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Top 10 Best North America Sailing Trips

Found 753 Sailing Trips activities in North America. Sort by Popularity. - Page 34
 

Land’s End Sunset Cruise – Open Bar & Tacos Included

(5 of 1 review)

Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, with approximately 40 minutes spent at each captivating point along the route. As you glide through the stunning landscapes of Cab... More

Start From $140.00
 
Land’s End Sunset Cruise – Open Bar & Tacos Included

Land’s End Sunset Cruise – Open Bar & Tacos Included

  • North America
  • Superb1 review5

Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, w....

    Start From $140.00
 
 

Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar

(5 of 1 review)

Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded group tours, this 2-hour cruise is exclusive to your party, giving you space to relax, celebrate, and enjoy the views in privacy. Sai... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar

Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar

  • North America
  • Superb1 review5

Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded grou....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Ultimate Miami Boat Party with Free Open Bar & Live DJ

(5 of 1 review)

Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience. This 3-hour Miami booze cruise offers a unique nightclub atmosphere on the water, complete with a FREE open bar serving unlimited... More

Free Cancellation
Private Tour
Start From $139.00
 
Ultimate Miami Boat Party with Free Open Bar & Live DJ

Ultimate Miami Boat Party with Free Open Bar & Live DJ

  • North America
  • Superb1 review5

Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience.....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Waikiki private Day Tour and Sunset sail for couples

(5 of 17 reviews)

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More

Free Cancellation
Private Tour
Start From $300.00
 
Waikiki private Day Tour and Sunset sail for couples Likely to Sell Out

Waikiki private Day Tour and Sunset sail for couples

  • North America
  • Superb17 reviews5

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay

(5 of 1 review)

This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become part of the crew. Our goal is to perform as a unit and get the boat to sail as fast as possible. However, if you are looking for a mo... More

Free Cancellation
Private Tour
Start From $600.00
 
Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay Likely to Sell Out

Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay

  • North America
  • Superb1 review5

This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become par....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Private Luxury Yacht in Miami

(5 of 1 review)

️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s top destinations—Haulover Sandbar, Oleta River State Park, Biscayne Bay & Sands Key, and Raccoon Island—in style! This sleek 3... More

Free Cancellation
Private Tour
Start From $830.00
 
Private Luxury Yacht in Miami Likely to Sell Out

Private Luxury Yacht in Miami

  • North America
  • Superb1 review5

️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s ....

    Free Cancellation
    Private Tour
    Start From $830.00
 
 

Jungle Tour

(5 of 1 review)

This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through Nichupte Lagoon and snorkel in the El Angel coral reef. Choose to take the driver’s seat or ride shotgun in a 2-seat speedboat a... More

Free Cancellation
Private Tour
Start From $115.00
 
Jungle Tour Likely to Sell Out

Jungle Tour

  • North America
  • Superb1 review5

This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through ....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers

(5 of 1 review)

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you explore stunning sites and Caribbean reefs. Experience the magic of the Mexican Caribbean, snorkeling in Isla Mujeres and Cancun's ... More

Free Cancellation
Private Tour
Start From $5,900.00
 
Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers Likely to Sell Out

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 ....

  • North America
  • Superb1 review5

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you e....

    Free Cancellation
    Private Tour
    Start From $5,900.00
 
 

3 Hours Private Afternoon Sail in Saint Petersburg

(5 of 1 review)

A private 42' Bali 4.2 catamaran charter for up to 6 people, featuring a custom route for cruising and sailing. Enjoy a comfortable trip with cushioned seating, shaded areas, music, and soft drinks. Tailor your day with optional a... More

Free Cancellation
Private Tour
Start From $780.00
 
3 Hours Private Afternoon Sail in Saint Petersburg Likely to Sell Out

3 Hours Private Afternoon Sail in Saint Petersburg

  • North America
  • Superb1 review5

A private 42' Bali 4.2 catamaran charter for up to 6 people, featuring a custom route for cruising a....

    Free Cancellation
    Private Tour
    Start From $780.00
 
 

San Diego Private Yacht Charter on a Classic Sailboat 6 Guests

(5 of 4 reviews)

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is a classic 41-ft Friendship sloop skippered by a USCG-licensed captain with 55 years of sailing exp... More

Free Cancellation
Private Tour
Start From $675.00
 
San Diego Private Yacht Charter on a Classic Sailboat 6 Guests Likely to Sell Out

San Diego Private Yacht Charter on a Classic Sailboat 6 Guests

  • North America
  • Superb4 reviews5

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Ph....

    Free Cancellation
    Private Tour
    Start From $675.00
 
 

Midmorning Whale Watch from Lahaina Harbor

(3.3 of 3 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Private Tour
Start From $100.22
 
Midmorning Whale Watch from Lahaina Harbor Likely to Sell Out

Midmorning Whale Watch from Lahaina Harbor

  • North America
  • Good3 reviews3.3

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $100.22
 
 

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

(5 of 2 reviews)

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on board sound system with Tiki-Oki, and the friendliest most fun captains around. You'll be sure to have... More

Free Cancellation
Private Tour
Start From $349.00
 
Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise Likely to Sell Out

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

  • North America
  • Superb2 reviews5

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, b....

