Top North America Sailing Trips

Q: What are the best options for North America Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best North America Sailing Trips are: San Diego Sailing Cruise Small Group 6 Guests Classic Yacht Whale-Watching Pirate Ship Cruise in Los Cabos El Cielo Snorkel by Private Boat El Cielo Cozumel snorkel by Private Boat JFarwell Adventure Yacht Sailing in the Halifax Harbour

Q: What are the best kid-friendly options for North America Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly North America Sailing Trips are: 3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya 4th of July Fireworks on Clipper City Tall Ship #1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson The Nāpali Coast Snorkel Excursion Pirate Ship by Day View all kid-friendly Tours →

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Private Luxury Yacht Charter aboard Tu Enamorado Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp Luxury Yacht 58 ft for up to 20 people 4 hrs Private Cruise Swim with Dolphin Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs View all Tours with Instant Confirmation →

Q: I need a ride! Which North America Sailing Trips have Hotel Pickup?

No problem. These North America Sailing Trips include Hotel Pickup: Private Cruise Swim with Dolphin Private Romantic Sailing Sunset Experience Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Private Luxury Sunset Sail in San Jose del Cabo Marina Private Luxury Yacht Charter with Snorkeling in Los Cabos View all Tours with Hotel Pickup →

Q: Got any more North America trip ideas?

We sure do. Check out our curated lists of hand-picked North America Tours. Top 10 North America 2026 Senior-friendly tours North America The best tours and activities for culture lovers in North America Top Day Trips from North America Things to do in North America this summer View all North America Trip Ideas →

Q: What are the most popular styles of Tours and Activities in North America?

Based on our sales data over the past year, the most popular styles of tours and activities in North America are: North America Luxury & Special Occasions North America Luxury Tours North America Tours & Sightseeing North America Kid Friendly North America Cruises, Sailing & Water Tours View all tour styles in North America →

St. Margarets Bay Sailing and Island Anchoring Adventure

Set sail on a 3-hour journey through the stunning St. Margarets Bay, blending sailing excitement with the beauty of Nova Scotia’s coastline. Departing from Shining …More

5.0 (4)

St. Margarets Bay Sailing and Island Anchoring Adventure

Set sail on a 3-hour journey through the stunning St. Margarets Bay, blending sailing excitement with the beauty of Nova Scotia’s coastline. Departing from Shining...

3 hours Free Cancellation

5.0 (4)

from
$162

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in …More

5.0 (22)

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in...

2 hours Free Cancellation

5.0 (22)

from
$160

From Sailboatcancun we offer sailing courses aboard a 75 feet sailboat with an experience of more than 25 thousand miles sailed by different oceans. The …More

Isla Mujeres, Mexico

5.0 (1)

Sailing Clases in Isla Mujeres

From Sailboatcancun we offer sailing courses aboard a 75 feet sailboat with an experience of more than 25 thousand miles sailed by different oceans. The...

4 hours Free Cancellation

5.0 (1)

from
$160

Mexico City: Xochimilco at sunrise + Breakfast and transportation

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for …More

Mexico City, Mexico

5.0 (130)

Mexico City: Xochimilco at sunrise + Breakfast and transportation

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for...

5 hours Hotel pickup offered Free Cancellation

5.0 (130)

from
$160

Waikoloa Signature Catamaran Sunset Sail

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers …More

Big Island of Hawaii, USA

4.8 (419)

Waikoloa Signature Catamaran Sunset Sail

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers...

90 to 120 minutes Free Cancellation

4.8 (419)

from
$159

Whale Shark Experience Lifetime Memory in Cancun (snack included)

Join one of the most wonderful wildlife experiences in Cancun during the whale shark season! Explore the Caribbean Sea aboard a small-group boat for a …More

Cancun, Mexico

4.2 (15)

Whale Shark Experience Lifetime Memory in Cancun (snack included)

Join one of the most wonderful wildlife experiences in Cancun during the whale shark season! Explore the Caribbean Sea aboard a small-group boat for a...

