Skip to content

Sail Tourer

Spain
The USA
Greece and Portugal
By Type
Best Sailing Tours
More Destinations

Sail Tourer

Spain
The USA
Greece and Portugal
By Type
Best Sailing Tours
More Destinations

USA

All USA Sailing Tours

Page 3 of 4

Afternoon Sail & Snorkel to the Captain Cook Monument - What the snorkeling is like

Big Island Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Afternoon Sail & Snorkel to the Captain Cook Monument

★ 5.0Afternoon Sail & Snorkel to the Captain Cook MonumentFrom $136246 reviews

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch - Raising the sails with the crew

Bay, Harbour and Coastal Sailing, Charleston Sailing Tours, Coastal Sailing Tours in the USA, Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, Tours, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

★ 4.6Schooner Sailing Harbor Tour & Dolphin WatchFrom $48255 reviews

Boston: Tall Ship Harbor Sail - The first minutes under sail

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Boston: Tall Ship Harbor Sail

★ 4.6Boston: Tall Ship Harbor SailFrom $35261 reviews

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea - Waikiki and Diamond Head from offshore

Oahu Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Swimming and Beach Sailing Trips, Tour Reviews, USA Sailing Tours

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

★ 5.0Board from Waikiki Beach for a scenic Sunset Sail on the HāweaFrom $72277 reviews

Sail & Splash Excursion in Ft. Lauderdale - The first 30 to 45 minutes: homes, yachts, and beach views

Sailing Tours, Tour Reviews, Tours, USA Sailing Tours

Sail & Splash Excursion in Ft. Lauderdale

★ 5.0Sail & Splash Excursion in Ft. LauderdaleFrom $99270 reviews

NYC: Sunset Sail Aboard Schooner Adirondack - Hudson River views without the usual sightseeing noise

New York City Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

NYC: Sunset Sail Aboard Schooner Adirondack

★ 4.9NYC: Sunset Sail Aboard Schooner AdirondackFrom $90283 reviews

Boston: Harbor Champagne Sunset Sail from Rowes Wharf - Boarding the Adirondack III or IV

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing Tours, Sailing Tours with an Open Bar, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours, Wine Tours

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

★ 4.8Boston: Harbor Champagne Sunset Sail from Rowes WharfFrom $82299 reviews

St. Augustine Live Music Cruise with Drinks and Sunset Option - Sunset, skyline, and the first stretch of the route

Concerts, Party and Music Sailing Cruises, Sailing Tours with an Open Bar, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

St. Augustine Live Music Cruise with Drinks and Sunset Option

★ 5.0St. Augustine Live Music Cruise with Drinks and Sunset OptionFrom $69315 reviews

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included - Meeting Liberty at Safe Harbor Sunroad

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in San Diego, Coastal Sailing Tours in the USA, Food & Drink, Sailing Tours, Sailing Yacht Charters, San Diego Sailing Tours, Tour Reviews, USA Sailing Tours, Wine Tours

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

★ 5.0San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine IncludedFrom $115331 reviews

Orange Beach Sunset Sailing Cruise - Two hours of bay views, music, and easy sailing

Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Swimming and Beach Sailing Trips, Tour Reviews, USA Sailing Tours

Orange Beach Sunset Sailing Cruise

★ 5.0Orange Beach Sunset Sailing CruiseFrom $75319 reviews

Waikiki Beach Sunset Sail - A sunset sail with a party-boat personality

Oahu Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Swimming and Beach Sailing Trips, Tour Reviews, USA Sailing Tours

Waikiki Beach Sunset Sail

★ 5.0Waikiki Beach Sunset SailFrom $70378 reviews

West Oahu Dolphin Watch and Snorkel Sail with Lunch - Six west-coast sights along the route

Lunch Experiences, Oahu Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in Oahu, Sailing and Snorkeling Trips in the USA, Sailing Tours, Sailing Tours with Lunch and BBQ, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in Oahu, Whale and Dolphin Watching Sails in the USA

West Oahu Dolphin Watch and Snorkel Sail with Lunch

★ 4.5West Oahu Dolphin Watch and Snorkel Sail with LunchFrom $125320 reviews

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail - A short but worthwhile snorkel session

Key West Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in Key West, Sailing and Snorkeling Trips in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

★ 4.5Key West Rum and Reggae: Reef Snorkel Adventure and Sunset SailFrom $59370 reviews

Key West Signature Sunset Sail with Live Music, Open Bar & Food - The open bar is the strongest value at $72

Concerts, Food, Food & Drink, Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Key West, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Signature Sunset Sail with Live Music, Open Bar & Food

★ 4.5Key West Signature Sunset Sail with Live Music, Open Bar & FoodFrom $72314 reviews

