By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
Page 10 of 39 • 920 listings
865
Miami
Florida
676
Cancún
Quintana Roo
490
Isla Mujeres
Quintana Roo
369
Tampa
Florida
359
Los Angeles
California
349
Lake Michigan
United States
329
Puerto Vallarta
Jalisco
311
Miami Beach
Florida
300
Cabo San Lucas
Baja California Sur
295
Nuevo Vallarta
Nayarit
288
Chicago
Illinois
285
Marina
Cabo San Lucas
243
Saint Petersburg
Florida
240
Tampa Bay
Florida
237
Marina Vallarta
Puerto Vallarta
227
Clearwater
Florida
224
Cartagena
Bolivar
209
Chesapeake Bay
United States

Vince
Set Sail on a classic 36' S2 in Chicago for up to 6 Guests
Highly recommend, Planned a surprised engagement, and Ted and Christy were awesome. Super accommodating, friendly, and went out of their way to make the experience very personal and fun. I wouldn’t want to experience a charter any other way.
TJ
Tushar
Luxury Italian Sailing Yacht on the Puget Sound — Seattle
Everything was perfect, Matt and JB made sure we had the perfect day! They made our day even more special, and were super accommodating and helpful, the perfect crew to sail with. As for the boat, Serafina is hands down the best boat on GetMyBoat, it is beautiful and very unique, it’s classy and we had a great time sailing.

Geoffrey
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.
ES
Edward
Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests
Our whole family, 3 generations, had a wonderful time. Skipper Dave is a knowledgeable, caring, and thoughtful host on his well equipped boat.
RM
Rachel
Let's Go Sail in Gloucester Point, Virginia
Had a wonderful and relaxing time on the boat! Learned a lot about Virginia and the water. Captain Bill was very communicative and allowed my group to reschedule due to the rain that morning. We all got a turn to drive the boat which was really fun and a new experience for all of us. The front of the boat felt like it was just me and the water. We brought our own drinks and snacks. I would definitely do it again.
RK
Richard
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Our group of four had a great three days onboard the Icarus. The boat was easy to sail and operate. No problems motoring around in the marinas, steers easy in reverse too. Jim was a great host, very responsive and knowledgeable. Highly recommend his boat to sail the Chesapeake!