Bermuda is at its best in April and May: warm enough for the beach, before the summer heat, the cruise season and the start of hurricane season in June. From next spring it also gets easier to reach from the American Midwest. On 28 October 2026 Aeroroutes reported that United has opened bookings for a new Chicago O’Hare to Bermuda route, once a week on Saturdays from 3 April 2027, with a Boeing 737 MAX 8. The outbound flight leaves Chicago at 09:05 and lands at 14:45; the return leaves Bermuda at 15:55 and arrives in Chicago at 18:02.
One flight a week sets the rhythm of the trip: Saturday to Saturday, seven nights. That is about right for an island chain that is small, but slow to cross without a car. If you are not starting in Chicago, O’Hare works as a connecting point from much of the United States.
Why spring, and what the weather is like
Bermuda is in the Atlantic, far north of the Caribbean, and its winters are much cooler. The climate chart on Wikivoyage gives average highs of 22.1°C in April and 24.3°C in May, against 30.1°C in August. April is also one of the driest months, with about 87 mm of rain. Hurricane season runs from June to November, and gales are common in winter, so spring is the calm, mild window.
The honest limit: with one flight a week, there is no next-day option if your plans change. If you want the warmest weather of the two months, May runs about 2°C warmer than April on the same chart.
Getting around without a car
Visitors cannot rent a normal car in Bermuda. According to Wikivoyage, rental cars are banned except for the Renault Twizy, a two-seat electric vehicle, and only residents can own cars. That shapes everything else:
- Buses and ferries connect the whole island to Hamilton, and ferries cross the Great Sound to the Royal Naval Dockyard and run between the Dockyard and St. George’s. Passes valid on both cover 1 to 31 days and cost $12 to $55, and a single trip is $5 in cash (prices listed on Wikivoyage, November 2026).
- Taxis are metered and wait at Hamilton’s Front Street and the main hotels.
- Mopeds and scooters are popular, but traffic drives on the left on narrow roads. Wikivoyage warns that “road rash” is a common injury among tourists.
Choosing where you sleep matters more than usual. Stay near a ferry stop or a main bus route, and the island opens up.
A week from Saturday to Saturday
The south shore beaches. Horseshoe Bay is the best-known stretch of pink sand. Elbow Beach, Tobacco Bay and St. Catherine’s Beach are other good swims.
St. George’s. Bermuda’s first capital, near the airport, is a UNESCO World Heritage site together with its forts. Give it a full day for the lanes, the old buildings cared for by the Bermuda National Trust and the beaches nearby.
The Royal Naval Dockyard. At the western tip, reached by ferry from Hamilton. It is where the largest cruise ships dock, so check the cruise calendar and go on a quieter day if you can.
The Bermuda Railway Trail. The island’s railway was dismantled in 1948, and its bed is now a walking trail from St. George’s towards Somerset in the west. You can walk short stretches between bus stops.
Underground. Crystal Caves and Fantasy Caves, in Hamilton Parish, are a good plan for a windy or rainy morning.
Before you book
Bermuda can be expensive. Wikivoyage explains that a steep import tax pushes up the price of goods in shops, and that airport charges make air fares higher than to many Caribbean islands. The transport pass is the easiest way to keep daily costs down.
Entry rules depend on your passport. For British passport holders, the UK Foreign Office says you can visit without a visa for up to 180 days in a 12-month period, with a return or onward ticket, and your passport must be valid for the length of your stay. All air passengers complete a Bermuda arrival card before landing, or on paper at the airport. If you need a visa for the United States, Canada or the United Kingdom, Wikivoyage notes that you must hold a valid multiple-entry visa for the country you transit through. Check the official rules for your own nationality before you travel.
For a longer trip, our ten-day USA itinerary can start or end in Chicago. Practical details on money, health and getting around are in our Bermuda travel guide, and nearby islands are in the Caribbean guides. If April or May works for you, book the Saturday seat first, then a room near a ferry stop.
Cover photo: P. Hughes, CC BY-SA 4.0, via Wikimedia Commons
