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
(4,950 Reviews)

Page 7 of 10240 listings

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
Limited Availability
Luxury Sailing Catamaran for up to 12
Sailing in Newport · 12 guests

Luxury Sailing Catamaran for up to 12

5.0
Snoozed - Active 02 Nov 2026
Limited Availability
Explore Newport Harbor on a Luxurious Beneteau Sense 55 Sailboat
Sailing in Newport · 6 guests

Explore Newport Harbor on a Luxurious Beneteau Sense 55 Sailboat

5.0
$400/hour
Limited Availability
Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat
Sailing in Newport · 6 guests

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

5.0
$195/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
$260+/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

5.0
$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
Limited Availability
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
$45+/hour
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
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
41' Catamaran Dolphin Cruise Along Panama City Beach
Sailing in Panama City Beach · 32 guests

41' Catamaran Dolphin Cruise Along Panama City Beach

New
$374/hour
52’ Sea Runner Sailing Catamaran Dolphin Cruise, Shell Island Adventure
Sailing in Panama City Beach · 78 guests

52’ Sea Runner Sailing Catamaran Dolphin Cruise, Shell Island Adventure

New
$1,950/hour

Local Sailing Reviews

  1. JR

    James

    43' Sailboat, Bristol RI & Beyond

    Captain Francis is very personable, and a great host on the water. He has taken very good care of his yacht, which is comfortable, ample in space and comfort, and everything operates as expected. He has a warm and laid-back demeanor, which makes for a very nice chemistry while sailing. Overall an A+.

  2. BH

    Betsy

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

    Oh what a night! We had a fantastic time on our sailing trip with Jake and his crew. They picked us up right on time, we had a perfect sale, and they even gave us some extra time at the end. The views of Boston were perfection, the sale was smooth and we felt very well taken care of by the entire crew the whole time! It really could not have been any more perfect. We highly recommend!

  3. 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 !

  4. LF

    Lena

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

  5. DW

    David

    43' Sailboat, Bristol RI & Beyond

    We were thrilled to be able to book Captain Francis again for a trip around the bay. Highly recommended!!!

  6. MS

    Matt

    Explore Newport Harbor on a Luxurious Beneteau Sense 55 Sailboat

    Absolutely top notch, great communication and excellent skill and handling. Gave a great tour and our whole family loved the day. Thank you!