Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Why travelers choose Greetwell

Curated by our team

Every experience is hand selected and approved by Greetwell.

Personal concierge

Real humans available to help before, during, and after your booking.

Intimate & authentic

Including unique in-home experiences you won't find anywhere else.

Easy booking & cancellation

Reserve in minutes with free cancellation on most experiences.

Greetwell

Experiences that stay with you long after the trip

Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

About

  • Our Story
  • For Experience Providers
  • For Hospitality Partners
  • For Developers

Resources

  • Travel Guides
  • Destinations
  • Categories
  • Experience Gift Cards
  • Help Center
[email protected]1-877-GREET-WELL

Safe & Secure Payments

© 2026 Greetwell, Inc. All rights reserved.
Privacy PolicyTerms
Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Best results for

Sailing

Showing 721-744 of 1,008 results
Key West, FL86Honolulu, HI65San Diego, CA35St. Augustine, FL28Traverse City, MI26
More
  • New York, NY24
  • Charleston, SC21
  • Chicago, IL18
  • Hilton Head Island, SC17
  • Boston, MA16
  • Newport, RI15
  • Saint Michaels, MD15
  • Pensacola Beach, FL14
  • Bluffton, SC13
  • Cocoa Beach, FL12
  • Salem, MA12
  • Destin, FL11
  • Marina del Rey, CA11
  • San Francisco, CA11
  • Irvington, VA10
  • Kennebunkport, ME10
  • Manteo, NC10
  • Oceanside, CA10
  • Boothbay Harbor, ME9
  • Camden, ME9
2-Hour Private Sail in West Grand Traverse Bay

2-Hour Private Sail in West Grand Traverse Bay

Charter a private 2-hour sail for up to 6 guests on West Grand Traverse Bay

5.0 • 188 reviews
$298
Private Sunset Sailing Charter on Grand Traverse Bay

Private Sunset Sailing Charter on Grand Traverse Bay

Sail Grand Traverse Bay at sunset on a private 2-hour charter for up to 6 guests

5.0 • 188 reviews
$359
Sail a 5-Hour Power Island Cruise From Traverse City

Sail a 5-Hour Power Island Cruise From Traverse City

Private 5-hour sail to Power Island with time to anchor and swim

5.0 • 188 reviews
$794
Private Sailboat Charter in Charleston

Private Sailboat Charter in Charleston

Learn the basics of sailing or relax on a private charter

5.0 • 187 reviews
$583
3-Hour Puget Sound Sailing Charter in Seattle

3-Hour Puget Sound Sailing Charter in Seattle

Sail Puget Sound on a private 3-hour charter for up to 6

5.0 • 179 reviews
$504
Sunset Sailing Charter on Puget Sound in Seattle

Sunset Sailing Charter on Puget Sound in Seattle

Private 3-hour sunset sail with views of Seattle and the Olympic Mountains

5.0 • 179 reviews
$504
2-Hour Salem Sound Schooner Sail

2-Hour Salem Sound Schooner Sail

Sail a 1930 schooner past Salem Sound lighthouses

5.0 • 180 reviews
$62/ person
Sail Salem Sound on a Classic Schooner Charter

Sail Salem Sound on a Classic Schooner Charter

Make Salem Sound your private escape aboard a classic schooner

5.0 • 180 reviews
$1,790
Historic Schooner Sunset Sail in Salem

Historic Schooner Sunset Sail in Salem

Sunset sailing aboard John Alden's racing yacht

5.0 • 180 reviews
$84
Sunset Sail Charter in Salem

Sunset Sail Charter in Salem

A private sunset outing aboard a historic schooner

5.0 • 180 reviews
$1,454
Private Sunset Sail in Salem

Private Sunset Sail in Salem

Charter a classic yacht for a relaxed Salem sunset sail

5.0 • 180 reviews
$1,229
Salem 2-Hour Morning Mimosa Sail

Salem 2-Hour Morning Mimosa Sail

Raise the sails and sip mimosas aboard a classic yacht on Salem Sound

5.0 • 180 reviews
$73/ person
Salem Sunday Bloody Mary Sail

Salem Sunday Bloody Mary Sail

Sail Salem Sound with Sunday Bloody Mary specials and hands-on sailing options

5.0 • 180 reviews
$73
Sunset Sail from Perkins Cove in Ogunquit

Sunset Sail from Perkins Cove in Ogunquit

Lounge on deck or lend a hand with the sails

5.0 • 180 reviews
$80/ person
Private Sailing Charter in Maalaea Bay

Private Sailing Charter in Maalaea Bay

Celebrate on a private catamaran with onboard appetizers and drinks

5.0 • 168 reviews
$2,729& up
2-Hour Daytime Sailing Cruise in Presque Isle Bay

2-Hour Daytime Sailing Cruise in Presque Isle Bay

Sail Presque Isle Bay with a captain and crew, plus two complimentary drinks

5.0 • 166 reviews
$170/ person
2-Hour Sunset Sailing Cruise in Presque Isle Bay

2-Hour Sunset Sailing Cruise in Presque Isle Bay

Sail Presque Isle Bay at sunset with wine and crew included

5.0 • 166 reviews
$201/ person
Full-Day Sailing Charter in Erie

Full-Day Sailing Charter in Erie

Take the helm and build practical sailing skills on Lake Erie

5.0 • 166 reviews
$1,903
Enjoy a 2-Hour Erie Sunset Sail & Couples Massage

Enjoy a 2-Hour Erie Sunset Sail & Couples Massage

Book a 1-hour couples massage plus a 2-hour Lake Erie sail for two

5.0 • 166 reviews
$779
Sailing Lesson at Wolverine Park Marina

Sailing Lesson at Wolverine Park Marina

Learn sailing basics with hands-on coaching tailored to your goals

5.0 • 166 reviews
$191/ person
Private 4-Hour Sailing Lesson in Lahaina

Private 4-Hour Sailing Lesson in Lahaina

Build sailing skills with instruction tailored to your experience

5.0 • 128 reviews
$2,729
Private Daytime Sailing Charter in Lahaina, Maui

Private Daytime Sailing Charter in Lahaina, Maui

A tailored private sail with Maui coastal views and onboard refreshments

5.0 • 128 reviews
$1,080& up
Gloucester Sunset Private Sailing Charter

Gloucester Sunset Private Sailing Charter

Reserve a traditional schooner for your celebration on Gloucester Harbor

5.0 • 107 reviews
$636& up
Gloucester Private Sailing Charter

Gloucester Private Sailing Charter

Private schooner sailing with captain and crew included

5.0 • 107 reviews
$477& up
1…303132…42