Visit Bermuda in the off-seasons for the cheapest airfare, hotel and cruise prices. Bermuda actually doesn't have Caribbean-like weather, contrary to popular belief. It is a semi-tropical island with moderate temperatures around the 60s and 70s for the bulk of the year. In the winter months, though, it can get in the 40s and 50s. Summer months are the most popular time to visit, so the prices will be at their highest. From March to April is the rainy season, which will be less expensive. Bermuda is susceptible to tropical storms and hurricanes from late June through October. For the cheapest prices, consider vacationing from February to late March. Try to book at least six months in advance for cheaper rates as well.
If you choose to fly to Bermuda, keep in mind that eight airlines serve Bermuda International Airport (BDA). Comparing these airlines will help you find the cheapest rates for your vacation. It is usually cheapest to fly directly from the East Coast, and some airlines offer summer packages if you want to fly during the high season.
Consider traveling to Bermuda on a cruise ship, as several cruise lines operate cruises every week, mainly from Boston, Fort Lauderdale, New York and Charleston (ports that offer flight deals from many states in the United States). Ships will dock at different locations in Bermuda, and you usually have a full day to explore that certain city or town. Many cruise lines offer deals, especially during the off-season. The benefit with cruises is that, although you don't spend all your time vacationing on Bermuda, your food is included in the cruise price, and you don't have to worry about figuring out how to jump from the different islands. You also have the advantage of booking discount excursions on the boat for Bermuda.
Cruise lines that routinely offer deals include Norwegian Cruise Line and Royal Caribbean, with prices that have been as low as $600 for seven days.
If you are a golfer, Bermuda is beneficial for you. The islands have nine golf courses--more than fast-food restaurants. This means that Bermuda has the most golf courses per square mile than any other place on Earth. You can reap the benefits of being a golfer here because the best time to play is in winter--the off-season when it isn't as hot. Some golf courses provide travel packages for hotel accommodations and golf rates, such as the government-owned Port Royal or Riddle's Bay.
Driving rental cars isn't allowed in Bermuda because of the dangerous road conditions, so the cheapest way to get around during your Bermuda holiday is via the transportation offered to travelers. Take a shuttle bus from the airport to your hotel (not a taxi as they are very expensive), and the Bermuda Breeze buses to get around the islands (an unlimited weekly pass runs around $45).
When you go off on your own to explore, you might not want to take the buses to go on normal routes. If this is the case, one of the best and cheapest ways to see Bermuda is by bicycle or moped. With 22 miles of bike paths, you can see the entire island with this method. The Bermuda Railway Trail (you can hike this trail on foot, too) follows an old rail bed and goes across the entire string of eight islands that make up the inhabited parts of Bermuda. This provides great views of the water, bluffs and houses. Bike rentals are about $50 per week and some hotels even offer the bicycles for no charge. If you don't like mopeds, ask for a "pedal bike" when renting.