Private crewed Sag Harbor Sail Boat rentals. Highest rated Charter Boat and Crew in Sag Harbor

Sag Harbor Boat Rental


Catamaran Sailing Yacht

Charter our 62’ Catamaran to cruise around Sag harbor with your family and friends for The Ultimate Luxury Yacht Charter experience. A Sag Harbor private boat rental with Captain Paul is the perfect way to take in the beautiful surroundings, and with Valkyrie Sailing every little detail is taken care of.
Our signature Sag Harbor private boat rental with Captain is a 4-hour cruise for up to twelve guests. Choose between a morning sail (our personal favorite way to start the day), Sag Harbor Day sail, or Sag Harbor Sunset cruise to relax onboard our luxury yacht and take in the views with your group, or turn the music up for an epic party aboard a Sag Harbor Private yacht with Captain 2022
Sit back and relax with ample room for all on our spacious 30’ wide deck sipping your favorite beverages, stop for a quick dip in the water, take advantage of the beautiful Golden Hour light, or even bring the kids along for a day of non stop fun and adventure.
Convenient pick up off Long Wharf, steps away from the heart of charming and historic Sag Harbor village. There are a wide variety of restaurants and shops located right nearby to pick up your favorite lunch or snacks to enjoy on board your private boat rental, if you need recommendations - don’t hesitate to ask!
Inquire about our fantastic Sag Harbor Booze Cruise or a Sag Harbor sunset cruise
Valkyrie Sailing Charters offer an affordable and fun way to spend a day on the water with activities for all. We cater our sailboat charters (with Captain and Crew) entirely to your needs. On our spacious and luxurious Sag Harbor Catamaran Rental you are sure to have the best day amidst the world famous, picturesque scenery of Eastern Long Island
...More info Hamptons Sailboat Charters

Sag Harbor Booze Cruise party valkyrie catamaran
Fun Sag Harbor booze cruise boat rental catamaran
Glorious sag harbor bachelorette party captain paul
July 2019

We had a wonderful time on a private sunset sail over labor day weekend, he was fast to respond (even though we booked our experience less than 24 hours beforehand). We loved it so much, we brought a larger crew with us the very next day. Would absolutely go sailing on the Valkyrie again!

James 5 Star Review with: Google

Sag Harbor Booze Cruise

62' x 30' Largest Sunset Yacht Rental in Sag Harbor in dual charter with 38' boat for up to 18 passengers
62'x30' Largest Sunset Yacht Rental in Sag Harbor with 38' partner
Photo by Pilot Paul


Whether you’re celebrating a milestone or special occasion or just need a day to let loose, you’re guaranteed to have fun on our spacious Luxurious Catamaran Rental, reviewed by many as the Best way to spend any day!

Weekday Sag Harbor Booze Cruise 2022

Weekend Sag Harbor Booze Cruise 2022

Get your party playlist ready, bring your funnest friends, plenty of drinks and snacks and prepare for an EPIC day on the water. We have the most powerful marine Stereo System. Your Booze cruise includes Captain and crew so you won’t have to worry about a thing while the drinks flow and the fun doesn’t stop for the duration of your Sag Harbor Boat Rental. Put up your OOO, don’t forget your swimsuit, and prepare to make memories that’ll last all summer long.
Valkyrie is engineered for 49 passengers, so while we are capped at 12 per private charter by the US Coast Guard - that means there is PLENTY of room for dancing, lounging, drinking and debauchery with your crew. Indoor and outdoor covered living/dining areas, as well as two trampolines give you plenty of room to spread out (no one wants to be on top of each other on a hot summer day). We provide coolers (with ice and water) located wherever is convenient so you won’t have to get up each time your drink needs refreshing, towels and pool noodles in case you’d like to stop and cool off in the water - we’ve got you covered. Pack light & get ready for the time of your life. Valkyrie Sailing Charters offer an affordable and fun way to spend a day on the water, amidst the world famous, picturesque scenery of Eastern Long Island. ...More info Hamptons Sailboat Charters

