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 →

San Diego Sailing Cruise Small Group 6 Guests 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

San Diego, USA

5.0 (85)

San Diego Sailing Cruise Small Group 6 Guests 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 (85)

from
$125

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and …More

Maui, USA

4.8 (85)

Maui: Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and...

2 hours Free Cancellation

4.8 (85)

from
$112

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego …More

San Diego, USA

5.0 (82)

Deluxe Day Sail in San Diego

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego...

2 hours 30 minutes Free Cancellation

5.0 (82)

from
$119

Isla Mujeres, Cancún Private Sunset Trip

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the …More

Isla Mujeres, Mexico

5.0 (82)

Isla Mujeres, Cancún Private Sunset Trip

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the...

5 hours Hotel pickup offered Free Cancellation

5.0 (82)

from
$450

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

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

Discover the magic of the Laguna de los 7 Colores aboard our sailboat. Enjoy 5 hours of sailing, good music, unlimited drinks, delicious food, and …More

Bacalar, Mexico

4.9 (80)

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch

Discover the magic of the Laguna de los 7 Colores aboard our sailboat. Enjoy 5 hours of sailing, good music, unlimited drinks, delicious food, and...

5 hours Free Cancellation

4.9 (80)

from
$72

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

Schooner Eastwind Sunset Sail to see the Maine Coastline

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and …More

4.8 (77)

Schooner Eastwind Sunset Sail to see the Maine Coastline

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and...

2 hours Free Cancellation

4.8 (77)

from
$75

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point …More

Oahu, USA

4.8 (76)

Waikiki Sunset Cruise from Oahu

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point...

2 hours Free Cancellation

4.8 (76)

from
$45

New York City Sunset Sail to the Statue of Liberty

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic …More

New York City, USA

4.9 (75)

New York City Sunset Sail to the Statue of Liberty

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic...

2 hours Free Cancellation

4.9 (75)

from
$90

Private Sunset Sail in San Diego Up to 6 guests

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking …More

La Jolla, USA

5.0 (74)

Private Sunset Sail in San Diego Up to 6 guests

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking...

2 hours Free Cancellation

5.0 (74)

from
$99

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay …More

Pensacola, USA

5.0 (73)

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay...

2 hours Free Cancellation

5.0 (73)

from
$114

Private Sunset Sail in San Diego up to 12 guests

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be …More

San Diego, USA

5.0 (73)

Private Sunset Sail in San Diego up to 12 guests

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be...

2 hours 30 minutes Free Cancellation

5.0 (73)

from
$85

Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the …More

Baltimore, USA

4.9 (72)

Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the...

1 hour 30 minutes Free Cancellation

4.9 (72)

from
$65

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed …More

Chicago, USA

5.0 (71)

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed...

2 hours Free Cancellation

5.0 (71)

from
$508

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in …More

Naples, USA

5.0 (71)

Sunset Cruise Tour

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in...

2 hours Free Cancellation

5.0 (71)

from
$54

Private Cabo San Lucas Sunset Cruise on 33´ sailboat

You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes …More

Cabo San Lucas, Mexico

4.9 (71)

Private Cabo San Lucas Sunset Cruise on 33´ sailboat

You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes...

2 hours 30 minutes Free Cancellation

4.9 (71)

from
$600

Private Day Sail in San Diego up to 12 guests

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San …More

San Diego, USA

5.0 (70)

Private Day Sail in San Diego up to 12 guests

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San...

2 hours 30 minutes Free Cancellation

5.0 (70)

from
$81

Private Sailing on the Miami Bay - Biscayne Bay

Let's go Sailing! Experience Miami's Biscayne Bay aboard one of Cool Shore Excursions Beneteau stylish vessels in the company of experienced, but mostly fun, well …More

Miami, USA

5.0 (67)

Private Sailing on the Miami Bay - Biscayne Bay

Let's go Sailing! Experience Miami's Biscayne Bay aboard one of Cool Shore Excursions Beneteau stylish vessels in the company of experienced, but mostly fun, well...

4 to 12 hours Free Cancellation

5.0 (67)

from
$175

Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion

Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty …More

Kennebunkport, USA

5.0 (66)

Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion

Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty...

2 hours Free Cancellation

5.0 (66)

from
$139