USA Sailing Trips

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party …More

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

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party...

3 hours Free Cancellation
4.9 (59)
from
$89
Key West Sunset Sail Aboard Legendary Schooner Appledore

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 (368)
from
$99
Classic Key West Schooner Sunset Sail with Full Open Bar

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 …More

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

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...

2 hours Free Cancellation
4.9 (282)
from
$109
Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers

Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This two-hour evening sail takes you into the picturesque ʻAuʻau Channel, where …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This two-hour evening sail takes you into the picturesque ʻAuʻau Channel, where...

2 hours Free Cancellation
5.0 (53)
from
$127
Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing...

2 hours Free Cancellation
5.0 (46)
from
$127
Private Guided Sunset and Eco Tour up to 6 Passengers

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset...

1 hour 30 minutes Free Cancellation
5.0 (81)
from
$250
Deluxe Day Sail in San Diego

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego...

2 hours 30 minutes Free Cancellation
5.0 (82)
from
$119
Private Luxury Yacht Charters, BYOB & Dolphins

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the …More

Charleston, USA

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the...

2 hours 30 minutes Free Cancellation
5.0 (430)
from
$525
Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion

Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty …More

Kennebunkport, USA

Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty...

2 hours Free Cancellation
5.0 (66)
from
$139
Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden …More

Oahu, USA

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden...

2 hours Free Cancellation
4.6 (87)
from
$68
Sunset Dolphin Sail Aboard the Daydreams Sailboat

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. …More

Panama City Beach, USA

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island....

2 hours Free Cancellation
5.0 (46)
from
$107
1.5-Hour San Francisco Bay Sailing Tour

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with …More

San Francisco, USA

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with...

1 hour 30 minutes Free Cancellation
4.8 (396)
from
$99
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat …More

San Diego, USA

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat...

2 hours Free Cancellation
4.9 (204)
from
$119
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed...

2 hours Free Cancellation
5.0 (71)
from
$508
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay …More

Likely to Sell Out
Likely to Sell Out
Pensacola, USA

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay...

2 hours Free Cancellation
5.0 (73)
from
$114
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the …More

Mount Pleasant, USA

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the...

2 hours Free Cancellation
4.9 (101)
from
$63
Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based …More

Maui, USA

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based...

5 hours Free Cancellation
5.0 (95)
from
$243
Sunset Cruise Tour

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in …More

Likely to Sell Out
Likely to Sell Out
Naples, USA

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in...

2 hours Free Cancellation
5.0 (71)
from
$54
Hawaiian Canoe Sailing Experience in Maui

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning...

2 hours Free Cancellation
4.9 (59)
from
$179
Kona Tradewind Catamaran Day Sail

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails …More

Big Island of Hawaii, USA

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails...

1 hour 30 minutes Free Cancellation
4.8 (51)
from
$89
Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a …More

New York City, USA

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a...

1 hour Free Cancellation
5.0 (43)
from
$350

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