Tobago Bay 9.5-Inch Shorts

Free Expedited Shipping on Orders $200+

FREE 3-DAY SHIPPING WITH $200 HURDLE VALID UNTIL 6:59AM PT JUNE 15, 2026. FREE 2-DAY SHIPPING WITH $200 HURDLE VALID FROM 7AM PT JUNE 15, 2026 UNTIL 6:59AM PT JUNE 17, 2026. Free Expedited Shipping offer is valid only for orders of $200 or more on eligible products, shipped within the U.S. (excluding U.S. territories). The $200 threshold must be met in a single, pre-tax transaction and after applicable discounts are applied. Purchase of Tommy Bahama furniture, packaging, shipping, handling, taxes and prior purchases do not qualify toward the $200 threshold. Orders will ship via FedEx 3-day air shipping or FedEx 2-day air shipping within the 48 contiguous states and FedEx 2-day air shipping to Alaska and Hawaii. If you choose another shipping option, additional charges will apply.

Free shipping is valid only for orders of $100-$199.99 on eligible products shipped within the U.S. (excluding U.S. territories). The $100 threshold must be met in a single, pre-tax transaction and after applicable discounts are applied. Purchase of Tommy Bahama furniture, packaging, shipping, handling, taxes and prior purchases do not qualify toward the $100 threshold. Orders will ship via FedEx Ground shipping within the 48 contiguous states and standard 2-day air shipping to Alaska and Hawaii. If you choose another shipping option, additional charges will apply.

Offers valid only at tommybahama.com. Not valid at Tommy Bahama full price stores, Tommy Bahama Outlets, Tommy Bahama Restaurants, Tommy Bahama Resorts, Tommy Bahama Home Store, or tommybahamafurniture.com. Offers do not apply to certain oversized items, certain flammable items, handling fees, out-of-stock items, previous purchases or Tommy Bahama furniture and cannot be combined with any other shipping offer. Shipping charges will be automatically taken off the invoice at the final stage of checkout. Items cannot be shipped to P.O. boxes or military APO/FPO addresses. Offer not available on all products and is subject to change without notice. Void where prohibited.

Flipside

TERMS & CONDITIONS

Earn a $50 Award for every $175 you spend in store or at tommybahama.com May 15 – June 21, 2026. Use your $50 Award during the redemption period, June 22 – July 12, 2026, toward a $100 minimum purchase at full-price retail stores, tommybahama.com, our Restaurants, and Marlin Bars.

THE OFFER

OFFER TO EARN AWARDS EXPIRES JUNE 21, 2026, ONLY WHILE SUPPLIES LAST. Awards may only be earned with purchases from U.S. Tommy Bahama full-price retail stores and tommybahama.com (U.S. shipments only, excluding U.S. territories). Awards may ship separately. Offer not valid at Tommy Bahama Resorts, Restaurants, Marlin Bars, Outlets, Home Stores, or tommybahamafurniture.com. Threshold must be met in a single, pretax transaction and after applicable discounts are applied. Purchase of gift cards, furniture, shipping, taxes, fees, donations, and prior purchases do not qualify toward the minimum purchase amount. Currency values are in U.S. Dollars. Tommy Bahama reserves the right to void an Award in the event the qualifying purchase is returned. Offer not valid for employees of Tommy Bahama. Offer void where prohibited. Offer subject to change, modification, or termination.

