Top North America Sailing Trips

632 Results
Sailing Charter around Vancouver Harbour Private Tour

Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and …More

Vancouver, Canada

Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and...

6 hours Free Cancellation
5.0 (2)
from
$2,342
Private Key West Morning Sail, Snorkel & Kayak Excursion

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge. …More

Special Offer
Special Offer
Key West, USA

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4 hours 30 minutes (approx.) Free Cancellation
$2,399
$2,270
Bertram Yacht 58 Feet Up to 25 People 4 hrs

This is a beautiful and comfortable Yacht, ideal for planning an excellent vacation and having a fun and spectacular party. The magnificent 58-foot-long boat has …More

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

This is a beautiful and comfortable Yacht, ideal for planning an excellent vacation and having a fun and spectacular party. The magnificent 58-foot-long boat has...

4 hours
from
$2,250
Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp

Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go on a trip to Isla Mujeres …More

Cancun, Mexico

Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go on a trip to Isla Mujeres...

4 to 7 hours Free Cancellation
4.7 (46)
from
$2,231
Private Yacht for up to 30 People

This ship is a wonderful option to plan unforgettable vacations and spectacular celebrations. With a length of 50 feet, it can accommodate up to 30 …More

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

This ship is a wonderful option to plan unforgettable vacations and spectacular celebrations. With a length of 50 feet, it can accommodate up to 30...

4 hours
from
$2,225
Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience

Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew …More

Cozumel, Mexico

Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew...

5 hours Free Cancellation
5.0 (644)
from
$2,200
All Inclusive Full Day and Sunset Private Catamaran in St. Pete

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

8 hours Free Cancellation
from
$2,200
Private Romantic Sailing Sunset Experience

Enjoy a romantic mix of sensations, views and tastes as you gaze at a caribbean sunset while colors or the sunset on the coats of …More

Playa del Carmen, Mexico

Enjoy a romantic mix of sensations, views and tastes as you gaze at a caribbean sunset while colors or the sunset on the coats of...

4 hours Hotel pickup offered Free Cancellation
3.0 (1)
from
$2,180
Premium Private 47ft Catamaran Snorkel & El Cielo (30p max)

Private 6-hour charter for up to 30 guests aboard Nemo, a spacious 47ft Nautitech catamaran, with El Cielo, guided snorkeling, fresh lunch, open bar and …More

Cozumel, Mexico

Private 6-hour charter for up to 30 guests aboard Nemo, a spacious 47ft Nautitech catamaran, with El Cielo, guided snorkeling, fresh lunch, open bar and...

6 hours Free Cancellation
4.8 (25)
from
$2,139
All Inclusive Full Day Luxury Catamaran Charter

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

7 hours Free Cancellation
5.0 (1)
from
$2,100
Private Atomic Catamaran Tour to Isla Mujeres

By booking this private service, you can design a completely tailored itinerary. You will have the freedom to navigate to the places of your choice …More

Cancun, Mexico

By booking this private service, you can design a completely tailored itinerary. You will have the freedom to navigate to the places of your choice...

7 hours Free Cancellation
4.9 (7)
from
$2,100
Private Yacht for up to 12 People

Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip that you will enjoy like no other, you …More

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

Imagine feeling the sea breeze aboard the wonderful Tiara 44 Yacht, it will definitely be a trip that you will enjoy like no other, you...

4 hours
from
$2,030
All Inclusive Half Day Sunset Catamaran Adventure

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

6 hours Free Cancellation
5.0 (1)
from
$2,000
3 Hour Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hours Free Cancellation
5.0 (1)
from
$1,995
Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous …More

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

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous...

4 hours Hotel pickup offered Free Cancellation
5.0 (390)
from
$1,799
All Inclusive St Pete Private Half Day Catamaran Charter

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

5 hours Free Cancellation
5.0 (1)
from
$1,700
4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres

This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we take care of customer during the all …More

Cancun, Mexico

This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we take care of customer during the all...

4 hours Free Cancellation
5.0 (6)
from
$1,700
Private Catamaran Ride in Los Cabos Food and Bar Outdoors

Enjoy a complete catamaran experience combining scenic sailing, snorkeling and onboard dining. Sail in front of the Cabo San Lucas Arch while enjoying open bar …More

Cabo San Lucas, Mexico

Enjoy a complete catamaran experience combining scenic sailing, snorkeling and onboard dining. Sail in front of the Cabo San Lucas Arch while enjoying open bar...

3 hours Free Cancellation
5.0 (18)
from
$1,687
Private Luxury Sunset Sail 39Ft Catamaran in Cozumel – 3 Hours

This is more than a sunset cruise it's a completely private evening aboard a spacious 39 foot Lagoon catamaran. Unlike shared sunset tours, your boat …More

Cozumel, Mexico

This is more than a sunset cruise it's a completely private evening aboard a spacious 39 foot Lagoon catamaran. Unlike shared sunset tours, your boat...

3 hours Free Cancellation
5.0 (26)
from
$1,600
Deluxe Private Boats - 40 ft Catamaran

We are a company that understands privacy, attention to detail, and quality in everything we get our hands-on. We want you to feel relaxed and …More

Cozumel, Mexico

We are a company that understands privacy, attention to detail, and quality in everything we get our hands-on. We want you to feel relaxed and...

3 to 8 hours Free Cancellation
5.0 (109)
from
$1,600

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