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
(4,730 Reviews)

Page 7 of 10240 listings

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
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
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
Lazy Daze Catamaran Dolphin Cruise
Sailing in Panama City Beach · 32 guests

Lazy Daze Catamaran Dolphin Cruise

New
$374/hour
47’ Beneteau Sailing Adventure with Dolphin Sightseeing
Sailing in Panama City Beach · 12 guests

47’ Beneteau Sailing Adventure with Dolphin Sightseeing

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

Footloose Catamaran Snorkel and Dolphin Cruise

New
$634/hour
52’ Privateer Catamaran Dolphin Cruise, Shell Island Adventure
Sailing in Panama City Beach · 78 guests

52’ Privateer Catamaran Dolphin Cruise, Shell Island Adventure

New
$1,950/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
Clean Modern Sailboat - Private Sailing Experience
Sailing in Pensacola · 6 guests

Clean Modern Sailboat - Private Sailing Experience

New
$207/hour

Local Sailing Reviews

  1. cC

    chris

    43' Sailboat, Bristol RI & Beyond

    This was an incredible sail. We had to cancel our initial trip due to very bad storms with 65 knot winds and flooding rains early in the season. We rebooked and had a fabulous, relaxing time. The Capt' is both entertaining and a wealth of information and just makes the entire experience what you would want.....sublime.

  2. AH

    Anne

    43' Sailboat, Bristol RI & Beyond

    Four of us had a great sail with Captain Francis. He struck the right balance between chatting with us and letting us talk amongst ourselves. We wanted to sail by a specific area and he graciously complied. I thought the value for the sailing experience was great. Highly recommend.

  3. BB

    Bryan

    43' Sailboat, Bristol RI & Beyond

    Table for Two and Captain Francis make for a great sail. We have sailed with him multiple times and will continue to do so yearly for our family sailing vacation. Safety, value, and his knowledge of sailing globally make it a great time and experience we return back to every year. I highly recommend his services.

  4. BE

    Bill

    43' Sailboat, Bristol RI & Beyond

    We had a delightful afternoon sail with Captain Francis! He was skilled and easygoing and his boat was very well equipped. Two of us were experienced sailors and he graciously allowed us to help crew and take the helm as much as we wished. We all shared stories of past adventures and had a wonderful day in Bristol and Narragansett Bay. Highly recommended!

  5. DW

    David

    43' Sailboat, Bristol RI & Beyond

    We had a wonderufl afternoon sailing on the bay with Captain Francis! Our kids had some prior sailing experience, and he was kind enough to let them crew a bit. He was personable and knowledgeable, we had a great time, and would definitely book through him again!

  6. BB

    Bryan

    43' Sailboat, Bristol RI & Beyond

    Our trip with Captain Francis was beyond our expectations. Two of my young adult kids were interested in learning to sail and Captain Francis spent the day with them teaching them all the basics with hands on training. Myself and my oldest daughter spent the day on the bow relaxing and enjoying the views and the sun. The boat was well equipped with all that we needed and Captain Francis was accommodating with any request. We will definitely be back and Table4Two will always be our first choice for sailing the Bristol/Newport waterways. Thanks for a Wonderful day on the water.