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Top 10 Best North America Sailing Trips

Found 707 Sailing Trips activities in North America. Sort by Popularity. - Page 15
 

4th of July Fireworks on Clipper City Tall Ship

(3.7 of 6 reviews)

TREAT YOURSELF TO SOMETHING SPECIAL Step aboard the massive Clipper City Tall Ship for a front-row seat as the Macy's July 4th Fireworks Spectacular lights up the night sky. You can’t get any closer to the action. Our team has ... More

Start From $570.00
 
4th of July Fireworks on Clipper City Tall Ship

4th of July Fireworks on Clipper City Tall Ship

  • North America
  • Very Good6 reviews3.7

TREAT YOURSELF TO SOMETHING SPECIAL Step aboard the massive Clipper City Tall Ship for a front-row ....

    Start From $570.00
 
 

Afternoon Ali'i Adventure

(5 of 5 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Start From $276.00
 
Afternoon Ali'i Adventure

Afternoon Ali'i Adventure

  • North America
  • Superb5 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Start From $276.00
 
 

Champagne Dolphin Sail and Reef Snorkel

(5 of 5 reviews)

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the ... More

Special Offer
Free Cancellation
Start From $98.01
(Saving 10% ) $108.91
 
-10% Champagne Dolphin Sail and Reef Snorkel Likely to Sell Out

Champagne Dolphin Sail and Reef Snorkel

  • North America
  • Superb5 reviews5

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now l....

    Special Offer
    Free Cancellation
    Start From $98.01
    (Saving 10% ) $108.91
 
 

Schooner Eastwind Sunset Sail to see the Maine Coastline

(4.6 of 46 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Start From $59.95
 
Schooner Eastwind Sunset Sail to see the Maine Coastline Likely to Sell Out

Schooner Eastwind Sunset Sail to see the Maine Coastline

  • North America
  • Superb46 reviews4.6

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Start From $59.95
 
 

Private Charter

(4.8 of 13 reviews)

The captain works with the guest to design a custom outing based on his 30 years of cruising experience in the local area. With knowledge of the local sea conditions and coastal ecology. you build a custom experience. Typically, G... More

Free Cancellation
Private Tour
Start From $775.00
 
Private Charter Likely to Sell Out

Private Charter

  • North America
  • Superb13 reviews4.8

The captain works with the guest to design a custom outing based on his 30 years of cruising experie....

    Free Cancellation
    Private Tour
    Start From $775.00
 
 

2-Hour Sunset Sailing With Wine In Stock Island

(5 of 85 reviews)

Sail with a smaller group of guests on our 65 foot schooner. Enjoy wines from around the world. Indulge in a variety of IPA, Import or domestic beers. Taste an assortment of appetizers. Enjoy a beautiful sunset while on the water.... More

Free Cancellation
Private Tour
Start From $115.00
 
2-Hour Sunset Sailing With Wine In Stock Island Likely to Sell Out

2-Hour Sunset Sailing With Wine In Stock Island

  • North America
  • Superb85 reviews5

Sail with a smaller group of guests on our 65 foot schooner. Enjoy wines from around the world. Indu....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

All Inclusive Beach Club, Water Sports HorseBack Ride Food Drinks

(4.5 of 4 reviews)

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatable experience with unlimited drinks, mouth-watering lunch, and your choice of two exciting activities. Whether you want to ride ho... More

Free Cancellation
Private Tour
Start From $55.00
 
All Inclusive Beach Club, Water Sports HorseBack Ride Food Drinks Likely to Sell Out

All Inclusive Beach Club, Water Sports HorseBack Ride Food Drinks

  • North America
  • Exellent4 reviews4.5

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatab....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Unforgettable Private Yacht Tour, Music, Drinks & Celebration Fun

(4.6 of 65 reviews)

Are you ready for an adventure? Join us for an unforgettable journey on our luxurious yacht, perfect for those who crave excitement and a deep connection with nature. Explore Miami's marine wonders aboard with all the comforts you... More

Free Cancellation
Private Tour
Start From $599.99
 
Unforgettable Private Yacht Tour, Music, Drinks & Celebration Fun Likely to Sell Out

Unforgettable Private Yacht Tour, Music, Drinks & Celebration Fun

  • North America
  • Superb65 reviews4.6

Are you ready for an adventure? Join us for an unforgettable journey on our luxurious yacht, perfect....

    Free Cancellation
    Private Tour
    Start From $599.99
 
 

Isla Mujeres, Cancún Private Sunset Trip

(5 of 75 reviews)

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the moment. We are here to bring you the the quality service you so rightly deserve. Our adored crew ensure... More

Free Cancellation
Private Tour
Start From $450.00
 
Isla Mujeres, Cancún Private Sunset Trip Likely to Sell Out

Isla Mujeres, Cancún Private Sunset Trip

  • North America
  • Superb75 reviews5

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

Milwaukee America's Cup Sailing Adventure

(3 of 2 reviews)

Set sail on the historic Red Witch II, an approximate replica of a classic 12-Meter America’s Cup yacht. Experience the thrill of sailing on Lake Michigan with a knowledgeable captain at the helm, ensuring a safe and enjoyable j... More

Special Offer
Free Cancellation
Private Tour
Start From $39.20
(Saving 20% ) $49.00
 
-20% Milwaukee America's Cup Sailing Adventure Likely to Sell Out

Milwaukee America's Cup Sailing Adventure

  • North America

Set sail on the historic Red Witch II, an approximate replica of a classic 12-Meter America’s Cup ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $39.20
    (Saving 20% ) $49.00
 
 

Key West Ultimate Beach Pass with Parasailing

(4.1 of 22 reviews)

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. ... More

Free Cancellation
Private Tour
Start From $109.95
 
Key West Ultimate Beach Pass with Parasailing Likely to Sell Out

Key West Ultimate Beach Pass with Parasailing

  • North America
  • Exellent22 reviews4.1

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are....

