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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,449 Reviews)

Page 36 of 38895 listings

⚓️ Lagoon 40' Cruising Catamaran in Puerto Vallarta (Includes food)
Sailing in Isla Iguana · 12 guests

⚓️ Lagoon 40' Cruising Catamaran in Puerto Vallarta (Includes food)

New
$365+/hour
 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
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
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
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
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
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
Sailing in Centro - Supmza. 001 · 16 guests

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

5.0
Snoozed - Active 07 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. 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.

  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. KB

    Kia

    Luxury Catamaran Lagoon 52' Capacity up to 40

    Jose’s boat was awesome! The boat itself was beautiful and spacious. The crew was helpful and knowledgeable and was able to make our full itinerary work! We had a wonderful time celebrating our friend’s bachelorette!