USA Sailing Trips

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

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, …More

Maui, USA

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,...

5 hours Free Cancellation
5.0 (140)
from
$193
Private Sailing Tour of Bodega Bay

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as …More

Napa & Sonoma, USA

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as...

3 hours Free Cancellation
4.9 (91)
from
$123
Private Catamaran Charter in Waikiki (1-6 Guests)

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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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...

2 hours Free Cancellation
5.0 (25)
from
$900
Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty …More

Honolulu, USA

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hours Free Cancellation
4.7 (242)
from
$79
Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations...

2 hours Free Cancellation
4.9 (29)
from
$110
Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear...

2 hours 30 minutes Free Cancellation
4.8 (42)
from
$127
2-Hour Relaxing Chesapeake Day Sail on Lady Patty

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in …More

Likely to Sell Out
Likely to Sell Out

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in...

2 hours Free Cancellation
5.0 (22)
from
$160
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

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, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

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,...

2 hours Free Cancellation
4.8 (19)
from
$279
Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

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 …More

Maui, USA

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...

2 hours Free Cancellation
4.9 (90)
from
$119
2hr. SUNSET Sailing Experience on San Francisco Bay

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get …More

Likely to Sell Out
Likely to Sell Out
Sausalito, USA

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get...

2 hours Free Cancellation
4.9 (35)
from
$149
Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hours Free Cancellation
5.0 (17)
from
$300
Private Morning Sail, Dolphin and History Tour on Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing …More

Charleston, USA

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing...

2 hours Free Cancellation
5.0 (86)
from
$525
San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by …More

San Diego, USA

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by...

2 hours 30 minutes Free Cancellation
4.9 (55)
from
$55
Schooner Appledore Day Sail with Full Bar in Key West

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hours Free Cancellation
5.0 (113)
from
$54
2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel …More

Likely to Sell Out
Likely to Sell Out

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel...

2 hours Free Cancellation
5.0 (17)
from
$245
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, …More

Oahu, USA

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hour Free Cancellation
4.8 (62)
from
$90
New York City Live Jazz Sail

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around …More

Likely to Sell Out
Likely to Sell Out
New York City, USA

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around...

2 hours Free Cancellation
4.9 (15)
from
$134
2 - Hour Private Hilton Head Morning Dolphin Watching / Sail

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions …More

Hilton Head Island, USA

This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions...

2 hours Free Cancellation
5.0 (37)
from
$465
Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also …More

Charleston, USA

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours Free Cancellation
5.0 (56)
from
$599
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step …More

Maui, USA

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes Free Cancellation
4.8 (63)
from
$249
Private Day Sail in San Diego up to 12 guests

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San …More

San Diego, USA

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San...

2 hours 30 minutes Free Cancellation
5.0 (70)
from
$81

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