Menu

Top 10 Best North America Sailing Trips

Found 756 Sailing Trips activities in North America. Sort by Popularity. - Page 17
 

Open Bar Boat Tour to Arcos, Animas, and Quimixto

(3 of 1 review)

This tour combines three of the bay’s most iconic locations in one all-inclusive adventure. Travelers love the balance of snorkeling, beach time, and jungle exploration—plus the comfort of a large double-deck boat with open ba... More

Free Cancellation
Start From $97.53
 
Open Bar Boat Tour to Arcos, Animas, and Quimixto

Open Bar Boat Tour to Arcos, Animas, and Quimixto

  • North America

This tour combines three of the bay’s most iconic locations in one all-inclusive adventure. Travel....

    Free Cancellation
    Start From $97.53
 
 

2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

(5 of 9 reviews)

Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking views of the city of Racine and on clear day views of Milwaukee and Kenosha You can lay back and relax to the sounds of the wave... More

Free Cancellation
Private Tour
Start From $95.00
 
2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

2 Hour Sailing Adventure in Lake Michigan (up to 6 people)

  • North America
  • Superb9 reviews5

Our trips are perfect for starters or advanced sailors. We offer a 2 -hour sailing trip overlooking ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Vintage Yacht Experience Small Group 6 passengers maximum

(5 of 81 reviews)

Skip the crowded boats and enjoy a quiet, small-group sail with just six guests onboard. Sail San Diego Bay with Captain Phil—a fun, easy going captain with decades of experience—aboard his classic yacht "Liberty". Enjoy craft... More

Free Cancellation
Private Tour
Start From $125.00
 
Vintage Yacht Experience Small Group 6 passengers maximum Likely to Sell Out

Vintage Yacht Experience Small Group 6 passengers maximum

  • North America
  • Superb81 reviews5

Skip the crowded boats and enjoy a quiet, small-group sail with just six guests onboard. Sail San Di....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

(4.9 of 42 reviews)

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More

Free Cancellation
Private Tour
Start From $59.95
 
Schooner Applejack Sunset Sail Tour in Boothbay Harbor Likely to Sell Out

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

  • North America
  • Superb42 reviews4.9

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Tiki Pub Glow Party Cruise (Adults only)

(4.9 of 16 reviews)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic of the moonlit waters, paired with tunes and laughter. Join us for the most memora... More

Free Cancellation
Private Tour
Start From $79.95
 
Tiki Pub Glow Party Cruise (Adults only) Likely to Sell Out

Tiki Pub Glow Party Cruise (Adults only)

  • North America
  • Superb16 reviews4.9

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, si....

    Free Cancellation
    Private Tour
    Start From $79.95
 
 

Adults-Only Sunset Catamaran Cruise to Isla Mujeres

(4.9 of 16 reviews)

Adults-Only Atmosphere Unlike typical family catamaran tours, this is exclusively for adults, creating a relaxed yet lively vibe perfect for couples, friends, and groups looking to unwind or celebrate. Stylish, Spacious Catamaran... More

Special Offer
Free Cancellation
Private Tour
Start From $98.10
(Saving 10% ) $109.00
 
-10% Adults-Only Sunset Catamaran Cruise to Isla Mujeres Likely to Sell Out

Adults-Only Sunset Catamaran Cruise to Isla Mujeres

  • North America
  • Superb16 reviews4.9

Adults-Only Atmosphere Unlike typical family catamaran tours, this is exclusively for adults, creati....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $98.10
    (Saving 10% ) $109.00
 
 

Speedboat and Snorkeling Adventure in Cancun

(4.9 of 16 reviews)

Pack your day with exciting water adventures in the vibrant Cancun jungle. Begin with a thrilling speedboat ride across the stunning Nichupte Lagoon. After the rush, ease into tranquility as you snorkel among the mesmerizing under... More

Special Offer
Free Cancellation
Private Tour
Start From $14.40
(Saving 20% ) $18.00
 
-20% Speedboat and Snorkeling Adventure in Cancun Likely to Sell Out

Speedboat and Snorkeling Adventure in Cancun

  • North America
  • Superb16 reviews4.9

Pack your day with exciting water adventures in the vibrant Cancun jungle. Begin with a thrilling sp....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $14.40
    (Saving 20% ) $18.00
 
 

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

(4.8 of 48 reviews)

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More

Free Cancellation
Private Tour
Start From $74.78
 
JFarwell Moonlight Yacht Cruise from Halifax Waterfront Likely to Sell Out

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

  • North America
  • Superb48 reviews4.8

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....

