Top North America Sailing Trips

Q: I need a ride! Which North America Sailing Trips have Hotel Pickup?

No problem. These North America Sailing Trips include Hotel Pickup: Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Waikiki Turtle Snorkeling Adventure(8am) 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 →

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

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity …More

Bacalar, Mexico

5.0 (128)

Private Paddle Tour at Sunrise

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity...

3 hours Free Cancellation

5.0 (128)

from
$32

Visit Private Beaches around Puerto Vallarta in a Private Yacht

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain …More

Puerto Vallarta, Mexico

5.0 (128)

Visit Private Beaches around Puerto Vallarta in a Private Yacht

Enjoy the most exclusive beaches just accessible by sea and reach places that other regular tours don’t go. Also enjoy the explanation from our captain...

4 hours

5.0 (128)

from
$1,500

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - …More

Hilton Head Island, USA

5.0 (125)

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island -...

2 hours Free Cancellation

5.0 (125)

from
$525

Shared Snorkeling Tour Playa El Cielo in Cozumel

We offer a tour with all security measures Our Guides are fully certified Visits to the Palancar reefs, Arrecife Colombia, as well as the visit …More

Cozumel, Mexico

4.9 (123)

Shared Snorkeling Tour Playa El Cielo in Cozumel

We offer a tour with all security measures Our Guides are fully certified Visits to the Palancar reefs, Arrecife Colombia, as well as the visit...

4 hours Free Cancellation

4.9 (123)

from
$51

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the …More

Hilton Head Island, USA

5.0 (121)

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the...

2 hours Free Cancellation

5.0 (121)

from
$485

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come …More

Oahu, USA

4.9 (121)

Small Group Waikiki Sunset Sailing Tour

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come...

2 hours Free Cancellation

4.9 (121)

from
$99

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your …More

Key West, USA

4.9 (119)

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...

5 hours Free Cancellation

4.9 (119)

from
$119

Suncoast Sailing's Day Sailing Experience!

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just …More

St Petersburg, USA

4.9 (118)

Suncoast Sailing's Day Sailing Experience!

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just...

2 hours 30 minutes Free Cancellation

4.9 (118)

from
$65

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play …More

Fort Myers, USA

5.0 (114)

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play...

2 hours Free Cancellation

5.0 (114)

from
$60

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on …More

La Jolla, USA

5.0 (114)

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on...

2 hours 30 minutes Free Cancellation

5.0 (114)

from
$119

Private Customizable Sailing Tour in Cancun

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be …More

Playa del Carmen, Mexico

4.9 (114)

Private Customizable Sailing Tour in Cancun

Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be...

4 to 8 hours Free Cancellation

4.9 (114)

from
$549

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed …More

Halifax, Canada

4.9 (113)

Best of Halifax Harbour Boat Tour

This 45' luxury boat is the perfect venue to learn about the history of Halifax. You are alongside our Captain and Deckhand throughout the relaxed...

1 hour Free Cancellation

4.9 (113)

from
$43

Schooner Appledore Day Sail with Full Bar in Key West

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern …More

Key West, USA

5.0 (113)

Schooner Appledore Day Sail with Full Bar in Key West

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hours Free Cancellation

5.0 (113)

from
$54

Costa Maya: Chacchoben & Bacalar sailing or Los Rápidos

Ideal for cruisers with at least 8 hours in Costa Maya. Chacchoben + Bacalar: Sailing or The Rapids Your adventure begins at Costa Maya Cruise …More

Costa Maya, Mexico

4.9 (113)

Costa Maya: Chacchoben & Bacalar sailing or Los Rápidos

Ideal for cruisers with at least 8 hours in Costa Maya. Chacchoben + Bacalar: Sailing or The Rapids Your adventure begins at Costa Maya Cruise...

5 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (113)

from
$165

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical …More

Bacalar, Mexico

4.9 (111)

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical...

3 hours Free Cancellation

4.9 (111)

from
$55

Vancouver Sailing Experience on a 50 Foot Sailboat

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for …More

Vancouver, Canada

5.0 (111)

Vancouver Sailing Experience on a 50 Foot Sailboat

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for...

2 hours 30 minutes Free Cancellation

5.0 (111)

from
$114

Within the activities of this tour, it will be bird watching, sailing in an ecological way without motor. We will swim in the places with …More

Bacalar, Mexico

5.0 (111)

Private Sailing between Mangroves

Within the activities of this tour, it will be bird watching, sailing in an ecological way without motor. We will swim in the places with...

3 hours Free Cancellation

5.0 (111)

from
$182

Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy …More

Big Island of Hawaii, USA

4.8 (109)

Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy...

3 hours Free Cancellation

4.8 (109)

from
$189