USA Sailing Trips

Buccaneer Pirate Cruise in Destin

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger...

90 to 120 minutes Free Cancellation
4.8 (146)
from
$62
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Experience one City Balloon Tours's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from …More

Oahu, USA

Experience one City Balloon Tours's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from...

2 hours Free Cancellation
4.9 (1,795)
from
$50
Sailing Charters in Wilmington

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on the historic Wilmington river walk. …More

Wilmington, USA

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on the historic Wilmington river walk....

2 hours Free Cancellation
5.0 (218)
from
$89
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, …More

Oahu, USA

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle,...

1 hour 30 minutes Free Cancellation
4.9 (256)
from
$45
Sunset Dolphin Sail Aboard the Footloose Catamaran

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 …More

Panama City Beach, USA

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...

1 hour 30 minutes Free Cancellation
4.9 (475)
from
$38
Sightseeing Day Sail around Boston Harbor

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of …More

Likely to Sell Out
Likely to Sell Out
Boston, USA

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of...

90 to 120 minutes Free Cancellation
4.8 (654)
from
$54
Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain …More

Big Island of Hawaii, USA

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain...

3 hours Free Cancellation
4.9 (737)
from
$136
Key West Day Sail on Schooner America 2.0 with 2 Drinks

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that …More

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

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...

1 hour 30 minutes Free Cancellation
5.0 (212)
from
$82
Sunset Sail Along the San Diego Skyline

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from …More

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

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from...

2 hours Free Cancellation
4.9 (658)
from
$99
Portland Tall Ship Cruise on Casco Bay

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this …More

Portland, USA

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this...

2 hours Free Cancellation
4.6 (242)
from
$101
Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean...

1 hour 30 minutes Free Cancellation
4.8 (382)
from
$109
Boston Harbor Sunset Sail Tour

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. …More

Likely to Sell Out
Likely to Sell Out
Boston, USA

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon....

2 hours Free Cancellation
4.9 (189)
from
$82
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

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

2 hours Free Cancellation
5.0 (114)
from
$60
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

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

2 hours Free Cancellation
4.9 (157)
from
$69
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our...

4 hours Free Cancellation
5.0 (713)
from
$189
San Diego Whale Watching Cruise

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off …More

San Diego, USA

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off...

3 hours 30 minutes Free Cancellation
4.6 (681)
from
$54
San Francisco Bay Cruise

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, …More

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island,...

1 hour Free Cancellation
4.6 (388)
from
$39
Suncoast Sailing's Day Sailing Experience!

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just …More

St Petersburg, USA

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just...

2 hours 30 minutes Free Cancellation
4.9 (118)
from
$65
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look …More

Kauai, USA

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look...

5 hours Free Cancellation
4.8 (1,559)
from
$223
Windjammer Classic Sunset Sail from Camden, Maine

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. …More

Camden, USA

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience....

2 hours Free Cancellation
4.9 (514)
from
$75
Monterey Bay Whale Watching

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey …More

Likely to Sell Out
Likely to Sell Out
Monterey & Carmel, USA

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey...

2 to 3 hours Free Cancellation
4.8 (366)
from
$70

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