Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings near me

Find Sailing Charters Near You

4.9
(4,955 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
Luxury Sailing Catamaran for up to 12
Sailing in Newport · 12 guests

Luxury Sailing Catamaran for up to 12

5.0
$350/hour
Limited Availability
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
Limited Availability
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
Limited Availability
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
Limited Availability
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
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
High Demand
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
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
47’ Beneteau Sailing Adventure with Dolphin Sightseeing in Panama City Beach
Sailing in Panama City Beach · 12 guests

47’ Beneteau Sailing Adventure with Dolphin Sightseeing in Panama City Beach

New
$460/hour
Footloose 40' Sailing Catamaran - Snorkel and Dolphin Cruise
Sailing in Panama City Beach · 38 guests

Footloose 40' Sailing Catamaran - Snorkel and Dolphin Cruise

New
$634/hour

Local Sailing Reviews

  1. KS

    Kevin

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    What an amazing trip. I’ve been coming to the waters on the Vineyard for years and Mason took us to places I’ve never seen before. The boat was perfect for a relaxing adventure. I would highly recommend for almost any type of group from a couple to a family or a small group. What an experience !

  2. LF

    Lena

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

    Amazing trip! Eric was fantastic. He asked us what we wanted to do, and he took us to his favorite spots. We went swimming and jumped off rocks. He told us very interesting stories and was extremely friendly. He made the whole experience better. He made us feel like the boat was our own. Great time, amazing boat. I’d definitely book him again!

  3. NK

    Nancy

    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    All round really fun, easy and pleasant experience! Fabulous day sailing!

  4. 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.

  5. 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.

  6. 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!