The 11th Annual Island Hopper Songwriter Fest: September 18 – 27, 2026
11th Annual Island Hopper Songwriter Fest. Returning Sept. 18-27, 2026, the award-winning, 10-day event will include star-studded performances by some of country music’s greatest singer-songwriters from Nashville and nationwide.
It kicks off on Captiva Island Sept. 18-20 2026; moves to Cape Coral Sept. 21-22; then to downtown Fort Myers Sept. 23-24; and ends at Fort Myers Beach Sept. 25-27.
Enjoy more than 60 artists and 80 shows. Most are free in small, intimate venues.
Limited-Time Offer: Stay 3 Nights, Get a 4th Night FREE!
Limited-Time Offer: Stay 3 Nights, Get a 4th Night FREE!
Make your Island Hopper experience even better with this exclusive offer! Enjoy an extra night on Captiva Island… Book a four night stay, use promo code STAYANDSAVE at checkout, and pay for only three nights!
To redeem this offer, select four consecutive nights when booking and enter coupon code STAYANDSAVE before completing your reservation. Your fourth night will be discounted automatically.
Relax, unwind, and enjoy more time exploring Captiva Island! Offer valid for stays Now through November 22, November 30 through December 18, 2026 (offer does not apply to the Harbour House). Book your stay today!
11th Annual Island Hopper Songwriter Fest. Returning Sept. 18-27, 2026, the award-winning, 10-day event will include star-studded performances by some of country music’s greatest singer-songwriters from Nashville and nationwide.
It kicks off on Captiva Island Sept. 18-20 2026; moves to Cape Coral Sept. 21-22; then to downtown Fort Myers Sept. 23-24; and ends at Fort Myers Beach Sept. 25-27.
Enjoy more than 60 artists and 80 shows. Most are free in small, intimate venues.
View a short video of last year’s Island Hopper Songwriter Fest: Link to video.
Limited-Time Offer: Stay 3 Nights, Get a 4th Night FREE!
Limited-Time Offer: Stay 3 Nights, Get a 4th Night FREE!
Make your Island Hopper experience even better with this exclusive offer! Enjoy an extra night on Captiva Island… Book a four night stay, use promo code STAYANDSAVE at checkout, and pay for only three nights!
To redeem this offer, select four consecutive nights when booking and enter coupon code STAYANDSAVE before completing your reservation. Your fourth night will be discounted automatically.
Relax, unwind, and enjoy more time exploring Captiva Island! Offer valid for stays Now through November 22, November 30 through December 18, 2026 (offer does not apply to the Harbour House). Book your stay today!
Hop on the Trolley… and Go. Stay at the Captiva Island Inn and enjoy FREE Transportation Around Captiva During Songwriter’s Fest on Captiva Island
The free hop-on, hop-off tram will run the festival route, with stops at South Seas, along Andy Rosse Lane and ‘Tween Waters Inn & Marina during the following times:
Friday, Sept. 18, 3pm – 10pm
Saturday, Sept. 19, 1:00pm – 10:00pm
Sunday, Sept. 20, 1:00pm – 6:00pm
Please Note: Uber/Lyft services are unavailable on the island. There are local transportation services, such as Sanibel Taxi, Sanibel Double D, and Majestic Transportation Services.
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1, 2 & 3 Bedroom Suites
1 Bedroom, 1 Bath, Full Kitchen, Sleeps 4.
$261.45 to $523.95/nt
1 Bedroom, 1 Bath, Full Kitchen, Sleeps 4.
$261.45 to $523.95/nt
2 Bedrooms, Bath & Full Kitchen. Sleeps 4.
$313.95 to $618.45/nt
2 Bedrooms, 2 Baths, Den & Full Kitchen.
$366.45 to $813.75/nt
3 Bedrooms, 3 Baths, Den & Full Kitchen..
$681.45 to $1,100/nt
Captiva Island 5-Bedroom Home Vacation Rentals
5 bedrooms, 2 fully-equipped kitchens and 2 dining areas, & outdoor pool.
$1,103.55 to $1,913.10/nt
5 Bedrooms, 4.5 Baths, Den & Full Kitchen.
$6,123.60 to $8,244.04/wk. Sat. to Sat.