Fort Lauderdale Sailing Charter - Raising the sails on the Atlantic

Private Sailing Charters, Sailing Tours, Tour Reviews, USA Sailing Tours

Fort Lauderdale Sailing Charter

★ 5.0Fort Lauderdale Sailing CharterFrom $150387 reviews

4-Hour Fort Lauderdale Sailing Charter - Meeting Captain Charlie at 750 SW 12th Avenue

Private Sailing Charters, Sailing Tours, Tour Reviews, USA Sailing Tours

4-Hour Fort Lauderdale Sailing Charter

★ 5.04-Hour Fort Lauderdale Sailing CharterFrom $148311 reviews

New York City: Sunset Sail Aboard a Schooner - Sailing South Along the Hudson River

New York City Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

New York City: Sunset Sail Aboard a Schooner

★ 4.9Sunset Sail Aboard a SchoonerFrom $101344 reviews

Key West: Sunset Sailing Trip with Open Bar, Food and Music - The Sandie Cat: room to move, plenty of company

Food, Food & Drink, Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Key West, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West: Sunset Sailing Trip with Open Bar, Food and Music

★ 4.5Sunset Sailing Trip with Open Bar, Food and MusicFrom $80310 reviews

Key West: Schooner Sunset Sail with Food & Drinks - America 2.0 brings the right kind of drama

Food, Food & Drink, Key West Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Key West, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in Key West, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Key West: Schooner Sunset Sail with Food & Drinks

★ 4.9Schooner Sunset Sail with Food & DrinksFrom $122318 reviews

From Ma'alaea: 'Alihilani Sunset Sail Catamaran Tour - Sailing the Auau Channel without a rushed schedule

Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Maui Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, Tours, USA Sailing Tours

From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

★ 4.8From Ma’alaea: ‘Alihilani Sunset Sail Catamaran TourFrom $114348 reviews

Seattle Sailing Harbor Tour - What the two-hour sailing feels like

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing Tours, Seattle Sailing Tours, Tour Reviews, Tours, USA Sailing Tours

Seattle Sailing Harbor Tour

★ 4.5Seattle Sailing Harbor TourFrom $39473 reviews

2-Hour Sunset Sail on the San Francisco Bay - Sunset views toward the Bay Bridge

2-Hour Experiences, Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing Tours, San Francisco Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

2-Hour Sunset Sail on the San Francisco Bay

★ 5.02-Hour Sunset Sail on the San Francisco BayFrom $129392 reviews

1.5-Hour San Francisco Bay Sailing Tour - Alcatraz, Angel Island, and the Bay Bridge

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing Tours, San Francisco Sailing Tours, Tour Reviews, Tours, USA Sailing Tours

1.5-Hour San Francisco Bay Sailing Tour

★ 5.01.5-Hour San Francisco Bay Sailing TourFrom $99393 reviews

Sunset Dolphin Sail Aboard the Footloose Catamaran - Ninety Minutes On The Gulf

Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Sunset Dolphin Sail Aboard the Footloose Catamaran

★ 5.0Sunset Dolphin Sail Aboard the Footloose CatamaranFrom $40442 reviews

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling - Biscayne National Park by Sail

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Miami Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

★ 5.0Sail Biscayne Bay: An Intimate Eco-Adventure with SnorkelingFrom $129441 reviews

Southwest Florida Sunset Sail - Sanibel Island Lighthouse and the first views

Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Southwest Florida Sunset Sail

★ 5.0Southwest Florida Sunset SailFrom $70476 reviews

Private Luxury Yacht Charters, BYOB & Dolphins - Fort Sumter from the water

Charleston Sailing Tours, Sailing Yacht Charters, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Private Luxury Yacht Charters, BYOB & Dolphins

★ 5.0Private Luxury Yacht Charters, BYOB & Dolphins395 reviews

Windjammer Classic Sunset Sail from Camden, Maine - Raising the sails with the crew

Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Windjammer Classic Sunset Sail from Camden, Maine

★ 5.0Windjammer Classic Sunset Sail from Camden, MaineFrom $64425 reviews

Windjammer Classic Day Sail from Camden, Maine - The Appledore II is part of the experience

Sailing Tours, Tour Reviews, USA Sailing Tours

Windjammer Classic Day Sail from Camden, Maine

★ 5.0Windjammer Classic Day Sail from Camden, MaineFrom $59406 reviews

Sunset Sailing Cruise on a Tall Ship in Boston Harbor - Boston Harbor at sunset, from the deck

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

★ 4.5Sunset Sailing Cruise on a Tall Ship in Boston HarborFrom $68414 reviews

Waikoloa Signature Catamaran Sunset Sail - A 53-foot catamaran with room to move

Big Island Sailing Tours, Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Waikoloa Signature Catamaran Sunset Sail

★ 4.5Waikoloa Signature Catamaran Sunset SailFrom $159396 reviews

Deluxe Sail & Snorkel to the Captain Cook Monument - Leaving Keauhou Bay at 8:15 a.m.

