Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 707 Sailing Trips activities in North America. Sort by Popularity. - Page 1612pm Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

12pm Turtle Canyon Snorkel Adventure
-
North America
-
Superb292 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
San Diego Afternoon Sail
Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military ves... More

San Diego Afternoon Sail
-
North America
-
Superb292 reviews4.8
Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna.....

Tulum: Snorkeling and Private Sailing Tour
-
North America
-
Superb153 reviews4.9
We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spect....
Private Tour
Private Morning Sail, Dolphin and History Tour on Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing yachts are the highest quality and operated by two professional ... More
Private Tour

Private Morning Sail, Dolphin and History Tour on Mystique
-
North America
-
Superb82 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Private Luxury Yacht in Miami
️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s top destinations—Haulover Sandbar, Oleta River State Park, Biscayne Bay & Sands Key, and Raccoon Island—in style! This sleek 3... More
Private Tour

Private Luxury Yacht in Miami
-
North America
-
Superb82 reviews5
️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s ....
Private Tour
2-Hour Sunset Sailing on San Diego Bay
Join Captain Doyle for an unforgettable 2-hour sunset sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and milit... More
Private Tour

2-Hour Sunset Sailing on San Diego Bay
-
North America
-
Superb1 review5
Join Captain Doyle for an unforgettable 2-hour sunset sailing experience aboard our 35-foot sailboat....
Private Tour
#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson
You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed so you learn faster and safer. We will share with you the best locations to launch f... More
Private Tour

#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson
-
North America
-
Superb4 reviews5
You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....
Private Tour
Snorkeling Tour in Los Cabos
Sail past Lover’s Beach, The Arch, and the Sea Lion Colony on your way to the beautiful Santa Maria Bay, on the Pez Gato, part of Cabo’s premier snorkeling tour. You will swim in the azure waters with colorful tropical fish. O... More
Private Tour

Snorkeling Tour in Los Cabos
-
North America
Sail past Lover’s Beach, The Arch, and the Sea Lion Colony on your way to the beautiful Santa Mari....
Private Tour
Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.
WELCOME to Mayan Paradise We are Liz (Biologist) and Danny (Sustainable Sailing) and we will guide you on this wonderful route created for you and your companions (Adventure Tourism, Nature and more). You are looking for TRANQUI... More
Private Tour

Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.
-
North America
-
Superb23 reviews5
WELCOME to Mayan Paradise We are Liz (Biologist) and Danny (Sustainable Sailing) and we will guide ....
Private Tour
Let's Go Sail the York River in Gloucester Point, Virginia
Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the cockpit or up on the bow of the boat for greater privacy. Great idea for engagement, bi... More
Private Tour

Let's Go Sail the York River in Gloucester Point, Virginia
-
North America
-
Superb127 reviews5
Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern ....
Private Tour
Tour to The Arch and Lover's Beach (optional) from Cabo
This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, and through the Marina. See it all in one tour! During this awesome experience, you will be able to see a great variety of tropical... More
Private Tour

Tour to The Arch and Lover's Beach (optional) from Cabo
-
North America
-
Superb8 reviews4.8
This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, a....
Private Tour
The Finest Private Yacht Experience in Cabo
This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some of the best things to do in Cabo such as whale watching and bathing on soothing crystal waters... More
Private Tour

The Finest Private Yacht Experience in Cabo
-
North America
-
Superb23 reviews4.6
This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30....
Private Tour
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 the booking process, service and follow up after the tour is performed. Customer´s feedback is ... More
Private Tour

4hrs / 46ft Catamaran Private Charter From Cancun to Isla Mujeres
-
North America
-
Superb3 reviews5
This catamaran has capacity up to 45 people. We provide a high quality service, nice boat and we tak....
Private Tour
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 at home. We understand you are here to be pampered and have the nicest drinks and lunc... More
Private Tour

Deluxe Private Boats - 40 ft Catamaran
-
North America
-
Superb109 reviews5
We are a company that understands privacy, attention to detail, and quality in everything we get our....
Private Tour
Private Statue of Liberty Sailing Tour
Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory, and curated amenities. Fully staffed by USCG licensed captain a... More
Private Tour

Private Statue of Liberty Sailing Tour
-
North America
-
Superb14 reviews5
Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with tabl....
Private Tour
Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch
Let yourself be carried away by the wind on an unforgettable adventure through the wonderful Lagoon of 7 Colors. A unique experience to enjoy with family or friends, open bar and lunch. Without engine noises, the sounds of nature... More
Private Tour

Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch
-
North America
-
Superb56 reviews4.9
Let yourself be carried away by the wind on an unforgettable adventure through the wonderful Lagoon ....
Private Tour
Luxury Catamaran tour to isla mujeres with transportation from Tulum
Excellent service on board Professional crew members Safety measures in all our activities Sanitary prevention protocols for all our guests and staff Once in a lifetime experience Delicious buffet lunch and drinks Beach club (beac... More
Private Tour

Luxury Catamaran tour to isla mujeres with transportation from Tu....
-
North America
-
Good62 reviews3.5
Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....
Private Tour
Discover Maine's Coastal Charms: Half-Day Scenic Sail
Set sail with us and immerse yourself in the unparalleled beauty of coastal Maine on our half-day excursion. Traverse the serene waters of the Saco River and Saco Bay with its eight gorgeous islands as you uncover their hidden sec... More
Private Tour

Discover Maine's Coastal Charms: Half-Day Scenic Sail
-
North America
-
Superb3 reviews5
Set sail with us and immerse yourself in the unparalleled beauty of coastal Maine on our half-day ex....
Private Tour
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More
Private Tour

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
-
North America
-
Superb12 reviews4.9
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....
Private Tour
Excursion to Reefs in a transparent boat from Cancun
It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine life, in addition, the colors of the blanquizal of Cancun are something spectacular and there is a great diversity of marine life... More
Private Tour

Excursion to Reefs in a transparent boat from Cancun
-
North America
-
Exellent7 reviews4.3
It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine l....
Private Tour