If you're in Watch Hill you absolutely must charter a trip on Trim Again with Captain Jack. We…read morewent out for a sail last week, this was our second time, and we couldn't have had a more enjoyable experience. Nothing recharges your batteries more than a quiet sail in the bay and out to Fisher's Island. Captain Jack knows everything about the area and he's happy to provide a guided tour. But if you want some islandy music or a quiet cruise, he's happy to accommodate that too as he did for us. We mixed up over our 3 hour charter. It's my opinion, but no trip to Watch Hill is complete without getting out on the water and Trim Again is the best way to do it. And it's surprisingly affordable as well.

Jack is a truly amazing captain. The experience on his boats are incredible and fun and full of…read morehistory as well! We have been out with Captain Jack 4 times now over the past 10 years and would do it every day if we could! He is a great captain and teaches you so much about the history of the area (and even if you think you don't like history, he will make it fun and interesting). We cannot say enough amazing things about Jack. On top of it all, he is really an amazing human being. Do NOT go to Watch Hill without going on a boat with Jack Spratt!

They cancelled our charter with 15 minutes notice to arrival time as we were already about to…read morearrive with a party of 15. "Mechanical issues on the charter prior." I bet. This was my plan for my 25th birthday. I had a party of 14 about to be there, and we all already paid. Beyond disappointed as this last minute cancellation has ruined my birthday and left a party of 14 in sag harbor with no backup plan since we received a final confirmation the night before. Thanks American Beauty. Not feeling beautiful.

Very nice boat ride around sag harbor with great views. David did.an excellent job telling and…read moreshowing us all the history around the area

Captain Erick was Fabulous.. very knowledgeable. Very…read morehelpful a pleasure. Would highly recommend any cruise with Captain Erick ..... If you book a cruise with Captain Eric, you will not be disappointed..

This private boat cruise was supposed to be the highlight of our trip and IT WAS. It was exactly…read morewhat we needed on our last day in Mystic. We had beautiful weather.. The "Novelty" boat was beautiful. Captain Eric was amazing. Communication leading up to our ride was great. Eric was personable and knowledgeable which made our morning tour unforgettable. We were offered cold water and umbrellas when the sun became intense. It was also nice to get so many ideas and recommendations for the area. Thank you

This was a highlight of our bougie Bachelorette party in Montauk! We rented our own private…read morecatamaran for six people for three hours. It was about $700+ after fees, tip, etc, and it was totally worth it. Our captain, Mason, was super cool. He was friendly, knowledgeable, and we felt comfortable being really annoying and weird in front of him. The sail itself was just a short ride in the bay, where we anchored close to a beach. We loved dancing on the boat, trying out the SUP board (included), basically chugging our BYOB drinks (no hard liquor allowed on board), taking pics lounging in the net, gawking at the yachts, and pretending the pool noodles were seahorses that we were riding. Bachelorette stuff! I think we had the Mon Mini boat, probably the smallest option. Included: one SUP board, bluetooth speaker, cooler, two pool noodles, the captain.

I booked the 26' catamaran for a Friday sunset cruise from 5-7pm. The catamaran was larger than I…read moreexpected. Also, the bean bag chairs were very comfortable compared to other boats. They provided two Yeti coolers and a Bluetooth speaker for music which was nice. The staff were very friendly and helpful. They helped take pictures for our group and the sailing was very smooth. I would definitely book again, probably earlier in the summer for the 3 hour cruise to be able to do the paddleboarding.

What a wonderful day for three of us out on the water. Captain Mike knows the area and guides you…read moreto the fish. We fished for fluke along the river and then out to the ocean for seabass, stripe bass, and lots of other fish in the sea! He knew where they were and where to catch them. Access to the river, the ocean and down to Rhode Island the twenty-one-foot Grady White cruised right along power by an ultra-quiet late model Yamaha 200 four stroke. After fishing and catching for hours, Captain Mike narrated a wonderful river cruise past the Back Eddy (a great stop for dinner after your charter), fresh oyster farmers market, fish house and quaint cottages, boat houses, and captains' residence of old. Picture perfect! We enjoyed every part of the day and had a smile on our face for many hours after. Highly recommend Westport Boat Charters with Captain Mike. Book it and you won't be disappointed.

From the owner: Westport Boat Charters provides charter services including sunsets cruises, river tours, and…read morefishing trips in the Westport River.

Sea dog picked us up from our wedding in Lloyd Harbor. They were a breeze to book with and helped…read moreto make my wedding day so special. Captain Burt and his wife were so accommodating and helpful getting us on and off the boat even in some rough seas. The boat in the excellent condition and made for a fairy tail send off with string lights and all!

From the owner: Sea Dog Cruising specializes in private charters up to six guests. We offer sightseeing tours of…read moresome of the most breathtaking natural and manmade sites. Experience the bluffs & lighthouses of Block Island. Secluded inlets, coves and beaches along the shore still offer vistas unspoiled by modern development, and the stately mansions and estates along the water give the region its nickname, "The Gold Coast". We also offer majestic tours of the Connecticut Coast Line. From photo shoots, to intimate gatherings, from special occasions to burials at sea, our dedicated crew ensures your charter will be an experience you won't soon forget.

Forgetta-bout it! Best charter I've ever booked. 10/10. Will sail Poet's Lounge again!!read more

What an unforgettable experience! Our crew loved our time on the water with Darin. He was an…read moreexcellent host, wonderful to chat with and very attentive when he realized one of us was feeling seasick. Two of us had been out with him before for a sunset cruise and we upped it to 3 hrs this time. Truly a great experience - highly recommend and will definitely be back!

We had a great time sailing with Ali. She was very knowledgeable about the area and it's history…read more It's a great way to spend a few hours on the water while being able to relax and take in the sights, all while sipping a cocktail. Highly recommend Sail Montauk.

Darius is great with kids and people in general. If you have kids then he's the guy to book with…read morebecause he involves them in the sailing and they have a blast. We had a great time even though the weather was not perfect which is saying a lot. He put us at ease and gave us just the right amount of information so that we got a sense of the boat and sailing. It was a really nice way to see the area and we'd do it again.

Beautiful clubhouse, very good food and fabulous service! Christine and Martha went above and…read morebeyond to meet our needs as we were visiting from RI on our vessel. SHYC is a must stop for proper yacht people!

We had our wedding reception here on October 27th. We worked with the manager, Chris Manfredi. He…read morewas SOOOO kind, funny and accommodating to us through the whole process. We sat down and talked about everything my husband and I dreamed about for the reception - and Chris and the SHYC made it all come true. It's a beautiful space. The fireplace was lit, we had a gelato sundae bar set up in the library, and all the rooms were open so our guests had plenty of room. We got to enjoy a sunset over the water through the windows that span the entire length of the club. I am still getting tons of compliments about the food. Chris worked with us to set up stations with made to order steak, pasta, veggies, and bacon scallops that were TO DIE FOR! All of the servers, bartenders, everyone involved was so kind, helpful and in a celebratory mood. It was absolutely perfect and VERY reasonable!! We felt like it was an incredible value for the experience. I can't rave enough. Thank you so much Chris and SHYC!!