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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 4
 

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

(4.7 of 2,135 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Start From $169.95
 
Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

  • North America
  • Superb2,135 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $169.95
 
 

Half-Day Luxury Sailing Experience in Tulum with Open Bar

(4.2 of 263 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
Start From $149.00
 
Half-Day Luxury Sailing Experience in Tulum with Open Bar

Half-Day Luxury Sailing Experience in Tulum with Open Bar

  • North America
  • Exellent263 reviews4.2

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

    Free Cancellation
    Start From $149.00
 
 

Halifax Sunset Cruise Ft. a Live Musician

(4.6 of 99 reviews)

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More

Free Cancellation
Start From $43.49
 
Halifax Sunset Cruise Ft. a Live Musician Likely to Sell Out

Halifax Sunset Cruise Ft. a Live Musician

  • North America
  • Superb99 reviews4.6

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....

    Free Cancellation
    Start From $43.49
 
 

4-Hour Private Fishing Charter in the Riviera Maya

(5 of 27 reviews)

Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully private experience, not a shared tour. The itinerary is flexible ... More

Free Cancellation
Private Tour
Start From $750.00
 
4-Hour Private Fishing Charter in the Riviera Maya Likely to Sell Out

4-Hour Private Fishing Charter in the Riviera Maya

  • North America
  • Superb27 reviews5

Unlike many destinations, your fishing time starts within minutes of departure—no long boat ridesâ....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

Nāpali Sunset Dinner Sail

(4.7 of 609 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Free Cancellation
Private Tour
Start From $263.82
 
Nāpali Sunset Dinner Sail Likely to Sell Out

Nāpali Sunset Dinner Sail

  • North America
  • Superb609 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Free Cancellation
    Private Tour
    Start From $263.82
 
 

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

(4.6 of 1,336 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Free Cancellation
Private Tour
Start From $53.31
 
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu Likely to Sell Out

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

  • North America
  • Superb1,336 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Free Cancellation
    Private Tour
    Start From $53.31
 
 

San Francisco Bay Sailing Cruise

(4.9 of 674 reviews)

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More

Free Cancellation
Private Tour
Start From $65.00
 
San Francisco Bay Sailing Cruise Likely to Sell Out

San Francisco Bay Sailing Cruise

  • North America
  • Superb674 reviews4.9

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Seattle Sailing Harbor Tour

(4.7 of 593 reviews)

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More

Free Cancellation
Private Tour
Start From $54.17
 
Seattle Sailing Harbor Tour Likely to Sell Out

Seattle Sailing Harbor Tour

  • North America
  • Superb593 reviews4.7

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....

    Free Cancellation
    Private Tour
    Start From $54.17
 
 

Puerto Vallarta Luxury Snorkel Sail with Open Bar and Lunch

(4.8 of 322 reviews)

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

Free Cancellation
Private Tour
Start From $79.00
 
Puerto Vallarta Luxury Snorkel Sail with Open Bar and Lunch Likely to Sell Out

Puerto Vallarta Luxury Snorkel Sail with Open Bar and Lunch

  • North America
  • Superb322 reviews4.8

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau sailboats, taking in br....

    Free Cancellation
    Private Tour
    Start From $79.00
 
 

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

(4.8 of 547 reviews)

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More

Free Cancellation
Private Tour
Start From $625.00
 
Private Fishing Trip Likely to Sell Out

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

  • North America
  • Superb547 reviews4.8

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Kona Morning Snorkel to Captain Cook Monument

(4.9 of 485 reviews)

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along the Kona coastline toward the Captain Cook Monument, where your adventure begins. Jump ... More

Free Cancellation
Private Tour
Start From $178.72
 
Kona Morning Snorkel to Captain Cook Monument Likely to Sell Out

Kona Morning Snorkel to Captain Cook Monument

  • North America
  • Superb485 reviews4.9

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leavi....

    Free Cancellation
    Private Tour
    Start From $178.72
 
 

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

(4.9 of 17 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

Special Offer
Free Cancellation
Private Tour
Start From $100.00
(Saving 20% ) $125.00
 
-20% 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
  • Superb17 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $100.00
    (Saving 20% ) $125.00
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 374 reviews)

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More

Special Offer
Free Cancellation
Private Tour
Start From $69.82
(Saving inf% ) $0.00
 
-inf% Key West Dolphin and Snorkel Experience Likely to Sell Out

Key West Dolphin and Snorkel Experience

  • North America
  • Exellent374 reviews4.4

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $69.82
    (Saving inf% ) $0.00
 
 

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

(4.7 of 210 reviews)

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

Special Offer
Free Cancellation
Private Tour
Start From $75.20
(Saving inf% ) $0.00
 
-inf% Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine Likely to Sell Out

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

  • North America
  • Superb210 reviews4.7

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $75.20
    (Saving inf% ) $0.00
 
 

Key West Sailing & Snorkeling: A Reef Adventure

(4.7 of 250 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

Special Offer
Free Cancellation
Private Tour
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Key West Sailing & Snorkeling: A Reef Adventure Likely to Sell Out

Key West Sailing & Snorkeling: A Reef Adventure

  • North America
  • Superb250 reviews4.7

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $79.00
    (Saving inf% ) $0.00
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 406 reviews)

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% 1.5-Hour San Francisco Bay Sailing Tour Likely to Sell Out

1.5-Hour San Francisco Bay Sailing Tour

  • North America
  • Superb406 reviews4.8

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

(4.4 of 398 reviews)

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More

Special Offer
Free Cancellation
Private Tour
Start From $57.32
(Saving inf% ) $0.00
 
-inf% Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail Likely to Sell Out

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

  • North America
  • Exellent398 reviews4.4

Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $57.32
    (Saving inf% ) $0.00
 
 

Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

(4.9 of 743 reviews)

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain Cook Monument at Kealakekua Bay, a Marine Life Conservation District on the Kona Coas... More

Special Offer
Free Cancellation
Private Tour
Start From $135.64
(Saving inf% ) $0.00
 
-inf% Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay Likely to Sell Out

Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

  • North America
  • Superb743 reviews4.9

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catama....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $135.64
    (Saving inf% ) $0.00
 
 

El Cielo Cozumel Snorkel trip by Catamaran

(4.4 of 286 reviews)

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More

Special Offer
Free Cancellation
Private Tour
Start From $94.60
(Saving 14% ) $110.00
 
-14% El Cielo Cozumel Snorkel trip by Catamaran Likely to Sell Out

El Cielo Cozumel Snorkel trip by Catamaran

  • North America
  • Exellent286 reviews4.4

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $94.60
    (Saving 14% ) $110.00
 
 

Boston Harbor Sunset Sail Tour

(4.8 of 199 reviews)

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More

Special Offer
Free Cancellation
Private Tour
Start From $82.27
(Saving inf% ) $0.00
 
-inf% Boston Harbor Sunset Sail Tour Likely to Sell Out

Boston Harbor Sunset Sail Tour

  • North America
  • Superb199 reviews4.8

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $82.27
    (Saving inf% ) $0.00
 
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