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 Port Royal, SC

Showing 1-24 of 34 results
America's Cup Yacht Sunset Sail on Hilton Head Island

America's Cup Yacht Sunset Sail on Hilton Head Island

Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes

4.8 • 8.1K reviews
$77/ person
Hilton Head Island Sunset Sail

Hilton Head Island Sunset Sail

Toast the evening aboard a relaxed coastal catamaran sail

4.9 • 51 reviews
$89/ person
Afternoon Sailing Charter in Hilton Head Island

Afternoon Sailing Charter in Hilton Head Island

A breezy private sail with island insights and room to unwind

5.0 • 390 reviews
$429
Private Dolphin Sailing Tour in Hilton Head Island

Private Dolphin Sailing Tour in Hilton Head Island

Private 2-hour sail to learn the salt marsh and watch for dolphins

4.9 • 118 reviews
$397
2.5-Hour Sailing Charter on Saint Helena Sound

2.5-Hour Sailing Charter on Saint Helena Sound

Private sailing with dolphin sightings on Saint Helena Sound

5.0 • 39 reviews
$371
Private Sailing Charter on Calibogue Sound, Hilton Head

Private Sailing Charter on Calibogue Sound, Hilton Head

Private captained sail on Calibogue Sound with room for your snacks and drinks

4.7 • 411 reviews
$371
Private Afternoon Sail & Dolphin Watch in Bluffton

Private Afternoon Sail & Dolphin Watch in Bluffton

Take the helm or relax on a private afternoon sail

5.0 • 390 reviews
$504& up
Hilton Head Sunset Dolphin Sailing Charter

Hilton Head Sunset Dolphin Sailing Charter

Sail into sunset with coastal wildlife and ecology insights

4.9 • 118 reviews
$442
Saint Helena Island Sunset Sailing Charter

Saint Helena Island Sunset Sailing Charter

Private sunset sailing with room below deck for passing weather

5.0 • 39 reviews
$398
Hilton Head Sailing on Historic America's Cup Yacht

Hilton Head Sailing on Historic America's Cup Yacht

Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht

4.8 • 8.1K reviews
$55/ person
Private Sailing Charter in Hilton Head Island

Private Sailing Charter in Hilton Head Island

Set sail on a private charter with room for your own food and drinks

4.9 • 51 reviews
$996& up
Afternoon Sailing Charter in Hilton Head Island

Afternoon Sailing Charter in Hilton Head Island

Shape your afternoon around ocean sailing or time in the water

5.0 • 390 reviews
$1,276& up
Dolphin & Monkey Sailing Cruise on Saint Helena Island

Dolphin & Monkey Sailing Cruise on Saint Helena Island

Sail quiet Lowcountry waterways while looking for dolphins and Morgan Island monkeys

5.0 • 39 reviews
$371
America's Cup Sailing Cruise in Hilton Head

America's Cup Sailing Cruise in Hilton Head

Sail Hilton Head’s coast aboard the historic Stars & Stripes

4.8 • 8.1K reviews
$1,445
Private Sunset Sail in Hilton Head Island

Private Sunset Sail in Hilton Head Island

An evening sailing charter with space for your own food and drinks

4.9 • 51 reviews
$1,550& up
Private Sunset Sail & Dolphin Watch in Bluffton

Private Sunset Sail & Dolphin Watch in Bluffton

An evening sail for sunset views and wildlife watching

5.0 • 390 reviews
$472
3.5-Hour Sailing Lesson in Saint Helena Island

3.5-Hour Sailing Lesson in Saint Helena Island

Take the helm with a private, customizable keelboat sailing lesson

5.0 • 39 reviews
$477
Hilton Head Island Sunset Sailing Cruise

Hilton Head Island Sunset Sailing Cruise

Sail the historic Stars & Stripes into a Hilton Head sunset

4.8 • 8.1K reviews
$1,766
Private Morning Sailing Charter in Bluffton

Private Morning Sailing Charter in Bluffton

Customize a private sail with offshore cruising or an anchored swim

5.0 • 390 reviews
$1,213& up
2-Hour Sailing Cruise in Hilton Head Island

2-Hour Sailing Cruise in Hilton Head Island

Enjoy a daytime sail and time on the water

4.9 • 51 reviews
$55/ person
4-Hour Sailing Charter in Hilton Head Island

4-Hour Sailing Charter in Hilton Head Island

Shape a private sail around your group’s ideal afternoon

5.0 • 390 reviews
$1,113
Brunch Sailing Cruise in Hilton Head Island

Brunch Sailing Cruise in Hilton Head Island

Savor brunch and drinks aboard a Lowcountry catamaran

4.9 • 51 reviews
$105/ person
Hilton Head Island Sunset Cruise

Hilton Head Island Sunset Cruise

Sail into sunset with room for your group and your own refreshments

4.9 • 51 reviews
$1,328& up
4-Hour Sailing Charter in Hilton Head Island

4-Hour Sailing Charter in Hilton Head Island

Tailor a private sail with time to anchor and swim

5.0 • 390 reviews
$1,113
12
Port Royal Things To Do
SailingBoat Tours70Fishing Charters55Bike Rentals53Dolphin Watching49
More
  • Kayaking Tours36
  • Yacht Charters23
  • Boat Rentals15
  • Dinner Cruises14
  • Ferries11
  • Historical Tours10
  • Sunrise and Sunset Tours9
Beach Tours
7
  • Horseback Riding7
  • Private Fishing Charters7
  • Stand Up Paddle Boarding7
  • Jet Skiing6
  • Museum Tours5
  • Canoeing4
  • Car Rentals4
  • Farm Visits4
  • Aquarium Visits3
  • Community and Heritage3
  • Ecotours3
  • Nature and Wildlife3