The Vacation Shop

Vacation-ready essentials, including men’s swimwear, beachwear, and summer layers built for wherever you’re headed.

19 Items
Man wearing turquoise swim trunks with dark blue wave pattern and drawstring waist.
Blue swim shorts with an all-over wave pattern in varying shades of blue and teal.
Men's swim trunks with blue and turquoise wave pattern throughout the fabric.
Man wearing blue wave-patterned swim trunks with drawstring waist and scalloped hem.
Men's swim trunks with blue wave pattern and gray compression shorts underneath.
Close-up of blue and teal fabric with wave-like pattern details woven throughout.
Man wearing teal and navy wave-patterned swim shorts with elastic waistband standing outdoors.

Anchor Trunk

$88
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Man wearing light blue seersucker swim trunks with vertical stripe pattern and drawstring waist.
Light blue seersucker Bayberry swim trunks with a drawstring elastic waistband.
Man wearing light blue and white striped seersucker swim trunk shorts, shown from back view.
Man wearing light blue seersucker swim trunks with vertical stripe pattern and drawstring waist.
Man wearing blue and white striped seersucker swim trunks with light blue inner shorts and drawstring.
Light blue and white seersucker fabric with diagonal striped texture pattern throughout.
Shirtless man wearing light blue seersucker swim trunks with drawstring standing outdoors.

Bayberry Trunk

$88
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sky-blue-leaves-bungalow-trunk
Light blue bungalow swim trunks with white tropical leaf pattern on a white background
Man wearing sky blue swim trunks with white leaf pattern shown from behind.
Sky blue swim trunks with cream leaf pattern and elastic waistband displayed on male model.
Man wearing sky blue swim trunks with white leaf pattern and green compression shorts underneath.
Man wearing sky blue swim shorts with white leaf pattern and drawstring waistband.
Sky blue fabric with white leaf patterns printed across textured folds.
Man wearing coral and cream checkered swim shorts with black palm tree print and tan drawstring.

Bungalow Trunk

$88
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Man wearing navy shibori-patterned swim trunk with cream drawstring, shown from waist down.
Blue diamond patterned Bayberry Trunk with a drawstring on a white background
Man wearing navy shibori patterned swim trunk with geometric diamond print design.
Man wearing navy shibori patterned swim trunk with diamond geometric design and drawstring.
Man wearing navy shibori patterned swim trunks with light blue liner shorts and drawstring waist.
Swatch of the Person wearing Blue diamond patterned Bayberry Trunk material
Man wearing navy shibori patterned swim shorts stands on sandy beach near dark foliage.
Man wearing navy seersucker swim trunks with geometric pattern and drawstring waist outdoors.

Bayberry Trunk

$88
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Black athletic hat with a Fair Harbor Surf Supply patch and mesh back panel.
Black athletic hat with perforated mesh panels throughout, adjustable back strap, and solid front panels.

Athletic Hat

$38

Bestseller

Man wearing a white oxford button-up shirt with rolled sleeves and a chest pocket.
White long-sleeved Oxford shirt with button front closure and navy trim at collar.
Man wearing a white button-up Oxford shirt with long sleeves and teal patterned shorts.
Man wearing a white oxford shirt with long sleeves and a collar, shown from behind.
Man wearing a light blue striped oxford shirt with button front and chest pocket detail.
Man wearing a light blue striped oxford shirt and dark navy pants standing in front of a truck.

Salty Oxford Shirt

$128
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Man wearing navy blue shorts with a zipper and button fly, paired with casual sneakers.
Navy blue shorts with a flat front, button closure, and side pockets displayed on a neutral background.
Man wearing navy blue shorts with rear pockets and button closure paired with canvas shoes.
Man wearing navy blue shorts with a beige long-sleeved shirt, showing front pocket detail.
Man wearing navy blue shorts with a beige long-sleeved hoodie and dark sneakers.
Close-up of navy ribbed fabric showing texture and diagonal folds in the material.
Man wearing a teal polo shirt and beige shorts standing outdoors near a wooden building.

Horizon Short

$98
Man wearing red and blue striped swim trunks with a drawstring waistband and blue elastic trim.
Red bayberry trunks with a navy waistband and subtle wave pattern with a white drawstring on a white background.
Man wearing red and blue wave-patterned swim trunks with blue waistband shown from behind.
Men's swim trunks with red and blue wave pattern, blue waistband, and drawstring closure.
Man wearing purple swim trunks with red wave pattern and blue waistband with drawstring.
Red and blue wave-patterned swim trunk with blue waistband and back pocket detail.
Red and blue wavy striped fabric with textured woven surface showing curved wave patterns.
Shirtless man wearing light blue seersucker swim trunks with drawstring standing outdoors.

Bayberry Trunk

$88
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Navy and red striped swim trunks with a white drawstring waistband on a man.
Navy and red striped swim trunks with drawstring waistband and side pockets.
Man wearing navy swim trunks with two red horizontal stripes across the back.
Navy swim trunk with horizontal red stripes across the thighs and a small patch detail.
Men's swim trunks with navy base, red horizontal stripes, and gray leg trim.
Man wearing navy swim trunks with red horizontal stripes and a drawstring waist.
Red and navy blue striped swim trunk fabric with textured weave detail displayed flat.
Man wearing navy swim shorts with red horizontal stripes standing on a beach.

Anchor Trunk

$88
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Man wearing a white crew neck short-sleeve t-shirt paired with dark blue jeans.
White kismet t-shirt on a white background
Man wearing a white short-sleeved crew neck t-shirt, shown from behind with dark jeans.
Close up of white kismet t-shirt, showing the fabric and brand logo patch. Paired with grey one pants.
Man wearing a white crew neck t-shirt with dark blue jeans and beige canvas shoes.
Man wearing a white short-sleeve tee with text graphic on the chest.
Man wearing white short-sleeve t-shirt with small text graphic on chest leaning against wooden railing.