    Free Cancellation
    Private Tour
    Start From $349.00
 
 

Private Sailboat Charter from San Pedro: Port of Los Angeles

(5 of 2 reviews)

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis (39ft) sailing yacht, perfect for couples or small groups looking for a memorable out... More

Free Cancellation
Private Tour
Start From $380.00
 
Private Sailboat Charter from San Pedro: Port of Los Angeles Likely to Sell Out

Private Sailboat Charter from San Pedro: Port of Los Angeles

  • North America
  • Superb2 reviews5

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a su....

    Free Cancellation
    Private Tour
    Start From $380.00
 
 

Luxury Yacht 58 ft for up to 20 people 4 hrs

(5 of 2 reviews)

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard this luxury yacht along the coast of Bahía de Banderas. You will enjoy every moment and every place in this tropical paradise. L... More

Free Cancellation
Private Tour
Start From $4,100.00
 
Luxury Yacht 58 ft for up to 20 people 4 hrs Likely to Sell Out

Luxury Yacht 58 ft for up to 20 people 4 hrs

  • North America
  • Superb2 reviews5

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard ....

    Free Cancellation
    Private Tour
    Start From $4,100.00
 
 

Cabo San Lucas Luxury Yacht to El Arco with Snorkeling Stop

(5 of 2 reviews)

Set sail from the lively Marina Cabo San Lucas aboard your private 45ft luxury yacht, perfect for up to 8 guests. A friendly crew welcomes you with a safety briefing before you glide past the stunning El Arco and Lover’s Beach. ... More

Free Cancellation
Private Tour
Start From $1,500.00
 
Cabo San Lucas Luxury Yacht to El Arco with Snorkeling Stop Likely to Sell Out

Cabo San Lucas Luxury Yacht to El Arco with Snorkeling Stop

  • North America
  • Superb2 reviews5

Set sail from the lively Marina Cabo San Lucas aboard your private 45ft luxury yacht, perfect for up....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
 

Original Cruisin Tikis Snorkeling Safari

(5 of 2 reviews)

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart of Destin Harbor while you soak in the scenery and the good vibes... More

Free Cancellation
Private Tour
Start From $89.00
 
Original Cruisin Tikis Snorkeling Safari Likely to Sell Out

Original Cruisin Tikis Snorkeling Safari

  • North America
  • Superb2 reviews5

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

JFarwell Sip & Sail aboard the Reverie

(5 of 19 reviews)

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or colleagues. Step aboard our 50’ Catamaran and be greeted with a perfect locally crafted bevera... More

Free Cancellation
Private Tour
Start From $862.93
 
JFarwell Sip & Sail aboard the Reverie Likely to Sell Out

JFarwell Sip & Sail aboard the Reverie

  • North America
  • Superb19 reviews5

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding ....

    Free Cancellation
    Private Tour
    Start From $862.93
 
 

Private Afternoon Snorkel with Sunset Sail in Key West

(5 of 4 reviews)

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More

Free Cancellation
Private Tour
Start From $995.00
 
Private Afternoon Snorkel with Sunset Sail in Key West Likely to Sell Out

Private Afternoon Snorkel with Sunset Sail in Key West

  • North America
  • Superb4 reviews5

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that sp....

    Free Cancellation
    Private Tour
    Start From $995.00
 
 

Luxury 40' Van Dutch Private Yacht Experience – Cancun 4 Hours

(4.8 of 22 reviews)

Enjoy an unforgettable day at sea with our exclusive 9-hour luxury yacht tour in Cancun. This full-day experience offers the perfect combination of relaxation, comfort, and first-class service. As the day winds down, guests will b... More

Free Cancellation
Private Tour
Start From $1,650.00
 
Luxury 40' Van Dutch Private Yacht Experience – Cancun 4 Hours Likely to Sell Out

Luxury 40' Van Dutch Private Yacht Experience – Cancun 4 Hours

  • North America
  • Superb22 reviews4.8

Enjoy an unforgettable day at sea with our exclusive 9-hour luxury yacht tour in Cancun. This full-d....

    Free Cancellation
    Private Tour
    Start From $1,650.00
 
 

Cabo San Lucas Private Custom Snorkel or Sunset Adventure

(5 of 1 review)

First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew will make sure that you have a drink in your hand within minutes. You will get to see the world famous Arch, Lover's Beach, Divorce... More

Free Cancellation
Private Tour
Start From $2,500.00
 
Cabo San Lucas Private Custom Snorkel or Sunset Adventure Likely to Sell Out

Cabo San Lucas Private Custom Snorkel or Sunset Adventure

  • North America
  • Superb1 review5

First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew w....

    Free Cancellation
    Private Tour
    Start From $2,500.00
 
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