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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 6
 

Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami

(5 of 19 reviews)

Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +1250 reviews on Google with a 4.9 score guarantee our quality. Immerse yourself in a unique adventure as you glide through the ... More

Free Cancellation
Private Tour
Start From $899.00
 
Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami

Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami

  • North America
  • Superb19 reviews5

Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our....

    Free Cancellation
    Private Tour
    Start From $899.00
 
 

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

(4.6 of 579 reviews)

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

Free Cancellation
Private Tour
Start From $55.00
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

  • North America
  • Superb579 reviews4.6

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Sunset Dolphin Sail Aboard the Footloose Catamaran

(4.8 of 486 reviews)

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More

Free Cancellation
Private Tour
Start From $38.45
 
Sunset Dolphin Sail Aboard the Footloose Catamaran

Sunset Dolphin Sail Aboard the Footloose Catamaran

  • North America
  • Superb486 reviews4.8

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....

    Free Cancellation
    Private Tour
    Start From $38.45
 
 

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(4.7 of 212 reviews)

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Free Cancellation
Private Tour
Start From $49.95
 
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

  • North America
  • Superb212 reviews4.7

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

    Free Cancellation
    Private Tour
    Start From $49.95
 
 

Premium Private 47ft Catamaran Snorkel & El Cielo (30p max)

(4.8 of 26 reviews)

Private 6-hour charter for up to 30 guests aboard Nemo, a spacious 47ft Nautitech catamaran, with El Cielo, guided snorkeling, fresh lunch, open bar and Marine Park fees included. Just 5–10 minutes by taxi from Cozumel’s cruis... More

Free Cancellation
Private Tour
Start From $2,139.00
 
Premium Private 47ft Catamaran Snorkel & El Cielo (30p max)

Premium Private 47ft Catamaran Snorkel & El Cielo (30p max)

  • North America
  • Superb26 reviews4.8

Private 6-hour charter for up to 30 guests aboard Nemo, a spacious 47ft Nautitech catamaran, with El....

    Free Cancellation
    Private Tour
    Start From $2,139.00
 
 
-15% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

(4.9 of 221 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

Special Offer
Free Cancellation
Private Tour
Start From $67.15
(Saving 15% ) $79.00
 
-15% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

  • North America
  • Superb221 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $67.15
    (Saving 15% ) $79.00
 
 
-inf% Laguna Grill - Private Boat with on-board BBQ and Drinks Included

Laguna Grill - Private Boat with on-board BBQ and Drinks Included

(5 of 151 reviews)

One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy nature away from crowds while enjoying an on board BBQ.... More

Special Offer
Free Cancellation
Private Tour
Start From $180.00
(Saving inf% ) $0.00
 
-inf% Laguna Grill - Private Boat with on-board BBQ and Drinks Included

Laguna Grill - Private Boat with on-board BBQ and Drinks Included

  • North America
  • Superb151 reviews5

One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy natu....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $180.00
    (Saving inf% ) $0.00
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 470 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

Special Offer
Free Cancellation
Private Tour
Start From $129.00
(Saving inf% ) $0.00
 
-inf% Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • North America
  • Superb470 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $129.00
    (Saving inf% ) $0.00
 
 

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

(4.9 of 89 reviews)

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Special Offer
Free Cancellation
Private Tour
Start From $119.00
(Saving inf% ) $0.00
 
-inf% Maui Premier Whale Watching Cruise - Luxury Catamaran Experience Likely to Sell Out

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

  • North America
  • Superb89 reviews4.9

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $119.00
    (Saving inf% ) $0.00
 
 

Sunset Sailing Cruise in Monterey Bay

(4.8 of 62 reviews)

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More

Special Offer
Free Cancellation
Private Tour
Start From $95.00
(Saving inf% ) $0.00
 
-inf% Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • North America
  • Superb62 reviews4.8

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $95.00
    (Saving inf% ) $0.00
 
 

Beach Island Shelling Cruise to Keewaydin Island Tour

(4.9 of 122 reviews)

Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommodate up to 44 passengers. Cruise along the Gordon River in Naples Bay and head out to Keewaydin Island, a 7-mile barrier island, wit... More

Special Offer
Free Cancellation
Private Tour
Start From $59.36
(Saving inf% ) $0.00
 
