Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,464 Reviews)

Page 39 of 39931 listings

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
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 14 Sep 2026
51ft Bavaria Cruiser – Shelter Island San Diego Luxury Ocean Charter
Sailing in San Diego · 12 guests

51ft Bavaria Cruiser – Shelter Island San Diego Luxury Ocean Charter

New
Snoozed - Active 02 Jan 2027
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
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
Sausalito: 41ft Jeanneau 410 Sun Odyssey Sailing Charter for Up to 10 Guests
Sailing in Sausalito · 10 guests

Sausalito: 41ft Jeanneau 410 Sun Odyssey Sailing Charter for Up to 10 Guests

New
Snoozed - Active 23 Sep 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 23 Sep 2026
The Gallivanders Ultimate Sailing Adventure
Sailing in Nassau · 12 guests

The Gallivanders Ultimate Sailing Adventure

New
Snoozed - Active 03 Jan 2027
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 23 Sep 2026
Lagoon 420 Hybrid Eco Friendly Electric Catamaran
Sailing in Guna Yala Comarca · 4 guests

Lagoon 420 Hybrid Eco Friendly Electric Catamaran

New
Snoozed - Active 27 Mar 2027
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 23 Sep 2026
Seattle Sailing Adventure – Wicked Wind Catalina 275 Sport
Sailing in Seattle · 4 guests

Seattle Sailing Adventure – Wicked Wind Catalina 275 Sport

New
Snoozed - Active 11 Sep 2026
Catalina Capri 22 Daysailer - Simple to Sail in Seattle
Sailing in Seattle · 5 guests

Catalina Capri 22 Daysailer - Simple to Sail in Seattle

New
Snoozed - Active 11 Sep 2026

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. 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.

  3. 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!!!

  4. TW

    Thomas

    Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

    Smooth sailing on a sunny afternoon; nothing but a balloon sail to cast you away along the beautiful Lake Pontchatrain coast way! Captain Jim provides a wonderful staycation that can’t be beat right here on the Northshore. His sailboat is a great way to go. Sailing on the lake at sunset in the moonlight is great for a fun relaxing afternoon.

  5. SG

    Sarah

    Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

    Jim was an amazing captain, the weather was on our side, and we couldn’t have asked for a better way to end our wedding night! He had snacks, water, chips, Gatorade, wine glasses, speakers, and MOST IMPORTANTLY, chairs for us to sit in ! It was an a amazing experience!

  6. MH

    Martin

    Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

    Captain Jim was terrific and we had a fantastic day on the lake. He was very thorough in explaining all of the safety requirements and we felt to be in good hands with him at the helm. We could not have had a better experience and will certainly be repeat customers. Many thanks to Captain Jim for making our excursion a memorable experience.