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Top 10 Best North America Sailing Trips

Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 19
 

Private Sailing Tour through the Ten Thousands Islands

(4.9 of 156 reviews)

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More

Private Tour
Start From $450.00
 
Private Sailing Tour through the Ten Thousands Islands

Private Sailing Tour through the Ten Thousands Islands

  • North America
  • Superb156 reviews4.9

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....

    Private Tour
    Start From $450.00
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.8 of 467 reviews)

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More

Free Cancellation
Private Tour
Start From $64.95
 
Windjammer Classic Day Sail from Camden, Maine

Windjammer Classic Day Sail from Camden, Maine

  • North America
  • Superb467 reviews4.8

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Private Tour
    Start From $64.95
 
 
-18% Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

(5 of 193 reviews)

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More

Special Offer
Free Cancellation
Private Tour
Start From $701.25
(Saving 18% ) $850.00
 
-18% Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

  • North America
  • Superb193 reviews5

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $701.25
    (Saving 18% ) $850.00
 
 
-inf% Miami Private Yacht Celebration Cruise with Captain

Miami Private Yacht Celebration Cruise with Captain

(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

Special Offer
Free Cancellation
Private Tour
Start From $799.00
(Saving inf% ) $0.00
 
-inf% Miami Private Yacht Celebration Cruise with Captain

Miami Private Yacht Celebration Cruise with Captain

  • North America
  • Superb65 reviews4.6

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $799.00
    (Saving inf% ) $0.00
 
 
-inf% Cozumel Private Snorkeling and Charter Experience

Cozumel Private Snorkeling and Charter Experience

(4.9 of 30 reviews)

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting the famous 'El Cielo' and other amazing destinations to give you... More

Special Offer
Free Cancellation
Private Tour
Start From $850.00
(Saving inf% ) $0.00
 
-inf% Cozumel Private Snorkeling and Charter Experience

Cozumel Private Snorkeling and Charter Experience

  • North America
  • Superb30 reviews4.9

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On th....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $850.00
    (Saving inf% ) $0.00
 
 
-inf% Tulum: Snorkeling and Private Sailing Tour

Tulum: Snorkeling and Private Sailing Tour

(4.9 of 172 reviews)

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spectacular view of the Tulum ruins from the sea... More

Special Offer
Free Cancellation
Private Tour
Start From $60.43
(Saving inf% ) $0.00
 
-inf% Tulum: Snorkeling and Private Sailing Tour

Tulum: Snorkeling and Private Sailing Tour

  • North America
  • Superb172 reviews4.9

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spect....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $60.43
    (Saving inf% ) $0.00
 
 
-inf% 2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

(4.9 of 20 reviews)

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, this intimate evening cruise offers stunning views of the coast... More

Special Offer
Free Cancellation
Private Tour
Start From $279.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

  • North America
  • Superb20 reviews4.9

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $279.00
    (Saving inf% ) $0.00
 
 
-inf% Private Customizable Sailing Tour in Cancun

Private Customizable Sailing Tour in Cancun

(4.7 of 123 reviews)

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be known by the sea. From a relaxing private sailing tour in the bay of Can... More

Special Offer
Free Cancellation
Private Tour
Start From $549.34
(Saving inf% ) $0.00
 
-inf% Private Customizable Sailing Tour in Cancun

Private Customizable Sailing Tour in Cancun

  • North America
  • Superb123 reviews4.7

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers th....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $549.34
    (Saving inf% ) $0.00
 
 
-inf% Private Sailboat + Captain for a Day Experience

Private Sailboat + Captain for a Day Experience

(5 of 612 reviews)

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride around the most relevant landmarks in the lagoon on board of a beautif... More

Special Offer
Free Cancellation
Private Tour
Start From $221.10
(Saving inf% ) $0.00
 
-inf% Private Sailboat + Captain for a Day Experience

Private Sailboat + Captain for a Day Experience

  • North America
  • Superb612 reviews5

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOI....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $221.10
    (Saving inf% ) $0.00
 
 
-inf% Luxury Snorkel Adventure in Cabo

Luxury Snorkel Adventure in Cabo

(4.9 of 60 reviews)

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at either one of this beach areas is where boat captain will make a stop for snorkeling at one ... More

Special Offer
Free Cancellation
Private Tour
Start From $149.00
(Saving inf% ) $0.00
 
-inf% Luxury Snorkel Adventure in Cabo

Luxury Snorkel Adventure in Cabo

  • North America
  • Superb60 reviews4.9

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located ....