-inf% Beach Island Shelling Cruise to Keewaydin Island Tour Likely to Sell Out

Beach Island Shelling Cruise to Keewaydin Island Tour

  • North America
  • Superb122 reviews4.9

Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommoda....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $59.36
    (Saving inf% ) $0.00
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 25 reviews)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More

Special Offer
Free Cancellation
Private Tour
Start From $900.00
(Saving inf% ) $0.00
 
-inf% Private Catamaran Charter in Waikiki (1-6 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (1-6 Guests)

  • North America
  • Superb25 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $900.00
    (Saving inf% ) $0.00
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 106 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Special Offer
Free Cancellation
Private Tour
Start From $149.00
(Saving inf% ) $0.00
 
-inf% 2hr. INTERACTIVE Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • North America
  • Superb106 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $149.00
    (Saving inf% ) $0.00
 
 

Private Luxury 42ft Sailing with Snorkeling in Los Cabos

(5 of 130 reviews)

Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful white beaches. Your yacht and crew will provide you with all the ameni... More

Special Offer
Free Cancellation
Private Tour
Start From $926.50
(Saving 15% ) $1,090.00
 
-15% Private Luxury 42ft Sailing with Snorkeling in Los Cabos Likely to Sell Out

Private Luxury 42ft Sailing with Snorkeling in Los Cabos

  • North America
  • Superb130 reviews5

Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Sno....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $926.50
    (Saving 15% ) $1,090.00
 
 

Costa Maya: Chacchoben & Bacalar sailing or Los Rápidos

(4.9 of 117 reviews)

Ideal for cruisers with at least 7 hours in Costa Maya. Chacchoben + Bacalar: Sailing or The Rapids Your adventure begins at Costa Maya Cruise Port, where our driver will pick you up at the agreed time. We will visit the Mayan R... More

Special Offer
Free Cancellation
Private Tour
Start From $175.00
(Saving inf% ) $0.00
 
-inf% Costa Maya: Chacchoben & Bacalar sailing or Los Rápidos Likely to Sell Out

Costa Maya: Chacchoben & Bacalar sailing or Los Rápidos

  • North America
  • Superb117 reviews4.9

Ideal for cruisers with at least 7 hours in Costa Maya. Chacchoben + Bacalar: Sailing or The Rapid....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $175.00
    (Saving inf% ) $0.00
 
 

Sunset Cruise Tour

(4.9 of 109 reviews)

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in Naples Bay and then set sail into the Gulf of Mexico to watch a breath... More

Special Offer
Free Cancellation
Private Tour
Start From $54.06
(Saving inf% ) $0.00
 
-inf% Sunset Cruise Tour Likely to Sell Out

Sunset Cruise Tour

  • North America
  • Superb109 reviews4.9

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $54.06
    (Saving inf% ) $0.00
 
 

Boat Ride to the Arch with Snorkeling in Cabo

(5 of 194 reviews)

This is more than a sightseeing cruise — it's a chance to see Cabo through the eyes of local marine experts. Your guide and captain are both trained biologists who share in-depth, science-backed insight into the marine life and ... More

Special Offer
Free Cancellation
Private Tour
Start From $75.81
(Saving inf% ) $0.00
 
-inf% Boat Ride to the Arch with Snorkeling in Cabo Likely to Sell Out

Boat Ride to the Arch with Snorkeling in Cabo

  • North America
  • Superb194 reviews5

This is more than a sightseeing cruise — it's a chance to see Cabo through the eyes of local marin....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $75.81
    (Saving inf% ) $0.00
 
 

Private Luxury Yacht Charters, BYOB & Dolphins

(5 of 430 reviews)

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More

Special Offer
Free Cancellation
Private Tour
Start From $525.00
(Saving inf% ) $0.00
 
-inf% Private Luxury Yacht Charters, BYOB & Dolphins Likely to Sell Out

Private Luxury Yacht Charters, BYOB & Dolphins

  • North America
  • Superb430 reviews5

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $525.00
    (Saving inf% ) $0.00
 
 

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

(5 of 143 reviews)

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More

Special Offer
Free Cancellation
Private Tour
Start From $192.98
(Saving inf% ) $0.00
 
-inf% Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar Likely to Sell Out

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

  • North America
  • Superb143 reviews5

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $192.98
    (Saving inf% ) $0.00
 
 

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

(4.9 of 156 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

Special Offer
Free Cancellation
Private Tour
Start From $69.00
(Saving inf% ) $0.00
 
-inf% 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
  • Superb156 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $69.00
    (Saving inf% ) $0.00
 
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