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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,244 Reviews)

Page 38 of 40948 listings

 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298/hour
Luxury Catamaran 52ft private charter for up to 40 people in Cartagena
Powerboats in Cartagena · 40 guests

Luxury Catamaran 52ft private charter for up to 40 people in Cartagena

New
$360/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
Key Largo Sailing with Dolphins on 35ft Legacy Catamaran
Sailing in Key Largo · 6 guests

Key Largo Sailing with Dolphins on 35ft Legacy Catamaran

New
$125/hour
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90/hour
Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI
Sailing in Milwaukee · 6 guests

Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI

New
$120/hour
SAILING IN ISLA MUJERES
Sailing in Isla Mujeres · 8 guests

SAILING IN ISLA MUJERES

New
$127/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
$250/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!!

5.0
$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
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
Snoozed - Active 20 Oct 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
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
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
Snoozed - Active 02 Nov 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
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

Sailing Reviews in United States

  1. AA

    AKINLOLU

    Luxury Catamaran Lagoon 52' Capacity up to 40

    The Yacht tour was great. The size of the boat was perfect for my crew of 33. The food services provided was great, and Eddy the live saver saved a member of my group which helped avoid a situation. In all it was a good experience to have in Cartagena.

  2. AD

    Alice

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

    Captain Lu is THE MAN ! We had an amazing time with him, he’s very nice and extremely knowledgeable. He adjusted the course of the cruise to an easier swell when our friend that is easily seasick started to feel dizzy, and she felt great the entire time! I can only recommend cruising with Captain Lu and will surely be back again !

  3. 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!

  4. 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!!!

  5. 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!

  6. MC

    Mev

    Luxury Catamaran Lagoon 52' Capacity up to 40

    Thank you! Captain, crew and chef were all phenomenal! Attentive, helpful and polite - all around great experience! Highly recommend this boat and crew. We had a group of 10 adults and 10 teens. Everyone raved about our day with the Sea Warriors. Just book them for a fun, luxury experience that is customizable for your group. 5 stars all the way.