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Best results for

Sailing

Showing 553-576 of 1,008 results
Key West, FL86Honolulu, HI65San Diego, CA35St. Augustine, FL28Traverse City, MI26
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  • New York, NY24
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Coastal Sailing Charter on a 31' Sailboat in Santa Barbara

Coastal Sailing Charter on a 31' Sailboat in Santa Barbara

Take in mountain and island views from the water

$636/ boat
Private 25' Sailboat Charter in Oak Harbor, Whidbey Island

Private 25' Sailboat Charter in Oak Harbor, Whidbey Island

Share a sail with friends or someone special

$201
Private Catalina 25 Sailing Charter in Oak Harbor

Private Catalina 25 Sailing Charter in Oak Harbor

Relax on board or get involved in sailing

$315
Private Sailing Charter in Oak Harbor, Whidbey Island

Private Sailing Charter in Oak Harbor, Whidbey Island

Sit back and relax or take an active role in sailing

$430
Full-Day Private Catalina 25 Sailing Charter in Oak Harbor

Full-Day Private Catalina 25 Sailing Charter in Oak Harbor

Relax on the water or take an active part in the sailing

$660
Private Sailing Lesson on the Hudson River in Hoboken

Private Sailing Lesson on the Hudson River in Hoboken

Build your sailing skills with an instructor guiding you throughout

$186/ boat
Private Sunset Sail on a Classic Yacht in Wilmington, NC

Private Sunset Sail on a Classic Yacht in Wilmington, NC

Sail into the evening with champagne and sabrage service included

$530
Private Sailboat Charter in St. Augustine

Private Sailboat Charter in St. Augustine

Leave the sailing to a professional captain and unwind on the water

$848
Private Tailored Sailing Lesson in Sag Harbor

Private Tailored Sailing Lesson in Sag Harbor

Focus your time on the sailing skills you want to develop

$1,166& up
Private Sailing Charter in Sag Harbor

Private Sailing Charter in Sag Harbor

Unwind on deck with paddle boards and pool toys on hand

$742& up
Private Classic Sailing Cruise in Sag Harbor

Private Classic Sailing Cruise in Sag Harbor

Relax on a private sail with onboard comforts

$954& up
Private Half-Day Catamaran Sail in Esperanza, Vieques

Private Half-Day Catamaran Sail in Esperanza, Vieques

Enjoy a catamaran all to yourselves, with optional beach time when conditions allow

$1,504
Shared Sunset Catamaran Sail in Vieques

Shared Sunset Catamaran Sail in Vieques

Stretch out on the bow as twilight settles over the Caribbean

$188/ person
Full-Day Private Sunset Sailing Charter in Vieques

Full-Day Private Sunset Sailing Charter in Vieques

Make a catamaran your private base for sailing, beach time, and a sunset return

$3,008
Full-Day Private Sailing & Snorkeling Charter in Vieques

Full-Day Private Sailing & Snorkeling Charter in Vieques

Enjoy two snorkeling stops, a full lunch, and unlimited drinks on your private charter

$1,357& up
Advanced Windsurfing Private Lesson in Kahului

Advanced Windsurfing Private Lesson in Kahului

2-hour private advanced windsurf lesson at Kanaha Beach Park

4.3 • 6 reviews
$377/ person
Kids' Windsurfing Lesson at Kanaha Beach Park

Kids' Windsurfing Lesson at Kanaha Beach Park

Build windsurfing skills with a lesson designed for young sailors

4.3 • 6 reviews
$227/ person
Santa Barbara 2-Hour Sailing Cruise

Santa Barbara 2-Hour Sailing Cruise

Sail past Santa Barbara's palm-lined coast aboard a 41-foot yacht

4.4 • 58 reviews
$74/ person
Santa Barbara Sunset Sailing Cruise

Santa Barbara Sunset Sailing Cruise

Sail Santa Barbara’s coast aboard a 41-foot yacht with panoramic shoreline views

4.4 • 58 reviews
$74/ person
Private Sailing Lesson in Oyster Bay

Private Sailing Lesson in Oyster Bay

Build sailing skills with a private lesson tailored to your goals

4.4 • 109 reviews
$292/ person
Cayo Levantado Island Catamaran Cruise From Punta Cana

Cayo Levantado Island Catamaran Cruise From Punta Cana

Sail Samaná Bay, swim at Cayo Levantado, and enjoy an island lunch

4.4 • 684 reviews
$122/ person
Hobie Wave Sailing Rental in Key Biscayne

Hobie Wave Sailing Rental in Key Biscayne

Sail Biscayne Bay on a stable Hobie Wave catamaran

4.2 • 219 reviews
$113/ boat
Key Biscayne 1-Hour Hobie Getaway Sailboat Rental

Key Biscayne 1-Hour Hobie Getaway Sailboat Rental

Cruise and swim aboard a stable Hobie Getaway catamaran

4.2 • 219 reviews
$170/ boat
Miami 40' Sailing Catamaran Cruise

Miami 40' Sailing Catamaran Cruise

Unwind on giant nets aboard a spacious sailing catamaran

4.0 • 165 reviews
$456/ hour
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