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

THE USA

All Sunset Sailing Cruises in the USA

Page 3 of 4

Charleston Harbor Sunset Cruise with Music & Onboard Bar - Boarding at Shem Creek

Bay, Harbour and Coastal Sailing, Charleston Sailing Tours, Coastal Sailing Tours in the USA, Party and Music Sailing Cruises, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Charleston Harbor Sunset Cruise with Music & Onboard Bar

★ 4.6Charleston Harbor Sunset Cruise with Music & Onboard BarFrom $6566 reviews

Chesapeake Beach: Sunset Sailing Cruise with Snacks - Two and a half hours on the Chesapeake

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

Chesapeake Beach: Sunset Sailing Cruise with Snacks

★ 4.7Chesapeake Beach: Sunset Sailing Cruise with SnacksFrom $1142 reviews

Charleston: Private Daytime or Sunset BYOB Sailing Charter - Meeting Captain Will at Ashley Marina

Charleston Sailing Tours, Private Sailing Charters, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Charleston: Private Daytime or Sunset BYOB Sailing Charter

★ 4.8Private Daytime or Sunset BYOB Sailing Charter18 reviews

Captain's Choice: Dolphin Watch Sunset Sail - Key West landmarks from the water

Key West Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Captain’s Choice: Dolphin Watch Sunset Sail

★ 4.5Captain’s Choice: Dolphin Watch Sunset SailFrom $8934 reviews

Camden: Sunset Sailing Cruise on a Wooden Schooner - Getting to know the Appledore II

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

Camden: Sunset Sailing Cruise on a Wooden Schooner

★ 4.8Camden: Sunset Sailing Cruise on a Wooden SchoonerFrom $64113 reviews

Camden: Schooner Surprise Sunset Sail - Key points at a glance

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

Camden: Schooner Surprise Sunset Sail

★ 4.5Camden: Schooner Surprise Sunset SailFrom $782 reviews

Boston: Sunset Tall Ship Harbor Cruise - Boston Harbor at sunset

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

Boston: Sunset Tall Ship Harbor Cruise

★ 4.8Boston: Sunset Tall Ship Harbor CruiseFrom $68115 reviews

Waikoloa: Catamaran Sunset Sail with Cocktails - Tropical drinks and island snacks

Catamaran Sailing Trips, Catamaran Sailing Trips 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

Waikoloa: Catamaran Sunset Sail with Cocktails

★ 4.8Waikoloa: Catamaran Sunset Sail with CocktailsFrom $15968 reviews

Wednesday Happy Hour Sunset Sail | Charleston Harbor - A social Wednesday evening without too much fuss

Bay, Harbour and Coastal Sailing, Charleston Sailing Tours, Coastal Sailing Tours in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Wednesday Happy Hour Sunset Sail | Charleston Harbor

★ 5.0Wednesday Happy Hour Sunset Sail | Charleston HarborFrom $792 reviews

Newport Sunset Sail on Schooner Adirondack - Watching the crew raise sail

Newport 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

Newport Sunset Sail on Schooner Adirondack

★ 5.0Newport Sunset Sail on Schooner AdirondackFrom $7480 reviews

2-Hour Oahu Sunset Catamaran Sail - What the 53-foot catamaran feels like underway

2-Hour Experiences, Catamaran Sailing Trips, Catamaran Sailing Trips in Oahu, Catamaran Sailing Trips in the USA, Oahu Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

2-Hour Oahu Sunset Catamaran Sail

★ 5.02-Hour Oahu Sunset Catamaran SailFrom $130122 reviews

Honolulu Sunset Sail from Kewalo Harbor Including Drinks - The ride from Kaka’ako to Waikiki

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, 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

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

★ 5.0Honolulu Sunset Sail from Kewalo Harbor Including DrinksFrom $61169 reviews

Sunset Catamaran Sail in Cocoa Beach - Cruising the Banana River Lagoon

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

Sunset Catamaran Sail in Cocoa Beach

★ 5.0Sunset Catamaran Sail in Cocoa BeachFrom $56176 reviews

Key West: Sunset Sail with Live Band, Drinks, and Appetizers - Checking in at 631 Greene Street

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, Tour Reviews, USA Sailing Tours

Key West: Sunset Sail with Live Band, Drinks, and Appetizers

★ 4.7Sunset Sail with Live Band, Drinks, and AppetizersFrom $79171 reviews

Seattle Sunset Sail BYOB - Why BYOB Changes the Evening

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

Seattle Sunset Sail BYOB

★ 5.0Seattle Sunset Sail BYOBFrom $71187 reviews

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming - Royal Hawaiian Hotel and Magic Island from offshore

