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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,462 Reviews)

Page 17 of 41 • 962 listings

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
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
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
$429/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
40ft Catamaran Private Charter / Capacity 30 people
Sailing in Cancún · 30 guests

40ft Catamaran Private Charter / Capacity 30 people

5.0
Superowner
$275+/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
42' Lagoon Luxury Catamaran Charter in Riviera Maya
Sailing in Puerto Aventuras · 25 guests

42' Lagoon Luxury Catamaran Charter in Riviera Maya

5.0
$338+/hour
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/hour
Boat for Groups of up to 60 People in Cancún, Quintana Roo
Events in Cancún · 61 guests

Boat for Groups of up to 60 People in Cancún, Quintana Roo

5.0
$188/hour
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/hour
44' Catamaran Party Boat In Grand Bahamas Island
Sailing in Bell Channel Bay · 45 guests

44' Catamaran Party Boat In Grand Bahamas Island

4.6
$140/hour
Fountaine Pajot 38ft Catamaran in Isla Mujeres Fountain Pajot
Sailing in Centro - Supmza. 001 · 18 guests

Fountaine Pajot 38ft Catamaran in Isla Mujeres Fountain Pajot

5.0
$250/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
100' Cruising Catamaran with Unlimited Food and Drinks in Cabo San Lucas
Sailing in Marina · 130 guests

100' Cruising Catamaran with Unlimited Food and Drinks in Cabo San Lucas

5.0
$60/day
Private Sailing Tours in Playa Flamingo, Guanacaste
Sailing in Playa Flamingo · 17 guests

Private Sailing Tours in Playa Flamingo, Guanacaste

5.0
Superowner
$186+/hour
20ft Bayliner VR5 Boat in Rockville, IN
Powerboats in Indiana · 6 guests

20ft Bayliner VR5 Boat in Rockville, IN

5.0
$510/day
Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”
Sailing in Chicago · 10 guests

Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”

5.0
$275/hour
Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat
Sailing in Marina · 10 guests

Sail Cabo in Style - Escape the Crowds on a Private 36ft Sailboat

5.0
$150/hour
Private sailing tour in Cancún Mexico
Sailing in Isla Mujeres · 8 guests

Private sailing tour in Cancún Mexico

5.0
$150/hour
23' Ranger Daysailer in Oakland, California
Sailing in Oakland · 5 guests

23' Ranger Daysailer in Oakland, California

5.0
$70/hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$450/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. BG

    Brittany

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

    BEST TRIP EVER! WOW! For my combined bach/bachelorette we were greeted with an amazing crew and best of all, SHOTS lol. The crew was clear about the rules and expectations on our trip and ensured our safety. We had the most amazing ride out on the ocean, the catamaran was gorgeous, clean, spacious, better than we could have imagined. The staff Aldo, Master P, Captain Juan, and Omar absolutely made our trip. They were joining in our fun and showing us how to enjoy the ocean safely. We were provided snorkeling gear, and were able to swim with and touch stingrays, this was a dream to say the least! The floating pad and paddle board were also amazing to hang out on. We didn't know what to expect with the food, and boy, they did not disappoint, the burgers were delicious, the guacamole was insane and the ceviche literally made this trip. Also, the photography skills of the staff, they had us in the best spots on the boat and made the funniest video for us. My group has been on several boats and this is BY FAR THE MOST AMAZING EXPERIENCE. Wish we could do it all over again. HIGHLY RECOMMEND!😊

  3. DC

    Donte

    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

    From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

  4. KB

    Kailee

    Rent 26ft Colgate Sailboat In Kemah, Texas

    Absolutely fantastic trip! I booked the boat for a graduation photoshoot for myself & Heidi & Colt were super great & accommodating during the trip! While I didn’t use the boat for a typical trip, I still had such a great time & would definitely recommend them!

  5. Ani

    Ani

    42' Lagoon Luxury Catamaran Charter in Riviera Maya

    We had the absolute pleasure of renting Chris’s catamaran for my husband’s 40th birthday in Tulum, and it was nothing short of phenomenal. The boat itself was beautiful and spacious, but what truly made the experience unforgettable was Chris and his incredible staff. They were superb—attentive, professional, and went above and beyond to make sure every detail was perfect. From start to finish, we felt taken care of, and our group had the best time out on the water. If you’re looking for an unforgettable experience in Tulum, I can’t recommend Chris and his team enough!

  6. Becca

    Becca

    Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

    Amazing in every way! Kip & Elizabeth were so kind and accommodating. We got to relax, snorkel, and even saw some dolphins which made the trip extra memorable. Kip was always responsive to messages and the process couldn’t have been more seamless from start to finish. Couldn’t recommend enough!