Filter
Top Rated
Only show top rated activities
Keyword
Price (USD)
$
-
$
Date(s)
September 2025
Sun
Mon
Tue
Wed
Thu
Fri
Sat
Today
Logo
Peek Pro for Business
peek-pro
Log In / Sign Up
Recently Viewed
peek-pro
Peek Pro for Business
Recently Viewed
  1. United States
  2. Florida
    3. Key West Guide
  3. Key West
Trending
On the Water
Families
Adventures
Tours
Dates
Night Owls
Food & Drink
Art & Culture
Shows
Filter
Showing results for Sailing View All
Booking Details
From $95
4.9
241 Ratings
4.9
241 Ratings
Key West Sunset Sail: Traditional Pirate Experience
Booking Details
From $116
4.9
730 Ratings
4.9
730 Ratings
Sunset Sailing: Key West Schooner America 2.0 Tour
Booking Details
From $230
Key West: Smathers Beach Sunset Catamaran Experience
Booking Details
From $100
5.0
1 Rating
5.0
1 Rating
Smathers Beach Day: Paddleboard, Kayak, Sail
Experiences just outside of Key West
Booking Details
From $89
5.0
211 Ratings
5.0
211 Ratings
Schooner Sunset Sail: Key West's Historic Voyage
Key West
Booking Details
From $350
Dock Side Adventure: Kayak, Paddle Boarding, Sunfish Sailboats
Naval Air Station Key West
Nearby destinations
United States Florida Marathon, Florida Monroe County, Florida Naval Air Station Key West, Florida Big Pine Key, Florida Stock Island, Florida Summerland Key, Florida Sugarloaf Key, Florida Little Torch Key, Florida
Things To Do In Key West
Top Locations
Top Destinations
  • Boat Tours, Rentals & Charters
  • Sightseeing
  • Historical Sites & Monuments
  • Day Trips
  • Fishing Charters & Trips
  • Walking Tours
  • Nature & Wildlife
  • Ghost & Haunted
  • Self Guided & Passes
  • Bus, Van & Limousine Tours
  • Other Water Sports
  • Ecotours
  • Jet Skiing
  • Scuba Diving & Snorkeling
  • Dining & Drink Experiences
  • Kayaking
  • Nightlife
  • Other Tours
  • Bar & Pub Crawl
  • Sailing
  • Parasailing
  • Food Tours
  • Music
  • Museums
  • Other Transportation
  • Photography
  • Community & Heritage
  • Neighborhood
  • Stand Up Paddle Boarding
  • Hop On Hop Off Tours
  • Seasonal & Holiday
  • Scavenger Hunts
  • Bike Tours & Rentals
  • Water Skiing
  • Concert & Special Events
  • Golf & Mini Golf
  • Immersive Experiences
  • Other Outdoor Activities
  • Swimming with Sharks
  • Escape Games
  • Waterfalls
  • Other Attractions & Entertainment
  • Shuttles & Rentals
  • Airport Transportation
  • Miami, Florida
  • Tampa, Florida
  • Miami Beach, Florida
  • St. Augustine, Florida
  • Key West, Florida
  • Key Largo, Florida
  • Tavernier, Florida
  • Naples, Florida
  • Florida
  • Big Pine Key, Florida
  • Sunny Isles Beach, Florida
  • Jacksonville Beach, Florida
  • United States
  • Ochopee, Florida
  • Everglades City, Florida
  • Homestead, Florida
  • Marathon, Florida
  • Palmetto, Florida
  • Monroe County, Florida
  • Islamorada, Florida
  • Naval Air Station Key West, Florida
  • Stock Island, Florida
  • Chokoloskee, Florida
  • Fort Lauderdale, Florida
  • Hollywood, Florida
  • Dania Beach, Florida
  • Florida City, Florida
  • Jerome, Florida
  • Duck Key, Florida
  • Weston, Florida
  • Juno Beach, Florida
  • Putnam County, Florida
  • Tamiami, Florida
  • Big Island
  • Boston
  • Cancun
  • Chicago
  • Kauai
  • Las Vegas
  • London
  • Los Angeles
  • Los Cabos
  • Maui
  • Miami
  • Napa and Sonoma
  • New Orleans
  • New York City
  • Oahu
  • Orlando
  • Paris
  • Philadelphia
  • San Diego
  • San Francisco
  • Savannah
  • Seattle
  • Tampa
  • Washington D.C.
© 2024 Peek Travel Inc.
Privacy
Terms
Peek
  • Jobs
  • Press Kit
Products
  • Peek Pro
  • MCP Server
Support
  • [email protected]
Over 25 million happy customers 
have used Peek to find the best experience
© 2025 Peek Travel Inc. All rights reserved.
| Privacy | Terms
Log In or Sign Up
Access and manage your tickets
Earn credits and activity discounts
Continue with Facebook
Continue with Google
or
Register Log in