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Find Sailboat Rentals Near You

4.9(Average of 206 reviews in this area)
Learn more about sail rentals and experiences
Page 1 of 2 (47 listings)
Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed Captain
Sailing in Havre de Grace · 6 guests

Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed Captain

New
$200hour
Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)
Tours in Havre de Grace · 2 guests

Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)

New
$200person
The most ROMANTIC sailboat on the Chesapeake Bay
Poquoson · 4 guests

The most ROMANTIC sailboat on the Chesapeake Bay

New
$250hour
Classic Sparkman & Stevens Sailboat: Choose Leisure Sailing or Hands-On Lessons
Sailing in Lacey Township · 6 guests

Classic Sparkman & Stevens Sailboat: Choose Leisure Sailing or Hands-On Lessons

New
$99hour
#1 Manhattan Sailboat! Captain, Crew, Champagne & Catering Service: 5-Star Luxury at Chelsea Piers
Sailing in Manhattan · 6 guests

#1 Manhattan Sailboat! Captain, Crew, Champagne & Catering Service: 5-Star Luxury at Chelsea Piers

5.0
Superowner
$325hour
Instant Book
Jeanneau 39i Julia Sailing Yacht in NY Harbor
Sailing in Manhattan · 9 guests

Jeanneau 39i Julia Sailing Yacht in NY Harbor

5.0
$300hour
Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC
Sailing in Manhattan · 6 guests

Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

5.0
$330hour
Hobie One 12 ft Sailboat for rent in Sag Harbor
Sailing in Sag Harbor · 3 guests

Hobie One 12 ft Sailboat for rent in Sag Harbor

New
$99hour
Sailing Charter in Toronto
Sailing in Toronto · 6 guests

Sailing Charter in Toronto

5.0
$75person
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$215hour
Tandem Sail on TWO Classic Sailboats (Or Just Charter One)
Sailing in Newport · 12 guests

Tandem Sail on TWO Classic Sailboats (Or Just Charter One)

New
$175hour
Sail Newport Rhode Island with Captain Kurt on 36' Pearson Sailboat
Sailing in Newport · 6 guests

Sail Newport Rhode Island with Captain Kurt on 36' Pearson Sailboat

New
$250hour
Tanzer 26' Small Sailboat for Day in Charlotte
Sailing in Charlotte · 6 guests

Tanzer 26' Small Sailboat for Day in Charlotte

New
$350day
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
Captained Sailing Charter in Charleston
Sailing in Charleston · 4 guests

Captained Sailing Charter in Charleston

New
$220hour
2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN GREENSBORO
Sailing in Georgia · 2 guests

2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN GREENSBORO

New
$40hour
Sail Aboard 148' Tall Ship Windy - The Official Ambassador of the City of Chicago - 1pm Daily ONLY
Tours in Chicago · 150 guests

Sail Aboard 148' Tall Ship Windy - The Official Ambassador of the City of Chicago - 1pm Daily ONLY

New
$42person
40' Luxury Cruiser/Racer Sailboat with Captain Monroe Harbor Chicago
Sailing in Chicago · 6 guests

40' Luxury Cruiser/Racer Sailboat with Captain Monroe Harbor Chicago

New
$400hour
2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN JACKSONVILLE
Sailing in Jacksonville · 2 guests

2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN JACKSONVILLE

New
$40hour
2022 Lexington Pontoon Boat rental in Fort Walton Beach/ Destin FL.
Powerboats in Fort Walton Beach · 5 guests

2022 Lexington Pontoon Boat rental in Fort Walton Beach/ Destin FL.

4.9
$75hour
38ft Sailing Catamaran in Clearwater Beach Day Sails and Sunset Cruises, Events, Celebrations!
Clearwater · 12 guests

38ft Sailing Catamaran in Clearwater Beach Day Sails and Sunset Cruises, Events, Celebrations!

New
$14-199hour
ALL FEES INCLUDED! 38’ Morgan Sailboat Rental in Miami Beach.
Sailing in Miami Beach · 6 guests

ALL FEES INCLUDED! 38’ Morgan Sailboat Rental in Miami Beach.

