Menu

Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 18
 

Vancouver Sailing Experience on a 50 Foot Sailboat

(5 of 114 reviews)

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More

Free Cancellation
Start From $114.71
 
Vancouver Sailing Experience on a 50 Foot Sailboat

Vancouver Sailing Experience on a 50 Foot Sailboat

  • North America
  • Superb114 reviews5

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....

    Free Cancellation
    Start From $114.71
 
 

Private Yacht Charter in Cabo for Up to 8 People

(5 of 4 reviews)

Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalized experience sailing in front of the iconic Arch, with a stop for snorkeling in crystal clear waters. Ideal for groups seeking pri... More

Free Cancellation
Private Tour
Start From $428.47
 
Private Yacht Charter in Cabo for Up to 8 People

Private Yacht Charter in Cabo for Up to 8 People

  • North America
  • Superb4 reviews5

Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalize....

    Free Cancellation
    Private Tour
    Start From $428.47
 
 

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

(5 of 206 reviews)

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More

Free Cancellation
Private Tour
Start From $870.00
 
Private Sailboat tour in Cabo San Lucas with Papillon Yachts

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

  • North America
  • Superb206 reviews5

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....

    Free Cancellation
    Private Tour
    Start From $870.00
 
 

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

(5 of 87 reviews)

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Private Tour
Start From $114.00
 
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

  • North America
  • Superb87 reviews5

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Private Tour
    Start From $114.00
 
 

Suncoast Sailing's Day Sailing Experience!

(4.9 of 117 reviews)

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just wind in the sails, salt in the air, and the kind of quiet glide across t... More

Free Cancellation
Private Tour
Start From $64.99
 
Suncoast Sailing's Day Sailing Experience!

Suncoast Sailing's Day Sailing Experience!

  • North America
  • Superb117 reviews4.9

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to fe....

    Free Cancellation
    Private Tour
    Start From $64.99
 
 

New York City Sunset Sail to the Statue of Liberty

(4.8 of 78 reviews)

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More

Free Cancellation
Private Tour
Start From $90.12
 
New York City Sunset Sail to the Statue of Liberty

New York City Sunset Sail to the Statue of Liberty

  • North America
  • Superb78 reviews4.8

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....

    Free Cancellation
    Private Tour
    Start From $90.12
 
 

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

(4.5 of 172 reviews)

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More

Free Cancellation
Private Tour
Start From $89.00
 
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

  • North America
  • Exellent172 reviews4.5

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Whale Watching with Lunch and transportation included

(4.4 of 20 reviews)

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll have front-row seats to witness the playful and majestic antics of whales in their natural habitat. Setting sail from the Marina, you... More

Free Cancellation
Private Tour
Start From $110.00
 
Whale Watching with Lunch and transportation included

Whale Watching with Lunch and transportation included

  • North America
  • Exellent20 reviews4.4

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll hav....

    Free Cancellation
    Private Tour
    Start From $110.00
 
 

Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

(5 of 12 reviews)

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, and set sail for a relaxing and refreshing 2-hour cruise through Charleston’s histor... More

Free Cancellation
Private Tour
Start From $63.00
 
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

  • North America
  • Superb12 reviews5

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard ou....

    Free Cancellation
    Private Tour
    Start From $63.00
 
 

Fort Lauderdale Sailing Charter

(5 of 404 reviews)

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a beautiful blend of natural mangroves, luxurious waterfront homes, and ... More

Free Cancellation
Private Tour
Start From $150.00
 
Fort Lauderdale Sailing Charter

Fort Lauderdale Sailing Charter

  • North America
  • Superb404 reviews5

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Private Sailing Charter in Savannah GA

(5 of 7 reviews)

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding, or a vibrant bachelorette party, enjoy the spacious and stable design of our boat,... More

Free Cancellation
Private Tour
Start From $650.00
 
Private Sailing Charter in Savannah GA

Private Sailing Charter in Savannah GA

  • North America
  • Superb7 reviews5

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whe....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

El Cielito beach by Private Boat

(4.8 of 142 reviews)

Awarded Private Snorkel Tour! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private tour will take you out to the most renowned ree... More

Free Cancellation
Private Tour
Start From $550.00
 
El Cielito beach by Private Boat

El Cielito beach by Private Boat

  • North America
  • Superb142 reviews4.8

Awarded Private Snorkel Tour! Have fun aboard your Private boat and experience Cozumel water treasu....

