Find Sailing Charters Near You

Local Sailing Reviews

1. MB

   Maria

   Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago

   I am new to the world of sailing, and this was an awesome experience. I was able to have hands-on learning about sailing in the midst of a safe environment and a competent captain. As I don’t own, my own boat, the cost was very reasonable. I plan to do this again then near future!

2. TF

   Todd

   Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

   This is the boat to book for a sweet sailing experience in Chicago. Super family friendly. Ocean-worthy vessel and Capt Bob and Gabby have been all over the hemisphere with it. They're more than willing to share as much knowledge as you'd like to know. I even pulled up the main sail! Bob and Gabby were great with our young children. Just wonderful people. Swimming spot they chose was excellent. If you're looking for the real deal, this is it. Loved hearing their stories about open ocean sailing and traversing the Caribbean Islands. Kids loved the aqua chair floaty. Worth every penny and more.

3. 

   Barb

   Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

   The boat is exactly as listed. Had a great night out watching the navy pier fireworks. Communication was excellent. The weather wasn’t cooperating and the captain was quick to reach out with details. We ended up rescheduling twice. Chicago weather what are you going to do. But once we got in the boat everything was so lovely. And there is a boat dog named, Piper. Piper kept us all entertained! Highly recommend!

4. JK

   James

   Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

   Ted was the captain of the boat and was excellent. He made our ride very enjoyable and stayed out for the fireworks at the end which was amazing. Kids loved the experience too!

5. NB

   Nicole

   20ft Bayliner VR5 Boat in Rockville, IN

   First time renting a boat through this platform - would definitely do it again. HIGHLY recommend Peter. Communication was excellent from the get go... easy to schedule, easy to pick up/meet, boat and equipment was in great condition...we had everything we needed for a great day on the lake. Would DEFINITELY rent from him again. As we stopped past the marina to fill up, the worker said, "nice boat." When we told him it was a rental he was shocked and said it was way nicer than anything they rented out. Highly recommend!

6. 

   Cindy

   2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

   Took our three grandchildren on a sailboat excursion with Captain Andy. Such a great, peaceful experience. Let the waves and breeze carry your troubles away. We’ve spent a good bit of time on the water but never in a sailboat and had me wanting to learn more. Such great hospitality, beautiful day, and magnificent lake. Dreading returning to the heat!