The Best Sailboat Rentals Near Spring Lake

50ft Catamaran Charter with Water Toys - Annapolis, MD

We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto and Grace are wonderful hosts and guides. They have a wealth of sailing and life experience to share during your trip. They were very flexible with us during a proposal event.

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!

41' Morgan Classic Sloop in Muskegon, Michigan!!!

This was our second time sailing with Jim My wife and I had a great time. Jim was easy to contact and responded very quickly to questions before the sail. We had to change our scheduled date and time because of weather, but Jim was very flexible and accommodating. We had a great conversation with him and heard some great stories about his sailing past. He even let me take the helm for a while, which i really enjoyed,

41' Morgan Classic Sloop in Muskegon, Michigan!!!

We had such a special day. Our captain was so attentive to everyone's comfort and went above and beyond for our member who was a first time sailor with motion sickness. His company was enjoyable and never intrusive and the day relaxing because he made sure no matter what each individual wanted to do, they got to do it. Thank you for your expertise and kindness Captain!!

41' Morgan Classic Sloop in Muskegon, Michigan!!!

I gave 5 stars on everything. Would have given 6 if it were an option. Jim was Quick to respond to questions. He was very accommodating and flexible on everything before and during the sailing trip. He was very friendly and has a ton of sailing experience. It was an extremely enjoyable trip.