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Find Sailing Charters Near You

4.9
(4,330 Reviews)

Page 7 of 10240 listings

1976 Classic Sailboat Charter out of Burlington Harbor
Sailing in Burlington · 4 guests

1976 Classic Sailboat Charter out of Burlington Harbor

5.0
$80-$100hour
4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!
Sailing in North Kingstown · 6 guests

4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!

5.0
$150hour
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
$200hour
Sail World-Famous Newport & Narragansett Bay Aboard Tartan 34 Classic
Sailing in East Providence · 6 guests

Sail World-Famous Newport & Narragansett Bay Aboard Tartan 34 Classic

4.0
$200hour
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
$260hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$290hour
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
$200hour
Private Sailing Charter Newport, Bristol RI | Captain and Crew
Sailing in Newport · 6 guests

Private Sailing Charter Newport, Bristol RI | Captain and Crew

New
$120-$175hour
Instant Book
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

New
$199hour
Private Sailing Charter Bristol/ Newport RI | Captain and Crew
Sailing in Bristol · 6 guests

Private Sailing Charter Bristol/ Newport RI | Captain and Crew

New
$120-$175hour
Instant Book
Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston
Sailing in Boston · 6 guests

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

New
$500hour
Sunset Sail Buzzards Bay in a Classic Sloop!
Sailing in Fairhaven · 4 guests

Sunset Sail Buzzards Bay in a Classic Sloop!

New
$150hour
30' Kurt Hughes Cruising Catamaran rental in Fernandina Beach, Florida
Sailing in Fernandina Beach · 6 guests

30' Kurt Hughes Cruising Catamaran rental in Fernandina Beach, Florida

4.8
$300hour
Spend the Day on Buzzards Bay - Sail on a J/105 or Cruise on a Dyer 29 Powerboat
Sailing in Mattapoisett · 6 guests

Spend the Day on Buzzards Bay - Sail on a J/105 or Cruise on a Dyer 29 Powerboat

New
$90person
Private Charters on Classic 80' Schooner yacht in Salem, Massachusetts
Sailing in Salem · 6 guests

Private Charters on Classic 80' Schooner yacht in Salem, Massachusetts

5.0
$498-$550hour
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$150hour
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-$95day
60' Cruising Monohull Ketch in Vineyard Haven, MA
Sailing in Tisbury · 12 guests

60' Cruising Monohull Ketch in Vineyard Haven, MA

5.0
$200-$275hour
Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!
Sailing in Gloucester · 6 guests

Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

New
$175-$225hour
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
$1,150-$1,300hour
Sail with us aboard ARTEMIS in Gloucester MA and New England
Sailing in Gloucester · 6 guests

Sail with us aboard ARTEMIS in Gloucester MA and New England

5.0
$250hour
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

New
$175-$220hour
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
$150hour
2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN JACKSONVILLE
Sailing in Jacksonville · 2 guests

2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN JACKSONVILLE

New
$40hour

Local Sailing Reviews

  1. Lauren

    Lauren

    Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

    Wonderful time out on the water with Captain Bill! Very accommodating, kind and knowledgeable. Weather wasn’t cooperative but he was able to be flexible and come up with an alternative itinerary. Definitely recommend!

  2. AL

    Albert

    1976 Classic Sailboat Charter out of Burlington Harbor

    Had a great time sailing with Eli. The location is right in downtown Burlington and the parking is right next to the boat very easy. Eli is very accommodating as he let me sail the boat for a good portion of the trip which is what I wanted. Eli was on time and communicated well. After the sail just walk into Burlington and have dinner or lunch great sail and location.

  3. Billy

    Billy

    1976 Classic Sailboat Charter out of Burlington Harbor

    Captain Eli was punctual, knowledgeable, and professional. The sailboat is a very well taken care of humble and small vessel but don’t let that hinder your party of four (max) from getting out on Lake Champlain and enjoying the scenery and sunset. Take some refreshments and music for a soundtrack to your trip.

  4. BM

    Bruce

    4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!

    Joe's 1978 cruising sailboat was just the right size and weight to balance comfort with sailing experience. Joe was highly knowledgeable as a sailor and with sharing the local lore. It felt more like a sail with friends than a "charter." As a former sailor myself, I felt totally at ease in his hands. We plan to make this a regular part of our visits to Providence.

  5. Ashley

    Ashley

    4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!

    Joe is an amazing sailor- he does not only take you out there in the water to sail but he also teaches you everything about his boat and how to operate it. He showed us around and picked us up closer to where we stayed instead of driving up to where he is. A very nice gentleman. You would always see him smile which is a very nice gesture.

  6. Yves

    Yves

    4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!

    Spectacular time with Joe! My wife and I absolutely loved the trip and specifically appreciated Joe’s knowledge, patience, and attention. We enthusiastically endorse Joe and his boat the Beluga! Thanks for sharing the day Joe and giving us wonderful memories of Newport and the Narragansett Bay!