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Sag Harbor Boat Rental video of Valkyrie Sailing 2022
Sag Harbor Boat Rental aerial drone video of Valkyrie Sailing Charters and Mega Yacht
Valkyrie Sailing Sag Harbor Mansion Boat Tour
Sag Harbor Mansion Tour and views of Valkyrie sailing in Sag Harbor. Aerial Drone video
private sag harbor sunset charter aboard Valkyrie with Captain Paul
Best Captain and Crew (Paul and Nicole) in Sag Harbor enjoying Sunset
Magnificent Sag Harbor sunset tour rental catamaran
guests enjoying cruise around Sag Harbor and Gardiners bay

Sag Harbor Sunset Cruise


A summer sunset in Sag Harbor is just about as good as it gets. The fiery orange sun disappearing on the horizon as the sky turns shades of cotton candy pink and purple, descriptions hardly do it justice. A reminder that magical moments occur all the time, nestled amidst the mundane of our day to day. Our dinner reservations are very often the highlight or culmination of our day, imagine how much MORE they can be following an epic sunset on the water!
During our Sag Harbor Sunset Cruise, bring your favorite bottle (or bottles!) of wine or champagne, maybe an appetizer charcuterie board, and enjoy one of life’s greatest simple pleasure aboard Valkyrie with your friends and loved ones. All as a precursor to what’s sure to be an amazing dinner or evening out on the town. Set the mood with spectacular golden hour light flooding in and let your worries float away… Sag Harbor Booze Cruise or a Hamptons Sunset Sail
Weekday Sag Harbor Sunset Cruise 2022

Weekend Sag Harbor Sunset Cruise 2022

Bachelorette Boat Party

Our most popular Sag Harbor boat charter!
Sag Harbor bachelorette party brides maids enjoying the sunset
sag harbor bachelorette sailing during sunset cruise
Best sag harbor bachelorette private boat tour with captain paul

Valkyrie Sailing provides the picture perfect setting for your ideal Sag Harbor Bachelorette Party Yacht Charter!

Included in your Private Sag Harbor Bachelorette Party Boat Rental:

  1. Half Day Boat Rental (full day options also available) aboard a beautiful 62 foot, 4 bedroom 4 bathroom Private Sailing Catamaran.
  2. Full staffing of the vessel, including USCG Licensed Captain Paul and crew
  3. Flexible pick-up/drop-off locations...Heading to dinner next in Montauk or Shelter Island? We’d be happy to drop you off!
  4. A variety of different routes to choose from depending on what things you’d like to do or sights you’d like to see!
  5. Day excursions, Sag Harbor sunset cruise, mansion tours, wine vineyards, Sag Harbor Booze Cruise...
  6. Access to our pool noodles & floats, refrigerators & freezer (don’t worry about lugging around a bulky cooler or accessories!).
Valkyrie Sailing provides a fully customizable private, crewed yacht charter experience in Sag Harbor catered entirely to your individual needs and desires. We are more than happy to work with you and we can’t wait to help you celebrate such a special time in your life. sag harbor bachelorette party boat 2022
If you are searching for the most spacious boat then a Sag Harbor Catamaran tour boat Rental with Valkyrie is The Highest rated.
Best of all, Renting a Private Yacht with Captain Paul - he is the boat owner and doesn’t work with charter brokers, so there are no hidden or added surcharges or fees!
Valkyrie is a wide, stable Catamaran tour boat operating in Sag Harbor. Certified by The US Coast Guard for 12 passengers. There is ample space in 3 separate areas all of which could fit 49 passengers: Front Deck with trampoline netting and comfy bean-bags, rear section under cover with ample seating, and Inside living room area.

New: Inquire about optional Aerial Drone Video and Photos

...Click for More Info on Ultimate Bachelorette Weekend Plan

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bachelorettes having fun at Sag harbor bachelorette party booze cruise

Model Location Shoots

Sunset Beach Shelter Island Sunset cruise
valkyrie sailing catamaran stern view
Sag Harbor model shoot boat

Valkyrie Sag Harbor Sailboat Rentals is the perfect platform for film, photo, and music video location shoots. At 62' long by 30' wide, with no heel, our vessel remains very flat and stable - perfect for shooting on the water. Our ample wide, accessible and flat deck space makes it easy to accommodate equipment and crew. In addition to our deck with ideal scenic background, inside you’ll find a well kept and pristinely clean luxury nautical interior.
Valkyrie Sag Harbor Sailing Catamaran is available to rent for location shoots during a Sag Harbor Boat Tour, with a variety of sailing routes throughout Eastern Long Island. Book for a full or half day, and our crew will assist with everything your crew might need. Picturesque, scenic, and private locations are available.
We’ll organize your choice of food and beverages, bring your equipment, feel free to tap into our sound system and prepare for a shoot that will stand the test of time.

