Sail Western Long Island Sound aboard this beautiful Pearson 386

 5.0 (21)

Pearson 386 (2003)


  • 38 feet

  • 10 guests

  • 3 cabins

  • 1 heads

  • Captained



No crowds, just you and your closest friends on board this classic beautiful 38 foot sailboat. Charter this boat for a gorgeous sail out of Mamaroneck Harbor, New York, and go to a destination of your choosing or wherever the wind takes us. You can take the wheel and trim the sheets or just lie back and enjoy the sun and gentle breeze. Whether you want to go on a simple sail, a romantic sunset cruise, or a longer voyage. It's all up to you.

RATES: $110 per person. $400 minimum 10 person maximum for trips lasting up to 8 hours.
Call for special wedding rates

This boat has 1 additional services available. View addons


  • Manufacturer
  • Model
  • Year
  • Guest Capacity
  • Cabins
  • Single Beds
  • Double Beds
  • Bathrooms
  • Number of engines
  • Horsepower per engine


This boat has 1 additional service(s) available for full day trips. You can select optional addons to customize your trip on the next page. Note that required addons are mandatory, and addons marked as payable at base need to be paid directly to the boat owner when you get to the boat.

Optional Extras (1)

  • Extra person
    per booking


  • Stereo AUX input mp3 hookup
  • Stove / grill
  • Autopilot
  • Microwave
  • Radar
  • Air conditioning
Navigation & Safety
  • Autopilot
  • Radar
  • Chart plotter
  • GPS
  • Generator
  • VHF Radio
  • Tender/Dinghy
  • Depth finder
  • Life jackets
  • Fire extinguisher
  • First aid kit
  • Torch light
  • Binoculars
  • Stereo AUX input mp3 hookup
  • CD Player
  • Speakers on deck
  • Stove / grill
  • Microwave
  • Air conditioning
  • Refrigerator
  • Bed linen
  • Towels
  • Freezer
  • Inverter
  • Warm water
  • Cockpit table
  • Outdoor shower
  • Overnight stay

21 Reviews

  • Nomä
    June 3rd, 2023

    Great Sailor, Great Boat, Great Person, Very Helpful. 10/10 experience

  • Lindsey
    June 22nd, 2022

    Our family had a great time sailing on Rick's boat for half a day. He made it especially fun for our 2 young kids on board! We would happily book again.

  • Mon
    June 4th, 2022

    We really enjoyed our trip with Captain Rick! I booked it for my birthday, and he was so flexible. The sailboat is AMAZING. Truly a highlight of my time. We want to do it again with more of an agenda.

  • Brittany
    May 24th, 2022

    Captain Rick was fantastic! I will definitely be booking with him again soon!

  • Shadia
    July 13th, 2021

    This was a truly wonderful experience and Captain Rick was extremely knowledgable, engaging and very accommodating. He provided us with some good options as to what we could do and we ended up being able to not only experience a wonderful boat trip across the Sound but also swim and have dinner at a fun restaurant on Long Island. I highly recommend this.

  • Leslie
    July 7th, 2021

    We went sailing with Rick and our 2 small children, and we couldn’t have had a nicer day. Rick was really great with the kids! Highly recommend.

  • Suzanne
    May 27th, 2021

    This truly was one of the best experiences of my life! I chartered the sailboat alone - I just wanted a day to reflect and enjoy the beauty of my surroundings. Well from the first minute to the last - it was simply wonderful. Rick was the absolute best captain - kind, funny, professional and simply a joy to share the day with! I felt like we were friends by the end of the trip. Don’t miss out on this opportunity with Rick! A++++ all around!

  • Emilia
    May 25th, 2021

    Rick was the best! Fun to be around and very knowledgeable. A beautiful and memorable day

  • L
    May 21st, 2021

    Captain Rick is a awesome guy our family had an amazing time.

    Highly recommended!!!

    Thank you for a great experience.

  • Edgar
    May 6th, 2021

    Rick is great! and he is extremely good with small kids too. Would highly recommend.

  • C
    Oct. 8th, 2020

    We had a wonderful day on the Long Island Sound with Captain Rick. We were blessed with beautiful fall weather and not that windy. Literally smooth sailing. The boat was clean, beautiful wood features it was a lovely all day cruise culminating into a beautiful sunset. Rick is a gifted story teller and we explored a parts of the coast and the mansions of Sands Point. Mostly we relaxed and enjoyed a day out with our party. We were three generations from age 13 to 76 and we all loved it. A great way to enjoy each other safely.

  • Saman
    Sept. 9th, 2020

    we had an awesome day! highly recommend it!

