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Top 10 Best USA Sailing Trips

Found 450 Sailing Trips activities in USA. Sort by Popularity. - Page 5
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 122 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • USA
  • Superb122 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Start From $289.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 617 reviews)

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More

Free Cancellation
Start From $127.00
 
Small-Group San Diego Sunset Sailing Excursion Likely to Sell Out

Small-Group San Diego Sunset Sailing Excursion

  • USA
  • Superb617 reviews4.9

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....

    Free Cancellation
    Start From $127.00
 
 

Sunset Catamaran Cruise in Ft. Lauderdale

(4.8 of 701 reviews)

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More

Free Cancellation
Start From $129.00
 
Sunset Catamaran Cruise in Ft. Lauderdale Likely to Sell Out

Sunset Catamaran Cruise in Ft. Lauderdale

  • USA
  • Superb701 reviews4.8

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Start From $129.00
 
 

Two Hour Coastal Sailing Cruise

(5 of 61 reviews)

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one of the largest and most stable sailing vessels in Savannah. Unlike crowded tour boats, our open-deck layout offers plenty of room... More

Free Cancellation
Start From $124.99
 
Two Hour Coastal Sailing Cruise Likely to Sell Out

Two Hour Coastal Sailing Cruise

  • USA
  • Superb61 reviews5

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one....

    Free Cancellation
    Start From $124.99
 
 

Luxury Sunset Sail on Serendipity Catamaran in Charleston

(5 of 4 reviews)

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local wildlife as the sun dips below the horizon. This up... More

Free Cancellation
Start From $150.00
 
Luxury Sunset Sail on Serendipity Catamaran in Charleston Likely to Sell Out

Luxury Sunset Sail on Serendipity Catamaran in Charleston

  • USA
  • Superb4 reviews5

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seab....

    Free Cancellation
    Start From $150.00
 
 

Maui Sunset Sail

(4.6 of 218 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More

Free Cancellation
Start From $137.82
 
Maui Sunset Sail Likely to Sell Out

Maui Sunset Sail

  • USA
  • Superb218 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Start From $137.82
 
 

San Francisco Bay Sailing Cruise

(4.9 of 641 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
Start From $65.00
 
San Francisco Bay Sailing Cruise Likely to Sell Out

San Francisco Bay Sailing Cruise

  • USA
  • Superb641 reviews4.9

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

    Free Cancellation
    Start From $65.00
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 300 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • USA
  • Superb300 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Start From $72.96
 
 

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

(4.7 of 326 reviews)

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More

Free Cancellation
Start From $66.67
 
4-Hour St. Pete Pier to Egmont Key Experience by Ferry Likely to Sell Out

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

  • USA
  • Superb326 reviews4.7

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....

    Free Cancellation
    Start From $66.67
 
 

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

(4.9 of 253 reviews)

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Partic... More

Free Cancellation
Start From $80.00
 
Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach Likely to Sell Out

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

  • USA
  • Superb253 reviews4.9

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wil....

    Free Cancellation
    Start From $80.00
 
 

Paragon Lahaina Sunset Sail

(4.6 of 10 reviews)

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More

Free Cancellation
Start From $102.00
 
Paragon Lahaina Sunset Sail Likely to Sell Out

Paragon Lahaina Sunset Sail

  • USA
  • Superb10 reviews4.6

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....

    Free Cancellation
    Start From $102.00
 
 

Sunset Dolphin Sail Aboard the Footloose Catamaran

(4.8 of 467 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
Start From $45.00
 
Sunset Dolphin Sail Aboard the Footloose Catamaran Likely to Sell Out

Sunset Dolphin Sail Aboard the Footloose Catamaran

  • USA
  • Superb467 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
    Start From $45.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 751 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Start From $141.57
 
Snorkel with Manta Rays Guaranteed Likely to Sell Out

Snorkel with Manta Rays Guaranteed

  • USA
  • Superb751 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Start From $141.57
 
 

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

(4.9 of 347 reviews)

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More

Free Cancellation
Start From $125.00
 
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests Likely to Sell Out

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

  • USA
  • Superb347 reviews4.9

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....

    Free Cancellation
    Start From $125.00
 
 

Sunset Sailing Cruise in Monterey Bay

(4.8 of 42 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

Free Cancellation
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • USA
  • Superb42 reviews4.8

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

    Free Cancellation
    Start From $95.00
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 127 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 $54.95
 
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor Likely to Sell Out

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • USA
  • Superb127 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 $54.95
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 241 reviews)

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More

Free Cancellation
Start From $109.00
 
Classic Key West Schooner Sunset Sail with Full Open Bar Likely to Sell Out

Classic Key West Schooner Sunset Sail with Full Open Bar

  • USA
  • Superb241 reviews4.9

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....

    Free Cancellation
    Start From $109.00
 
 

Sunset Sail from Traverse City with Food, Wine & Cocktails

(4.8 of 227 reviews)

Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stories about the history of the lands, people, and waters of the Grand Traverse Bay area. Enjoy complimentary locally sourced food, w... More

Free Cancellation
Start From $229.00
 
Sunset Sail from Traverse City with Food, Wine & Cocktails Likely to Sell Out

Sunset Sail from Traverse City with Food, Wine & Cocktails

  • USA
  • Superb227 reviews4.8

Wind down and relax as our captain and crewmates teach you about our elegant schooner and share stor....

    Free Cancellation
    Start From $229.00
 
 

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

(4.6 of 534 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
Start From $55.00
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head Likely to Sell Out

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

  • USA
  • Superb534 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
    Start From $55.00
 
 

Afternoon Windjammer Cruise Along the Coast of Portland Maine

(4.6 of 187 reviews)

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour,... More

Free Cancellation
Start From $69.00
 
Afternoon Windjammer Cruise Along the Coast of Portland Maine Likely to Sell Out

Afternoon Windjammer Cruise Along the Coast of Portland Maine

  • USA
  • Superb187 reviews4.6

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to e....

    Free Cancellation
    Start From $69.00
 
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