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All listings near me

Find Sailing Charters Near You

4.9
(4,703 Reviews)

Page 8 of 10240 listings

Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$290/hour
Instant Book
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
$199/hour
Sail Away on Our Passion: Your 42-Foot Pearson for a Day or Weekend Adventure
Sailing in Dartmouth · 6 guests

Sail Away on Our Passion: Your 42-Foot Pearson for a Day or Weekend Adventure

New
$150/hour
Instant Book
Come Sail & Party on Maybellene our well cared for 34' Beneteau Yacht
Sailing in New Bedford · 6 guests

Come Sail & Party on Maybellene our well cared for 34' Beneteau Yacht

5.0
$150/hour
Instant Book
Elegant 43ft Catamaran: Experience Boston Harbor in Style!
Sailing in Boston · 6 guests

Elegant 43ft Catamaran: Experience Boston Harbor in Style!

5.0
$313+/hour
Sunset Sail Buzzards Bay in a Classic Sloop!
Sailing in Fairhaven · 4 guests

Sunset Sail Buzzards Bay in a Classic Sloop!

5.0
$150/hour
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
$300/hour
Spend the Day on Buzzards Bay - Sail on "Hamlet" a 35 '  J/105 racer/cruiser
Sailing in Mattapoisett · 6 guests

Spend the Day on Buzzards Bay - Sail on "Hamlet" a 35 ' J/105 racer/cruiser

5.0
$195/hour
41ft Island Packet Sailing Adventures
Sailing in Fernandina Beach · 6 guests

41ft Island Packet Sailing Adventures

New
$249/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
Instant Book
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$150/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

New
$125/hour
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+/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
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
4 Hour Private Charter in Destin, FL! Crab Island, Snorkeling, Dolphins & More!
Sailing in Destin · 6 guests

4 Hour Private Charter in Destin, FL! Crab Island, Snorkeling, Dolphins & More!

5.0
$150/hour
3-Hour Daytime Cruise in Destin, Florida
Sailing in Destin · 6 guests

3-Hour Daytime Cruise in Destin, Florida

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
Instant Book
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

Local Sailing Reviews

  1. sk

    sarah

    Custom Sailing Charter - Newport/ Block Island

    Captain Candace, Captain Don and Stephanie were an absolute delight to work with from start to finish. Capt. Candace was very easy to communicate with and worked to accommodate our age diverse group. Great directions and instructions as to how to find the boat, the boat was in pristine condition and VERY comfortable accommodations for our sail. Captain Don and Stephanie were very clear about safety first at all times, very knowledgable sailers and wonderful tour guides and historians when the wind was not working with us. We could not have asked for anything more - the boat and the crew are top notch. We hope to have the opportunity to sail with Candace and crew again. Our sailing experience was the highlight of our trip to Newport.

  2. Madison

    Madison

    Custom Sailing Charter - Newport/ Block Island

    Candace is an amazing host & captain and her boat is absolutely beautiful! The space in the back was more than enough room for our bachelorette party of 6. She lets us BYOB, food, and connect to her bluetooth to play our own music. Not to mention her crew mate Stephanie was also more than happy to be our personal photographer the whole time lol!! 100% recommend sailing with Serendipity Sailing we had SO much fun!

  3. 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.

  4. MF

    Margaret

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

    Six of us took a lovely sail with Dave as our captain. We sailed out to listen to some of the Newport Jazz Festival and then took a turn around the area. We had so much fun, and Dave was great! He's friendly and knowledgeable about points of interest in the area. We will definitely sail with him on the Hurrah again. Thanks Dave!

  5. HR

    Haley

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

    David was the best!!! His boat is beautiful, he had so much knowledge and was so great to talk to, he gave us an unforgettable experience! We’re definitely coming back annually to do more boat tours with David! We took our engagement photos on the boat, had champagne and enjoyed the beautiful weather!

  6. Tyra

    Tyra

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

    A great experience. David is so communicative and made the entire experience perfect! We had some set back due to a passing shower but David called with updates and made sure everything was safe before it began. He was so full of information and made the experience that much better. Look forward to next time!!