8 hours Free Cancellation

4.2 (15)

from
$159

Enjoy a high-speed Jet Ski adventure in Cancun using powerful Sea-Doo watercraft. Ride with a certified guide who leads you through the mangroves of Nichupte …More

Cancun, Mexico

5.0 (1)

Cancun Mangrove Jet Ski Tour

Enjoy a high-speed Jet Ski adventure in Cancun using powerful Sea-Doo watercraft. Ride with a certified guide who leads you through the mangroves of Nichupte...

1 hour Free Cancellation

5.0 (1)

from
$159

Whale Shark Encounter Experience from Cancun

Experience an unforgettable encounter with the world's largest fish in the crystal-clear waters of the Mexican Caribbean! Enjoy a small-group experience with a maximum of …More

Cancun, Mexico

4.3 (4)

Whale Shark Encounter Experience from Cancun

Experience an unforgettable encounter with the world's largest fish in the crystal-clear waters of the Mexican Caribbean! Enjoy a small-group experience with a maximum of...

8 hours Free Cancellation

4.3 (4)

from
$159

Private Half Day Sailing Charter in Portland Maine

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, …More

Portland, USA

5.0 (1)

Private Half Day Sailing Charter in Portland Maine

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa,...

4 hours Free Cancellation

5.0 (1)

from
$158

Xoximilco Flaoting Fiesta in Canals of Cancun

Celebrate Mexican culture like never before at Xoximilco by Xcaret—a one-of-a-kind floating fiesta through the canals of Cancun! Step aboard a colorful trajinera (traditional gondola-style …More

Cancun, Mexico

5.0 (8)

Xoximilco Flaoting Fiesta in Canals of Cancun

Celebrate Mexican culture like never before at Xoximilco by Xcaret—a one-of-a-kind floating fiesta through the canals of Cancun! Step aboard a colorful trajinera (traditional gondola-style...

4 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$155

Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of …More

Big Island of Hawaii, USA

4.9 (856)

Sunset and Manta Ray Snorkel Adventure

Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of...

2 hours 15 minutes Free Cancellation

4.9 (856)

from
$155

Spectacular Sunset Sail on San Diego Bay

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas …More

La Jolla, USA

5.0 (41)

Spectacular Sunset Sail on San Diego Bay

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas...

2 hours Free Cancellation

5.0 (41)

from
$150

Experience Oceanside Sailing with Whales and dolphins!

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the …More

Carlsbad, USA

5.0 (18)

Experience Oceanside Sailing with Whales and dolphins!

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the...

2 hours Free Cancellation

5.0 (18)

from
$150

Miami Private Boat Tour- Millionaire’s Row and Celebration Cruise

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google. …More

Miami, USA

4.9 (259)

Miami Private Boat Tour- Millionaire’s Row and Celebration Cruise

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google....

4 hours Free Cancellation

4.9 (259)

from
$150

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

5.0 (24)

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...

2 hours Free Cancellation

5.0 (24)

from
$150

Luxury Sunset Sail on Serendipity Catamaran in Charleston

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local …More

Charleston, USA

5.0 (26)

Luxury Sunset Sail on Serendipity Catamaran in Charleston

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local...

2 hours Free Cancellation

5.0 (26)

from
$150

To cross the calm waters of the Caribbean, there is no better means of transportation than a catamaran. These specialized sailboats have multiple hulls so …More

Cancun, Mexico

5.0 (1)

Luxury Sailboat at Sunset in Cancun

To cross the calm waters of the Caribbean, there is no better means of transportation than a catamaran. These specialized sailboats have multiple hulls so...

2 hours 30 minutes Hotel pickup offered

5.0 (1)

from
$150

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

5.0 (21)

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...

2 hours Free Cancellation

5.0 (21)

from
$150