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The best time of year to go to Lisbon is in the late spring/early summer, or autumn months. April, May, and June will give you great weather without the massive crowds that flock here in July and August. September and October can also be very pleasant, with warm temperatures so you can still swim and enjoy water activities in Lisbon.
Some of the best sailing trips you can enjoy in Lisbon are on cruising catamarans. Book yourself a ticket on a group catamaran tour or even charter a whole catamaran to yourself and see the gorgeous coastline around Lisbon. See the Tower of Belem, enjoy lunch while cruising, stop for a swim, see the beaches of Cascais and enjoy seeing the city from the Tagus River.
Yes! Surfing is a popular activity in Lisbon. Some of the best beaches for surfing include:
Surfing lessons in Lisbon start around $30 per person per hour. You can also rent surfboards and go on your own for as little as $20/hour in Lisbon.