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All listings near me

Find Sailing Charters Near You

4.9
(4,950 Reviews)

Page 7 of 10240 listings

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
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. 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. SS

    Simon

    Luxury Sailing Catamaran for up to 12

    Unforgettable Post-Wedding Sail!! We spent a half-day with Aaron on the Catamaran Quest right after our wedding in St. Thomas, and it was easily one of the highlights of our entire trip. From the moment we stepped on board, Aaron made us feel incredibly special. He was super attentive and helpful, ensuring we had everything we needed to just relax and soak in the "just married" bliss. The food and drinks he served were fantastic—well-prepared and exactly what we needed for a day on the water. The boat itself is awesome and very well-equipped with everything you’d want for a comfortable excursion. We did encounter some minor technical issues with the engines during our trip, but Aaron handled it with total professionalism and didn't let it dampen the experience at all. If you are looking for a captain who truly cares about his guests' experience, book with Aaron. Thank you for making our celebration so memorable! PS: Aaron’s mango salsa is to die for - awesome stuff!!

  5. MS

    Megan

    Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

    Captain Dave is awesome. He’s knowledgeable, accommodating, friendly and down to earth. My 5 friends and I had an amazing time sailing in Newport as part of a Bachelorette party, but we all agreed we would do it again any time because it was so fun! I’d highly recommend this experience to anyone!

  6. MB

    Mark

    Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

    Our sail with David was great! Even though we had light winds, we still covered a lot of ground. David is very capable and knowledgeable, and he also knows a lot about the area and the maritime region. The boat is in very good condition and very roomy. We ended up with 4 guests and were very comfortable. We expect to sail again with David in the future.