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
  • 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 in Key West St Thomas

Showing 1-24 of 26 results
Sail & Snorkel Jost Van Dyke 9-Hour Cruise

Sail & Snorkel Jost Van Dyke 9-Hour Cruise

Catamaran sail to Jost Van Dyke with snorkeling, breakfast and an open bar

5.0 • 1.7K reviews
$307/ person
Private Sunset Sail on a 55' Yacht in St. Thomas

Private Sunset Sail on a 55' Yacht in St. Thomas

Sunset views, premium drinks, and hors d'oeuvres aboard a private yacht

5.0 • 77 reviews
$949
St. Thomas Match Racing Sailing Lesson

St. Thomas Match Racing Sailing Lesson

Learn racing skills and sail one-design boats at a private yacht club

4.9 • 1.3K reviews
$172/ person
Sunset Sail Around Charlotte Amalie Harbour

Sunset Sail Around Charlotte Amalie Harbour

Sunset sailing with appetizers, drinks and pirate tattoos

4.7 • 128 reviews
$94/ person
Full-Day Sailing & Snorkeling Charter in Red Hook

Full-Day Sailing & Snorkeling Charter in Red Hook

Customize a Caribbean catamaran day with snorkeling, beach stops and onboard comforts

4.5 • 272 reviews
$1,704
3.5-Hour Sailing Charter in St. Thomas

3.5-Hour Sailing Charter in St. Thomas

Private sailing with snorkeling, open bar, and a Christmas Cove option

$795
65' Catamaran Sunset Sail in St. John

65' Catamaran Sunset Sail in St. John

Ease into the evening with sunset sailing and an open bar

$84/ person
Private Sailing Catamaran Charter from St Thomas

Private Sailing Catamaran Charter from St Thomas

Sail the US Virgin Islands with a private crew and open bar

5.0 • 1.7K reviews
$2,014& up
Sunset Catamaran Charter in St. Thomas

Sunset Catamaran Charter in St. Thomas

Sail into sunset aboard a spacious luxury catamaran with champagne and music

4.5 • 272 reviews
$1,134
Private Sunset Sail on a Classic Yacht in St. Thomas

Private Sunset Sail on a Classic Yacht in St. Thomas

Sail into sunset colors with sparkling wine and coastal bites

$795
Catamaran Sail & Snorkel to St. John from St. Thomas

Catamaran Sail & Snorkel to St. John from St. Thomas

Pair an island escape with the comforts of a luxury catamaran

$116/ person
Sunset Sail & Snorkel in St. Thomas

Sunset Sail & Snorkel in St. Thomas

Sail into sunset with sparkling wine on a private catamaran

5.0 • 1.7K reviews
$1,590
4-Hour Sailing Charter in St. Thomas

4-Hour Sailing Charter in St. Thomas

Private sailing, snorkeling, and watersports in the US Virgin Islands

5.0 • 1.7K reviews
$1,749
Luxury Catamaran Sunset Sail in St. Thomas

Luxury Catamaran Sunset Sail in St. Thomas

Wind down under sail with hors d'oeuvres and an open bar

$116/ person
Luxury Catamaran Sunset Sail in St. Thomas

Luxury Catamaran Sunset Sail in St. Thomas

Unwind under sail with harbor views, hors d’oeuvres, and an open bar

$84/ person
Jost Van Dyke Catamaran & Snorkel Day Trip from St. John

Jost Van Dyke Catamaran & Snorkel Day Trip from St. John

Pair national park snorkeling with a sailing escape to the British Virgin Islands

$276/ person
Full-Day Catamaran Sail to Jost Van Dyke from St. Thomas

Full-Day Catamaran Sail to Jost Van Dyke from St. Thomas

Combine national park snorkeling with a British Virgin Islands beach escape

$244/ person
Full-Day Jost Van Dyke Catamaran & Snorkel from St. Thomas

Full-Day Jost Van Dyke Catamaran & Snorkel from St. Thomas

Pair national park snorkeling with an island escape to the British Virgin Islands

$298/ person
St. John Catamaran Sail, Snorkel & Shop from St. Thomas

St. John Catamaran Sail, Snorkel & Shop from St. Thomas

Pair a luxury catamaran sail with time to explore St. John at your own pace

$127/ person
Buck Island & Water Island Snorkel Sail from St. Thomas

Buck Island & Water Island Snorkel Sail from St. Thomas

Explore the Virgin Islands by luxury catamaran

$170/ person
Sunset Catamaran Dinner Sail from St. Thomas to St. John

Sunset Catamaran Dinner Sail from St. Thomas to St. John

Pair an evening on the water with your choice of dining in St. John

$138/ person
Sunset Cruise in St. Thomas

Sunset Cruise in St. Thomas

A private evening sail for sunset views from the water

5.0 • 105 reviews
$491
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
12
Key West St Thomas Things To Do
SailingYacht Charters89Snorkeling52Boat Tours30Kayaking Tours19
More
  • Beach Tours16
  • Scuba Diving14
  • Fishing Charters10
  • Jeep Tours8
  • Sightseeing8
  • ATV Tours7
  • Parasailing7
Scavenger Hunts
6
  • Private Transfers5
  • Stand Up Paddle Boarding5
  • Boat Rentals4
  • Jet Skiing4
  • Paddleboarding4
  • Aquarium Visits3
  • Historical Tours3
  • Swimming with Dolphins3