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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,447 Reviews)

Page 16 of 40 • 951 listings

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
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
$465+/hour
Leopard 53 Power Catamaran (25-ft wide deck space)
Powerboats in Fort Lauderdale · 13 guests

Leopard 53 Power Catamaran (25-ft wide deck space)

New
$575+/hour
Catalina 30 sailboat  in Portland, Oregon
Sailing in Portland · 12 guests

Catalina 30 sailboat in Portland, Oregon

5.0
$199/hour
San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440
Sailing in Brisbane · 6 guests

San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440

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
Luxury Lagoon 450 Sailing Catamaran in Oceanside
Sailing in Oceanside · 6 guests

Luxury Lagoon 450 Sailing Catamaran in Oceanside

5.0
$250/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
Limited Availability
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
55ft Private Catamaran Charter for Up to 55 Guests in Cancún, Quintana Roo
Sailing in Cancún · 55 guests

55ft Private Catamaran Charter for Up to 55 Guests in Cancún, Quintana Roo

5.0
Superowner
$400+/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
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
Cruising Monohull Charter in Samaná, Dominican Republic
Sailing in Samana · 10 guests

Cruising Monohull Charter in Samaná, Dominican Republic

4.0
$1,586/day
63' Catamaran - Newport, RI - Luxury Sailing For Large Groups!
Sailing in Newport · 40 guests

63' Catamaran - Newport, RI - Luxury Sailing For Large Groups!

5.0
$833/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
$434/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
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
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
Rent 26ft Colgate Sailboat In Kemah, Texas
Sailing in Seabrook · 5 guests

Rent 26ft Colgate Sailboat In Kemah, Texas

5.0
$85/hour
EXCLUSIVE ISLAND CRUISE ENTERTAINMENT MUSIC DANCE PARTY CAPTAIN CHARTER 🏝
Events in La Romana · 150 guests

EXCLUSIVE ISLAND CRUISE ENTERTAINMENT MUSIC DANCE PARTY CAPTAIN CHARTER 🏝

New
Superowner
Best of 2026
$17/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
40ft Catamaran Private Charter / Capacity 30 people
Sailing in Cancún · 30 guests

40ft Catamaran Private Charter / Capacity 30 people

5.0
Superowner
$275+/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. JS

    Janessa

    63' Catamaran - Newport, RI - Luxury Sailing For Large Groups!

    Thank you so much for having us last night! It was truly the BEST boat experience any of us had ! The Captaint and Kiki were the best hosts ! Super helpful and fun !! They exceeded our expectations and the boat was amazing ! Will definitely make this a yearly thing !!!

  2. 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!

  3. 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.

  4. ML

    Michelle

    San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440

    Excellent trip with Captain Joseph! He was so easy to plan the itinerary with beforehand and very fun on board. He made us feel safe and we had a wonderful time sailing around the bay with friends and our dogs! Would go out again with Captain Joseph soon! Definitely a wonderful trip and gorgeous and cozy boat.

  5. DK

    Dmitri

    Charter 36ft Sloop In Westbrook, Connecticut

    We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!

  6. FG

    Frank

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

    Thank you for such an amazing and memorable time. Our family had a blast. It was exactly what we were looking for! Boat was gorgeous and the staff was attentive, friendly and knowledgeable ! Anyone looking to charter, you guys will be our go to recommendation for sure!