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

Polynesian Canoe Sunset Sail

(4.9 of 129 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More

Special Offer
Free Cancellation
Private Tour
Start From $250.00
(Saving inf% ) $0.00
 
-inf% Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • North America
  • Superb129 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $250.00
    (Saving inf% ) $0.00
 
 

Deluxe Private Boats - 40 ft Catamaran

(5 of 132 reviews)

We are a company that understands privacy, attention to detail, and quality in everything we get our hands-on. We want you to feel relaxed and at home. We understand you are here to be pampered and have the nicest drinks and lunc... More

Special Offer
Free Cancellation
Private Tour
Start From $1,600.00
(Saving inf% ) $0.00
 
-inf% Deluxe Private Boats - 40 ft Catamaran Likely to Sell Out

Deluxe Private Boats - 40 ft Catamaran

  • North America
  • Superb132 reviews5

We are a company that understands privacy, attention to detail, and quality in everything we get our....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,600.00
    (Saving inf% ) $0.00
 
 

Visit Private Beaches around Puerto Vallarta in a Private Yacht

(5 of 135 reviews)

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain on the art of sailing. This is not a boat trip, this is an experience to enj... More

Special Offer
Free Cancellation
Private Tour
Start From $1,500.00
(Saving inf% ) $0.00
 
-inf% Visit Private Beaches around Puerto Vallarta in a Private Yacht Likely to Sell Out

Visit Private Beaches around Puerto Vallarta in a Private Yacht

  • North America
  • Superb135 reviews5

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours do....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,500.00
    (Saving inf% ) $0.00
 
 

Luxury Catamaran tour to isla mujeres with transportation from Tulum

(3.5 of 66 reviews)

Excellent service on board Professional crew members Safety measures in all our activities Sanitary prevention protocols for all our guests and staff Once in a lifetime experience Delicious buffet lunch and drinks Beach club (beac... More

Special Offer
Free Cancellation
Private Tour
Start From $110.77
(Saving inf% ) $0.00
 
-inf% Luxury Catamaran tour to isla mujeres with transportation from Tulum Likely to Sell Out

Luxury Catamaran tour to isla mujeres with transportation from Tu....

  • North America
  • Good66 reviews3.5

Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $110.77
    (Saving inf% ) $0.00
 
 

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

(4.7 of 52 reviews)

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More

Special Offer
Free Cancellation
Private Tour
Start From $72.83
(Saving inf% ) $0.00
 
-inf% JFarwell Moonlight Yacht Cruise from Halifax Waterfront Likely to Sell Out

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

  • North America
  • Superb52 reviews4.7

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $72.83
    (Saving inf% ) $0.00
 
 

The Finest Private Yacht Experience in Cabo

(4.6 of 23 reviews)

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some of the best things to do in Cabo such as whale watching and bathing on soothing crystal waters... More

Special Offer
Free Cancellation
Private Tour
Start From $738.83
(Saving inf% ) $0.00
 
-inf% The Finest Private Yacht Experience in Cabo Likely to Sell Out

The Finest Private Yacht Experience in Cabo

  • North America
  • Superb23 reviews4.6

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $738.83
    (Saving inf% ) $0.00
 
 

2hr Shared Sailing Experience in Toronto

(5 of 27 reviews)

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to be the shortest commercial one in the world. Below the water is a walking tunnel connecting the two for t... More

Special Offer
Free Cancellation
Private Tour
Start From $581.95
(Saving inf% ) $0.00
 
-inf% 2hr Shared Sailing Experience in Toronto Likely to Sell Out

2hr Shared Sailing Experience in Toronto

  • North America
  • Superb27 reviews5

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out fo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $581.95
    (Saving inf% ) $0.00
 
 

Key West: Sunset Sail + Reef Snorkel & Sandbar

(5 of 56 reviews)

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More

Special Offer
Free Cancellation
Private Tour
Start From $143.05
(Saving inf% ) $0.00
 
-inf% Key West: Sunset Sail + Reef Snorkel & Sandbar Likely to Sell Out

Key West: Sunset Sail + Reef Snorkel & Sandbar

  • North America
  • Superb56 reviews5

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $143.05
    (Saving inf% ) $0.00
 
 

Experience Oceanside Sailing with Whales and dolphins!

(5 of 18 reviews)

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the Oceanside harbor. We cater to guests from many of the five star hotels in the area. We serve an up... More

Special Offer
Free Cancellation
Private Tour
Start From $150.00
(Saving inf% ) $0.00
 
-inf% Experience Oceanside Sailing with Whales and dolphins! Likely to Sell Out

Experience Oceanside Sailing with Whales and dolphins!

  • North America
  • Superb18 reviews5

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $150.00
    (Saving inf% ) $0.00
 
 

Snorkeling Adventure in Puerto Morelos with snack and round trip

(3.9 of 95 reviews)

You must live this experience once in your life, This activity is only for travelers that love to be in a unique place in the world. You will discover the 2nd biggest reef wall in the world, you will see a huge variety of fish of... More

Special Offer
Free Cancellation
Private Tour
Start From $44.25
(Saving inf% ) $0.00
 
-inf% Snorkeling Adventure in Puerto Morelos with snack and round trip Likely to Sell Out

Snorkeling Adventure in Puerto Morelos with snack and round trip

  • North America
  • Very Good95 reviews3.9

You must live this experience once in your life, This activity is only for travelers that love to be....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $44.25
    (Saving inf% ) $0.00
 
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