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Rest Roam Reset: 2026 Anguilla Retreat
Nov 5–8, 2026 · 3 nights

Rest Roam Reset: 2026 Anguilla Retreat

South Hill Nov 5–8, 2026
Rest Roam Reset LLC
Organized by Rest Roam Reset LLC
About this trip
A 4-day luxury retreat in Anguilla designed for rest, ease, and soft adventure. Curated experiences, wellness moments, and golden hour views—every detail invites you to reset, your way.
Itinerary
Day 1 · Thu, Nov 5
Shores of Serenity: Welcome to Anguilla + 2 more
Shores of Serenity: Welcome to Anguilla — ✨ The Art of Arrival – Ease Into Island Life 🏝 Your Journey Begins. Private group transfer from Anguilla airport (AXA) or Anguilla Ferry Terminal Port to your 5-star hotel & spa—your ocean view room is ready and waiting.
Sunkissed Soirée — 🍹 Sunset Welcome Reception Enjoy handcrafted welcome cocktails and light bites with a stunning ocean backdrop. This is your moment to breathe, soften, and ease into the retreat.
Beneath the Moonlit Sky — 🌙 Evening at Your Pace Concierge is available to assist with dinner plans at one of the resort’s top restaurants. Or opt for in-room dining and a night to yourself.
Day 2 · Fri, Nov 6
Grounded Luxury & Curated Connection + 4 more
Grounded Luxury & Curated Connection — ✨🌅 Morning Reset Ritual Begin the day slowly with a light wellness experience designed to set intention and calm the mind.
Daybreak Indulgence — 🍽 Gourmet Breakfast Enjoy a fresh tropical breakfast with island ingredients and ocean breeze.
Beach Bliss & Fairway Dreams — 🏝 Choose Your Flow – Beach or Golf Spend your afternoon on the soft sands of the resort’s private beach or Tee off with complimentary golf access at a championship course.
OPTIONAL ADD-ON: Private boat transfer to Prickly Pear Cays – $250 pp — ⛵️Sail to the serene Prickly Pear Cay for a day of sun, snorkeling, and island charm. Enjoy crystal-clear waters, white sand beaches, vibrant marine life, and a relaxed beachside lunch in paradise.
Island Essence: A Culinary Affair — 🍽 Signature Curated Group Dinner A curated dining experience with local flavors, fine wine, and unforgettable ambiance.
Day 3 · Sat, Nov 7
🍽 Breakfast at Your Leisure + 2 more
🍽 Breakfast at Your Leisure — ✨Wake when you’re ready and enjoy a relaxed morning meal overlooking the sea.
Roam & Reset – A Day of Island Indulgence — 🚗 VIP Beach Club & Moke Takeover Cruise Anguilla in your personal open-air Moke, stopping at curated beach clubs with pre-arranged lounge seating and elevated cocktails. 🏖 Luxury Beach Crawl Visit the island’s most stunning beach clubs, ending with sunset drinks at a cliffside jazz lounge.
🌙 Evening at Your Pace — Concierge is available to assist with dinner plans at one of the resort’s top restaurants. Or opt for in-room dining and a night to yourself.
Day 4 · Sun, Nov 8
✨Departure: Sunkissed & Refreshed
🍽 Farewell Breakfast Gathering A final slow morning with fresh juices, tropical fruit, and connection. 🚘 VIP Departure Transfer Private transportation arranged for a seamless journey home.
Choose your package
Cancellation policy
Very Strict Refund Policy Set by Rest Roam Reset LLC
50% refund, minus the 6.25% + $0.55 processing fee (and commitment fee, if applicable), if canceled 60 days or more before the trip start date.
No refund if canceled less than 60 days before the trip start date.
These refund policies are designed to protect both the group leader and participants. All cancellations are subject to the terms outlined above. If you have specific questions about your refund eligibility, please contact us before canceling. Refunds will be processed within 7-10 business days of receiving a cancellation request. Prices include payment processing; if a refund is issued, the processing portion (6.25% + $0.55 per payment) is not returned. Travel insurance is strongly recommended.
Read the full policy
Questions about this trip? Message Rest
From
$2,600 / traveler
— 6 packages available · Processing included
🔒 Secure, encrypted checkout · By reserving you agree to Let's Gravel's Terms & Conditions and the organizer's cancellation policy
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