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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,374 Reviews)

Page 21 of 38889 listings

45' Sea Ray Yacht Charter in Turks & Caicos
Powerboats in The Bight Settlement · 15 guests

45' Sea Ray Yacht Charter in Turks & Caicos

New
$500/hour
Sailing Adventure on Bay in Miami on Tartan Sailboat!
Sailing in Key Biscayne · 4 guests

Sailing Adventure on Bay in Miami on Tartan Sailboat!

5.0
$100/hour
45' Lagoon Luxury Catamaran Charter in Riviera Maya
Sailing in Puerto Aventuras · 30 guests

45' Lagoon Luxury Catamaran Charter in Riviera Maya

5.0
$366+/hour
Instant Book
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 2025
$183/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
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
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
Charter this  53ft Cruising Catamaran for a Boat Party in Cancún, Quintana Roo
Sailing in Cancún · 55 guests

Charter this 53ft Cruising Catamaran for a Boat Party in Cancún, Quintana Roo

New
$457/hour
Experience Maine on 65ft Classic Schooner Yacht
Sailing in Rockport · 30 guests

Experience Maine on 65ft Classic Schooner Yacht

5.0
$500/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
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
Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish
Sailing in Negril · 100 guests

Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish

New
$1,800/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
Luxury Yacht Sailing Tour inclusive of Lunch and Drinks on board Aquila 44’
Events in Nassau · 12 guests

Luxury Yacht Sailing Tour inclusive of Lunch and Drinks on board Aquila 44’

New
$700/hour
The Only Vessel For Big Groups in Cancun (Up To 60 people)
Events in Cancún · 60 guests

The Only Vessel For Big Groups in Cancun (Up To 60 people)

New
$394+/hour
46ft Luxury Sail Catamaran - Single & Multi-Day Catamaran Expeditions | PVR
Sailing in Nuevo Vallarta · 25 guests

46ft Luxury Sail Catamaran - Single & Multi-Day Catamaran Expeditions | PVR

New
$624+/hour
Instant Book
2019 Hudson 48' Yacht Charter!! Wider than a 70ft yacht !
Events in Cancún · 14 guests

2019 Hudson 48' Yacht Charter!! Wider than a 70ft yacht !

New
$699/hour
MAXICAT 65ft Private Party Catamaran in Cartagena
Sailing in Cartagena · 80 guests

MAXICAT 65ft Private Party Catamaran in Cartagena

New
Superowner
Best of 2025
$6,700/day
Private overnight Charter on a Luxurious Fountaine Pajot 47 up to 8 guests
Sailing in Nassau · 9 guests

Private overnight Charter on a Luxurious Fountaine Pajot 47 up to 8 guests

New
Best of 2025
$3,715+/night
Catalina 27 Sailboat Rental in Olga, Washington
Sailing in Anacortes · 6 guests

Catalina 27 Sailboat Rental in Olga, Washington

5.0
$90+/hour
Amazing Day On Catamaran 43 FT With Unlimited Open Bar Cancun and Isla Mujeres
Sailing in Cancún · 35 guests

Amazing Day On Catamaran 43 FT With Unlimited Open Bar Cancun and Isla Mujeres

New
$280/hour
Rent This Lux Sea Ray 33’ Miami Experience
Events in Miami · 12 guests

Rent This Lux Sea Ray 33’ Miami Experience

New
$130+/hour
42' Luxury Catamaran Sailboat
Sailing in Miami · 6 guests

42' Luxury Catamaran Sailboat

New
$285/hour
Sailing Catamaran Rental in West Bay
Sailing in West Bay · 50 guests

Sailing Catamaran Rental in West Bay

5.0
$288/hour

Sailing Reviews in United States

  1. 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.

  2. 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 .

  3. 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.

  4. 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

  5. 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

  6. Sreenivasan

    Sreenivasan

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

    Excellent sail boat and amazing crew. We had an unforgettable experience. The When & If… is a beauty! Thank you Capt. Seth & team of pirates :)..