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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,192 Reviews)

Page 38 of 40945 listings

41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90/hour
SAILING IN ISLA MUJERES
Sailing in Isla Mujeres · 8 guests

SAILING IN ISLA MUJERES

New
$125/hour
All Inclusive 45´ Luxury Catamaran in Baja California Sur
Sailing in Centro · 8 guests

All Inclusive 45´ Luxury Catamaran in Baja California Sur

New
$246/hour
Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!
Sailing in Gloucester · 6 guests

Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

New
$175+/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
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$200+/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
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 Feb 2026
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
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
Catamaran #GMB37MIA in Isla Mujeres Fountain Pajot
Sailing in Centro - Supmza. 001 · 18 guests

Catamaran #GMB37MIA in Isla Mujeres Fountain Pajot

5.0
Snoozed - Active 07 Oct 2025
Catamaran 38' Private tour to Isla Mujeres / Cancun / Playa del Carmen #GMB38CAT
Sailing in Centro - Supmza. 001 · 16 guests

Catamaran 38' Private tour to Isla Mujeres / Cancun / Playa del Carmen #GMB38CAT

5.0
Snoozed - Active 07 Oct 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. 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!

  4. 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.

  5. 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!

  6. Dennese

    Dennese

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

    Sailing with Captain James was a dream!! You will not regret this experience! Not only is he hospitable, he is full of life and passion which only made our trip better. We enjoyed every part of our trip the only sad part was that we didn’t book longer. 100/10 would book with Captain James again!!