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Model Location Shoot aboard Valkyrie Sailing Catamaran

Wedding Proposals

Sag Harbor Sunset Cruise Proposal aboard Valkyrie Sailing Charters
valkyrie sailing catamaran stern view
private Sag Harbor Sunset Cruise Proposal aboard Valkyrie Sailing Charters

Propose at Sea
A Luxury Private Yacht rental is the perfect location to propose to your sweetheart. Use your imagination and envision yourself bending down on one knee to propose to your significant other aboard Valkyrie Sailing Catamaran with a beautifully romantic Sag Harbor setting in the background. The sun sets in the distance while the breeze moves through your soon-to-be fiance's hair as you pull out the ring and ask for her (or his) hand in marriage.
It simply does not get any more romantic than that.
Our crew is here to provide you with whatever you need to make your wedding proposal on the water absolutely perfect. Either Day Sail, or Sunset Cruise. After all, the subtleties of this important moment matter a great deal. Tell us exactly what you envision for your wedding proposal and we will bring your vision to life, setting the stage for a truly unforgettable proposal on the water and a lifetime of love.
Bring Your Own Photographer, or Incorporate our New Highest Quality Drone to memorialize sweeping shots on the Deck of the Private Catamaran SailBoat Rental

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Romantic Proposal during Sag harbor Sailing Cruise aboard Valkyrie Sailing Catamaran Rental

Family Friendly Fun & Adventures

Treasure hunt pirate-booty boat party aboard valkyrie sailing Sag Harbor Boat Rental
Sag Harbor Boat Tour Valkyrie Sailing Boat Charter kids pirate treasure hunt adventure
Kids tubing adventure aboard sailing charter Sag Harbor

Pirate Treasure Hunts, snorkeling, tubing, sailing camp
At Valkyrie Sailing, we pride ourselves on offering fully customizable charters, designed with something for everyone in mind. Can’t get a sitter, or just want to bring your kids along? We’ve got you covered! Click here for more info … ...More Info Pirate Treasure Hunt by Boat

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Treasure hunt pirate-booty fun boat party aboard valkyrie sailing charters

Valkyrie Sailing Charters 5 Star Reviews

Sag Harbor Sail Boat Rentals - Over 100 5 Star Reviews from Google and other verified Sources. For The Best Sag Harbor Sunset Cruise, Fun Sag Harbor Booze Cruise, and Family Day Sails around Picturesque Sag Habor Bays, including Manion Tours, and Mega Yachts Click to View all Reviews

September 2021

Captain Paul did a great job with communicating throughout the whole experience. The boat was a fun time, with music and fridge available to hold our snacks and drink. We stopped to swim at nice locations and it was an overall fun and memorable sail!

Cynthia Raimondi 5 Star Review with: Google

September 2021

Absolutely wonderful! The boat looks even better than the photos. We had 8 girls but could have fit many more. Captain Paul and Nicole were awesome- so helpful, so friendly- the boat was super clean and relaxing, we even stopped and went swimming. Highly recommended!!!!!! We had a bachelorette trip but this would be lovely for any occasion

maggie politi 5 Star Review with: Google

July 2021

We had an amazing day with Captain Paul on his gorgeous boat!! We were a group of 9 celebrating a bachelorette party and it was the perfect afternoon. We did a sunset sail from 4-8 pm and had the best time. Paul was so accommodating, helpful and easy to communicate with leading up to the day. Thank you so much Paul!!

Olivia Zysman 5 Star Review with: Google

October 2020

My husband and I booked a sunset sail with Captain Paul for our anniversary, and we couldn’t be happier with this experience. Captain Paul made us feel welcome, comfortable, and safe. The boat was clean and spacious, allowing guests to have a good amount of privacy. This this is a good value for a 3-hour sail with breathtaking views of the mansions in North Fork and Shelter Island. We capped off the day watching the most majestic sunset I’ve ever seen. Another sailing charter with Captain Paul would surely be part of the itinerary for our next Sag Harbor escape!

