Top North America Sailing Trips

633 Results
Half-Day Luxury Sailing Experience in Tulum with Open Bar

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so …More

Tulum, Mexico

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so...

4 hours Hotel pickup offered Free Cancellation
4.5 (225)
from
$149
Key West Sail and Snorkel Day Trip from Fort Lauderdale

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from …More

Fort Lauderdale, USA

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from...

15 hours Free Cancellation
3.4 (14)
from
$149
2hr. SUNSET Sailing Experience on San Francisco Bay

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get …More

Likely to Sell Out
Likely to Sell Out
Sausalito, USA

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get...

2 hours Free Cancellation
4.9 (35)
from
$149
Luxury Snorkel Adventure in Cabo

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at …More

Cabo San Lucas, Mexico

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at...

3 hours 30 minutes Hotel pickup offered Free Cancellation
4.9 (60)
from
$149
Private Luxury Adventure Tours in Cabo San Lucas

Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy this amazing adventure for 2 …More

Cabo San Lucas, Mexico

Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy this amazing adventure for 2...

2 hours Hotel pickup offered Free Cancellation
4.9 (16)
from
$149
Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the...

2 hours 30 minutes Free Cancellation
5.0 (12)
from
$149
Riviera Maya Half-Day Sailing Experience with Lunch and Open Bar

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so …More

Playa del Carmen, Mexico

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so...

4 hours Hotel pickup offered Free Cancellation
4.7 (69)
from
$149
Whale Watching Sailboat Tour in San Jose del Cabo

Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cruise past the iconic landmarks of San …More

Likely to Sell Out
Likely to Sell Out
San Jose del Cabo, Mexico

Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cruise past the iconic landmarks of San...

2 hours Free Cancellation
5.0 (3)
from
$149
Snorkel Adventure through the Sea of Cortez

Sail through the Sea of Cortez, a blue and shimmering spectacle around Cabo San Lucas. You will ride a luxurious and comfortable catamaran along the …More

Cabo San Lucas, Mexico

Sail through the Sea of Cortez, a blue and shimmering spectacle around Cabo San Lucas. You will ride a luxurious and comfortable catamaran along the...

4 hours Hotel pickup offered Free Cancellation
5.0 (8)
from
$149
Sailing Snorkel Adventure

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value. …More

Cabo San Lucas, Mexico

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value....

4 hours Free Cancellation
4.5 (6)
from
$149
Half-Day Luxury Sailing in Puerto Morelos with Open Bar

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforgettable half-day adventure. This experience offers a guided snorkeling …More

Tulum, Mexico

Set sail on the tranquil turquoise waters of Puerto Morelos aboard a luxury catamaran for an unforgettable half-day adventure. This experience offers a guided snorkeling...

5 hours Hotel pickup offered Free Cancellation
4.8 (4)
from
$149
Isla Mujeres Sailing Adventure from Riviera Maya

Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel.
Surrounded by all the scale of blue colors, you'll relax and chill, …More

Playa del Carmen, Mexico

Enjoy an amazing sailing journey to Isla Mujeres on a 40ft Fountaine Pajot luxury vessel.
Surrounded by all the scale of blue colors, you'll relax and chill,...

7 hours Hotel pickup offered
4.2 (9)
from
$149
Relaxing Saco River Public Sunset Sail

Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. Glide along the Saco River and take in the picturesque …More

Kennebunkport, USA

Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. Glide along the Saco River and take in the picturesque...

2 hours Free Cancellation
5.0 (2)
from
$149
Isla Mujeres Sailing Adventure from Cancun

Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard of an exclusive catamaran...!! This tour is recommended for …More

Cancun, Mexico

Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard of an exclusive catamaran...!! This tour is recommended for...

7 hours Hotel pickup offered
4.0 (4)
from
$149
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours Free Cancellation
4.7 (90)
from
$148
JFarwell Sunset Wine and Cheese Yacht Sailing

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved …More

Halifax, Canada

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved...

2 hours 30 minutes Free Cancellation
5.0 (171)
from
$146
JFarwell Private Yacht Wine & Cheese Sunset Sail

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine …More

Halifax, Canada

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine...

2 hours 30 minutes Free Cancellation
4.9 (18)
from
$146
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

Likely to Sell Out
Likely to Sell Out
Vancouver Island, Canada

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
2hr Shared Sailing Experience in Toronto

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to …More

Toronto, Canada

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to...

2 hours Free Cancellation
5.0 (24)
from
$146
Sunset Sailboat Cruise on Winyah Bay

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for couples, relaxed evenings, and anyone …More

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for couples, relaxed evenings, and anyone...

2 hours Free Cancellation
5.0 (2)
from
$145

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