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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,392 Reviews)

Page 38 of 39914 listings

22ft SeaSwirl Striper Center Console
Fishing in Los Angeles · 8 guests

22ft SeaSwirl Striper Center Console

New
$175/hour
Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan
Sailing in Holland · 6 guests

Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan

New
$150/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
Stay Warm and dry, year-round cruising San Juan’s and Seattle charters
Sailing in Seattle · 6 guests

Stay Warm and dry, year-round cruising San Juan’s and Seattle charters

New
$350+/hour
Luxury 47' Lagoon Catamaran Charter - Snorkel, Sunset, Overnight Stays
Sailing in Marina Vallarta · 25 guests

Luxury 47' Lagoon Catamaran Charter - Snorkel, Sunset, Overnight Stays

New
$234/hour
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$50/hour
Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!
Sailing in Gloucester · 60 guests

Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!

New
$1,200+/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

5.0
Snoozed - Active 17 Sep 2026
Enjoy Luxury Catamaran for Islands, Sunsets and Night Events
Sailing in Cartagena · 20 guests

Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

5.0
Superowner
Snoozed - Active 09 Sep 2026
Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!
Sailing in New Orleans · 6 guests

Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!

5.0
Snoozed - Active 02 Jan 2027
52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

5.0
Snoozed - Active 02 Jan 2027
Efoiling at deer creek reservoir
Adventures in Salt Lake City · 1 guest

Efoiling at deer creek reservoir

5.0
Snoozed - Active 15 Jan 2027
Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

5.0
Snoozed - Active 02 Jan 2027
SeaDoo Switch Sport *5 ADULTS*
Powerboats in Texas · 9 guests

SeaDoo Switch Sport *5 ADULTS*

5.0
Snoozed - Active 02 Oct 2026
Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.
Sailing in Brooklyn · 6 guests

Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.

5.0
Snoozed - Active 02 Jan 2027
Bali 43 Complete comfort Catamaran
Sailing in Marina del Rey · 12 guests

Bali 43 Complete comfort Catamaran

5.0
Snoozed - Active 17 Aug 2026
Luxury Sailing Catamaran for up to 12
Sailing in Newport · 12 guests

Luxury Sailing Catamaran for up to 12

5.0
Snoozed - Active 02 Nov 2026
46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica
Sailing in Playa Flamingo · 40 guests

46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica

5.0
Snoozed - Active 02 Nov 2026
Islander 36 - The Perfect Sailing Yacht for San Francisco Bay
Sailing in Sausalito · 6 guests

Islander 36 - The Perfect Sailing Yacht for San Francisco Bay

5.0
Snoozed - Active 02 Jan 2027
Beautiful Sailboat for Private Outings, South Bay LA, King Harbor Marina
Sailing in Redondo Beach · 6 guests

Beautiful Sailboat for Private Outings, South Bay LA, King Harbor Marina

5.0
Snoozed - Active 02 Sep 2026
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
Snoozed - Active 17 Sep 2026
Axe 1 Center Console Boat Rental in Montego Bay, Jamaica
Events in Montego Bay · 8 guests

Axe 1 Center Console Boat Rental in Montego Bay, Jamaica

New
Snoozed - Active 03 Sep 2026
The Gallivanders Ultimate Sailing Adventure
Sailing in Nassau · 12 guests

The Gallivanders Ultimate Sailing Adventure

New
Snoozed - Active 03 Jan 2027

Sailing Reviews in United States

  1. Irene

    Irene

    Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

    Nina is a fantastic person, fantastic captain and a fantastic company. 2 of us and a doggie went on a short adventure with her and it couldn’t have been a better experience. We had so much fun, laughter and comfort with her on her boat that i can barely put this in words. We will definitely do this over and over again. Highly recommend!

  2. MP

    Meredith

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    Amory and his team were wonderful from start to finish. We wanted a relaxing girls boat day, away from vendors and clubs, and they delivered! They also recommended a fantastic catering option and arranged it for us. We loved his captain Demer and first mate Wayne. They made us feel safe without overstepping.

  3. SD

    Sam

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    ⭐️⭐️⭐️⭐️⭐️ 5/5 — An Unforgettable Anniversary Celebration! We rented this catamaran in Cartagena last week to celebrate our 25th anniversary with a group of 20 people, and it was truly an incredible experience from start to finish. The boat was spacious, clean, and extremely comfortable—perfect for hosting a group our size without ever feeling crowded. The crew went above and beyond to make the day special. They were friendly, attentive, and professional, always checking in to make sure we had everything we needed. The captain knew all the best spots, and the views of Cartagena from the water were absolutely stunning. We enjoyed great music, smooth sailing, and plenty of time to relax, swim, and celebrate. It was the perfect mix of luxury and fun, and our entire group left with amazing memories. If you're looking for a memorable experience on the water in Cartagena—whether for a celebration or just a fantastic day out—I highly recommend this catamaran. It truly made our 25th anniversary celebration unforgettable!

  4. AP

    Alexis

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    My group had an incredible experience from start to finish! Amory was so helpful with planning our trip and organizing everything ahead of time. He responded quickly to all of my questions and made the whole process smooth and stress-free. The day before, he sent detailed instructions with the meeting point and helpful tips, which made everything super easy to find. The boat was clean, spacious, and well-kept, and Captain Demer and crew member Wayne were fantastic. They made sure everyone was comfortable and having a great time the entire day. We stopped to swim and explore at Cholon, which was definitely a highlight of the trip. Everything was perfectly organized, and we couldn’t have asked for a better crew or experience. Highly recommend booking through Amory for an amazing day on the water in Cartagena!

  5. CL

    Chloe

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    We booked the full-day rental for a bachelorette party and had a wonderful time. Amory was very responsive, answered all of our questions, and even offered to decorate the boat for the celebration. The crew on board was nice and attentive throughout the day. The catamaran itself was spacious with plenty of room for our group of 10, and one of the girls especially loved how comfortable the bed was for a nap. The highlight of the day was the beautiful sunset on the ride back, an unforgettable experience!

  6. NG

    Nate

    Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!

    The boat is amazing. The interior is a gorgeous wood finish and navigating the exterior of the boat was very doable for us! We had a blast on all sides of the boat. Jim was also an amazing host! Flexible and even though we were late he let us still get our full time on the water. Engaging when engaged with such great conversation, but willing to let us sit back and just hang out together. Highly recommend.