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
(4,805 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
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
$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
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
Pensacola Private Sailing Experience for Up to 6 Guests
Sailing in Pensacola · 6 guests

Pensacola Private Sailing Experience for Up to 6 Guests

New
$138+/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

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. VS

    Vicky

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    We had a great day out exploring the bay with Captain Tony. It was a wonderful sailboat experience, that included a swim in a quiet cove and tour of notable homes on the coast. The ride come with a free lesson on the History of Newport, if you would like one. We look forward to seeing the Captain again soon!

  3. SS

    Susan

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    Anthony was kind enough to take us out on super short notice when a different boat canceled us. We were traveling for the sole purpose of an afternoon sail and had nonrefundable travel and hotel. i am so grateful the other boat canceled because Anthony and his J42 were simply the best! i recommend him highly to anyone who wants to sail. He appeals to all levels of sailors and has great knowledge of the area and is willing to share. We got some history lessons as well as the sail. Fantastic!

  4. MM

    Martez

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    Captain Anthony created a wonderful experience for my family -- fun stories and sailing tutorials for the kids and knowledge information about sailing physics and "hands on" experience for the adults. A masterful conversationalist and a natural with people of all ages. Truly a gentleman and a terrific sailor. We highly recommend him to parties of all types, but especially families.

  5. MB

    Matt

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    Couldn’t be happier with our experience with Tony and Parker. Easy communication, and Tony is a great host. We had so much fun, saw the beauty of Newport by boat, and even got some fun history lessons. Will definitely be booking with Tony again next time we’re in Newport!

  6. MS

    Mitchell

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    Captain Tony and Parker were excellent! We had an incredible day out on the water, even with some rough wind. Not only did they provide an awesome experience and we’re incredibly accommodating to our itinerary requests, they even taught us a thing or two about sailing. I’d definitely recommend them and hope to charter them again in the future!