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 →

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable …More

Cabo San Lucas, Mexico

5.0 (172)

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable...

3 hours Free Cancellation

5.0 (172)

from
$870

Private Luxury 42ft Sailing with Snorkeling in Los Cabos

Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful …More

Cabo San Lucas, Mexico

5.0 (129)

Private Luxury 42ft Sailing with Snorkeling in Los Cabos

Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful...

3 hours Free Cancellation

5.0 (129)

from
$872

Private Yacht 32 FT 8 PAX with Food and Bar Los Cabos

Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalized experience sailing in front of the iconic Arch, …More

Cabo San Lucas, Mexico

5.0 (1)

Private Yacht 32 FT 8 PAX with Food and Bar Los Cabos

Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalized experience sailing in front of the iconic Arch,...

3 hours Free Cancellation

5.0 (1)

from
$880

Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami

Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +1250 reviews on Google with a …More

Miami, USA

5.0 (19)

Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami

Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +1250 reviews on Google with a...

3 hours Free Cancellation

5.0 (19)

from
$899

Enjoy a day cruising with friends and family on the open water, explore local scenery, and experience the beautiful Cancun weather! Charter this amazing luxury …More

Cancun, Mexico

5.0 (1)

Sea Daddy Private Yacht - 50 ft

Enjoy a day cruising with friends and family on the open water, explore local scenery, and experience the beautiful Cancun weather! Charter this amazing luxury...

2 hours Free Cancellation

5.0 (1)

from
$899

Private Catamaran Charter in Waikiki (1-6 Guests)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on …More

Oahu, USA

5.0 (25)

Private Catamaran Charter in Waikiki (1-6 Guests)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on...

2 hours Free Cancellation

5.0 (25)

from
$900

Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which …More

Oahu, USA

5.0 (11)

Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which...

2 hours Free Cancellation

5.0 (11)

from
$900

Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with us you will know the …More

Puerto Vallarta, Mexico

5.0 (2)

Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with us you will know the...

6 hours

5.0 (2)

from
$935

Key West Private Charter: Sandbar and Snorkeling

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a …More

Key West, USA

5.0 (20)

Key West Private Charter: Sandbar and Snorkeling

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a...

4 hours

5.0 (20)

from
$950

Private Charleston Harbor Catamaran Sail

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a …More

Mount Pleasant, USA

5.0 (30)

Private Charleston Harbor Catamaran Sail

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a...

2 hours 30 minutes Free Cancellation

5.0 (30)

from
$950

Private Luxury Catamaran Moonlight Party in Halifax

The ultimate private sailing experience! The Reverie is the newest boat in our fleet. The Reverie is the perfect balance of luxury and space to …More

Halifax, Canada

5.0 (1)

Private Luxury Catamaran Moonlight Party in Halifax

The ultimate private sailing experience! The Reverie is the newest boat in our fleet. The Reverie is the perfect balance of luxury and space to...

2 hours Free Cancellation

5.0 (1)

from
$942

Full-Day Private Sailing & Los Arcos Snorkeling, Puerto Vallarta

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim …More

Puerto Vallarta, Mexico

4.9 (108)

Full-Day Private Sailing & Los Arcos Snorkeling, Puerto Vallarta

Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim...

6 hours

4.9 (108)

from
$963

Private Swim, Snorkel & Sail on the Daydreams Sailboat

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area …More

Panama City Beach, USA

5.0 (33)

Private Swim, Snorkel & Sail on the Daydreams Sailboat

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

3 hours Free Cancellation

5.0 (33)

from
$963

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline, …More

Monterey & Carmel, USA

5.0 (1)

Private Sailing Trip on Monterey Bay

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline,...

2 hours Free Cancellation

5.0 (1)

from
$965

Private Sunset Sail on San Diego Bay with Champagne

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully …More

San Diego, USA

5.0 (1)

Private Sunset Sail on San Diego Bay with Champagne

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$975

San Diego's first ever Family Sailing Tours

We are based in San Diego and we are designed for families. Our whole mission is to bring families closer together. We want to put …More

La Jolla, USA

5.0 (6)

San Diego's first ever Family Sailing Tours

We are based in San Diego and we are designed for families. Our whole mission is to bring families closer together. We want to put...

2 hours 30 minutes Free Cancellation

5.0 (6)

from
$975

Private Family Catamaran From Isla Mujeres

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? …More

Isla Mujeres, Mexico

5.0 (1)

Private Family Catamaran From Isla Mujeres

Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time?...

3 hours Free Cancellation

5.0 (1)

from
$985

Our starting point is Carmelita Lagoon Club, a privileged space on the shores of Bacalar Lagoon, with incredible views and an ideal atmosphere to begin …More

Bacalar, Mexico

5.0 (175)

Private Catamaran Tour

Our starting point is Carmelita Lagoon Club, a privileged space on the shores of Bacalar Lagoon, with incredible views and an ideal atmosphere to begin...

4 hours Free Cancellation

5.0 (175)

from
$990

Premium Isla Mujeres Tour by Private Catamaran

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, …More

Cancun, Mexico

5.0 (251)

Premium Isla Mujeres Tour by Private Catamaran

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired,...

5 hours Free Cancellation

5.0 (251)

from
$990

Private Sailboat Charter on San Francisco Bay

Fall and winter typically provide lighter breezes on SF Bay. Great days on the Bay. 3 hour PRIVATE Charter with a unique experience aboard Carmelita, …More

5.0 (9)

Private Sailboat Charter on San Francisco Bay

Fall and winter typically provide lighter breezes on SF Bay. Great days on the Bay. 3 hour PRIVATE Charter with a unique experience aboard Carmelita,...

3 hours Free Cancellation

5.0 (9)

from
$995