Key West Boat Guide

Key West sunset cruises

Watch the sun go down from the water. Compare schooner sails, catamarans, dinner cruises and private sunset charters.

Compare sunset cruises

111 tours

Full Moon Sail Aboard Schooner America 2.0

Full Moon Sail Aboard Schooner America 2.0

From $64Book
Key West Stargazing Cruise Aboard Schooner America 2.0

Key West Stargazing Cruise Aboard Schooner America 2.0

From $64Book
Sunset Cruise - Mac's Place Dock

Sunset Cruise - Mac's Place Dock

From $79.95Book
Astronomer Guided Stargazing Cruise Aboard Schooner America 2.0

Astronomer Guided Stargazing Cruise Aboard Schooner America 2.0

From $82Book
Conch Republic- Bloody Battle - Parade/Battle Viewing/Sunset

Conch Republic- Bloody Battle - Parade/Battle Viewing/Sunset

From $89.95Book
Historic Schooner Sunset Sail from Downtown Key West

Historic Schooner Sunset Sail from Downtown Key West

From $109 / personBook
Tropical Drift: A Key West Sunset Cruise

Tropical Drift: A Key West Sunset Cruise

From $299.95Book
Overnight Charter - Includes Chef & Food

Overnight Charter - Includes Chef & Food

From $1,500Book
Multi-Day Charter - Includes Food & Chef

Multi-Day Charter - Includes Food & Chef

From $1,500 / personBook
Multi-Day Charter - Includes Chef and food

Multi-Day Charter - Includes Chef and food

From $1,500 / personBook
Sunset Sail + Wine School with Cayo Provisions

Sunset Sail + Wine School with Cayo Provisions

Price on booking pageBook
Private Powerboat Sunset Cruise

Private Powerboat Sunset Cruise

Price on booking pageBook
Private Sunset Sail

Private Sunset Sail

Price on booking pageBook
Sunset Sail

Sunset Sail

Price on booking pageBook
Sunset Cruise - Still Dreamin'

Sunset Cruise - Still Dreamin'

Price on booking pageBook
2 hour sunset trip

2 hour sunset trip

Price on booking pageBook
Sushi & Sunset Cruise

Sushi & Sunset Cruise

Price on booking pageBook
Women’s Sunset + Swim Sail

Women’s Sunset + Swim Sail

Price on booking pageBook
8/24/21 Sunset Cruise Sail For Tails SPCA Fundraiser

8/24/21 Sunset Cruise Sail For Tails SPCA Fundraiser

Price on booking pageBook
Sandbar, Dolphins, Sunset Combo

Sandbar, Dolphins, Sunset Combo

Price on booking pageBook
Conch Republic Bloody Battle on When And If

Conch Republic Bloody Battle on When And If

Price on booking pageBook
Land's End Sunset Sail

Land's End Sunset Sail

Price on booking pageBook
Private Sailing Cruise

Private Sailing Cruise

Price on booking pageBook
Tiki Bar, Snipes, Sandbar & Sunset

Tiki Bar, Snipes, Sandbar & Sunset

Price on booking pageBook

How to pick a sunset cruise

  • Under sail: classic schooners and sailboats. Quieter, and the crew often lets guests help raise the sails.
  • Big catamarans: more room to move around, often with a bar, music and the lowest price per person.
  • Dinner and champagne cruises: food or drinks included. Check the listing for what's in the price.
  • Private charters: the whole boat for your group, good for proposals, birthdays and families.

Most sunset cruises last about two hours and leave around an hour before sunset, so the start time moves through the year.