Kismet Tee

$48
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Bestseller

Person wearing a pair of green wave Bayberry swim trunks with a drawstring waistband.
A pair of green wave Bayberry swim trunks with a drawstring waistband.
Man wearing teal swim trunks with horizontal wave pattern, shown from behind.
Man wearing teal green wave-patterned swim trunks with drawstring waistband and side pocket.
Man wearing teal textured swim trunks with light blue contrast liner and white drawstring.
Man wearing teal green swim trunks with a textured wave pattern and drawstring waistband.
Swatch of green waves fabric
Shirtless man wearing light blue seersucker swim trunks with drawstring standing outdoors.

Bayberry Trunk

$88
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Navy swim trunks with light blue horizontal stripes and a white drawstring waistband.
Navy and light blue striped swim trunk with white drawstring and elastic waistband.
Men's swim trunks in navy with light blue horizontal stripes and elastic waistband.
Men's swim trunk with light blue and navy horizontal stripes and drawstring waistband shown from the side.
Man wearing navy swim trunks with light blue horizontal stripes and gray panel on right leg.
Man wearing navy swim trunks with light blue horizontal stripes and drawstring waistband.
Light blue and dark blue striped fabric with diagonal ribbed texture and natural folds.
Man wearing navy swim shorts with red horizontal stripes standing on a beach.

Anchor Trunk

$88
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Bestseller

Man wearing a light blue striped oxford shirt with long sleeves and button-front closure.
Light blue and white striped oxford button-down shirt with long sleeves and chest pocket.
Man wearing a light blue striped oxford shirt with long sleeves and a collar, shown from behind.
Man wearing a light blue and white striped oxford shirt with long sleeves and button front closure.
Man wearing light blue striped oxford shirt with gray pants and dark sneakers.
Man wearing a light blue striped oxford shirt with button front and chest pocket detail.
Man wearing a light blue striped oxford shirt and dark navy pants standing in front of a truck.

Salty Oxford Shirt

$128
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Bestseller

Man wearing khaki five-pocket pants with a patterned belt and casual sneakers.
Khaki five-pocket pants with a flat front, button closure, and straight leg silhouette.
Man wearing khaki five-pocket pants with back pockets visible and woven belt detail.
Man wearing khaki five-pocket pants with a braided leather belt and pink shirt.
Man wearing a coral polo shirt and khaki five-pocket pants with a brown belt.
Close-up of khaki cotton twill fabric showing diagonal weave pattern and soft texture.
Man wearing khaki five-pocket pants and gray shirt leaning against blue vintage truck.
Man wearing khaki five-pocket pants with a gray button-up shirt and brown leather boots.

Horizon 5-Pocket Pant

$138
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Man wearing sky blue swim trunks with an all-over shell pattern and tan drawstring.
Sky blue swim shorts with an all-over shell print pattern and tan drawstring waistband.
Sky blue swim trunks with an all-over shell pattern and back pocket detail displayed on a man.
Man wearing light blue swim trunks with a repeating shell pattern and drawstring waistband.
Man wearing sky blue swim trunks with shell pattern and built-in inner shorts.
Sky blue fabric with an all-over shell pattern featuring radiating line details throughout.
Man wearing navy polo shirt and light blue patterned shorts standing in garden setting.
Man wearing sky blue shorts with an all-over shell pattern and front pocket detail.

Bayberry Trunk

$88
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Person wearing a pair of blue 8 inch one shorts with a drawstring on a white background. Paired with a tshirt and white sneakers.
Navy 8 inch one shorts with a drawstring on a white background
Person wearing a pair of navy 8 inch one shorts with a drawstring on a white background. Showing the liner underneath.
Person wearing a pair of navy 8 inch one shorts with a drawstring on a white background. Showing the side view.
Man standing on patio wearing navy one short and tshirt, with drink in hand. Colorful table and chairs behind him.

One Short

$78
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Washed red long-sleeve rashguard with crew neckline and raglan sleeves displayed flat against white background.

Kids Anchor Rashguard

$48
Man wearing blue swim trunks with vertical red and white stripes and drawstring waist.
Blue and red striped swim trunks with a drawstring waist and vertical ribbed texture pattern.
Men's swim trunks with blue, red, and white vertical stripes and elastic waistband.
Men's swim trunk with blue and red vertical stripe pattern and drawstring waist.
Man wearing blue striped swim trunk with red vertical stripes and turquoise mesh lining detail.
Fabric with horizontal stripes in blue, coral, and navy blue tones arranged diagonally across the surface.
Man standing in bungalow patterned short outside by edge of pool looking across the pool.
Man wearing colorful swim shorts with a palm tree pattern outdoors with pool behind him.

Bungalow Trunk

$88
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Man wearing a gray long-sleeved rashguard with an anchor graphic on the chest.
Gray long-sleeve rashguard with crew neckline and raglan sleeves displayed flat against white background.
Man wearing light gray long-sleeve rashguard viewed from behind against white background.
Man wearing a light gray long-sleeve rashguard with a crew neckline and contrasting seams.
Gray long-sleeved rashguard worn with blue wave-patterned swim trunks, showing chest and side view.
Man wearing a gray long-sleeve rashguard with blue patterned swim shorts and tan sandals.
Gray rashguard fabric with textured weave and diagonal folds creating subtle shadows.
Man wearing a white long-sleeve rashguard and patterned swim shorts standing outdoors.

Anchor Rashguard

$68