Cheska Marie 5 Star Review with: AirBnB

September 2019

What an AWESOME experience! My wife and I took a sunset cruise aboard the Valkyrie with Captain Paul. We had originally scheduled for the night prior but some weather rolled through and Paul was very accommodating. We met where his instructions had laid out and boarded his dinghy right away. A quick 2 minute jaunt to the Valkyrie! We sailed for 3+ hours and it culminated in an unbelievable sunset. Prettier than our pictures showed! Captain Paul made sure we had everything we needed - including blankets when it got chilly - and was the perfect host. We hope to sail with him again and would suggest this experience to anyone. Thanks, Captain!

Whitney 5 Star Review with: AirBnB

August 2021

I booked Valkyrie Sailing with Captain Paul for my sisters bachelorette party. By far the easiest process to book. Captain Paul was very responsive in all emails, and very helpful with recommendations for lunch suggestions in the area as well. The experience on the boat exceeding all expectations. It was clean, and very spacious. We sailed around Sag Harbor area and even anchored in a beautiful place to swim. Captain Paul and assistant Nicole helped to blow up floats we brought and supplied noodles too. All of the bachelorette party guests had a great time. Highly recommend Valkyrie Sailing with Captain Paul! In fact will be booking again for a family boating trip in the near future. Beautiful day for all!

Jennifer O'Neill 5 Star Review with: Google

August 2021

Had an amazing time with Captain Paul and Nicole aboard the Valkyrie. We had eight 30-something ladies onboard for a morning sail during my best friend's bachelorette weekend. The weather was great and all of the seating/tanning areas super comfortable and large enough for us all to sit together. We stopped a few times to swim and really appreciated the Paul/Nicole keeping an eye on us in the water and making sure we were safe. As we walked off the 4 hour cruise we were all talking about re-booking again for another weekend since it was so much fun and relaxing!

Marisa Rodriguez-McGill 5 Star Review with: Google

June 2021

What an amazing experience!! From the beginning, Paul made our reservation easy and answered all of my questions quickly. I was delighted to find he had availability as he was the best price in the area. I had concerns due to COVID-19 and he assured me that the tour would still happen with no issues. Captain Paul went above and beyond for our group. When we found out about thunderstorms on the day of our sail, Paul sprung into action and worked with us to figure out a plan B. He was very flexible and was able to drop us off on the North Fork so we could continue on with our wine tour after the sail. The boat itself is SO spacious and truly an amazing experience! The speakers are great, and the front of the boat with the bean bags is so comfy. Paul didn't hesitate to help us blow up our floats and provide us with life jackets and pool noodles. I absolutely recommend for a bachelorette party, birthday party, or any type of group outing! Thanks Captain Paul!

Alex Siegal 5 Star Review with: Google

sag harbor bachelorette party boat
Sag Harbor boat rental catamaran
Sag Harbor Booze Cruise party valkyrie catamaran
captain paul yacht day sail valkyrie sailing charters
Guest enjoying Sag Harbor Sunset Sail aboard private boat rental Noyack Bay
Glorious Aerial Drone View of sag harbor boat rental Deck area
Valkyre Sag Harbor Boat Rental Frequently Asked Questions (FAQs)

Valkyrie is engineered for 49 passengers, so while we are capped at 12 per private charter by the US Coast Guard - that means there is PLENTY of room for dancing, lounging, drinking and debauchery with your crew.

Get your party playlist ready, bring your funnest friends, plenty of drinks and snacks and prepare for an EPIC day on the water. We have the most powerful marine Stereo System.

Indoor and outdoor covered living/dining areas, as well as two trampolines give you plenty of room to spread out (no one wants to be on top of each other on a hot summer day).

We provide coolers (with ice and water) located wherever is convenient so you won’t have to get up each time your drink needs refreshing, towels and pool noodles in case you’d like to stop and cool off in the water - we’ve got you covered. Pack light & get ready for the time of your life.