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
(8,463 Reviews)

Page 16 of 39932 listings

Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California
Sailing in Newport Beach · 6 guests

Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California

5.0
$160/hour
Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco
Sailing in San Francisco · 6 guests

Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco

5.0
Superowner
$400+/hour
Instant Book
41ft Sailing Charters from Costa Mujeres, Cancun
Sailing in Isla Mujeres · 32 guests

41ft Sailing Charters from Costa Mujeres, Cancun

5.0
Superowner
$248/hour
Private 53' Sailing Catamaran with Cool Crew - Up to 55 People, Open Bar
Sailing in Cancún · 55 guests

Private 53' Sailing Catamaran with Cool Crew - Up to 55 People, Open Bar

5.0
$498+/hour
Catalina 30 sailboat  in Portland, Oregon
Sailing in Portland · 12 guests

Catalina 30 sailboat in Portland, Oregon

5.0
$199/hour
Cancun Shared Catamaran: Isla Mujeres, Snorkeling, Drinks & Buffet Lunch
Sailing in Cancún · 40 guests

Cancun Shared Catamaran: Isla Mujeres, Snorkeling, Drinks & Buffet Lunch

5.0
$60/day
Luxury Lagoon 450 Sailing Catamaran in Oceanside
Sailing in Oceanside · 6 guests

Luxury Lagoon 450 Sailing Catamaran in Oceanside

5.0
$250/hour
Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht
Sailing in New Bedford · 6 guests

Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht

5.0
$260+/hour
Cruising Monohull Charter in Samaná, Dominican Republic
Sailing in Samana · 10 guests

Cruising Monohull Charter in Samaná, Dominican Republic

4.0
$1,586/day
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
Dream sailing a wonderful experience on the water | 40'  Sun Odyssey Sailboat
Sailing in Marina del Rey · 6 guests

Dream sailing a wonderful experience on the water | 40' Sun Odyssey Sailboat

New
$250/hour
42' Wanderlust - The Best Sailing Cat in the Market - Sarasota
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

5.0
$499+/hour
All-Inclusive Luxury Catamaran in Puerto Vallarta
Sailing in Nuevo Vallarta · 14 guests

All-Inclusive Luxury Catamaran in Puerto Vallarta

5.0
$918/hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
$315+/hour
Private Luxury Sunset Sailing Cruise in Cozumel, Mexico
Sailing in San Miguel de Cozumel · 35 guests

Private Luxury Sunset Sailing Cruise in Cozumel, Mexico

5.0
$464/hour
Limited Availability
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 12 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
Rent 26ft Colgate Sailboat In Kemah, Texas
Sailing in Seabrook · 5 guests

Rent 26ft Colgate Sailboat In Kemah, Texas

5.0
$85/hour
Private 44ft Catamaran Charter for Up to 45 Guests
Sailing in Cancún · 45 guests

Private 44ft Catamaran Charter for Up to 45 Guests

5.0
Superowner
$343+/hour
44' Leopard Catamaran All-Inclusive Charter in Tulum Beach.
Sailing in Tulum · 35 guests

44' Leopard Catamaran All-Inclusive Charter in Tulum Beach.

4.5
Superowner
Best of 2026
$520/hour
Now available: 53" Carver Yacht for spring and summer sunset & day cruises
Events in Galveston · 12 guests

Now available: 53" Carver Yacht for spring and summer sunset & day cruises

5.0
$400/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
Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!
Events in Cabarete · 100 guests

Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!

New
Superowner
Best of 2026
$17/hour
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/hour

Sailing Reviews in United States

  1. LA

    LisaMarie

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

    We had the pleasure of sailing with Nat over the 4th of July weekend, and it was a fantastic experience from start to finish. He was punctual, courteous, and instantly put us at ease with his friendly demeanor. What stood out most was how attentive he was to our individual experience levels on the water — he adjusted his approach throughout the day so that everyone, regardless of sailing background, felt comfortable and included. Nat is clearly a highly accomplished sailor, but he wears that expertise lightly. The day felt relaxed as we navigated the waters of the San Juan Islands. — great conversation, great skill, and a great time on the water.

  2. Lauren

    Lauren

    Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California

    We had a really fun trip through the harbor and down the coast for my husband’s Birthday. Captain Andrew was able to find the sweet spot between sharing interesting information and allowing us to enjoy the natural scenery. The kids loved how all the other boats wanted to sail up to ours to yell “Argghhhh!l” and “Ahoy!!!”

  3. Shubhobroto

    Shubhobroto

    Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California

    The trip was very interesting, particularly for my 5 year old as he wanted a pirate ship experience on his birthday. The captain and crew were very professional and made sure we were comfortable. Our needs were take care off. We had a great great time. I would suggest to stay in and around the bay and less of deep waters, as it gets a bit bumpy in deep waters. We enjoyed every bit of the trip. We will surely want to do it again😀.

  4. SC

    SHONTEK

    Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California

    The crew, lead by Captain Andrew, was incredibly professional. They made the trip very fun. The small boat that took us to the big boat was impressive, but, the big boat was amazing. Truly breathtaking when the sails went up. My 5yr old had so much fun. Great trip!!! Will do it again.

  5. NA

    Nicole

    Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco

    Everyone I worked with while planning a sailing excursion for my team was amazing. I called lots of times to get answers to questions regarding the itinerary and the team was very helpful and responsive. The team went above and beyond in all aspects and the trip was fantastic. I would highly recommend this company!

  6. Ana

    Ana

    Catalina 30 sailboat in Portland, Oregon

    Captain Shane warmly welcomed us into his boat. He was really accommodating throughout the course of sailing. I love the conversations and trivia he tells us about the views. The boat was superb and amazing! I love it with or without the mainsail. Overall, our experience was really great! We will definitely want to do this again with him as our Captain.