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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,144 Reviews)

Page 38 of 39923 listings

Sailing Catamaran Adventures 50' Catamaran La Paz, BCS MX (6 Cabin, Max 12 Pass)
Sailing in Las Garzas · 12 guests

Sailing Catamaran Adventures 50' Catamaran La Paz, BCS MX (6 Cabin, Max 12 Pass)

New
$332/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$200+/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
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$50/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
27' Oday Sailboat for Easy Sailing and Bay Adventures
Sailing in Redwood City · 6 guests

27' Oday Sailboat for Easy Sailing and Bay Adventures

New
$99/hour
Karisma 45 ft Sun Odyssey Jeanneau
Sailing in Seabrook · 6 guests

Karisma 45 ft Sun Odyssey Jeanneau

5.0
Snoozed - Active 13 Apr 2026
Woman-owned luxury with transparent pricing - read our 5-star reviews!
Sailing in Manhattan · 6 guests

Woman-owned luxury with transparent pricing - read our 5-star reviews!

5.0
Snoozed - Active 03 May 2026
Efoiling at deer creek reservoir
Adventures in Salt Lake City · 1 guest

Efoiling at deer creek reservoir

5.0
Snoozed - Active 15 Jan 2027
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
Snoozed - Active 17 Apr 2026
Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.
Sailing in Brooklyn · 6 guests

Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.

5.0
Snoozed - Active 02 Jan 2027
Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)
Powerboats in Cartagena · 16 guests

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)

5.0
Snoozed - Active 02 Aug 2026
1980 Catalina 38ft Sparkman & Stephens Sailboat in Long Beach
Sailing in Long Beach · 10 guests

1980 Catalina 38ft Sparkman & Stephens Sailboat in Long Beach

3.7
Snoozed - Active 02 May 2026
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

5.0
Snoozed - Active 03 May 2026
Islander 36 - The Perfect Sailing Yacht for San Francisco Bay
Sailing in Sausalito · 6 guests

Islander 36 - The Perfect Sailing Yacht for San Francisco Bay

5.0
Snoozed - Active 02 Jul 2026
Beautiful Sailboat for Private Outings, South Bay LA, King Harbor Marina
Sailing in Redondo Beach · 6 guests

Beautiful Sailboat for Private Outings, South Bay LA, King Harbor Marina

5.0
Snoozed - Active 02 Sep 2026
North River Sailing - See NYC from a Classic Racing Yacht
Sailing in Manhattan · 6 guests

North River Sailing - See NYC from a Classic Racing Yacht

5.0
Snoozed - Active 03 May 2026
Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida
Sailing in West Palm Beach · 12 guests

Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida

5.0
Snoozed - Active 31 Jul 2026
⚓️ Luxury 45' Catamaran Charter 2019 in Puerto Vallarta
Sailing in Marina Vallarta · 16 guests

⚓️ Luxury 45' Catamaran Charter 2019 in Puerto Vallarta

4.0
Snoozed - Active 02 May 2026
Private Sailing Charter on Martha's Vineyard
Sailing in Tisbury · 6 guests

Private Sailing Charter on Martha's Vineyard

5.0
Snoozed - Active 02 Jul 2026
40' Luxury Cruising Sailboat – Private Charters for 8 Guests
Sailing in Richmond · 8 guests

40' Luxury Cruising Sailboat – Private Charters for 8 Guests

New
Snoozed - Active 19 Apr 2026
Axe 1 Center Console Boat Rental in Montego Bay, Jamaica
Events in Montego Bay · 8 guests

Axe 1 Center Console Boat Rental in Montego Bay, Jamaica

New
Snoozed - Active 03 Sep 2026
Catamaran boat Party La Paz
Events in Zona Comercial · 12 guests

Catamaran boat Party La Paz

New
Superowner
Snoozed - Active 03 Oct 2026

Sailing Reviews in United States

  1. AB

    Annie

    Woman-owned luxury with transparent pricing - read our 5-star reviews!

    We had such a good experience with Jessica and Captain Dan! The boat was supplied with basic needs and a bathroom! There is a Bluetooth speaker and a bean bag in the front of the boat so that you can lounge there if you'd like. The communication up front was excellent and easy to follow. I highly recommend this experience. Myself and the 5 others in tow had the best time! Thank you!

  2. JC

    Julia

    Woman-owned luxury with transparent pricing - read our 5-star reviews!

    Highly Recommend!!! Jessica was very responsive and helpful with helping me plan our last minute sailing. Everything was exactly as described. The ship was clean with nice amenities for our entire party. Captain Kevin was extremely knowledgeable and provided a great experience with plenty of photo opportunities! We can’t wait to do this again!!

  3. Demi

    Demi

    Woman-owned luxury with transparent pricing - read our 5-star reviews!

    Wish I could give 6 stars on every category. This is my second year booking a trip with Jessica and I won’t look elsewhere for this kind of trip. Every captain is kind and helpful and makes the experience even better. Can’t say enough good things!

  4. JF

    Joseph

    Woman-owned luxury with transparent pricing - read our 5-star reviews!

    Jessica and Captain Kevin were exceptional. This was my first charter, it was a last minute booking on a holiday weekend, and for a special occasion (proposal). Jessica was more than prepared and made it so simple! We literally just had to show up. She already communicated the details to the Captain when we arrived. Captain Kevin had the boat prepped and ready to go. We arrived at the private parking, got on the boat (which was beautiful and a perfect size), and enjoyed our experience! Captain Kevin took care of setup, clean up, and even acted as our impromptu photographer at the moment of the proposal. Jessica and her crew are a well oiled machine and I wouldn't hesitate to book with her again for special occasions or simply a day out with friends. I'm living proof, no experience necessary. I look forward to the opportunity to sail aboard Sailing Islander in the future!

  5. Alexandra

    Alexandra

    Woman-owned luxury with transparent pricing - read our 5-star reviews!

    We had an amazing time on Jessica’s boat & Captain Jack was very accommodating. At night the city looked like it was floating on water & the views were absolutely breathtaking… Made both my girlfriend & I cry it was so magical (and we’re not criers lol) The sailboat was very clean & we will definitely rent with Jessica again!

  6. MM

    Melissa

    Woman-owned luxury with transparent pricing - read our 5-star reviews!

    This was a surprise birthday present for my sister-in-law. She always wanted to be on a boat. Upon planning this I didn’t know where to start but as soon as I got in contact with Jessica everything fell into place. Every step was clear Jessica went through everything with me. The day of it went smooth better than I ever thought. Our captain Christa was so sweet she was so friendly and inviting. She answered every question we had. She went over everything with us. We started at Jersey city and went to NY and back. We got to look at the sunset, saw other boats pass us (ours was better of course) it was an amazing experience. Christa let us do our thing and made us feel comfortable it honestly felt like she was one of our friends who happen to have a boat. That’s my girl, I love her. My sister-in-law loved it, it was a great time. We ate, listened to music, and just vibed. Our Captain even said my daughters Mac and cheese was bomb.