USA Sailing Trips

Spectacular Afternoon Sail on San Diego Bay

A unique two-hour sailing Experience aboard our 35-foot sailboat, Luna. Limited to six people. Watch for playful dolphins, sea lions, and pelicans. Get hands-on or …More

La Jolla, USA

A unique two-hour sailing Experience aboard our 35-foot sailboat, Luna. Limited to six people. Watch for playful dolphins, sea lions, and pelicans. Get hands-on or...

2 hours Free Cancellation
5.0 (24)
from
$150
Polynesian Canoe Day Sail

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 …More

Oahu, USA

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...

2 hours Free Cancellation
5.0 (28)
from
$170
Golden Hour Escape: Private Sunset Sail in Coastal Maine

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined …More

Kennebunkport, USA

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined...

2 hours Free Cancellation
5.0 (23)
from
$849
Private Swim, Snorkel & Sail on the Daydreams Sailboat

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area …More

Panama City Beach, USA

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

3 hours Free Cancellation
5.0 (33)
from
$963
Moana’s Luxury semi-private Sunset Cruise on Nalu

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback …More

Oahu, USA

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback...

2 hours Free Cancellation
5.0 (21)
from
$150
Baltimore Inner Harbor Sail on the Unforgettable

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling …More

Baltimore, USA

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...

1 hour 30 minutes Free Cancellation
4.8 (25)
from
$65
Polynesian Canoe Morning Sail

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 …More

Oahu, USA

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...

2 hours Free Cancellation
5.0 (18)
from
$180
Waikiki Friday Night Fireworks Cruise NYE SPECIAL CRUISE!

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring …More

Oahu, USA

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring...

1 hour Free Cancellation
4.7 (30)
from
$60
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from …More

Oahu, USA

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from...

2 hours Free Cancellation
4.9 (18)
from
$70
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hours Free Cancellation
4.8 (14)
from
$1,150
Public Sunset Sailing Cruise on Lake Champlain

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack...

2 hours
5.0 (23)
from
$95
Sunset Sail Aboard the Liberty Clipper

Set sail into the golden hues of sunset on the 125' Schooner Liberty Clipper. This 2-hour adventure lets you glide through the tranquil waters while …More

Long Island, USA

Set sail into the golden hues of sunset on the 125' Schooner Liberty Clipper. This 2-hour adventure lets you glide through the tranquil waters while...

2 hours Free Cancellation
5.0 (18)
from
$89
Maui: Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and …More

Maui, USA

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and...

2 hours Free Cancellation
4.8 (85)
from
$112
Key West Nighttime Full Moon Sail

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or …More

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

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or...

1 hour 30 minutes Free Cancellation
5.0 (10)
from
$89
Private Key West Sunset Sail

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for …More

Key West, USA

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for...

2 hours
4.9 (50)
from
$693
Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which...

2 hours Free Cancellation
5.0 (11)
from
$900
Private Sailboat Charter on San Francisco Bay

Fall and winter typically provide lighter breezes on SF Bay. Great days on the Bay. 3 hour PRIVATE Charter with a unique experience aboard Carmelita, …More

Likely to Sell Out
Likely to Sell Out

Fall and winter typically provide lighter breezes on SF Bay. Great days on the Bay. 3 hour PRIVATE Charter with a unique experience aboard Carmelita,...

3 hours Free Cancellation
5.0 (9)
from
$995
Private Statue of Liberty Sailing Tour

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory, …More

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

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory,...

2 hours
5.0 (14)
from
$800
Champagne Dolphin Sail and Reef Snorkel

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 …More

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

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...

3 hours
5.0 (10)
from
$109
Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the...

2 hours 30 minutes Free Cancellation
5.0 (12)
from
$149
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment …More

Miami, USA

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment...

3 to 30 minutes Free Cancellation
4.9 (12)
from
$600

Frequently Asked Questions

These answers are based on answers previously given to Key West Private Charters customers' questions.

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