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

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

★ 5.0Best Waikiki Sunset Cruise:BYOB Sunset Sail with SwimmingFrom $71191 reviews

San Diego: San Diego Bay Sunset & Daytime Sailing Experience - The Downtown Skyline from San Diego Bay

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in San Diego, Coastal Sailing Tours in the USA, 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

San Diego: San Diego Bay Sunset & Daytime Sailing Experience

★ 5.0San Diego Bay Sunset & Daytime Sailing ExperienceFrom $89181 reviews

Sunset Sail from Traverse City with Food, Wine & Cocktails - A proper schooner, not just a floating restaurant

Food, Food & Drink, Sailing Tours, Sailing Tours with an Open Bar, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours, Wine Tours

Sunset Sail from Traverse City with Food, Wine & Cocktails

★ 5.0Sunset Sail from Traverse City with Food, Wine & Cocktails226 reviews

2.5-Hour Small-Group Catamaran Sunset Sail with Drinks - USS Midway and the downtown waterfront

Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing Tours, Sailing Tours with an Open Bar, San Diego Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in San Diego, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

2.5-Hour Small-Group Catamaran Sunset Sail with Drinks

★ 5.02.5-Hour Small-Group Catamaran Sunset Sail with DrinksFrom $119223 reviews

New York Sunset Schooner Cruise on the Hudson River - What makes the Schooner Adirondack different

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 Sunset Schooner Cruise on the Hudson River

★ 5.0New York Sunset Schooner Cruise on the Hudson RiverFrom $90221 reviews

Sunset Sail in Miami: Complimentary Champagne Toast - The ocean route past PortMiami and South Beach

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

Sunset Sail in Miami: Complimentary Champagne Toast

★ 5.0Sunset Sail in Miami: Complimentary Champagne ToastFrom $99232 reviews

Sunset Sail from Ma'alaea Harbor - What Comes With the $151 Price

Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Maui Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Sunset Sail from Ma’alaea Harbor

★ 4.5Sunset Sail from Ma’alaea HarborFrom $151207 reviews

Classic Key West Schooner Sunset Sail with Full Open Bar - The sunset route around Mallory Square and Fort Zachary Taylor

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

Classic Key West Schooner Sunset Sail with Full Open Bar

★ 5.0Classic Key West Schooner Sunset Sail with Full Open Bar213 reviews

Kona Signature Catamaran Sunset Sail - What the 90-minute route actually offers

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

Kona Signature Catamaran Sunset Sail

★ 5.0Kona Signature Catamaran Sunset SailFrom $109218 reviews

Seattle: Tall Sailboat Sunset Harbor Cruise - The first hour: Seattle from the water

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

Seattle: Tall Sailboat Sunset Harbor Cruise

★ 4.8Tall Sailboat Sunset Harbor CruiseFrom $79223 reviews

Kauai: Napali Coast Sunset Sailboat Tour with Dinner - The ride toward the Nāpali Coast

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

Kauai: Napali Coast Sunset Sailboat Tour with Dinner

★ 4.6Kauai: Napali Coast Sunset Sailboat Tour with DinnerFrom $247207 reviews

Board from Waikiki Beach: Scenic Sunset Sail on the Hāwea - Meeting near the Duke Kahanamoku Statue

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

Board from Waikiki Beach: Scenic Sunset Sail on the Hāwea

★ 4.9Board from Waikiki Beach: Scenic Sunset Sail on the HāweaFrom $68217 reviews

Suncoast Sailing's Sunset Sailing Experience! - The sunset near Treasure Island

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

Suncoast Sailing’s Sunset Sailing Experience!

★ 5.0Suncoast Sailing’s Sunset Sailing Experience!From $69254 reviews

Deluxe Sunset & Day Sail Small Group - Leaving Harbor Island for golden hour

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

Deluxe Sunset & Day Sail Small Group

★ 5.0Deluxe Sunset & Day Sail Small GroupFrom $119245 reviews

Sunset Sail Cruise in Key West - Man O War Harbor and the Historic Seaport

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

Sunset Sail Cruise in Key West

★ 5.0Sunset Sail Cruise in Key West260 reviews

Key West Sunset Sail Aboard Legendary Schooner Appledore - Helping raise the sails

Key West Sailing Tours, Sailing Tours, 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 Sunset Sail Aboard Legendary Schooner Appledore

★ 5.0Key West Sunset Sail Aboard Legendary Schooner Appledore251 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

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

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

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

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

Keep browsing

Sailing Tours2055 Sunset Sailing Cruises476 Catamaran Sailing Trips228 Island Hopping Sailing Trips229 Sailing and Snorkeling Trips214 Bay, Harbour and Coastal Sailing234

← 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