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Come sail away on our North America sailing trips. Enjoy sailing on your vacation and spend the day out on the water. Our North America sailing tours are a great activity for any traveler. You can relax and ride or learn to sail at one of our sailing schools. Our sailing adventures are a great addition to any vacation. Browse our North America sailing and plan your vacation today!


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Featured Listings

1 - 20 of 41 for Sailing & Yacht Charters in North America
Ketchikan Charter Boats Ketchikan, Alaska Sailing & Yacht Charters

Ketchikan Charter Boats

Ketchikan, Alaska Sailing & Yacht Charters
We offer 4,6,8 hour fishing charters in the salmon capital of the world! Ketchikan Alaska...
From USD $200 per trip pp
Charter Service, Sailing School & Romantic Getaway St. Petersburg, Florida Sailing & Yacht Charters

Charter Service, Sailing School & Romantic Getaway

St. Petersburg, Florida Sailing & Yacht Charters
Sailing Florida Charter's & Sailing School located on Tampa Bay, downtown St. Petersburg, Florida. ASA sailing classes, Coast Guard licensed captains, bareboat charters, romantic getaway packages, res...
From USD $60 per trip

Luxury Yacht Charter Cancun Riviera Maya Mexico Cancun, Mexico Sailing & Yacht Charters

Luxury Yacht Charter Cancun Riviera Maya Mexico

Cancun, Mexico Sailing & Yacht Charters
Luxury Yacht Charter Cancun Dotkom Company for rental, sailboats catamaran yachts fishing boats and private Cruise yacht charter for Caribbean islands Honemoon, celebrations, meetings, fishing, divin...
From USD $400 per trip
Sound Sailing- Crewed Sailboat Charters in Alaska Sitka, Alaska Sailing & Yacht Charters

Sound Sailing- Crewed Sailboat Charters in Alaska

Sitka, Alaska Sailing & Yacht Charters
Hear the spouts of an orca pod or a family of humpback whales and their rumbling songs. Sail to the calving glaciers and remote towering fjords. Providing safe, comfortable, exciting adventures for ov...
From USD $300 per night
Pacific Yellowfin Private Charters Vancouver, British Columbia Sailing & Yacht Charters

Pacific Yellowfin Private Charters

Vancouver, British Columbia Sailing & Yacht Charters
Pacific Yellowfin Charters offers private, luxury adventures along the beautiful British Columbia coastline. Get up close with killer whales, dolphins, black bears and brown bears, all while enjoying ...
From USD $62,845 per week
Classic Harbor Line Key West, Florida Sailing & Yacht Charters

Classic Harbor Line

Key West, Florida Sailing & Yacht Charters
Classic Harbor Line proudly runs Schooner America 2.0, the premier sailing vessel in Key West, featuring two-hour sunset and day sails. Complimentary drinks and hors d'oeuvres provided....
From USD $55 per trip
Luxe Yacht Charters Miami  Beach, Florida Sailing & Yacht Charters

Luxe Yacht Charters

Miami Beach, Florida Sailing & Yacht Charters
Enjoy your party on our luxury Miami Yachts. It might be party yacht rental in Miami you are looking for, a private yacht charter in Florida, an anniversary celebration, Bar Mitzvah or even to have y...
From USD $600 per trip
Alaska Cruises Juneau, Alaska Sailing & Yacht Charters

Alaska Cruises

Juneau, Alaska Sailing & Yacht Charters
Alaska small ship cruising company that provides private yacht charters throughout the Inside Passage....
Contact For Rates & Specials!
Maine Windjammer Sailing Adventures Blue Hill, Maine Sailing & Yacht Charters

Maine Windjammer Sailing Adventures

Blue Hill, Maine Sailing & Yacht Charters
The Maine Windjammer Association's nine historic ships offer exciting 3- to 6-day sailing vacations along the Maine coast from May to October. Includes great food, spectacular scenery, abundant wildli...
From USD $180 per night
Chardonnay Sailing Charters Santa Cruz, California Sailing & Yacht Charters

Chardonnay Sailing Charters

Santa Cruz, California Sailing & Yacht Charters
Excursions aboard Chardonnay Sailing Charters are perfect for any age group and fun for everyone from seasoned sailors to first-time adventures....
From USD $60 per trip pp

Alaska's Liveaboard Glacier Bay Cruises, 5-7 days Glacier Bay, Alaska Sailing & Yacht Charters

Alaska's Liveaboard Glacier Bay Cruises, 5-7 days

Glacier Bay, Alaska Sailing & Yacht Charters
Private, custom cruises for 2-6 people, all inclusive onboard; Glacier Bay Nat'l Park, wildlife, whales, fishing, glaciers, Elfin Cove, Gustavus, Excursion Inlet, incredible scenery, meals, snacks, Ju...
From USD $3,375 per trip
Adventure Charters and Dive Moss Point, Mississippi Sailing & Yacht Charters

Adventure Charters and Dive

Moss Point, Mississippi Sailing & Yacht Charters
Adventure Charters and Dive. Fishing, Scuba, Boating. We specialize in Adaptive Services in Scuba Diving, Fishing, Kayaking, and Boating. Fun half day or all day trips. We can design trips to fi...
From USD $100 per trip
The Boat Company, Celebrating 30 Years of Cruising Far North, Alaska Sailing & Yacht Charters

The Boat Company, Celebrating 30 Years of Cruising

Far North, Alaska Sailing & Yacht Charters
Celebrating 30 years of Cruising, Conservation, Education & Fishing in The Tongass National Forest, Southeast Alaska, Our Nations Largest National Forest. Explore Southeast Alaska with the Original "...
From USD $13,590 per trip
S.E. Alaska up and close on the 'Northern Dream' Juneau, Alaska Sailing & Yacht Charters

S.E. Alaska up and close on the 'Northern Dream'

Juneau, Alaska Sailing & Yacht Charters
Enjoy S.E. Alaska up and close aboard your own exclusive yacht! Aboard the "Northern Dream" a 65' Sea Ranger, you can plan your tip to your wishes. Fishing, kayaking, exploring, sight seeing and more....
From USD $3,000 per trip
Sail the Maine Coast on the Schooner Stephen Taber Rockland, Maine Sailing & Yacht Charters

Sail the Maine Coast on the Schooner Stephen Taber

Rockland, Maine Sailing & Yacht Charters
The Schooner Stephen Taber offers 3-6 day sailing trips off the coast of Maine. Built in 1871 and based in Rockland, a trip aboard the Taber is unique, authentic, personal and relaxing. The ship carri...
From USD $550 per trip
hot travel deals
Hornblower Cruises & Events Newport Beach, California Sailing & Yacht Charters

Hornblower Cruises & Events

Newport Beach, California Sailing & Yacht Charters
As one of the country’s most recognized dinner cruise and yacht charter companies, we host daily dinner cruises and unforgettable, customized charters designed just to fit any budget....
From USD $35 per trip
Alaska Yacht Charters Aboard Alaskan Song Sitka, Alaska Sailing & Yacht Charters

Alaska Yacht Charters Aboard Alaskan Song

Sitka, Alaska Sailing & Yacht Charters
Yacht Charters in Southeast Alaska - A Classic Yacht with Professional crew offering whales and wildlife, fishing, kayaking, hot-springs and gourmet cuisine. Custom Itineraries & Menus since 1995....
Contact For Rates & Specials!


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