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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,341 Reviews)

Page 38 of 39915 listings

All Inclusive 45´ Luxury Catamaran in Baja California Sur
Sailing in Centro · 8 guests

All Inclusive 45´ Luxury Catamaran in Baja California Sur

New
$263/hour
SAILING THE GULF OF NICOYA ON A LUXURY 37" YACHT
Sailing in Punta Arenas · 4 guests

SAILING THE GULF OF NICOYA ON A LUXURY 37" YACHT

New
$150/hour
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
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
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
$229/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
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
Beneteau 36’ Cruising Monohull in Redondo Beach
Sailing in Redondo Beach · 6 guests

Beneteau 36’ Cruising Monohull in Redondo Beach

5.0
Snoozed - Active 08 Aug 2026
Bali 43 Complete comfort Catamaran
Sailing in Marina del Rey · 12 guests

Bali 43 Complete comfort Catamaran

5.0
Snoozed - Active 17 Aug 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
Limited Availability
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
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

Sailing Reviews in United States

  1. MA

    Mina

    Beneteau 36’ Cruising Monohull in Redondo Beach

    Brasher was very kind and patient, even we showed up late due to certain circumstances, he never took it off our booked time and gave us an awesome ride!!

  2. AH

    Aileenka

    Beneteau 36’ Cruising Monohull in Redondo Beach

    Booked Brasher and his boat for my 30th birthday and it did not disappoint! From the very beginning he had excellent communication and assured me I would have a great time. I definitely did! He had a cooler aboard for drinks, he took us to a lovely anchorage spot to swim and inflated the cube. I would 100% book this trip again.

  3. OA

    Omar

    Beneteau 36’ Cruising Monohull in Redondo Beach

    We had an absolutely wonderful Mother’s Day sail today, and our captain made the entire experience unforgettable. From the moment we stepped aboard, he was professional, relaxed, knowledgeable, and incredibly accommodating. He made everyone feel comfortable and safe while still keeping the trip fun and memorable. The boat was beautiful, the sailing was smooth, and he knew exactly how to create the perfect atmosphere for a special family day on the water. You can tell he genuinely loves what he does, and that energy made all the difference. Highly recommend to anyone looking for a relaxing, first-class sailing experience. We’ll definitely be back. Thank you again for making Mother’s Day so special!

  4. 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!

  5. 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.

  6. TK

    Taylor

    Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!

    This was my second time booking Captain Jim’s sailboat for a photoshoot and it was a great experience- as always! He’s so kind, provides a great and professional experience. He always has snacks and drinks for myself and my clients - along with other great accommodations! Will definitely be booking again!!!