Big Island Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Deluxe Sail & Snorkel to the Captain Cook Monument

★ 5.0Deluxe Sail & Snorkel to the Captain Cook MonumentFrom $179472 reviews

Evening Colors Sunset Sail Tour in Seattle - Seattle’s skyline from the sound

Sailing Tours, Seattle Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, Tours, USA Sailing Tours

Evening Colors Sunset Sail Tour in Seattle

★ 5.0Evening Colors Sunset Sail Tour in SeattleFrom $59593 reviews

Small-Group San Diego Afternoon Sailing Excursion - From Shelter Island to open water

Sailing Tours, San Diego Sailing Tours, Tour Reviews, Tours, USA Sailing Tours

Small-Group San Diego Afternoon Sailing Excursion

★ 5.0Small-Group San Diego Afternoon Sailing ExcursionFrom $116531 reviews

Small-Group San Diego Sunset Sailing Excursion - Settling Into The Catalina-Style Sailboat

Sailing Tours, San Diego Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in San Diego, Sunset Sailing Cruises in the USA, Tour Reviews, Tours, USA Sailing Tours

Small-Group San Diego Sunset Sailing Excursion

★ 5.0Small-Group San Diego Sunset Sailing ExcursionFrom $127592 reviews

Sunset Sail Along the San Diego Skyline - Settling into the bean bag seats

Sailing Tours, San Diego Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in San Diego, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Sunset Sail Along the San Diego Skyline

★ 5.0Sunset Sail Along the San Diego SkylineFrom $109603 reviews

Schooner Fame Sailing Tour - Raising sails, steering, and firing the cannon

Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, Tours, USA Sailing Tours

Schooner Fame Sailing Tour

★ 5.0Schooner Fame Sailing TourFrom $50571 reviews

Waikiki Sunset Cocktail Sail with Open Bar - The open bar and the value of the price

Oahu Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Oahu, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Waikiki Sunset Cocktail Sail with Open Bar

★ 4.5Waikiki Sunset Cocktail Sail with Open BarFrom $84554 reviews

Key West Reef Snorkel & Sail Adventure - My booking advice

Key West Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in Key West, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Key West Reef Snorkel & Sail Adventure

★ 4.5Key West Reef Snorkel & Sail AdventureFrom $79540 reviews

Kauai: Leila Na Pali Sunset Dinner Sail - The four-hour Na Pali sightseeing run

Dining Experiences, Dinner and Evening Sailing Cruises, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Kauai: Leila Na Pali Sunset Dinner Sail

★ 4.5Kauai: Leila Na Pali Sunset Dinner SailFrom $263524 reviews

Kauai’s Na Pali Coast Snorkel and Sail Tour - Seeing the Na Pali Coast from Leila

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, Tours, USA Sailing Tours

Kauai’s Na Pali Coast Snorkel and Sail Tour

★ 5.0Kauai’s Na Pali Coast Snorkel and Sail TourFrom $292541 reviews

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head - What the 90-minute sail is really like

Sailing Tours, Sailing Yacht Charters, Tour Reviews, USA Sailing Tours

America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head

★ 4.5America’s Cup 12-Meter Yacht Afternoon Sail from Hilton HeadFrom $55504 reviews

Keep browsing

Sailing Tours636 Sunset Sailing Cruises168 Catamaran Sailing Trips103 Island Hopping Sailing Trips74 Sailing and Snorkeling Trips99 Bay, Harbour and Coastal Sailing104

← Previous 1 2 3 4 Next →

Scroll to Top

Every kind of day on the water

Pick a rig, a coast or an afternoon.

Kinds of day

Sunset Sails Catamaran Trips Sail and Snorkel Island Hopping Bays and Harbours

On board

Open Bar Sailings Lunch and BBQ Dinner Sailings Swim Stops Party Boats

Boats

Tall Ships Yacht Charters Private Charters Nile Feluccas Whales and Dolphins

Best of

Best Sailing Trips Sunset Sails in the USA US Coastal Sailing Portuguese Sunset Sails Greek Island Hopping

Sail Tourer

Sheets easing, an anchorage nobody can drive to, and salt drying on the deck by the time you head in.

Europe

Spain Portugal Greece Italy Croatia France

The Americas

The USA Mexico US Virgin Islands Aruba Puerto Rico Canada

Asia Pacific and Africa

Australia New Zealand French Polynesia Vietnam Egypt

Harbours

Barcelona Lisbon Key West Mallorca Oahu Airlie Beach

Home Sailing Tours Sunset Sailing Cruises Catamaran Sailing Trips USA Sailing Tours Spain Sailing Tours Island Hopping Sailing Trips

© 2026 Sail TourerSailing trips on every coast with a harbour