AWARD CARD REDEMPTION

ALL AWARDS EXPIRE JULY 12, 2026. Valid only at Tommy Bahama U.S and Canadian full-price retail stores, Tommy Bahama Restaurants and Marlin Bars (dine-in only, not during Happy Hour, not valid on alcohol, not valid at Grapefruit Basil®), and tommybahama.com (U.S and Canadian shipments only, excluding U.S. territories and Quebec). Not valid at Tommy Bahama Resorts, Outlets, Home Stores, or tommybahamafurniture.com. Valid only for a single transaction with a $100 minimum purchase. Limit one (1) Award per transaction, and in restaurants per table. Purchase of gift cards, furniture, shipping, taxes, fees, donations, gratuity, and prior purchases do not qualify toward the $100 threshold. Not valid toward purchases of gift cards, furniture, shipping, taxes, fees, donations, gratuity, and prior purchases. Must be presented at time of purchase and may not be combined with any other promotion or discount. Currency values are in U.S. Dollars. When used in Canada, the transaction total is converted from local currency to U.S. Dollars, at prevailing OANDA published exchange rates, and deducted from the card’s balance. Void if altered or transferred for value. Awards are intended as a free promotion from the merchant to the individual and are not redeemable for cash. Merchandise purchased in connection with Awards may not be returned for a cash refund unless prohibited by law. Tommy Bahama reserves the right to void an Award in the event the qualifying purchase is returned. Not replaceable if lost, stolen, or destroyed. May not be used by employees of Tommy Bahama. For questions, please call Guest Services at 866.986.8282. Use constitutes acceptance of these terms and conditions. Offer void where prohibited.

Flipside

TERMS & CONDITIONS

Earn a CAD $65 Award for every CAD $225 you spend in store or at tommybahama.com May 15 – June 21, 2026. Use your CAD $65 Award during the redemption period, June 22 – July 12, 2026, toward a CAD $130 minimum purchase at full-price retail stores and tommybahama.com.

THE OFFER

OFFER TO EARN AWARDS EXPIRES JUNE 21, 2026, ONLY WHILE SUPPLIES LAST. Awards may only be earned with purchases from Canadian Tommy Bahama full-price retail stores and tommybahama.com (Canadian shipments only, excluding Quebec). Awards may ship separately. Offer not valid at Tommy Bahama Resorts, Restaurants, Marlin Bars, Outlets, Home Stores, or tommybahamafurniture.com. Threshold must be met in a single, pretax transaction and after applicable discounts are applied. Purchase of gift cards, furniture, shipping, donations, taxes, fees, and prior purchases do not qualify toward the minimum purchase amount. Currency values are in Canadian Dollars. Tommy Bahama reserves the right to void an Award in the event the qualifying purchase is returned. Offer not valid for employees of Tommy Bahama. Offer void where prohibited. Offer subject to change, modification, or termination.

AWARD CARD REDEMPTION

ALL AWARDS EXPIRE JULY 12, 2026. Valid only at Tommy Bahama Canadian and U.S. full-price retail stores, Tommy Bahama Restaurants and Marlin Bars (dine-in only, not during Happy Hour, not valid on alcohol, not valid at Grapefruit Basil®), and tommybahama.com (Canadian and U.S. shipments only, excluding Quebec and U.S. territories). Not valid at Tommy Bahama Resorts, Outlets, Home Stores, or tommybahamafurniture.com. Valid only for a single transaction with a CAD $130 minimum purchase. Limit one (1) Award per transaction, and in restaurants per table. Purchase of gift cards, furniture, shipping, taxes, fees, donations, gratuity, and prior purchases do not qualify toward the CAD $130 threshold. Not valid toward purchases of gift cards, furniture, shipping, taxes, fees, donations, gratuity, and prior purchases. Must be presented at time of purchase and may not be combined with any other promotion or discount. Currency values are in Canadian Dollars. When used in the U.S., the transaction total is converted from local currency to Canadian Dollars, at prevailing OANDA published exchange rates, and deducted from the card’s balance. Void if altered or transferred for value. Awards are intended as a free promotion from the merchant to the individual and are not redeemable for cash. Merchandise purchased in connection with an Award may not be returned for a cash refund unless prohibited by law. Tommy Bahama reserves the right to void Awards in the event the qualifying purchase is returned. Not replaceable if lost, stolen, or destroyed. May not be used by employees of Tommy Bahama. For questions, please call Guest Services at 866.986.8282. Use constitutes acceptance of these terms and conditions. Offer void where prohibited.

Early Holiday Booking Promotion

Book your holiday party with us before November 15 and get a $50 award for every $250 you spend on it.

