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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,285 Reviews)

Page 19 of 40939 listings

Experience Ultimate Tropical Luxury on 38' Lagoon Catamaran in Nuevo Vallarta
Sailing in Nuevo Vallarta · 23 guests

Experience Ultimate Tropical Luxury on 38' Lagoon Catamaran in Nuevo Vallarta

5.0
$350+/hour
32ft Irwin Citation Sailboat for Beautiful Sail on Lake Erie (Cleveland area)
Sailing in Cleveland · 6 guests

32ft Irwin Citation Sailboat for Beautiful Sail on Lake Erie (Cleveland area)

5.0
$325+/hour
30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida
Powerboats in Deerfield Beach · 10 guests

30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

5.0
$200/hour
Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!
Sailing in Manhattan · 6 guests

Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!

5.0
$224+/hour
Relax, feel free & sail into a nautical world of Wonder - Hunter 36 Sailboat
Sailing in Berkeley Township · 6 guests

Relax, feel free & sail into a nautical world of Wonder - Hunter 36 Sailboat

New
$125/hour
60ft Luxury Catamaran Private Charter / Capacity 60 people
Sailing in Cancún · 60 guests

60ft Luxury Catamaran Private Charter / Capacity 60 people

5.0
Superowner
$442+/hour
Pajot 46 Sailing Catamaran in Tulum and Playa!!
Sailing in Tulum · 15 guests

Pajot 46 Sailing Catamaran in Tulum and Playa!!

5.0
Superowner
$450/hour
Sailing Lessons on the San Francisco Bay
Tours in Berkeley · 4 guests

Sailing Lessons on the San Francisco Bay

5.0
$123+/day
26ft Beach Cat Private Charter in Savannah GA *COI Vessel
Powerboats in Savannah · 17 guests

26ft Beach Cat Private Charter in Savannah GA *COI Vessel

5.0
$450/hour
La Paz Island Adventure Sailing Cruiser
Sailing in Zona Comercial · 8 guests

La Paz Island Adventure Sailing Cruiser

5.0
$235/hour
Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC
Sailing in Wilmington · 6 guests

Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC

5.0
$350/hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Annapolis · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
★Midcoast Maine aboard the Schooner Yacht Meteor ★
Sailing in Rockland · 4 guests

★Midcoast Maine aboard the Schooner Yacht Meteor ★

5.0
$175/hour
Gorgeous 42' Bali Catamaran in Marina del Rey
Sailing in Marina del Rey · 12 guests

Gorgeous 42' Bali Catamaran in Marina del Rey

New
Superowner
$575/hour
Private 44ft Trimaran in Los Cabos for 50 Guests
Sailing in Juárez · 50 guests

Private 44ft Trimaran in Los Cabos for 50 Guests

New
Superowner
Best of 2026
$250/hour
Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
Sailing in Salisbury · 4 guests

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

5.0
$160/hour
78ft Catamaran Private Charter / Capacity 100 people in Cancún, Quintana Roo
Sailing in Cancún · 100 guests

78ft Catamaran Private Charter / Capacity 100 people in Cancún, Quintana Roo

5.0
Superowner
$750+/hour
77 ft Catamaran Cruise With Drinks, food and Waterslide In Cancún, Mexico
Sailing in Cancún · 280 guests

77 ft Catamaran Cruise With Drinks, food and Waterslide In Cancún, Mexico

5.0
$1,227/hour
50ft Sailing Catamaran Private Charter / Capacity 50 people
Sailing in Cancún · 50 guests

50ft Sailing Catamaran Private Charter / Capacity 50 people

5.0
Superowner
$314+/hour
45’ Leopard 2020 Cruising Catamaran in Cancun - Isla Mujeres!
Sailing in Cancún · 18 guests

45’ Leopard 2020 Cruising Catamaran in Cancun - Isla Mujeres!

5.0
Superowner
$515/hour
Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!
Powerboats in Sosúa · 80 guests

Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!

New
Superowner
Best of 2026
$50/hour
Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia
Sailing in Cartagena · 60 guests

Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia

5.0
$3,500/day
Sailing Catamaran Rental in West Bay
Sailing in West Bay · 50 guests

Sailing Catamaran Rental in West Bay

5.0
$288/hour
65ft Sailing Catamaran in Playa del Coco
Sailing in Coco · 70 guests

65ft Sailing Catamaran in Playa del Coco

5.0
$532/hour

Sailing Reviews in United States

  1. Lauren

    Lauren

    Charter 42' Lagoon Catamaran in Annapolis, MD

    We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!

  2. LP

    Luke

    Sailing Lessons on the San Francisco Bay

    This was so fun! We were happy to learn the basics of sailing. It was awesome and we had a blast, despite the low winds up the channel. Would sail again and recommend!

  3. PA

    Peggy

    30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

    Our party of six adults and three children had the best time with Mike and his beautiful Jupiter 30. The boat was in immaculate order, had plenty of seating for all of us, and was safe for the kids to roam around on. A great sound system kept both kids and adults entertained. Mike truly is the best captain one can ask for. Quick to respond to our requests before the trip, and attentive, safe and positive during it. 10/10 from our whole party of nine

  4. Jennifer

    Jennifer

    Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!

    Dave and his boat are fantastic! We booked for some sailing instruction, and while there wasn’t much wind, it was still amazing. Dave explained the boat setup, the electronics, and other relevant things to consider when sailing in the harbor while giving us a beautiful tour around lower Manhattan. We also set sail and took the wheel for a bit. I would 100% recommend going out on Dave’s boat with him whether for a sightseeing tour or to learn from him, or both.

  5. MA

    Megan

    Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC

    James was so accommodating for our elopement on his sailboat. He was always quick to respond and great at communicating with us. We really enjoyed our trip on the water and James made it easy for us to be comfortable and sit and relax. It was perfect!

  6. AD

    Andrew

    ★Midcoast Maine aboard the Schooner Yacht Meteor ★

    We just got back from a wonderful day on the water :) We bareboat chartered the Meteor. Captain Neal was able to be flexible on our timing since our original day was bad weather and he did not have many bookings around the same time. He made perfect suggestions regarding weather, currents, tides and routes to help us learn the area quickly and be able to navigate a beautiful day on Penobscot Bay. 100% we will be back again! Treat his boat well and Capt Neal will treat you well in return! Thanks so much for a wonderful day!