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 Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and …More

Panama City Beach, USA

5.0 (3)

Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and...

2 hours Free Cancellation

5.0 (3)

from
$749

Discover the wonders of Capeh Chen Lagoon In Sian Ka’an. Glide through calm waters and see gentle manatees. Spot crocodiles resting along the banks. Watch …More

Tulum, Mexico

5.0 (3)

Breathtaking Sunset at Sian Ka'an

Discover the wonders of Capeh Chen Lagoon In Sian Ka’an. Glide through calm waters and see gentle manatees. Spot crocodiles resting along the banks. Watch...

6 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$214

Old Plank Adventures: Sail into Deep Tranquility

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica …More

Santa Monica, USA

5.0 (3)

Old Plank Adventures: Sail into Deep Tranquility

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica...

2 hours Free Cancellation

5.0 (3)

from
$400

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought …More

Cabo San Lucas, Mexico

5.0 (3)

Sunset Cruise Tequila Tasting

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought...

2 hours Free Cancellation

5.0 (3)

from
$115

Private Sailing Experience along the Southern Maine Coastline

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you …More

Kennebunkport, USA

5.0 (3)

Private Sailing Experience along the Southern Maine Coastline

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you...

2 to 6 hours Free Cancellation

5.0 (3)

from
$747

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area …More

Panama City Beach, USA

5.0 (3)

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

3 hours Free Cancellation

5.0 (3)

from
$124

Baltimore Harbor Moonlight Sail on the Summer Wind

Find your own slice of paradise on this 1.5-hour moonlight sail around Baltimore Harbor. Listen to music inspired by the Caribbean as you enjoy the …More

Baltimore, USA

5.0 (3)

Baltimore Harbor Moonlight Sail on the Summer Wind

Find your own slice of paradise on this 1.5-hour moonlight sail around Baltimore Harbor. Listen to music inspired by the Caribbean as you enjoy the...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$75

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet. …More

Oahu, USA

5.0 (3)

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet....

1 hour Free Cancellation

5.0 (3)

from
$60

Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from …More

Oahu, USA

5.0 (3)

Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$69

Glass Bottom Boat Morning Coffee Cruise in Waikiki

Wake up to the serene beauty of Waikiki on the Morning Coffee Cruise, where you can savor locally roasted Ali’i Coffee Co. and fresh pastries …More

Oahu, USA

5.0 (3)

Glass Bottom Boat Morning Coffee Cruise in Waikiki

Wake up to the serene beauty of Waikiki on the Morning Coffee Cruise, where you can savor locally roasted Ali’i Coffee Co. and fresh pastries...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$69

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting …More

Key Largo, USA

5.0 (2)

SUNSET CRUISE in Key Largo,FL.

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$389

Private Daytime Picnic Boat Cruise (Up to 6 Passengers)

Set sail on Lake Champlain for a one-of-a-kind adventure where the route is guided entirely by the wind—ensuring no two cruises are ever the same. …More

Burlington, USA

5.0 (2)

Private Daytime Picnic Boat Cruise (Up to 6 Passengers)

Set sail on Lake Champlain for a one-of-a-kind adventure where the route is guided entirely by the wind—ensuring no two cruises are ever the same....

2 hours

5.0 (2)

from
$550

Private Sunset Catamaran Sail in Cocoa Beach

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of …More

Cocoa Beach, USA

5.0 (2)

Private Sunset Catamaran Sail in Cocoa Beach

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of...

2 hours Free Cancellation

5.0 (2)

from
$338

Private Sailing Charter: Up to 24 Passengers

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco …More

San Francisco, USA

5.0 (2)

Private Sailing Charter: Up to 24 Passengers

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco...

1 hour 30 minutes

5.0 (2)

from
$1,425

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Oahu, USA

5.0 (2)

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hours Free Cancellation

5.0 (2)

from
$1,595

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 …More

Oahu, USA

5.0 (2)

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6...

2 hours Free Cancellation

5.0 (2)

from
$1,200

Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything …More

Fort Myers, USA

5.0 (2)

Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything...

3 hours Free Cancellation

5.0 (2)

from
$599

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

Welcome to an incredible adventure, if what you like is getting to know new places and being in contact with nature, then this activity is …More

Punta Sam, Mexico

5.0 (2)

Guided Tour of Puerto Morelos Reefs with Snorkeling Experience

Welcome to an incredible adventure, if what you like is getting to know new places and being in contact with nature, then this activity is...

5 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$44

Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink …More

Portland, USA

5.0 (2)

Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink...

3 hours Free Cancellation

5.0 (2)

from
$185

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in …More

Mount Pleasant, USA

5.0 (2)

Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in...

2 hours Free Cancellation

5.0 (2)

from
$38