THE OFFER

OFFER TO RECEIVE AWARDS EXPIRES NOVEMBER 15, 2025. AWARDS CANNOT BE USED AS PAYMENT TOWARD THE EVENT FOR WHICH THEY WERE EARNED. AWARDS MAY ONLY BE REDEEMED JANUARY 1–31, 2026 AT TOMMY BAHAMA RESTAURANTS AND MARLIN BARS. $500 Food and Beverage minimum applies. To take advantage of this offer, your contracted event must occur between November 15, 2025 and January 15, 2026 (excluding December 31, 2025). A signed contract must be received by Tommy Bahama no later than 11:59 pm PST on November 15, 2025. The number of Awards earned will be based on actual food and beverage charges only after any applicable discounts are applied; additional charges such as rentals, floral, valet, tax or gratuity are excluded. Awards will be issued approximately 72 hours after the event. This offer cannot be combined with any other offer. Tommy Bahama reserves the right to change or revoke this offer at any time and to void Awards in the event the contracted event is cancelled. Additional restrictions apply, see “Redemption of Awards” below. Offer void where prohibited.

AWARD CARD REDEMPTION

EOFFER TO REDEEM AWARDS EXPIRES JANUARY 31, 2026. AWARDS CANNOT BE USED AS PAYMENT TOWARD THE EVENT FOR WHICH THEY WERE EARNED. AWARDS MAY ONLY BE REDEEMED JANUARY 1–31, 2026 AT TOMMY BAHAMA RESTAURANTS AND MARLIN BARS (DINE IN ONLY, EXCLUDES HAPPY HOUR AND ALCOHOL). Not valid at Grapefruit Basil®, Tommy Bahama full-price retail stores, Outlets or Resorts, tommybahama.com, tommybahamafurniture.com or the Tommy Bahama Home Store. Maximum of one Award can be redeemed in a single transaction. Awards not valid toward purchases of gift cards, gift services, alcohol, shipping, handling, taxes, gratuity, and prior purchases. Awards must be presented at time of purchase and may not be combined with any other promotion or discount. Void if altered or transferred for value. Awards not redeemable for cash. Awards are not replaceable if lost, stolen, or destroyed. May not be used by employees of Tommy Bahama. For questions, please call Guest Services at (866) 986-8282. Use constitutes acceptance of these terms and conditions. Awards are void where prohibited.

Rated 5 out of 5 by jake8282 from Best Shorts Ever Designed!! PLEASE PLEASE bring back all these Tobago Bay 9.5 inch shorts. Especially Light Sky Color. Please, I beg you. Greatest shorts ever.

Date published: 2026-06-11

Rated 5 out of 5 by Nahh from My favorite What?!? Discontinued??? I lost weight wand wa going to order 6 pair to replace my old ones. Nooooo

Date published: 2026-04-11

Rated 5 out of 5 by RANDYLL from BRING BACK TOBAGO BAY SHORTS!!! You really need to bring back the Tobago bay shorts. I have both the New Cirrus version which seems to have taken their place, but the Tobago Bay shorts are much better. Just rename them Montego Bay shorts & bring them back. The Cirrus version seem to loosen up & tend start to fall off of you even when tied. Never have that problem w/ the Tobago Bay. BRING THEM BACK!

Date published: 2026-04-02

Rated 5 out of 5 by RBreview from Extremely comfortable shorts. Extremely comfortable shorts. Tommy Bahama absolutely needs to get the Tobago Bay 9.5-Inch Shorts back in stock! I would buy three pairs of each color just in case they get discontinued (hopefully they’re not ready).

Date published: 2025-10-09

Rated 5 out of 5 by H J R from Nice shorts Extremely comfortable shorts! I have them in every color I could find.

Date published: 2025-06-29

Tobago Bay 9.5-Inch Shorts Reviews - page 2

Tobago Bay 9.5-Inch Shorts

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Tobago Bay 9.5-Inch Shorts

Shipping Restrictions

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