    Free Cancellation
    Private Tour
    Start From $74.78
 
 

Isla Mujeres Catamaran Tour with Snorkeling Spinnaker and Lunch

(4.8 of 48 reviews)

Discover the beauty of Isla Mujeres on this 7-hour catamaran adventure from Cancun. Sail the vibrant Caribbean waters while snorkeling in a stunning reef, then take to the skies with a thrilling spinnaker ride. Once you reach Isla... More

Special Offer
Free Cancellation
Private Tour
Start From $14.40
(Saving 20% ) $18.00
 
-20% Isla Mujeres Catamaran Tour with Snorkeling Spinnaker and Lunch Likely to Sell Out

Isla Mujeres Catamaran Tour with Snorkeling Spinnaker and Lunch

  • North America
  • Superb48 reviews4.8

Discover the beauty of Isla Mujeres on this 7-hour catamaran adventure from Cancun. Sail the vibrant....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $14.40
    (Saving 20% ) $18.00
 
 

Full Day Luxury Catamaran Charter

(4.8 of 48 reviews)

Spend a full day exploring Tampa Bay aboard a private luxury catamaran! Swim, snorkel, and paddle at hidden islands like Egmont Key and Fort De Soto. Enjoy onboard charcuterie, a champagne or wine toast, and full crew service for ... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Full Day Luxury Catamaran Charter Likely to Sell Out

Full Day Luxury Catamaran Charter

  • North America
  • Superb48 reviews4.8

Spend a full day exploring Tampa Bay aboard a private luxury catamaran! Swim, snorkel, and paddle at....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar

(4.9 of 383 reviews)

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous Arch, Land's end, and Sea Lion Colony before you head out of the bay.  Visit a secl... More

Free Cancellation
Private Tour
Start From $2,299.00
 
Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Likely to Sell Out

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Ba....

  • North America
  • Superb383 reviews4.9

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great ph....

    Free Cancellation
    Private Tour
    Start From $2,299.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 126 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More

Free Cancellation
Private Tour
Start From $250.00
 
Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • North America
  • Superb126 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....

    Free Cancellation
    Private Tour
    Start From $250.00
 
 

Fun Boat Rental with Captain in Miami Beach - up to 6 people

(4.9 of 53 reviews)

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straightforward bareboat charter. Now, let's talk logistics. The captain's compensation is a separate matter, settled directly at the ... More

Free Cancellation
Private Tour
Start From $260.00
 
Fun Boat Rental with Captain in Miami Beach - up to 6 people Likely to Sell Out

Fun Boat Rental with Captain in Miami Beach - up to 6 people

  • North America
  • Superb53 reviews4.9

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straig....

    Free Cancellation
    Private Tour
    Start From $260.00
 
 

America's Cup Evening Sailing Adventure Newport, RI

(4.9 of 28 reviews)

Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around Narragansett Bay passed many iconic sights including New York Yacht Club, Ida Lewis Light, Fort Adams, Eisenhower House, Hammersm... More

Free Cancellation
Private Tour
Start From $125.00
 
America's Cup Evening Sailing Adventure Newport, RI Likely to Sell Out

America's Cup Evening Sailing Adventure Newport, RI

  • North America
  • Superb28 reviews4.9

Get on board for the best hands-on sailing experience Newport, RI has to offer. A 2 hour sail around....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Key West Nighttime Full Moon Sail

(5 of 8 reviews)

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 an evening out with family and friends. Departing in the evening as the moo... More

Free Cancellation
Private Tour
Start From $83.85
 
Key West Nighttime Full Moon Sail Likely to Sell Out

Key West Nighttime Full Moon Sail

  • North America
  • Superb8 reviews5

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1....

    Free Cancellation
    Private Tour
    Start From $83.85
 
 

Cabo Blast Sunset Cruise: Iconic Views, Group Joy, Food and Drink

(5 of 8 reviews)

What Makes This Tour Unique? This isn’t just another sunset cruise—it’s the Cabo experience travelers dream about. You’ll sail right up to the legendary Arch, capturing postcard‑perfect photos as the colors of the sky s... More

Free Cancellation
Private Tour
Start From $99.00
 
Cabo Blast Sunset Cruise: Iconic Views, Group Joy, Food and Drink Likely to Sell Out

Cabo Blast Sunset Cruise: Iconic Views, Group Joy, Food and Drink

  • North America
  • Superb8 reviews5

What Makes This Tour Unique? This isn’t just another sunset cruise—it’s the Cabo experience t....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Harbor Sail Aboard the Tall Ship Denis Sullivan

(5 of 8 reviews)

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this pub... More

Free Cancellation
Private Tour
Start From $55.00
 
Harbor Sail Aboard the Tall Ship Denis Sullivan Likely to Sell Out

Harbor Sail Aboard the Tall Ship Denis Sullivan

  • North America
  • Superb8 reviews5

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique oppor....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.7 of 60 reviews)

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 Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Private Tour
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • North America
  • Superb60 reviews4.7

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Golden Hour Escape: Private Sunset Sail in Coastal Maine

(5 of 20 reviews)

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 to endure. Set sail along Maine's exquisite coastline aboar... More

Free Cancellation
Private Tour
Start From $849.00
 
Golden Hour Escape: Private Sunset Sail in Coastal Maine Likely to Sell Out

Golden Hour Escape: Private Sunset Sail in Coastal Maine

  • North America
  • Superb20 reviews5

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the settin....

    Free Cancellation
    Private Tour
    Start From $849.00
 
 

Key West Sail and Snorkel Day Trip from Fort Lauderdale

(3.1 of 16 reviews)

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from Fort Lauderdale promises thrilling experiences and breathtaking sights both above and ... More

Free Cancellation
Private Tour
Start From $149.00
 
Key West Sail and Snorkel Day Trip from Fort Lauderdale Likely to Sell Out

Key West Sail and Snorkel Day Trip from Fort Lauderdale

  • North America
  • Good16 reviews3.1

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it....

    Free Cancellation
    Private Tour
    Start From $149.00
 
Booking.com
Booking.com
Booking.com