Top North America Sailing Trips

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 →

Wednesday Happy Hour Sunset Sail - Drinks Included

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha …More

Mount Pleasant, USA

5.0 (10)

Wednesday Happy Hour Sunset Sail - Drinks Included

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha...

2 hours Free Cancellation

5.0 (10)

from
$76

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 …More

Key West, USA

5.0 (10)

Key West Nighttime Full Moon Sail

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...

1 hour 30 minutes Free Cancellation

5.0 (10)

from
$89

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with …More

Key West, USA

5.0 (10)

Champagne Dolphin Sail and Reef Snorkel

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with...

3 hours

5.0 (10)

from
$109

Private Sail Around New York City and The Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are …More

Jersey City, USA

5.0 (10)

Private Sail Around New York City and The Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are...

2 hours Free Cancellation

5.0 (10)

from
$650

Puerto Vallarta Private Yacht Adventure 5 hours + 1 hour Free

Sail on a private trip on board our private yacht 50 feet, ideal for up to 18 passengers. We are sure that with us you …More

Puerto Vallarta, Mexico

5.0 (10)

Puerto Vallarta Private Yacht Adventure 5 hours + 1 hour Free

Sail on a private trip on board our private yacht 50 feet, ideal for up to 18 passengers. We are sure that with us you...

6 hours

5.0 (10)

from
$1,452

Discover Hobie-Cat Sailing and Fish your own Lunch

Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freedom that only the ocean …More

Puerto Vallarta, Mexico

5.0 (10)

Discover Hobie-Cat Sailing and Fish your own Lunch

Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freedom that only the ocean...

2 hours 30 minutes Free Cancellation

5.0 (10)

from
$225

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend …More

Port Angeles, USA

5.0 (9)

Sailing Charter

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend...

1 to 3 hours Free Cancellation

5.0 (9)

from
$240

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adventure waiting for you! Departing from Brooklyn …More

Brooklyn, USA

5.0 (9)

Private Sailing Charter in Brooklyn

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adventure waiting for you! Departing from Brooklyn...

2 hours Free Cancellation

5.0 (9)

from
$630

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

Two Hour Scenic Sail on the Liberty Clipper

A voyage aboard the 125' Schooner Liberty Clipper offers a unique opportunity to connect with maritime history while exploring the stunning views of Long Island …More

Long Island, USA

5.0 (9)

Two Hour Scenic Sail on the Liberty Clipper

A voyage aboard the 125' Schooner Liberty Clipper offers a unique opportunity to connect with maritime history while exploring the stunning views of Long Island...

2 hours Free Cancellation

5.0 (9)

from
$69

Beyond Bacalar: Pirate Route Exploration + River Float + Lunch

The Hidden Gem Tour! Explore Bacalar’s secret lagoons and the historic Pirate Route, float gently in peaceful currents, spot wildlife, and enjoy fresh snacks and …More

Bacalar, Mexico

4.9 (9)

Beyond Bacalar: Pirate Route Exploration + River Float + Lunch

The Hidden Gem Tour! Explore Bacalar’s secret lagoons and the historic Pirate Route, float gently in peaceful currents, spot wildlife, and enjoy fresh snacks and...

5 hours Free Cancellation

4.9 (9)

from
$84

Private Isla Mujeres Adventure & Free Time

If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres, the women’s Island. Your day starts with …More

Playa del Carmen, Mexico

4.9 (9)

Private Isla Mujeres Adventure & Free Time

If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres, the women’s Island. Your day starts with...

6 hours Hotel pickup offered Free Cancellation

4.9 (9)

from
$120

San Diego Sailing Sunset and Afternoon Classic Yacht

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

La Jolla, USA

5.0 (9)

San Diego Sailing Sunset and Afternoon Classic Yacht

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation

5.0 (9)

from
$125

Introduction to Sailing in Saint John, NB

Set sail on the tranquil waters of the Saint John River aboard our O'Day 34 sailing yacht, for a 2.5 to 3-hour introduction to boating …More

Saint John, Canada

5.0 (9)

Introduction to Sailing in Saint John, NB

Set sail on the tranquil waters of the Saint John River aboard our O'Day 34 sailing yacht, for a 2.5 to 3-hour introduction to boating...

2 hours 30 minutes Free Cancellation

5.0 (9)

from
$73

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

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

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to …More

St Augustine, USA

4.8 (8)

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to...

2 hours Free Cancellation

4.8 (8)

from
$199

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a capacity of up to …More

Cabo San Lucas, Mexico

5.0 (8)

Luxury Private Yacht Charter in Cabo San Lucas Mexico

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a capacity of up to...

2 hours Free Cancellation

5.0 (8)

from
$400

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding, …More

Savannah, USA

5.0 (7)

Private Sailing Charter in Savannah GA

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding,...

2 hours Free Cancellation

5.0 (7)

from
$650

Public Sunset Picnic Boat Cruise on Lake Champlain

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food …More

Burlington, USA

5.0 (7)

Public Sunset Picnic Boat Cruise on Lake Champlain

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food...

2 hours Free Cancellation

5.0 (7)

from
$95