Top North America Sailing Trips

632 Results
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 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
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
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
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 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
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
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 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
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
4hrs/60ft Luxury Catamaran Private Charter Cancun to Isla Mujeres

Sail Away on Our Luxury Catamaran: The Ultimate Caribbean Experience Set sail on our spacious catamaran, with room for up to 60 guests, and enjoy …More

Cancun, Mexico

Sail Away on Our Luxury Catamaran: The Ultimate Caribbean Experience Set sail on our spacious catamaran, with room for up to 60 guests, and enjoy...

4 hours Free Cancellation
4.0 (1)
from
$2,400
5 Hr Private Catamaran Cruise with lunch and drinks to 15-20 ppl

Choices for your private occasion in a catamaran different sizes as well as Yachts depending on the amount of people and your experience. Also inclusive …More

Cozumel, Mexico

Choices for your private occasion in a catamaran different sizes as well as Yachts depending on the amount of people and your experience. Also inclusive...

5 hours
4.9 (15)
from
$2,500
Cabo San Lucas Private Custom Snorkel or Sunset Adventure

First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew will make sure that …More

Cabo San Lucas, Mexico

First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew will make sure that...

3 hours Free Cancellation
5.0 (1)
from
$2,500
Luxury All Inclusive Catamaran Charter in Cabo San Lucas

Welcome aboard our new, luxury Catamaran; all-inclusive and all-private! We have both a large outdoor area with a large seating area in the front and …More

Cabo San Lucas, Mexico

Welcome aboard our new, luxury Catamaran; all-inclusive and all-private! We have both a large outdoor area with a large seating area in the front and...

3 hours Free Cancellation
4.9 (60)
from
$2,552
Private Luxury Catamaran in Tulum with Snacks and Open Bar

It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and delicious dishes and our host will serve …More

Tulum, Mexico

It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and delicious dishes and our host will serve...

4 hours Free Cancellation
5.0 (238)
from
$2,700
Private Luxurious Sailing Cruise in San Diego Bay

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll …More

La Jolla, USA

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll...

2 hours Free Cancellation
5.0 (13)
from
$2,700
Private Catamaran Sailboat 4hrs 15Pax

Sail through the bay of Puerto Vallarta celebrating any occasion. A birthday, an engagement, bachelor party or alone enjoy a private sunset with your friends. …More

Puerto Vallarta, Mexico

Sail through the bay of Puerto Vallarta celebrating any occasion. A birthday, an engagement, bachelor party or alone enjoy a private sunset with your friends....

4 hours
from
$3,058
Private Luxury Yacht for up to 12 people

A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, luxurious and sophisticated, it is specially designed to satisfy …More

Puerto Vallarta, Mexico

A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, luxurious and sophisticated, it is specially designed to satisfy...

4 hours
from
$3,250

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