5.0
Superowner
$92-100hour
65ft Searay Power Mega Yacht Rental in Miami, Florida
Miami · 13 guests

65ft Searay Power Mega Yacht Rental in Miami, Florida

New
$275hour
Enjoy Miami In Our Luxury 75ft Sunseeker Sport Yacht
Events in Miami · 13 guests

Enjoy Miami In Our Luxury 75ft Sunseeker Sport Yacht

New
$300hour

Time to set sail in the most beautiful locations in the world.

Rent or charter a sailboat for your next water experience. Whether you're looking for a small sailboat, a luxury sailing yacht, a catamaran, or a racing sailboat, you're sure to find the perfect vessel for your desired experience on GetMyBoat. Sailboat rentals are a great way to explore if you're traveling to top sailing destinations like the Chesapeake Bay, Mission Bay, Lake Tahoe, or Cape Cod. Book a sailboat to fit your budget and itinerary with GetMyBoat.

Local Sail Reviews

  1. Gizem
    Gizem
    #1 Manhattan Sailboat! Captain, Crew, Champagne & Catering Service: 5-Star Luxury at Chelsea Piers

    This is our third boat ride on captain Martins boat and as always we had the absolute best time. I’m always so glad I choose to sail with them and always leave, planning on when is the soonest time I could come and book again. Captain Martin was extremely accommodating & professional throughout the entire booking process and his boat has everything you could ever need. The boat is extremely clean and in great condition. Highly recommend to every single person. Captain Caleb and Gino also made our experience so much more enjoyable & went above and beyond for us. 10/10 - 5 stars isn’t enough to explain what a beautiful experience this is. Runnnnn - don’t walk to book!

  2. FH
    Faraji
    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

    Captain Paul was the absolute best he and his wife just showed so much grace and hospitality. The highlight...Captain Paul let me take the wheel. The Statue of Liberty at sunset was just breathtaking. What an experience and end to Summer 22' I will definitely connect with him again!!!!

  3. Joey
    Joey
    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

    As a native born and raised New Yorker i can honestly say this is a must do for anyone visiting or just looking to do something for the day. Great boat, great time and great crew. Will book again.

  4. LR
    Leonela
    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

    Paul and Melisa were so amazing. I celebrated my birthday on their boat and had a blast. We were able to bring our own food, they did offer providing that as well. Melisa was a great host and made sure we had everything we needed, she was so attentive; our cups were never empty =) We played our own music. The boat had speakers through out. The pictures do not do the boat justice, it is even more amazing in person. My pictures came out perfect. Paul stopped wherever possible so we could get the perfect picture. They were so pleasant and kind and accommodating. I would definitely recommend for any couples looking for a date, friends getting together or even a family gathering as well. It was definitely a birthday to remember and am looking forward to sailing with them again this summer! XOXO Leonela

  5. LA
    Loany
    2022 Lexington Pontoon Boat rental in Fort Walton Beach/ Destin FL.

    Christopher was a great captain, he was very communicative and helpful and made sure everything went smoothly.

  6. Amber
    Amber
    ALL FEES INCLUDED! 38’ Morgan Sailboat Rental in Miami Beach.

    As natives of the Appalachians, our son has always dreamt of having a sailboat one day, yet we know absolutely nothing about boats. Instead of paying an extravagant amount for senior pictures, as he is going to the U of Miami in the fall we decided to book this sailboat adventure while visiting campus, that would allow our son to learn about sailboats as well as provide an opportunity for us to take his senior pictures ourselves while on the boat. Alexei and his girlfriend were more than accommodating to our family, answering any questions we had and making sure we stayed comfortable the entire time. The Bluetooth speaker provided, while unexpected, was such an added bonus to our magical time on the water! If you do absolutely nothing else during your time while in Miami, BOOK THIS JOURNEY, as I promise it’s something you will never regret.

Boating Guide - Sail

Time to set sail in the most beautiful locations in the world.

Rent or charter a sailboat for your next water experience. Whether you're looking for a small sailboat, a luxury sailing yacht, a catamaran, or a racing sailboat, you're sure to find the perfect vessel for your desired experience on GetMyBoat. Sailboat rentals are a great way to explore if you're traveling to top sailing destinations like the Chesapeake Bay, Mission Bay, Lake Tahoe, or Cape Cod. Book a sailboat to fit your budget and itinerary with GetMyBoat.

GetMyBoat has 47 listings for Sail experiences in this location with 206 reviews.

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