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 Dunedin, FL

Showing 1-14 of 14 results
Private 40' Sailing Catamaran Charter in St. Petersburg

Private 40' Sailing Catamaran Charter in St. Petersburg

Private catamaran sailing with space to swim, paddle, and unwind

4.9 • 517 reviews
$2,916
Classic Schooner Sailing Cruise in Treasure Island

Classic Schooner Sailing Cruise in Treasure Island

Classic schooner sailing with open-deck Gulf views

4.9 • 209 reviews
$68/ person
4-5 Hour Private Daytime Sail in St. Petersburg

4-5 Hour Private Daytime Sail in St. Petersburg

Private daytime sail with dinghy access for island exploring

5.0 • 25 reviews
$1,356& up
Sunset Sailing Charter in St. Pete

Sunset Sailing Charter in St. Pete

Sail Tampa Bay at golden hour aboard a 40-foot luxury catamaran

4.9 • 517 reviews
$1,744
Treasure Island Sunset Sailing Cruise

Treasure Island Sunset Sailing Cruise

Watch the Gulf sunset aboard a traditional schooner

4.9 • 209 reviews
$73/ person
Gulfport Sunset Sail Charter

Gulfport Sunset Sail Charter

Private evening sailing with sunset views across Tampa Bay

5.0 • 25 reviews
$1,356
Private 48' Sailing Yacht Charter in St. Petersburg

Private 48' Sailing Yacht Charter in St. Petersburg

Private, wind-driven sailing aboard a 48-foot Jeanneau yacht

4.9 • 517 reviews
$1,705
Gaff-Rigged Schooner Charter in Treasure Island

Gaff-Rigged Schooner Charter in Treasure Island

Sail Boca Ciega Bay on a private schooner with drinks and a restroom aboard

4.9 • 209 reviews
$1,836
Private 48' Sailing Yacht Charter in St. Petersburg

Private 48' Sailing Yacht Charter in St. Petersburg

Sail Tampa Bay aboard a private 48-foot Jeanneau yacht

4.9 • 517 reviews
$1,211
Sunset Sailing Charter in Treasure Island

Sunset Sailing Charter in Treasure Island

Private evening sailing with sunset views on Boca Ciega Bay and the Gulf of Mexico

4.9 • 209 reviews
$1,836
Private Sailing Charter in Treasure Island

Private Sailing Charter in Treasure Island

Sail Boca Ciega Bay and the Gulf while watching for dolphins

4.9 • 209 reviews
$792
Sunset Sailing Charter in St. Petersburg

Sunset Sailing Charter in St. Petersburg

Private 2-hour sunset sail with downtown St. Petersburg views

5.0 • 4 reviews
$559
3-Hour Daytime Sailing Cruise in St. Petersburg

3-Hour Daytime Sailing Cruise in St. Petersburg

Relax on a 3-hour sail with a U.S. Coast Guard–licensed captain from downtown St. Pete

5.0 • 4 reviews
$559
Morning Sailing Cruise on Tampa Bay

Morning Sailing Cruise on Tampa Bay

Start the day aboard a classic yacht with optional sailing instruction

5.0 • 4 reviews
$480
Dunedin Things To Do
SailingBoat Tours136Fishing Charters50Kayaking Tours38Yacht Charters36
More
  • Jet Skiing33
  • Boat Rentals31
  • Dolphin Watching21
  • Bike Rentals19
  • Snorkeling16
  • Ghost and Haunted11
  • Sunrise and Sunset Tours11
  • Paddleboarding9
  • Dinner Cruises8
Ferries
8
  • Helicopter Tours8
  • Car Rentals6
  • Food Tours5
  • Day Trips4
  • Seasonal and Holiday4
  • Surfing Lessons4
  • Tubing4
  • Horseback Riding3
  • Kiteboarding3
  • Scuba Diving3