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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,648 Reviews)

Page 26 of 451,074 listings

Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions
Sailing in Fort Myers Beach · 12 guests

Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions

New
$300hour
44ft Sea Ray Sundancer Motor Yacht Rental in Quintana Roo, Mexico
Events in Cancún · 14 guests

44ft Sea Ray Sundancer Motor Yacht Rental in Quintana Roo, Mexico

New
$400hour
2 Hours Sailing Tour For Bloggers in Marina Del Rey, California
Sailing in Marina del Rey · 6 guests

2 Hours Sailing Tour For Bloggers in Marina Del Rey, California

New
$167hour
Cruising Catamaran Charter in Cabarete, Dominican Republic
Sailing in Cabarete · 80 guests

Cruising Catamaran Charter in Cabarete, Dominican Republic

New
$75hour
Beatiful Catalina 42' Yacht Rental in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Beatiful Catalina 42' Yacht Rental in Puerto Vallarta

New
Superowner
Best of 2023
$138-$148hour
Classic rowboat photoshoot
Sailing in Vancouver · 2 guests

Classic rowboat photoshoot

New
$194hour
San Francisco Sailing Awesomeness aboard Custom 42' Globetrotting Sloop
Sailing in Sausalito · 6 guests

San Francisco Sailing Awesomeness aboard Custom 42' Globetrotting Sloop

5.0
$125hour
Sailing Cataraman 48ft "Bubble"
Sailing in Miami · 12 guests

Sailing Cataraman 48ft "Bubble"

New
$177person
Lagoon 42’ 2019 for sleep-aboard island hop in Puerto Aventuras.
Sailing in Puerto Aventuras · 6 guests

Lagoon 42’ 2019 for sleep-aboard island hop in Puerto Aventuras.

New
Best of 2023
$639hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$290hour
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$250-$349hour
Enjoy 139' - Luxury Charter Schooner in San Diego
Sailing in San Diego · 77 guests

Enjoy 139' - Luxury Charter Schooner in San Diego

5.0
$1,750hour
MAXICAT 65ft Private Party Catamaran in Cartagena
Sailing in Cartagena · 80 guests

MAXICAT 65ft Private Party Catamaran in Cartagena

New
Superowner
Best of 2023
$3,500day
All-Inclusive Private Yacht Charter on 62' Luxury Sunreef Yacht *Captain & Chef*
Sailing in Nassau · 25 guests

All-Inclusive Private Yacht Charter on 62' Luxury Sunreef Yacht *Captain & Chef*

New
$800hour
All Inclusive Luxury Power Vessel holds up to 30 people. Best Vessel Ever!
Powerboats in Tulum · 30 guests

All Inclusive Luxury Power Vessel holds up to 30 people. Best Vessel Ever!

New
$593hour
35.5' Hunter-Legend Cruising Monohull
Sailing in Oakland · 6 guests

35.5' Hunter-Legend Cruising Monohull

5.0
$115hour
Cozy, Fast, and Fun Sailboat in Vancouver!
Sailing in Vancouver · 4 guests

Cozy, Fast, and Fun Sailboat in Vancouver!

5.0
$146hour
Lagoon 470 extended in 52'
Sailing in Guna Yala Comarca · 12 guests

Lagoon 470 extended in 52'

New
$1,300night
Sailing Catamaran Rental in West Bay
Sailing in West Bay · 50 guests

Sailing Catamaran Rental in West Bay

5.0
$90person
Sailing Lesson in Little River, South Carolina
Tours in Little River · 1 guest

Sailing Lesson in Little River, South Carolina

New
$360hour
64' Luxury Horizon Sport Yacht Rental in Fort Myers Beach, Florida
Events in Fort Myers Beach · 12 guests

64' Luxury Horizon Sport Yacht Rental in Fort Myers Beach, Florida

New
$500-$825hour
All Inclusive Luxury Sailing Vacation in Belize
Sailing in Stann Creek District · 6 guests

All Inclusive Luxury Sailing Vacation in Belize

New
$3,395night
PRIVATE BOAT-VIP EXPERIENCE 🤩🛥ENJOY A BEAUTIFULL PARTY BOAT in Puerto Plata
Events in Sosúa · 25 guests

PRIVATE BOAT-VIP EXPERIENCE 🤩🛥ENJOY A BEAUTIFULL PARTY BOAT in Puerto Plata

New
Superowner
$59person
50' Cruising Catamaran in Casa de Campo, La Romana
Sailing in La Romana · 20 guests

50' Cruising Catamaran in Casa de Campo, La Romana

New
$2,395day

Sailing Reviews in United States

  1. LK

    Levko

    San Francisco Sailing Awesomeness aboard Custom 42' Globetrotting Sloop

    Wonderful trip. Really appreciated Evan letting us reschedule initially due to some really bad weather. We did a big loop and saw amazing views of the Golden Gate bridge, Presidio, and Angel Island. Evan had great stories and anecdotes the whole way. Would absolutely recommend Evan!

  2. PV

    Piet

    San Francisco Sailing Awesomeness aboard Custom 42' Globetrotting Sloop

    Evan did a fantastic job making our trip amazing! The boat, the itinerary, the attention to detail, and the experience he clearly had all made this an unforgettably fantastic trip. The boat was beautiful and Evan even let us drive and taught the group about sailing! I can't recommend sailing with Evan enough, you will not be disappointed!

  3. 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!

  4. Pamela

    Pamela

    Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

    We booked this experience for my husbands birthday and it was PERFECT! The Selina II IS STUNNING, and Captain Iris and her crew were absolutely wonderful. Captain Matt was fantastic! He took such good care of us while we sailed across the Chesapeake Bay and celebrated with a couple of glasses of delicious champagne! Look no further and book the Selina II, you won’t regret it, it’s absolutely worth it !!

  5. KR

    Kristin

    San Francisco Sailing Awesomeness aboard Custom 42' Globetrotting Sloop

    Our expereince was so much fun! Evan provided a safe and knowledgeable environment all while taking in the views of the bay! This was an amazing first time sailing - 10/10 would recommend!

  6. Tori

    Tori

    Cozy, Fast, and Fun Sailboat in Vancouver!

    Aidan was an incredibly friendly and fun captain/host. Him and his great lil sailboat made my moms 60th Birthday feel really special! Would definitely book again :)