It is always smart to plan in an extra day at the beginning of a cruise to account for potential delays based on flight schedules or potential weather.  Whenever we travel during winter, we always plan to arrive in the departure port a day early.  We either stay close to the airport so we can take advantage of the cruise line transfers or stay close to the port at a hotel with a cruise line shuttle.  We are fortunate that we live near a major airport with direct flights to many locations.  At most, we plan for only one layover and choose our airports carefully.  Watch the airline schedules carefully, as they may change the itinerary without notification.

If you don’t plan extra time at your embarkation and debarkation port, you may not experience the the location at any level.  This happened on our first Mediterranean cruise that ended in Barcelona.  The cruise line did not have an excursion that we could take, so we went directly to the airport.  On our second Mediterranean cruise we departed from Barcelona, so we spent an extra three days prior to the cruise to see Barcelona.  That was really worth the extra time and cost.  We have arranged similar stays at the end of a cruise.  For example, on a cruise the ended in Yokohama (Tokyo), we decided to stay three extra days in Tokyo since is it unlikely we will visit Japan anytime again soon.  When planning extra days, I have some suggestions:

Ask the cruise line

Ask your agent or check with the cruise line to see whether they have any pre- or post-cruise excursions.  Many lines offer 2-5 day packages which include someone to help you get around.  These are often called Cruisetours.  Cruisetours have been popular for many years, providing a chance to see the rugged terrain and wild animals in Alaska.  South American cruises offer tours to see inland locations (e.g., Iguazu Falls or Machu Picchu).  The same is true about cruises to other parts of the world.  Keep in mind that these tours may cost more than ones you can book on your own, but they guarantee you will get to your ship and they are packaged with your cruise.

If you plan to stay in the same city for a few days, check with the cruise line to find out whether they have hotel packages.  Be ware that the cruise line package may be more expensive, but they may include extras, such as meals, tours, guides, and transfers to/from airport/ship.  Compare your prices to determine which is best.

Book your own tour

There are many third-party excursion providers and many cater to cruisers, promising that they will get you back to your ship on time.  However, the burden is still on you as the traveler to make sure you get back on time.  Likewise, check out the reputation of the tour provider and always allow sufficient time to get to the ship.

Book you own hotel

This is less risky than booking a third-party multi-day tour.  It is easy to research hotels on the Internet.  Many offer packages that include meals, theater tickets, or other extras.  If you are not booking directly with the hotel (e.g., booking.com, hotels.com, priceline.com, etc.), verify your reservation directly with the hotel, especially in foreign country.  I never pay for the hotel in advance, even though it saves money, since I may want to change the reservation closer to the cruise date.  On a final note, make sure you consider hidden costs, such as taxes/fees, meals not included, transfer to/from the airport/ship.  Note that taxi to the airport in London or Sydney can cost $100.  Since you will have a lot of baggage, public transit is not normally a good option.  Check in advance with the hotel whether they have a shuttle you can use – whether free or for a small fee.

I prefer to book hotels when I am staying in the same city the the ship uses.  I have done this for Barcelona, Venice, London, Hong Kong, Tokyo, Sydney, Auckland, and San Francisco.  We have a preference for certain hotel chains or local hotels.  For example, in Tokyo, we stayed at the Gate Hotel Asakusa Kaminarimon, which is a local hotel located at the gate of Sensō-ji, a large Buddhist temple,  and easy walking or subway access to many locations.  We took a post-cruise excursion that went by our hotel and asked them to drop us off nearby, which they did.  This way, we got our transport to the hotel plus an escorted tour of city locations not close to the hotel.  Really worked out great.  We have found that the cruise lines will work with us to facilitate our experience. Visit our Destination Tokyo post to learn more of our experiences in Tokyo.

Most large cities now have hop-on hop-off buses.  Get a two-day pass, then ride a circuit the entire route (usually about 2-3 hours).  You can then stay on the bus and get off where you wish.  We search for hotels that are fairly close to a bus stop to make it easier on ourselves.

Tell us about you pre- and post-cruise experiences, but commenting below.