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 →

Private Charter Day Sail For up to 6 People

Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to …More

Salem, USA

5.0 (7)

Private Charter Day Sail For up to 6 People

Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to...

1 hour 30 minutes Free Cancellation

5.0 (7)

from
$225

Private Atomic Catamaran Tour to Isla Mujeres

By booking this private service, you can design a completely tailored itinerary. You will have the freedom to navigate to the places of your choice …More

Cancun, Mexico

4.9 (7)

Private Atomic Catamaran Tour to Isla Mujeres

By booking this private service, you can design a completely tailored itinerary. You will have the freedom to navigate to the places of your choice...

7 hours Free Cancellation

4.9 (7)

from
$2,100

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing in the kayak in calm waters, we have contact with …More

Huatulco, Mexico

5.0 (7)

kayaking in Huatulco

The geographical position favors us to observe whales, dolphins, turtles and much more while sailing in the kayak in calm waters, we have contact with...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (7)

from
$72

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of …More

Panama City Beach, USA

5.0 (6)

Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of...

1 hour 30 minutes Free Cancellation

5.0 (6)

from
$38

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

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, …More

5.0 (6)

Chesapeake Bay Private Cruise

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water,...

2 hours 30 minutes Free Cancellation

5.0 (6)

from
$736

3.5 hour Sailing Adventure in Nanoose Bay

Immerse yourself in the beauty of the Salish Sea. Listen to seabirds as you take in breathtaking mountain vistas and island shorelines. Sea Lions are …More

Vancouver Island, Canada

5.0 (6)

3.5 hour Sailing Adventure in Nanoose Bay

Immerse yourself in the beauty of the Salish Sea. Listen to seabirds as you take in breathtaking mountain vistas and island shorelines. Sea Lions are...

3 hours 30 minutes Free Cancellation

5.0 (6)

from
$146

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, …More

Big Island of Hawaii, USA

5.0 (6)

Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests,...

3 hours Free Cancellation

5.0 (6)

from
$276

Sunset Sail Experience by Catamaran in Waikiki

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu …More

Oahu, USA

4.8 (6)

Sunset Sail Experience by Catamaran in Waikiki

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu...

2 hours Free Cancellation

4.8 (6)

from
$92

Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this half-day tour on a beautiful and comfortable sailboat while you …More

Puerto Vallarta, Mexico

5.0 (6)

Private Whale Watching Sailing Tour

Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this half-day tour on a beautiful and comfortable sailboat while you...

4 hours

5.0 (6)

from
$770

4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres

This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we take care of customer during the all …More

Cancun, Mexico

5.0 (6)

4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres

This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we take care of customer during the all...

4 hours Free Cancellation

5.0 (6)

from
$1,700

Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy …More

Key West, USA

5.0 (5)

Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy...

1 hour 45 minutes Free Cancellation

5.0 (5)

from
$89

Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our …More

Key West, USA

5.0 (5)

Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$98

Private - Bacalar sailing across the mesmerizing waters

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon …More

Tulum, Mexico

5.0 (5)

Private - Bacalar sailing across the mesmerizing waters

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon...

12 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$274

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights …More

Oahu, USA

5.0 (5)

BYOB Friday Night Fireworks Cruise

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights...

2 hours 30 minutes Free Cancellation

5.0 (5)

from
$139

Private Yacht in Tulum with Snacks and Open Bar

What truly sets this tour apart is the level of privacy and customization we offer. Whether you're celebrating a special occasion or simply seeking a …More

Playa del Carmen, Mexico

5.0 (5)

Private Yacht in Tulum with Snacks and Open Bar

What truly sets this tour apart is the level of privacy and customization we offer. Whether you're celebrating a special occasion or simply seeking a...

4 hours Free Cancellation

5.0 (5)

from
$1,400

Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of …More

Baltimore, USA

5.0 (5)

Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$75

Private Classic Sailboat Tour in New York City

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll …More

New York City, USA

5.0 (4)

Private Classic Sailboat Tour in New York City

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll...

2 hours Free Cancellation

5.0 (4)

from
$700

Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where the winds are perfect for an afternoon adventure. Guests can …More

Newport, USA

5.0 (4)

Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where the winds are perfect for an afternoon adventure. Guests can...

1 hour 40 minutes Free Cancellation

5.0 (4)

from
$55