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: Toronto Tall Ship Boat Cruise Day Sails and Sunset tours on Schooner Surprise in Camden Maine Fort Lauderdale Sailing Charter Cabo San Lucas Sunset Sailing Shared Cruise Sunset Sail Cruise in Key West

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 →

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

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

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

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

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 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

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 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 Dolphin Sightseeing Sail on the Lazy Daze Catamaran

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of …More

Panama City Beach, USA

Private Dolphin Sightseeing Sail on the Lazy Daze Catamaran

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of...

1 hour 30 minutes Free Cancellation

from
$857

Private Sunset Sailing Cruise with Drinks in Puerto Vallarta

On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains …More

Puerto Vallarta, Mexico

5.0 (27)

Private Sunset Sailing Cruise with Drinks in Puerto Vallarta

On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains...

3 hours 30 minutes

5.0 (27)

from
$853

Cozumel Private Snorkeling and Charter Experience

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting …More

Cozumel, Mexico

5.0 (25)

Cozumel Private Snorkeling and Charter Experience

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting...

5 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$850

Golden Hour Escape: Private Sunset Sail in Coastal Maine

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 …More

Kennebunkport, USA

5.0 (23)

Golden Hour Escape: Private Sunset Sail in Coastal Maine

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...

2 hours Free Cancellation

5.0 (23)

from
$849

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or …More

Halifax, Canada

5.0 (19)

JFarwell Sip & Sail aboard the Reverie

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or...

1 hour 30 minutes Free Cancellation

5.0 (19)

from
$844

Cabo Private Catamaran: Arch, Sea Lions and Beach for Up to 12

Our boat excursions in Cabo San Lucas are the perfect way to explore the wonders of the Sea of Cortez. Our well-trained bilingual crew will …More

Cabo San Lucas, Mexico

5.0 (17)

Cabo Private Catamaran: Arch, Sea Lions and Beach for Up to 12

Our boat excursions in Cabo San Lucas are the perfect way to explore the wonders of the Sea of Cortez. Our well-trained bilingual crew will...

3 hours 30 minutes Free Cancellation

5.0 (17)

from
$840

San Diego Private Yacht Charter on a Classic Sailboat

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is …More

San Diego, USA

5.0 (4)

San Diego Private Yacht Charter on a Classic Sailboat

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is...

2 hours 30 minutes Free Cancellation

5.0 (4)

from
$810

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

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore los arcos area while savoring fresh guacamole and a …More

Puerto Vallarta, Mexico

5.0 (104)

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

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore los arcos area while savoring fresh guacamole and a...

4 hours

5.0 (104)

from
$803