    Free Cancellation
    Private Tour
    Start From $550.00
 
 

Sunset Sail in Miami: Complimentary Champagne Toast

(4.8 of 241 reviews)

Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for sun dresses, sandals and chilled wine. Take advantage of one of Florida's finest highlights upon our comfortable 80 ft catamaran a... More

Free Cancellation
Private Tour
Start From $129.00
 
Sunset Sail in Miami: Complimentary Champagne Toast

Sunset Sail in Miami: Complimentary Champagne Toast

  • North America
  • Superb241 reviews4.8

Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Riviera Maya Half-Day Sailing Experience with Lunch and Open Bar

(4.4 of 80 reviews)

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More

Free Cancellation
Private Tour
Start From $149.00
 
Riviera Maya Half-Day Sailing Experience with Lunch and Open Bar

Riviera Maya Half-Day Sailing Experience with Lunch and Open Bar

  • North America
  • Exellent80 reviews4.4

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Shallow Water Snorkeling and Dolphin Watching in Key West

(4.6 of 476 reviews)

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s weather refunds of course. Premium drinks & snacks included! Enjoy a premium sha... More

Free Cancellation
Private Tour
Start From $108.91
 
Shallow Water Snorkeling and Dolphin Watching in Key West

Shallow Water Snorkeling and Dolphin Watching in Key West

  • North America
  • Superb476 reviews4.6

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 wee....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Full-Day Private Sailing & Los Arcos Snorkeling, Puerto Vallarta

(4.9 of 114 reviews)

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim and even Paddelboard in Los Arcos National Park, capturing beautiful views ... More

Free Cancellation
Private Tour
Start From $961.31
 
Full-Day Private Sailing & Los Arcos Snorkeling, Puerto Vallarta

Full-Day Private Sailing & Los Arcos Snorkeling, Puerto Vallarta

  • North America
  • Superb114 reviews4.9

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....

    Free Cancellation
    Private Tour
    Start From $961.31
 
 

Chicago's Fireworks Show aboard Tall Ship Windy!

(4.7 of 26 reviews)

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Free Cancellation
Private Tour
Start From $113.73
 
Chicago's Fireworks Show aboard Tall Ship Windy!

Chicago's Fireworks Show aboard Tall Ship Windy!

  • North America
  • Superb26 reviews4.7

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....

    Free Cancellation
    Private Tour
    Start From $113.73
 
 

Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB

(4.9 of 217 reviews)

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to race around the world, and now are perfectly at home on Puget Sound. Sit back and relax as our trained crew hoist the sails and turn... More

Free Cancellation
Private Tour
Start From $60.00
 
Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB Likely to Sell Out

Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - B....

  • North America
  • Superb217 reviews4.9

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to ra....

    Free Cancellation
    Private Tour
    Start From $60.00
 
 

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

(5 of 114 reviews)

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. 2.5 hour tour length is perfect for seeing all the beautiful sights. Catamarans reall... More

Free Cancellation
Private Tour
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

  • North America
  • Superb114 reviews5

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Newport Sunset Sail on Classic Sailboat

(4.7 of 60 reviews)

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More

Free Cancellation
Private Tour
Start From $74.20
 
Newport Sunset Sail on Classic Sailboat Likely to Sell Out

Newport Sunset Sail on Classic Sailboat

  • North America
  • Superb60 reviews4.7

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....

    Free Cancellation
    Private Tour
    Start From $74.20
 
Booking.com
Booking.com
Booking.com