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: Waikiki small group turtle snorkeling & sailing Shared Snorkeling Tour Playa El Cielo in Cozumel Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt Private Sailing Charter in Savannah GA New York City Sailboat Day Cruise to the Statue of Liberty

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 →

LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and …More

Long Beach, USA

4.6 (8)

LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and...

1 hour

4.6 (8)

from
$255

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA

5.0 (128)

Polynesian Canoe Sunset Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours Free Cancellation

5.0 (128)

from
$250

Private Guided Sunset and Eco Tour up to 6 Passengers

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset …More

Destin, USA

5.0 (81)

Private Guided Sunset and Eco Tour up to 6 Passengers

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset...

1 hour 30 minutes Free Cancellation

5.0 (81)

from
$250

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, …More

Oahu, USA

4.8 (37)

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May,...

2 hours Free Cancellation

4.8 (37)

from
$250

Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step …More

Maui, USA

4.8 (63)

Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes Free Cancellation

4.8 (63)

from
$249

2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel …More

5.0 (17)

2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel...

2 hours Free Cancellation

5.0 (17)

from
$245

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based …More

Maui, USA

5.0 (95)

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based...

5 hours Free Cancellation

5.0 (95)

from
$243

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

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a …More

Bacalar, Mexico

5.0 (432)

Private sailing tour of Bacalar Lagoon

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a...

3 hours Free Cancellation

5.0 (432)

from
$240

Los Cabos Seasonal Whale Watch and Snorkel Tour

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the …More

San Jose del Cabo, Mexico

4.9 (19)

Los Cabos Seasonal Whale Watch and Snorkel Tour

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the...

4 hours Hotel pickup offered Free Cancellation

4.9 (19)

from
$239

If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the dates of December 15th thru April …More

Cabo San Lucas, Mexico

4.9 (12)

Platinum Private Catamaran Sailing Tour

If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the dates of December 15th thru April...

2 hours Hotel pickup offered Free Cancellation

4.9 (12)

from
$237

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff …More

Bacalar, Mexico

5.0 (78)

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff...

4 hours Free Cancellation

5.0 (78)

from
$237

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

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

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look …More

Kauai, USA

4.8 (1,559)

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look...

5 hours Free Cancellation

4.8 (1,559)

from
$223

Private Sailboat + Captain for a Day Experience

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY Cool Shore Excursions TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride …More

Bacalar, Mexico

5.0 (304)

Private Sailboat + Captain for a Day Experience

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY Cool Shore Excursions TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride...

3 hours Free Cancellation

5.0 (304)

from
$222

Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, …More

Maui, USA

4.9 (220)

Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hours Free Cancellation

4.9 (220)

from
$221

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

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and …More

Maui, USA

5.0 (40)

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and...

5 hours Free Cancellation

5.0 (40)

from
$214

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in …More

Maui, USA

4.8 (836)

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in...

5 hours Free Cancellation

4.8 (836)

from
$213