, and provided a custom experience (finding a good spot to swim), he even let the kids steer the boat. The Mariah is a beautiful vessel with comfortable seating as well as roomy and shady as needed. I would book with Ken again no questions. Thank you, Ken!!

  6. DS

    Danielle

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    From start to finish, Kenneth was incredibly friendly and engaging, making the entire experience unforgettable. He truly made us feel like part of the sailing adventure, sharing his knowledge and ensuring we had the best time possible. I would rate this experience a 10 out of 10 and would gladly book with him again next time we're in town. Highly recommend!