Top North America Sailing Trips

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Speedboat and Snorkeling Adventure in Cancun Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun Paddle at Dawn with visit to Cenotes and Islands Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor Sunrise by Paddle or Kayak with Floating Picnic View all Tours with Instant Confirmation →

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 →

Half-Day Luxury Sailing Experience in Tulum with Open Bar

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so …More

Tulum, Mexico

4.5 (225)

Half-Day Luxury Sailing Experience in Tulum with Open Bar

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so...

4 hours Hotel pickup offered Free Cancellation

4.5 (225)

from
$149

Key West Sail and Snorkel Day Trip from Fort Lauderdale

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 …More

Fort Lauderdale, USA

3.4 (14)

Key West Sail and Snorkel Day Trip from Fort Lauderdale

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...

15 hours Free Cancellation

3.4 (14)

from
$149

2hr. SUNSET Sailing Experience on San Francisco Bay

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get …More

Sausalito, USA

4.9 (35)

2hr. SUNSET Sailing Experience on San Francisco Bay

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get...

2 hours Free Cancellation

4.9 (35)

from
$149

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at …More

Cabo San Lucas, Mexico

4.9 (60)

Luxury Snorkel Adventure in Cabo

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (60)

from
$149

Private Luxury Adventure Tours in Cabo San Lucas

Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy this amazing adventure for 2 …More

Cabo San Lucas, Mexico

4.9 (16)

Private Luxury Adventure Tours in Cabo San Lucas

Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy this amazing adventure for 2...

2 hours Hotel pickup offered Free Cancellation

4.9 (16)

from
$149

Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the …More

Fort Myers, USA

5.0 (12)

Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the...

2 hours 30 minutes Free Cancellation

5.0 (12)

from
$149

Riviera Maya Half-Day Sailing Experience with Lunch and Open Bar

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so …More

Playa del Carmen, Mexico

4.7 (69)

Riviera Maya Half-Day Sailing Experience with Lunch and Open Bar

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so...

4 hours Hotel pickup offered Free Cancellation

4.7 (69)

from
$149

Whale Watching Sailboat Tour in San Jose del Cabo

Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cruise past the iconic landmarks of San …More

San Jose del Cabo, Mexico

5.0 (3)

Whale Watching Sailboat Tour in San Jose del Cabo

Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cruise past the iconic landmarks of San...

2 hours Free Cancellation

5.0 (3)

from
$149

Snorkel Adventure through the Sea of Cortez

Sail through the Sea of Cortez, a blue and shimmering spectacle around Cabo San Lucas. You will ride a luxurious and comfortable catamaran along the …More

Cabo San Lucas, Mexico

5.0 (8)

Snorkel Adventure through the Sea of Cortez

Sail through the Sea of Cortez, a blue and shimmering spectacle around Cabo San Lucas. You will ride a luxurious and comfortable catamaran along the...

4 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$149

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value. …More

Cabo San Lucas, Mexico

4.5 (6)

Sailing Snorkel Adventure

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value....

4 hours Free Cancellation

4.5 (6)

from
$149

Half-Day Luxury Sailing in Puerto Morelos with Open Bar

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforgettable half-day adventure. This experience offers a guided snorkeling …More

Tulum, Mexico

4.8 (4)

Half-Day Luxury Sailing in Puerto Morelos with Open Bar

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforgettable half-day adventure. This experience offers a guided snorkeling...

5 hours Hotel pickup offered Free Cancellation

4.8 (4)

from
$149

Isla Mujeres Sailing Adventure from Riviera Maya

Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel. Surrounded by all the scale of blue colors, you'll relax and chill, …More

Playa del Carmen, Mexico

4.2 (9)

Isla Mujeres Sailing Adventure from Riviera Maya

Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel. Surrounded by all the scale of blue colors, you'll relax and chill,...

7 hours Hotel pickup offered

4.2 (9)

from
$149

Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. Glide along the Saco River and take in the picturesque …More

Kennebunkport, USA

5.0 (2)

Relaxing Saco River Public Sunset Sail

Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. Glide along the Saco River and take in the picturesque...

2 hours Free Cancellation

5.0 (2)

from
$149

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

Isla Mujeres Sailing Adventure from Cancun

Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard of an exclusive catamaran...!! This tour is recommended for …More

Cancun, Mexico

4.0 (4)

Isla Mujeres Sailing Adventure from Cancun

Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard of an exclusive catamaran...!! This tour is recommended for...

7 hours Hotel pickup offered

4.0 (4)

from
$149

Key West: Sunset Sail + Reef Snorkel & Sandbar

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • …More

Key West, USA

5.0 (56)

Key West: Sunset Sail + Reef Snorkel & Sandbar

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? •...

4 hours 30 minutes Free Cancellation

5.0 (56)

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

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