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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,069 Reviews)

Page 38 of 39917 listings

34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
27' Oday Sailboat for Easy Sailing and Bay Adventures
Sailing in Redwood City · 6 guests

27' Oday Sailboat for Easy Sailing and Bay Adventures

New
$99/hour
Karisma 45 ft Sun Odyssey Jeanneau
Sailing in Seabrook · 6 guests

Karisma 45 ft Sun Odyssey Jeanneau

5.0
Snoozed - Active 13 Apr 2026
Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL
Sailing in West Palm Beach · 12 guests

Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL

4.3
Superowner
Snoozed - Active 02 May 2026
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
Snoozed - Active 17 Apr 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
Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)
Powerboats in Cartagena · 16 guests

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)

5.0
Snoozed - Active 02 Aug 2026
1980 Catalina 38ft Sparkman & Stephens Sailboat in Long Beach
Sailing in Long Beach · 10 guests

1980 Catalina 38ft Sparkman & Stephens Sailboat in Long Beach

3.7
Snoozed - Active 02 May 2026
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

5.0
Snoozed - Active 03 May 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 Jul 2026
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
North River Sailing - See NYC from a Classic Racing Yacht
Sailing in Manhattan · 6 guests

North River Sailing - See NYC from a Classic Racing Yacht

5.0
Snoozed - Active 03 May 2026
Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida
Sailing in West Palm Beach · 12 guests

Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida

5.0
Snoozed - Active 31 Jul 2026
⚓️ Luxury 45' Catamaran Charter 2019 in Puerto Vallarta
Sailing in Marina Vallarta · 16 guests

⚓️ Luxury 45' Catamaran Charter 2019 in Puerto Vallarta

4.0
Snoozed - Active 02 May 2026
Private Sailing Charter on Martha's Vineyard
Sailing in Tisbury · 6 guests

Private Sailing Charter on Martha's Vineyard

5.0
Snoozed - Active 02 Jul 2026
40' Luxury Cruising Sailboat – Private Charters for 8 Guests
Sailing in Richmond · 8 guests

40' Luxury Cruising Sailboat – Private Charters for 8 Guests

New
Snoozed - Active 19 Apr 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
Catamaran boat Party La Paz
Events in Zona Comercial · 12 guests

Catamaran boat Party La Paz

New
Superowner
Snoozed - Active 03 Oct 2026
Premium Experience in Exclusive Panga in La Crucecita
Powerboats in La Crucecita · 8 guests

Premium Experience in Exclusive Panga in La Crucecita

New
Snoozed - Active 02 May 2026
Luxury Bay Sailing Experience – Private 42' Yacht, Comfortably Seats 10 Guests
Sailing in Oakland · 10 guests

Luxury Bay Sailing Experience – Private 42' Yacht, Comfortably Seats 10 Guests

New
Snoozed - Active 19 Apr 2026
42' Luxury Catamaran – Private San Francisco Bay Charters for 12 - Oakland
Sailing in Oakland · 12 guests

42' Luxury Catamaran – Private San Francisco Bay Charters for 12 - Oakland

New
Snoozed - Active 19 Apr 2026
⚓️ Suri 36' Cruising Catamaran Charter in Cruz de Huanacaxtle
Sailing in La Cruz de Huanacaxtle · 30 guests

⚓️ Suri 36' Cruising Catamaran Charter in Cruz de Huanacaxtle

New
Snoozed - Active 02 May 2026
Private Sail Charter of NYC Skyline and Statue of Liberty
Sailing in Manhattan · 6 guests

Private Sail Charter of NYC Skyline and Statue of Liberty

New
Snoozed - Active 02 May 2026
Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1
Sailing in Fort Lauderdale · 4 guests

Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1

New
Snoozed - Active 02 May 2026

Sailing Reviews in United States

  1. GK

    George

    Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL

    Capt Mark is not just a skilled boatman, he is a gentleman of many talents. What a delight to spend the day on his Naked Truth (thankfully, Capt stayed fully clothed!). This was a sailing experience even staying in the intracoastal. You made our day memorable! I look forward to our next voyage.

  2. ES

    Emily

    Sail in downtown Toronto

    We had an incredible trip on Dom's boat! We went out for my partner's birthday (2 of us). Dom is an amazing host and made us feel welcome from the start. He let us help with the sails and asked our input on where to go based on the wind. We had such a great experience and would recommend him to anyone!

  3. ZF

    Zachary

    Sail in downtown Toronto

    Captain Dom was an incredible host! If I could give 6/5 stars I would. He communication was excellent, he was welcoming, kind, safe and wanted to ensure we all got we needed when on board. His boat is excellent quality and we definitely got more than we asked for. 100% would recommend to anyone, and definitely will do again. Cheers!

  4. Janelle

    Janelle

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

    Captain Ed is fantastic! I e had such an amazing time for our 1 year anniversary! He built a wonderful itinerary for us and took beautiful photos for us. His sail boat is immaculately maintained and beautiful! We highly recommend and will ensure to sail with him again! Thank you!

  5. Pablo

    Pablo

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

    I had an absolutely fantastic time sailing on this remarkable boat! The captain's (Ed Navitski) expertise and professionalism made the experience truly memorable. Sharing this adventure with friends only added to the enjoyment. I can't recommend this sailing experience highly enough – it was an excellent time all around.

  6. AL

    Ami

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

    Everything about this sail was perfect. Captain Ed regularly communicated with us pre sail to ensure we got to where we needed to be. On board he oriented us to the boat. The boat is beautiful and had everything we needed such as cups, ice, cooler, comfortable seating. The sail was the best and Captain Ed made sure we didn’t miss out on key photo opportunities. I highly recommend!!! Thanks Captain Ed!!