Top North America Sailing Trips

633 Results
Private Tour Isla Mujeres excursion in Transparent Boat

We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our 100% transparent boat. It will be a …More

Isla Mujeres, Mexico

We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our 100% transparent boat. It will be a...

1 hour Free Cancellation
4.5 (2)
from
$374
Guided Seattle Sailing Adventure from Bainbridge Island

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we …More

Seattle, USA

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we...

2 hours Free Cancellation
5.0 (86)
from
$360
Private Catamaran Sunset Cruise with Dolphin watching

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain …More

Destin, USA

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain...

2 hours Free Cancellation
5.0 (4)
from
$360
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
Private Sailing Charters: Island Adventures and Sunset Cruises

Set sail on a private charter with Water Music Charters, offering an unforgettable experience along Folly Beach and Charleston's vibrant waters. With over 25 years …More

Folly Beach, USA

Set sail on a private charter with Water Music Charters, offering an unforgettable experience along Folly Beach and Charleston's vibrant waters. With over 25 years...

2 hours Free Cancellation
5.0 (2)
from
$350
Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on …More

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

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on...

2 hours Free Cancellation
5.0 (3)
from
$349
Private Sunset Catamaran Sail in Cocoa Beach

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of …More

Likely to Sell Out
Likely to Sell Out
Cocoa Beach, USA

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of...

2 hours Free Cancellation
5.0 (2)
from
$338
Private luxury sailing catamaran experience in Bacalar lagoon

Our Stiletto catamaran stands out due to several unique features: 1. Speed and Stability : Unlike traditional catamarans, the Stiletto combines the thrill of speed …More

Bacalar, Mexico

Our Stiletto catamaran stands out due to several unique features: 1. Speed and Stability : Unlike traditional catamarans, the Stiletto combines the thrill of speed...

4 hours
5.0 (4)
from
$303
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
The Nāpali Coast Snorkel Excursion

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making...

6 hours Free Cancellation
4.9 (559)
from
$292
Pirate Ship by Day

Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboard an incredible 700-ton Galleon, full of adventure and …More

Puerto Vallarta, Mexico

Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboard an incredible 700-ton Galleon, full of adventure and...

6 hours
5.0 (2)
from
$280
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
Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, …More

Big Island of Hawaii, USA

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests,...

3 hours Free Cancellation
5.0 (6)
from
$276
Private Sailing Excursions, Nice Spacious Sailboats

Bacalar's lagoon is explored by sailboat with up to six guests, giving families and friends space to tailor the trip. Sail to cenotes, Bird Island, …More

Bacalar, Mexico

Bacalar's lagoon is explored by sailboat with up to six guests, giving families and friends space to tailor the trip. Sail to cenotes, Bird Island,...

4 hours Free Cancellation
4.9 (33)
from
$275
Bacalar - Gourmet Tour in Private Catamaran with Cocktails Included

During this experience you will try star dishes from the best restaurants in the area aboard a comfortable private boat. You will enjoy a rich …More

Bacalar, Mexico

During this experience you will try star dishes from the best restaurants in the area aboard a comfortable private boat. You will enjoy a rich...

4 hours Free Cancellation
5.0 (22)
from
$275
Private - Bacalar sailing across the mesmerizing waters

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon …More

Tulum, Mexico

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon...

12 hours Hotel pickup offered Free Cancellation
5.0 (5)
from
$274
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

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 …More

Maui, USA

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...

5 hours Free Cancellation
5.0 (135)
from
$269
Bimini or Grand Bahama Island Day Cruise

Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands, this tropical paradise is famous for white-sand beaches, crystal-clear …More

Likely to Sell Out
Likely to Sell Out
Fort Lauderdale, USA

Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands, this tropical paradise is famous for white-sand beaches, crystal-clear...

12 hours Free Cancellation
3.7 (24)
from
$265
Sailboat with Shade Private Adventure in Bacalar

Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We explore mangroves, shoreline and Cenotes. Our …More

Bacalar, Mexico

Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We explore mangroves, shoreline and Cenotes. Our...

3 hours 30 minutes Free Cancellation
5.0 (22)
from
$264
Nāpali Sunset Dinner Sail

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa...

4 to 5 hours Free Cancellation
4.8 (563)
from
$264

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