    Free Cancellation
    Private Tour
    Start From $109.95
 
 

New Historic Palm Beach Sightseeing on Motunui Catamaran Cruise

(3.7 of 3 reviews)

Relax on a comfortable, shaded 2-hour Intracoastal Waterway Sightseeing Cruise aboard Motunui, a 50-ft open breeze catamaran with cushioned seating, tables, and deck-level restrooms. Enjoy a fully narrated tour showcasing Palm Bea... More

Free Cancellation
Private Tour
Start From $56.71
 
New Historic Palm Beach Sightseeing on Motunui Catamaran Cruise Likely to Sell Out

New Historic Palm Beach Sightseeing on Motunui Catamaran Cruise

  • North America
  • Very Good3 reviews3.7

Relax on a comfortable, shaded 2-hour Intracoastal Waterway Sightseeing Cruise aboard Motunui, a 50-....

    Free Cancellation
    Private Tour
    Start From $56.71
 
 

HipHop Catamaran Party from Cancun to Isla Mujeres

(3.4 of 7 reviews)

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snorkeling in one of the Caribbean's top reefs, surrounded by vibrant marine life. Then, head to a secluded sandbank—a hidden gem pe... More

Free Cancellation
Private Tour
Start From $42.00
 
HipHop Catamaran Party from Cancun to Isla Mujeres Likely to Sell Out

HipHop Catamaran Party from Cancun to Isla Mujeres

  • North America
  • Good7 reviews3.4

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snor....

    Free Cancellation
    Private Tour
    Start From $42.00
 
 

Guided Seattle Sailing Adventure from Bainbridge Island

(5 of 82 reviews)

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we could see a nuclear submarine, inbound container ships, or century-old schooners... More

Free Cancellation
Private Tour
Start From $295.00
 
Guided Seattle Sailing Adventure from Bainbridge Island Likely to Sell Out

Guided Seattle Sailing Adventure from Bainbridge Island

  • North America
  • Superb82 reviews5

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning wa....

    Free Cancellation
    Private Tour
    Start From $295.00
 
 

New York Harbor Wine and Jazz Sail aboard Clipper City

(4.4 of 21 reviews)

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of New York City on this entertaining evening jazz sail. From the decks of the boat, you will enjoy breathtaking views of the Manha... More

Free Cancellation
Private Tour
Start From $140.08
 
New York Harbor Wine and Jazz Sail aboard Clipper City Likely to Sell Out

New York Harbor Wine and Jazz Sail aboard Clipper City

  • North America
  • Exellent21 reviews4.4

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views o....

    Free Cancellation
    Private Tour
    Start From $140.08
 
 

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

(5 of 39 reviews)

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More

Free Cancellation
Private Tour
Start From $599.00
 
Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering Likely to Sell Out

Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

  • North America
  • Superb39 reviews5

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht ....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

4 hours Sailboat Tour for 2 people along the Los Angeles Coastline

(3.7 of 3 reviews)

The coastal line of Los Angeles. You will see Marina Del Rey, head for Santa Monica, sail past Venice Beach, Airport, Malibu beach, go into the open ocean, anchor (if desired) and return back to Marina Del Rey.... More

Free Cancellation
Private Tour
Start From $599.00
 
4 hours Sailboat Tour for 2 people along the Los Angeles Coastline Likely to Sell Out

4 hours Sailboat Tour for 2 people along the Los Angeles Coastlin....

  • North America
  • Very Good3 reviews3.7

The coastal line of Los Angeles. You will see Marina Del Rey, head for Santa Monica, sail past Venic....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Polynesian Canoe Day Sail

(4.9 of 28 reviews)

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

Free Cancellation
Private Tour
Start From $200.00
 
Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • North America
  • Superb28 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Private Classic Sailboat Tour in New York City

(5 of 1 review)

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll enjoy stunning views of iconic landmarks like the Statue of Liberty, E... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Classic Sailboat Tour in New York City Likely to Sell Out

Private Classic Sailboat Tour in New York City

  • North America
  • Superb1 review5

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a ....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Fort Lauderdale Sailing Charter

(5 of 367 reviews)

Your PRIVATE or SEMI-PRIVATE sailboat charter is hosted by Captain Dan, a licensed captain with 20 years of local sailing experience. For PRIVATE charters, call directly to make arrangements. One to Three passengers bookings are s... More

Free Cancellation
Private Tour
Start From $150.00
 
Fort Lauderdale Sailing Charter Likely to Sell Out

Fort Lauderdale Sailing Charter

  • North America
  • Superb367 reviews5

Your PRIVATE or SEMI-PRIVATE sailboat charter is hosted by Captain Dan, a licensed captain with 20 y....

    Free Cancellation
    Private Tour
    Start From $150.00
 
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