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 2025
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
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: | View All 123 Reviews. Best Boat Rental in Sag Harbor
Sag Harbor Booze Cruise
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 2025
Weekend Sag Harbor Booze Cruise 2025
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
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 2025
Weekend Sag Harbor Sunset Cruise 2025
Bachelorette Boat Party
Our most popular Sag Harbor boat charter!
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:
- Half Day Boat Rental (full day options also available) aboard a beautiful 62 foot, 4 bedroom 4 bathroom Private Sailing Catamaran.
- Full staffing of the vessel, including USCG Licensed Captain Paul and crew
- Flexible pick-up/drop-off locations...Heading to dinner next in Montauk or Shelter Island? We’d be happy to drop you off!
- A variety of different routes to choose from depending on what things you’d like to do or sights you’d like to see!
- Day excursions, Sag Harbor sunset cruise, mansion tours, wine vineyards, Sag Harbor Booze Cruise...
- Access to our pool noodles & floats, refrigerators & freezer (don’t worry about lugging around a bulky cooler or accessories!).
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!
New: Inquire about optional Aerial Drone Video and Photos
...Click for More Info on Bachelorette Boat Rental or...Click for More Info about Hamptons Bachelorette Party Weekend Plan
Model Location Shoots
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.
Wedding Proposals
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
Family Friendly Fun & Adventures
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
Valkyrie Sailing Charters 5 Star Reviews
Sag Harbor Sail Boat Rentals - Over 123 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 ReviewsCaptain 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 Google
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 Google
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 Google
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 AirBnB
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 AirBnB
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 Google
Valkyrie Sag Harbor Boat Rental Frequently Asked Questions (FAQs)
How many passengers permitted on The Boat?
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.
Do you Have Speakers, Sound-System?
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.
How much Space on The Boat?
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).
What do you provide?
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.