Menu

Top 10 Best North America Sailing Trips

Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 6
 

Newport Sunset Sail on Schooner Adirondack

(4.9 of 80 reviews)

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! 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 sailbo... More

Start From $67.84
 
Newport Sunset Sail on Schooner Adirondack Likely to Sell Out

Newport Sunset Sail on Schooner Adirondack

  • North America
  • Superb80 reviews4.9

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....

    Start From $67.84
 
 

Sunset Sail Cruise in Key West

(4.9 of 276 reviews)

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Free Cancellation
Start From $95.00
 
Sunset Sail Cruise in Key West Likely to Sell Out

Sunset Sail Cruise in Key West

  • North America
  • Superb276 reviews4.9

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

    Free Cancellation
    Start From $95.00
 
 

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

(5 of 44 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $599.00
 
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique Likely to Sell Out

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

  • North America
  • Superb44 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(4.9 of 197 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Private Tour
Start From $79.00
 
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming Likely to Sell Out

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

  • North America
  • Superb197 reviews4.9

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 178 reviews)

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More

Free Cancellation
Private Tour
Start From $75.00
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans Likely to Sell Out

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • North America
  • Superb178 reviews4.9

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....

    Free Cancellation
    Private Tour
    Start From $75.00
 
 

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

(4.9 of 1,506 reviews)

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More

Free Cancellation
Private Tour
Start From $35.00
 
1-Hour Interactive Pirate Cruise (arrive 30 minutes early) Likely to Sell Out

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

  • North America
  • Superb1,506 reviews4.9

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

Private Sailing Charter with Captain, BYOB

(5 of 69 reviews)

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More

Free Cancellation
Private Tour
Start From $500.00
 
Private Sailing Charter with Captain, BYOB Likely to Sell Out

Private Sailing Charter with Captain, BYOB

  • North America
  • Superb69 reviews5

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....

    Free Cancellation
    Private Tour
    Start From $500.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 250 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb250 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Waikiki Sunset Cruise from Oahu

(4.8 of 53 reviews)

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More

Free Cancellation
Private Tour
Start From $45.00
 
Waikiki Sunset Cruise from Oahu Likely to Sell Out

Waikiki Sunset Cruise from Oahu

  • North America
  • Superb53 reviews4.8

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

(4.9 of 124 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Private Tour
Start From $69.00
 
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

  • North America
  • Superb124 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales

(4.9 of 14 reviews)

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky to get the rare opportunity to hear the whale songs live! Our RABEN (Me... More

Free Cancellation
Private Tour
Start From $99.00
 
Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales Likely to Sell Out

Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales

  • North America
  • Superb14 reviews4.9

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade h....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Southwest Florida Sunset Sail

(4.9 of 494 reviews)

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More

Free Cancellation
Private Tour
Start From $70.00
 
Southwest Florida Sunset Sail Likely to Sell Out

Southwest Florida Sunset Sail

  • North America
  • Superb494 reviews4.9

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

(4.5 of 85 reviews)

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More

Free Cancellation
Private Tour
Start From $109.00
 
Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar Likely to Sell Out

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....

  • North America
  • Exellent85 reviews4.5

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres

(4.4 of 305 reviews)

Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More

Free Cancellation
Private Tour
Start From $62.00
 
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres Likely to Sell Out

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres

  • North America
  • Exellent305 reviews4.4

Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....

    Free Cancellation
    Private Tour
    Start From $62.00
 
 

Key West Reef Snorkel & Sail Adventure

(4.7 of 548 reviews)

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Free Cancellation
Private Tour
Start From $79.00
 
Key West Reef Snorkel & Sail Adventure Likely to Sell Out

Key West Reef Snorkel & Sail Adventure

  • North America
  • Superb548 reviews4.7

Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

(4.8 of 308 reviews)

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More

Free Cancellation
Private Tour
Start From $89.00
 
Puerto Vallarta Luxury Sailing with Premium Open bar & lunch Likely to Sell Out

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch

  • North America
  • Superb308 reviews4.8

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventure

(3 of 4 reviews)

Discover an unforgettable side of O‘ahu most visitors never experience! Our Kāneʻohe Sandbar Splash & Snorkeling Adventure takes you beyond Waikiki to the serene waters of Kāneʻohe Bay, framed by the dramatic Ko‘olau mount... More

Free Cancellation
Private Tour
Start From $155.93
 
Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventure Likely to Sell Out

Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventur....

  • North America

Discover an unforgettable side of O‘ahu most visitors never experience! Our Kāneʻohe Sandbar Spl....

    Free Cancellation
    Private Tour
    Start From $155.93
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 453 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Private Tour
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • North America
  • Superb453 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Suncoast Sailing's Sunset Sailing Experience!

(4.9 of 267 reviews)

Step aboard Suncoast Horizon, a real working 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 ... More

Free Cancellation
Private Tour
Start From $69.99
 
Suncoast Sailing's Sunset Sailing Experience! Likely to Sell Out

Suncoast Sailing's Sunset Sailing Experience!

  • North America
  • Superb267 reviews4.9

Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually suppos....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Your Private Miami Yacht Charter with Music and Fun

(4.6 of 65 reviews)

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is designed for fun, style, and unforgettable memories with your group. Adventure Highlig... More

Free Cancellation
Private Tour
Start From $600.00
 
Your Private Miami Yacht Charter with Music and Fun Likely to Sell Out

Your Private Miami Yacht Charter with Music and Fun

  • North America
  • Superb65 reviews4.6

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate....

    Free Cancellation
    Private Tour
    Start From $600.00
 
4 5 6 7 8
Booking.com
Booking.com
Booking.com