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 in the United States

Awesome sailboat rentals in United States.

4.9
(8,052 Reviews)

Page 22 of 39920 listings

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
45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay
Sailing in San Diego · 6 guests

45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay

5.0
$550+/hour
43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0
$150+/hour
Manuel Antonio Catamaran Private ''Spanish Dancer''
Sailing in Quepos · 12 guests

Manuel Antonio Catamaran Private ''Spanish Dancer''

5.0
$1,500/hour
Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne
Tours in Miami Beach · 10 guests

Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne

New
Superowner
$159+/hour
Newport Private Day Sail onboard 28' Sabre Yacht Serenity
Sailing in Newport · 4 guests

Newport Private Day Sail onboard 28' Sabre Yacht Serenity

New
$150/hour
Catamaran |15 People |Choptank River
Sailing in Maryland · 15 guests

Catamaran |15 People |Choptank River

New
Superowner
$700/hour
Experience Maine on 65ft Classic Schooner Yacht
Sailing in Rockport · 30 guests

Experience Maine on 65ft Classic Schooner Yacht

5.0
$500/hour
Cruising Catamaran Rental in Puerto Plata, Puerto Plata
Sailing in Barrio Las Yaguitas · 80 guests

Cruising Catamaran Rental in Puerto Plata, Puerto Plata

1.0
Superowner
Best of 2026
$183/hour
Sailing Adventure on Bay in Miami on Tartan Sailboat!
Sailing in Key Biscayne · 6 guests

Sailing Adventure on Bay in Miami on Tartan Sailboat!

5.0
$100/hour
65 People - All inclusive service aboard the 65ft Power Catamaran
Events in Marina · 65 guests

65 People - All inclusive service aboard the 65ft Power Catamaran

New
$548/hour
Cabo Private Sail & Snorkel Tour Arch & Open Bar
Sailing in Marina · 8 guests

Cabo Private Sail & Snorkel Tour Arch & Open Bar

New
$200/hour
Maxicat 65ft Private Party Catamaran in Cartagena
Sailing in Cartagena · 80 guests

Maxicat 65ft Private Party Catamaran in Cartagena

New
Superowner
$838/hour
Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington
Tours in Anacortes · 6 guests

Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington

5.0
$200/hour
Isla Mujeres Eco Catamaran Experience with Snorkeling & Beach Club
Sailing in Cancún · 30 guests

Isla Mujeres Eco Catamaran Experience with Snorkeling & Beach Club

New
Superowner
Best of 2026
$75/hour
Hunter 'Legend' Sailboat, 36ft in Seabrook, Texas
Sailing in Seabrook · 8 guests

Hunter 'Legend' Sailboat, 36ft in Seabrook, Texas

5.0
$151+/hour
Dunn’s River Falls Private Catamaran Cruise – Ocho Rios
Powerboats in Ocho Rios · 100 guests

Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

New
$654/hour
Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami
Events in Miami · 13 guests

Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami

New
$250/hour
Discover the magic of the sea | Westsail 43' Private Sailing Tours
Sailing in San Diego · 12 guests

Discover the magic of the sea | Westsail 43' Private Sailing Tours

New
$280/hour
Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience
Events in Sosúa · 25 guests

Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience

New
$135/hour
French 42ft Sailboat for Romantic and All Inclusive Sailing Experience in Cabo
Sailing in Marina · 12 guests

French 42ft Sailboat for Romantic and All Inclusive Sailing Experience in Cabo

New
$377/hour
Custom 40ft Sail Boat Rental in Cozumel
Sailing in Centro · 12 guests

Custom 40ft Sail Boat Rental in Cozumel

New
$181+/hour
Luxury Catamaran Belize, Private Chef & Hol Chan Snorkeling
Powerboats in San Pedro · 12 guests

Luxury Catamaran Belize, Private Chef & Hol Chan Snorkeling

New
$882/hour
Catalina 27 Sailboat Rental in Olga, Washington
Sailing in Anacortes · 6 guests

Catalina 27 Sailboat Rental in Olga, Washington

5.0
$90+/hour

Sailing Reviews in United States

  1. JM

    Julie

    Hunter 'Legend' Sailboat, 36ft in Seabrook, Texas

    The girls had such a great time! They appreciated the upgrade (when y'all found out it was a bachelorette party they got the upgrade) and said the boat driver was very attentive and super nice! It was the best part of their bachelorette weekend! Thank you!

  2. AA

    Adam

    45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay

    What can I say except a big thank you for the best experience I’ve had before! It’s been an adventure holiday and for me personally, an awakening. You gave it your all for me and it's been totally great. Your new friend, Adam.

  3. Rachel

    Rachel

    Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington

    What a fun day sailing around the orcas . Nat was an amazing sailing instructor and we loved learning about sailing and checking out the islands by water . Would highly recommend doing this - highlight of the trip .

  4. MS

    Michelle

    Catalina 27 Sailboat Rental in Olga, Washington

    Lots to learn of you're new at sailing. Great teacher. Guess over it until you get it. Did a wonderful job explaining everything. The who what when where and why's. Also gave us a great dinner ideas.

  5. MH

    Madeline

    Experience Maine on 65ft Classic Schooner Yacht

    It was an absolutely beautiful sail! The captain and crew were so personable, sweet and accommodating! Gorgeous day and a BREATHTAKING boat! 10000/10 would recommend

  6. LT

    Lloyd

    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

    Davis was our captain, he was great . Very informative and knowledgeable . We went on a 31/2 hour sail in the Chesapeake bay. Would definitely do it again