Private Sailing Trips with Captain Gregg on Apostle Islands

Cruising Monohull
6 Guests

About This Boat

Enjoy sailing on Apostle Islands with USCG Captain 


• All Day Charter for up to 6 people: $839
• 5 Hour Charter for up to 6 people: $645
• Private Sunset Charter for up to 6 people (2 hours): $374

What You Can Expect:

Welcome to Bayfield and the Apostle Islands!!

There are 22 Apostle Islands, with 21 of the 22 islands and 12 miles of mainland shoreline, that are included in the National Lakeshore Park at Lake Superior's southwest end. These forested, sheltered islands, on the world's most expansive fresh water lake, provides a paradise for sailors, divers & fisherman in an area rich with history. Madeline Island, is the only year-around inhabited island, which is not part of the National Shoreline Park, but it is an island most find very exciting to visit.
Come experience why countless boaters and sailing enthusiasts consider Bayfield and the Apostle Islands for some of the best sailing and recreational boating in the world. Bayfield was named "One of America's 10 Best Places to Sail", by Sail Magazine and one of the "50 Best Yachting Destinations" by Yachting Magazine readers in 2012.

Our Sail Offerings

Private All - Day and 5 Hour Adventure Sails 

Sailing at its best. From morning, an All day sailing adventure, want to include an Anchoring/Lunch stop? Not a problem! Plus, enjoy a relaxing sail all the way back to Pier 121 and an evening sunset. It has been a great day enjoying Central Texas.

This 5 hour trip is the for people wanting to truly relax.  You could help navigate the boat, learn to sail, or just sit back and let the Captain do the work for you.  It's your private trip  9:00 am or 11:00 am Departures.

Private 3 Hours Get-Away Sail and Sunset Charters 

This is one of the best trips on Lake Lewisville. We will sailing out into Lake Lewisville for a leisurely sail, meanwhile enjoying lunch or just relax. 9:30 am and 1:30 pm departure times

For your personal party (max 4 people) and usually last 2 - 2.5 hours depending on season and weather. We can customize these trips anyway you would like, with refreshments and food, wine, champagne, etc.

If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.


  • Type: Cruising Monohull
  • Capacity: 6 People
  • Rental Minimum: 3 hours
  • Cancellation: Full Refund 5 Days Prior


  • Life jackets/required safety gear
  • Cabin
  • Wheel steering
  • Inboard Engine
  • Autopilot
  • CD Player
  • Dodger
  • Single Engine
  • Fuel type: Diesel
  • Berth
  • Head
  • Furling Headsail
  • Furling Mainsail

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Meet Captain Gregg

Captain Gregg

From Lewisville

Member Since Dec 2015

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Phone Number
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