Island Hopper Songwriter’s Festival, a two-week event throughout Sanibel, Captiva and Fort Myers beaches, is kicking off this upcoming weekend! We invite you to enjoy exclusive performances from more than 40 nationally-acclaimed songwriters at venues across our islands—with West Wind Island Resort as the perfect spot to relax and retreat between the non-stop entertainment.With FREE performances from some of the greatest nationally-acclaimed and Billboard chart songwriters, you sure won’t want to miss this event!

In celebration for the upcoming festival, we’ve compiled the ultimate “411” guide to your weekend at the Island Hopper Songwriters Fest including a list of venues with distance from West Wind Island Resort, schedule of events, transportation information, and other useful tips to make your first Island Hopper experience something to remember! Island Hopper Logo


West Wind Island Resort is less than 20 minutes away from each venue (which is only about a 50-minute bike ride), but far enough away so you can still find that peaceful beach setting when you need it when you stay with us. For a printable version of the full schedule of events, Click here!

Old Captiva House and Crow’s Nest
15951 Captiva Dr. Captiva, 16 min car ride

Doc Fords
5400 Plantation Road, Captiva, 20 min car ride

Captiva Island Inn
11508 Andy Rosse Ln., Captiva, 20 min car ride

Cantina Captiva
14970 Captiva Drive, Captiva, 19 min car ride

Key Lime Bistro
11509 Andy Rosse Ln., Captiva, 20 min car ride

Mucky Duck
11546 Andy Rosse Ln., Captiva, 20 min car ride

RC Otters
11509 Andy Rosse Ln., Captiva, 19 min car ride

South Seas Island Resort
5400 Plantation Rd., Captiva, 21 min car ride


Toll Info

If you’re planning on going off and on the island, don’t forget to have some cash on you for the Sanibel Causeway Toll. There are no performances off Island for the first weekend, but just in case you feel like exploring the area, make sure to have the $6 on you.



Bicycling is a very popular activity on the island. While you may not be able to walk to and from these destinations, we have plenty of recommendations on how to get you where you need to go!

  • Park and Ride from Chadwicks Square, stopping at Andy Rosse Lane, which will get you to Keylime Bistro, Mucky Duck and RC Otters. (5400 Plantation Rd, Captiva, FL)
  • Eat at RC Otters, Cantina Captiva, Captiva Pizza or Keylime Bistro and get a free ride on the S Car Go back to your hotel, or the beach!
  • Bicycle or Segway Rentals

o   Billy’s Bikes & Rentals located at 1509 Periwinkle Way, Sanibel (Closed Sunday)

o   Finnimore’s Cycle Shop located at 2353 Periwinkle Way, Sanibel (Open 7 days a week


Need a taxi?

o   Sanibel Taxi Toll Free: (888) 527-7806

o   Sanibel Cab Company Phone: (239) 472-0151

o   Tip: the cost of a taxi from Southwest Florida International Airport (RSW) to Fort Myers would be approximately $35 for 1 to 3 passengers


Biking Info

If you are going to be biking to and from your destinations, click here to view more information on biking paths and road rules.

Click here for a map of Sanibel and Captiva, provided by The Sanibel Chamber of Commerce.



If you’re heading to the beach, public parking lots have park-and-pay machines. The cost is $2 per hour, and each machine produces a receipt for you to put on your dash.  The machines do not make change, but they accept $1, $5 and $10 bills, as well as Visa and MasterCard credit cards. Handicapped parking is free on Sanibel.

Roadside parking is not allowed, and some areas are restricted to those with permits.  Permits are available to non-residents at a cost of $80 to $160.  They are available at the Sanibel Recreation Center located at 3880 Sanibel-Captiva Road, Sanibel Island, FL.

Shopping, restaurants, and local attractions have their own free parking available, but it may be limited if a performance is popular. It’s best to carpool, take a taxi, or carve out some extra time for a bike ride if the event is packed.


Local Tips

  • Be sure to apply sunscreen frequently avoid getting a sunburn while outdoors. Even if it seems overcast for a while, it’s still important to protect your skin from harmful rays. In addition to sunscreen, wearing a hat would also be a good idea.
  • Hydrate often. Don’t go on a long bike ride without a bottle of water or sports drink.
  • Turns out, it’s pretty sunny in the sunshine state. Especially on Sanibel Island! Don’t forget to protect your eyes with shades.
  • Attire is pretty casual and laid back on Sanibel Island.
  • Up until October 31st, it’s turtle nesting season. Please do not pick up or move any of the turtles you may find on the beach.


If you need downtime from all of the festivities, enjoy relaxing by our pool, take a walk down the beach, or click here to find out more about the different adventures that await you in the Southwest Florida area.

If you still haven’t booked your room for the festival, there is still time! Take advantage of our specials and receive a free night’s stay—click here for details.


…And most importantly, Enjoy!

Contact our front desk at (800) 824-0476 or (239) 472-1541 check on room availability, so you can TRULY enjoy this great event while experiencing TRUE Sanibel at West Wind Island Resort.