  • Young Mi
    Young Mi
    Aug. 15th, 2020

    We had the best time with Captain Rick. He was so kind and funny. The kids and adults loved him. The boat was great too!

    He was so flexible with your schedule and patient with our needs. We will definitely book again. Thanks for a great time!!

  • Nyeema
    July 20th, 2020

    Boat was well
    Taken care of the owner was nice it was a peaceful successful boat ride

  • Steven
    July 13th, 2020

    I booked Rick for a half day sail as a present for my wife's 50th, along with our two young kids and family friend. Rick was the consummate host from start to finish. He was especially good with our very demanding kids (2.5 and 7.5) and incredibly patient and engaging with them. We had a great day and are already looking forward to booking Rick for another trip. I would not hesitate in the slightest to recommend Rick to anyone. The boat was fantastic, everything went smoothly, safely and we were all talking about it for the rest of the day. Thank you Rick for a great day on the water.

  • Haiwen
    July 7th, 2020

    We had a great time on Rick’s boat. He was extremely quick in responding to inquiries prior to the trip. We started the trip with blue sky. But the weather turned stormy an hour+ later. Rick was very calm and experienced in dealing with the situation. He was also very nice and accommodating in responding to our requests. Thank you, Rick.

  • Wendy
    June 26th, 2020

    It was such a great experience! Rick was very accommodating and an expert in what he does. He ensured our safety throughout the entire trip. Will definitely book him again! Thank you so much Rick!

  • Gennyne
    Sept. 3rd, 2019

    Captain Rick was great! We had an amazing adventure!

  • Alexandra
    July 1st, 2019

    Rick was incredible!! I can't say enough how amazing our trip out on Nirvana was for my father's 70th birthday. Something we will remember forever as a family. The sailboat was beyond beautiful and Rick is such a pro and super reliable in communication. He is also a great host! We hope to be able to board Nirvana again one day soon. Thank you Rick and Nirvana!

  • Ariana
    Sept. 6th, 2018

    Our trip far exceeded our expectations! Rick is an incredible captain and he made the experience fun and memorable! He was amazing with our kids, and my husband who I got the gift for described the trip as the best day of our summer. I cannot say enough good things about Rick and his boat! Anybody would be lucky to spend a day on board this boat!

  • Vivian
    Aug. 14th, 2018

    Absolutely wonderful experience. Rick was very friendly, attentive, and a seasoned sailor. Very flexible & responsive. We had a wonderful time! Weather was beautiful -- warm & windy - a great day to be on the water. Would highly recommend Rick and his boat.

Boat Owner


Member since October 2015

Rick has a long sailing history with costal and blue water experience. He is Coast Guard licensed to Captain up to a 100 ton vessel so you'll be safe and sound under his watch. He's been offering private charters on the sloop Nirvana for the past 5 years. With coastal and blue water experience, Rick can insure that your time on the water is safe and fun.

Response rate: 92.0%
Response time: within 7 hours
Message owner

Location and Destination Guide

Usually this boat operates around Mamaroneck, NY.

New York City looks great from the ground, but that view from the water is something else! Jump aboard a Sailo boat rental from the Big Apple and experience the thrill of the sea - and snap plenty of incredible pictures. Sailing in NYC is a must on your summer bucket list, whether you are visiting or a New Yorker.

It might not be the first thing you think of when finding things to do in New York City, but renting a boat for a full day or just a few hours is a truly memorable experience.

Customer Questions & Answers

Ask general questions about this boat. For questions related to a specific booking request click here to Message the Boat Owner directly.


Can you do a Manhattan pickup?


0 votes
No, this boat rental is not available for pickup in Manhattan.
by Janet on July 6th 2018


Are there speakers?


0 votes
Yes, there are speakers that guests may connect to play their own music for this boat rental.
by Janet on July 23rd 2018


What could we do on a boat for a full day?


0 votes
You determine the start and end times for this boat rental. On Friday’s the captain would suggest the following. We start at about 3:00 pm we sail across the Sound to a restaurant that has been very popular with my clients after dinner we sail up to Rye swimming and relaxing along the way. We reach Rye by 8:00 to get a good spot to view their extensive fireworks display. We leave Rye around 10:00 and get back to the dock around 11:00 pm. That’s just one suggested itinerary.
by Janet on July 16th 2018


Can I bring alcohol?


0 votes
For this boat rental, guests may bring any food or drink onboard.
by Janet on July 23rd 2018


Cancelation policy - Standard
Full refund if renter cancels 6 days or more before the trip start date.
No refund if renter cancels 5 days or less before the trip start date.