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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,186 Reviews)

Page 39 of 40937 listings

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

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$50/hour
Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise
Sailing in West Bay · 12 guests

Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise

5.0
Snoozed - Active 10 Aug 2026
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

4.7
Snoozed - Active 02 Jan 2026
Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran
Sailing in Nassau · 12 guests

Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

4.9
Snoozed - Active 02 Mar 2026
50ft Catamaran Charter with Water Toys -Boca Raton, FL
Sailing in Boca Raton · 12 guests

50ft Catamaran Charter with Water Toys -Boca Raton, FL

5.0
Snoozed - Active 03 Nov 2025
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0
Snoozed - Active 02 Jan 2026
Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389
Sailing in West Palm Beach · 8 guests

Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389

5.0
Snoozed - Active 16 Sep 2025
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 Sep 2025
41ft Metta Sailing Catamaran in Turks and Caicos Islands
Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

5.0
Snoozed - Active 08 Oct 2025
Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast
Sailing in Friendship · 6 guests

Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast

5.0
Snoozed - Active 19 Sep 2025
36' PDQ Catamaran Charter in Puerto Aventuras, Mexico
Sailing in Puerto Aventuras · 15 guests

36' PDQ Catamaran Charter in Puerto Aventuras, Mexico

5.0
Snoozed - Active 02 Oct 2025
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0
Snoozed - Active 02 Oct 2025
38' Sailing catamaran for parties / events in Long Beach! DISCOUNT WEEK DAYS
Sailing in Long Beach · 12 guests

38' Sailing catamaran for parties / events in Long Beach! DISCOUNT WEEK DAYS

5.0
Superowner
Snoozed - Active 02 Sep 2025
Sail to Fishers Island on a fast and classy 35' Sailboat
Sailing in New London · 6 guests

Sail to Fishers Island on a fast and classy 35' Sailboat

5.0
Snoozed - Active 02 Jun 2026
Classic Sparkman & Stevens Sailboat: Choose Leisure Sailing or Hands-On Lessons
Sailing in Lacey Township · 6 guests

Classic Sparkman & Stevens Sailboat: Choose Leisure Sailing or Hands-On Lessons

5.0
Snoozed - Active 02 Jan 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
40ft party catamaran for 13 on sand bar!
Sailing in Sunny Isles Beach · 12 guests

40ft party catamaran for 13 on sand bar!

New
Superowner
Snoozed - Active 12 Sep 2025
Sail on a classy and fast Sailing Yacht in the Hamptons, New York
Sailing in East Hampton · 6 guests

Sail on a classy and fast Sailing Yacht in the Hamptons, New York

5.0
Snoozed - Active 17 Jun 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 02 Oct 2025
Hanse 418 Cruising Monohull Rental in Hollywood, Florida
Sailing in Hollywood · 12 guests

Hanse 418 Cruising Monohull Rental in Hollywood, Florida

New
Snoozed - Active 02 Nov 2025
Catamaran boat Party La Paz
Events in Zona Comercial · 12 guests

Catamaran boat Party La Paz

New
Superowner
Snoozed - Active 17 Oct 2025
Private 65ft Catamaran for Charter Trips in Montego Bay
Sailing in Montego Bay · 40 guests

Private 65ft Catamaran for Charter Trips in Montego Bay

New
Snoozed - Active 02 Nov 2025
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

New
Snoozed - Active 23 Sep 2025

Sailing Reviews in United States

  1. JS

    Jen

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!

  2. KN

    Karen

    Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

    I had ever used this app before, but glad I did! Johnathan had amazing communication prior to our charter and was very helpful and transparent of what was included and answered all of our questions. The crew was AMAZING too! We saw sea turtles, sunfish, and more! Found a gorgeous conch shell near Rose Island and the kids LOVED the slide. The food was also AMAZING and the fully stocked bar was a winner!!! Boat was incredible and they also has sea scooters!!!

  3. CW

    Chelsea

    38' Sailing catamaran for parties / events in Long Beach! DISCOUNT WEEK DAYS

    This was my first time ever chartering a boat or using this website. I was nervous about it since I don’t know much about any of this, so I’m here to tell you to do it. If you want to have a fantastic boating experience, choose David! We had an amazing time celebrating my birthday on this boat and I would 100% book it again. Everything went as planned (except when the unicorn floatie was whisked away off the boat and we then had to recover it in windy conditions- it was a very funny and memorable time).

  4. LB

    Leanna

    Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

    I truly cannot say enough great things about Anthony and Mile. From the moment we stepped on board, everything exceeded our expectations. The boat was absolutely stunning—beautifully maintained and equipped with all the fun extras that made the day unforgettable. The food was not only delicious but thoughtfully prepared and presented. Most importantly, the entire experience was filled with fun, laughter, and amazing memories. Every detail was perfect, and it was worth every single penny. Thank you both for an incredible day on the water—we’ll definitely be back!

  5. JA

    Jeremy

    Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast

    Ralph made bareboating a great experience end to end. His Morgan 36-5 Nelson Marek was just right, in working order and easy to sail for just my wife who does not sail and me. The equipment was all good, including a new and simple to use chart plotter mounted right at the helm. Beautiful location, conditions and waters made for great sailing. Convenient getting answers in advance, getting started and finished. All good. Highly recommendation. And there’s a super lobster place right nearby.

  6. TW

    Terry

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    A perfect day on the Metta. After messaging about our grandkids interests, the captain took us to the boat wreck to snorkel and then to a great coral reef! Snacks, drinks and gear were provided and they were very helpful. Last, we swam and played on the most beautiful beach and the kids saw iguanas! Great hosts! We will book the Metta again!