Top North America Sailing Trips

632 Results
Sunset in Private Sailboat 4 hrs up to 15 pax

Sail around the bay, celebrating your birthday, bachelorette party, anniversary or any other important event. You will receive the best service where you will see …More

Puerto Vallarta, Mexico

Sail around the bay, celebrating your birthday, bachelorette party, anniversary or any other important event. You will receive the best service where you will see...

3 hours
4.6 (11)
from
$3,295
Private Luxury Catamaran Cancun to Isla Mujeres | For up to 30 pp

Experience the ultimate luxury tour to Isla Mujeres from Cancun with our exclusive catamaran tour. Explore the stunning turquoise waters of the Caribbean, take in …More

Cancun, Mexico

Experience the ultimate luxury tour to Isla Mujeres from Cancun with our exclusive catamaran tour. Explore the stunning turquoise waters of the Caribbean, take in...

4 hours Free Cancellation
4.8 (41)
from
$3,485
Key West Private Wind & Wine Charter

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset …More

Key West, USA

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset...

2 hours (approx.) Free Cancellation
5.0 (1,717)
from
$3,499
Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs

Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting nautical activities! If you are looking to live a …More

Likely to Sell Out
Likely to Sell Out
Puerto Vallarta, Mexico

Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting nautical activities! If you are looking to live a...

4 hours
from
$3,708
Private Cruise Swim with Dolphin

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild...

3 hours Hotel pickup offered
from
$3,901
Luxury Yacht 58 ft for up to 20 people 4 hrs

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard this luxury yacht along the coast of Bahía de …More

Likely to Sell Out
Likely to Sell Out
Puerto Vallarta, Mexico

Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard this luxury yacht along the coast of Bahía de...

4 hours
from
$4,100
Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp

Experience the Caribbean like never before with our sophisticated seafarer guiding you through its pristine waters. During this tour, you will have one snorkel stop …More

Cancun, Mexico

Experience the Caribbean like never before with our sophisticated seafarer guiding you through its pristine waters. During this tour, you will have one snorkel stop...

4 hours Free Cancellation
4.6 (28)
from
$5,290
Private Luxury Yacht Charter aboard Tu Enamorado

Pamper yourself, your friends and family to an unforgettable sailing cruise around scenic Cabo San Lucas Bay aboard the beautifully crafted Tu Enamorado. Live the …More

Cabo San Lucas, Mexico

Pamper yourself, your friends and family to an unforgettable sailing cruise around scenic Cabo San Lucas Bay aboard the beautifully crafted Tu Enamorado. Live the...

3 hours Free Cancellation
3.0 (5)
from
$5,572
Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you explore stunning sites and Caribbean reefs. Experience the magic …More

Cancun, Mexico

Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you explore stunning sites and Caribbean reefs. Experience the magic...

6 hours Free Cancellation
from
$5,900
Sail Charter Along the Mexico Riviera and Costa Alegre

Set sail on a sail adventure along the stunning Riviera Nayarit or Costa Alegre departing and returning from the Grand Isla Navidad Resort in Barra …More

Set sail on a sail adventure along the stunning Riviera Nayarit or Costa Alegre departing and returning from the Grand Isla Navidad Resort in Barra...

7 days
from
$7,999
3-Night Private Charter in Lake Clark National Park

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group …More

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group...

4 days
5.0 (1)
from
$20,513
6-Night Private Charter in Lake Clark National Park

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group …More

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group...

7 days
5.0 (1)
from
$30,769

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