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 961-984 of 1,004 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
Private Snorkel Day Sail & Sunset Cruise from St. Thomas

Private Snorkel Day Sail & Sunset Cruise from St. Thomas

Enjoy a day at sea without missing the sunset sail

5.0 • 1 reviews
$1,952
Private Full-Day Sailing & Snorkel Charter in St. Thomas

Private Full-Day Sailing & Snorkel Charter in St. Thomas

Sail your own catamaran with lunch options from floating food spots to a private island

5.0 • 1 reviews
$1,789/ boat
Private Day Sail & Sunset Cruise in St. Thomas & St. John

Private Day Sail & Sunset Cruise in St. Thomas & St. John

Combine an afternoon at sea with a sunset sail on your own private catamaran

5.0 • 1 reviews
$1,952
Private Full-Day Jost Van Dyke Sailing Trip from St. Thomas

Private Full-Day Jost Van Dyke Sailing Trip from St. Thomas

Sail to White Bay with your own catamaran, snorkel stops, and time ashore

5.0 • 1 reviews
$2,548
Intro Sailing Lesson for First-Timers in New Orleans

Intro Sailing Lesson for First-Timers in New Orleans

Try sailing before committing to further lessons

5.0 • 1 reviews
$56/ person
Evening Wine and Jazz Concert Sail on Clipper City

Evening Wine and Jazz Concert Sail on Clipper City

Sail past the NYC skyline with live jazz and two glasses of wine on a summer evening

4.5 • 723 reviews
$157
New York Golden Hour Cocktail Sail

New York Golden Hour Cocktail Sail

See New York Harbor from a historic tall ship in pre-sunset light

4.5 • 723 reviews
$104/ person
City Lights Sailing Cruise in New York City

City Lights Sailing Cruise in New York City

Sail past NYC’s lit-up skyline on the Clipper City at night

4.5 • 723 reviews
$94/ person
New York Sunset Jazz Sail

New York Sunset Jazz Sail

Live jazz, harbor landmarks, and sunset views aboard a tall ship

4.5 • 723 reviews
$106/ person
Private 2-Hour Sailing Lesson in Honolulu

Private 2-Hour Sailing Lesson in Honolulu

Build sailing skills with hands-on instruction from Captain Al

$424& up
Sunset Sailing Cruise on a 53' Catamaran in Washington DC

Sunset Sailing Cruise on a 53' Catamaran in Washington DC

Trade city bustle for a relaxed evening under sail

$85/ person
Lunchtime Sailing Tour of Buffalo Harbor

Lunchtime Sailing Tour of Buffalo Harbor

Explore Buffalo Harbor under sail

$46/ person
Buffalo Harbor Sunset Sail

Buffalo Harbor Sunset Sail

Step aboard SV Foxy Maxie for a sunset on the water

$46/ person
Sailing Trip to Angel Island From Berkeley

Sailing Trip to Angel Island From Berkeley

Spend less time sailing and more time exploring ashore

$476& up
Private Half-Day Sailing Cruise on San Francisco Bay

Private Half-Day Sailing Cruise on San Francisco Bay

Sail aboard a 30-foot monohull with your own group and a captain

$455& up
Sailing Crew Overboard Recovery Workshop in Berkeley

Sailing Crew Overboard Recovery Workshop in Berkeley

Build practical overboard recovery skills beyond a basic sailing class

$207/ person
Intro to Sailing Lesson in Berkeley

Intro to Sailing Lesson in Berkeley

Learn how sails, wind, and boat handling work together in a hands-on lesson

$196/ person
Semi-Private Sailing Cruise with Alcatraz Views in Berkeley

Semi-Private Sailing Cruise with Alcatraz Views in Berkeley

Take in San Francisco and island views under sail

$413& up
Full-Day Historic Ketch Sail & Snorkel Tour in St. John

Full-Day Historic Ketch Sail & Snorkel Tour in St. John

Reach secluded snorkel spots under sail aboard a historic vessel

$848
Sunset Sail on a Historic Monohull in St. John

Sunset Sail on a Historic Monohull in St. John

Wind down on the water with an evening under sail

$424
Half-Day Sail & Snorkel Eco Tour in St. John

Half-Day Sail & Snorkel Eco Tour in St. John

Pair sailing and snorkeling with lunch and drinks included

$530
Penobscot Bay Schooner Day Sail in Camden, Maine

Penobscot Bay Schooner Day Sail in Camden, Maine

See Maine's coast from the deck of a schooner

$64/ person
Bring Your Own Picnic Sailing Cruise in Old Saybrook

Bring Your Own Picnic Sailing Cruise in Old Saybrook

Enjoy your own picnic on the water with a choice of cruising routes

$371& up
War of 1812 Tall Ship Sail on St Simons Island

War of 1812 Tall Ship Sail on St Simons Island

Help set the sails and haul the lines aboard a historic-style tall ship

$70/ person
1…3839404142