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Best Affordable Milestone and Special Occasion Trips

Whether you’re looking to celebrate a birthday, anniversary or the birth of your child, we’ve got the perfect celebratory getaway for you this winter.

Anniversary: Hotel Madeline, Telluride, CO

Located at the base of Telluride in Mountain Village, this hotel has 95 guestrooms outfitted with leather armchairs, plush beds, and soaking tubs. Getting onto the slopes is easy with the ski valet who can help you get outfitted with all equipment and gear you’ll need. Consider visiting in early December before prices go up for the holidays and high ski season. After a day on the mountain, enjoy the hotel’s restaurant, Rev, which serves only produce and meat sourced from farms located within a 100-mile radius and seafood from sustainable fisheries. Doubles from $199/night (through December 19).

Honeymoon: Copamarina Beach Resort & Spa, Puerto Rico

Ninety miles from San Juan, this romantic beachfront retreat on the southern coast is set on 20 acres of gardens and half mile of beach with 106 guestrooms and suites. Get some post-wedding relaxation in at the full-service spa and the two swimming pools with Jacuzzis. If you’re looking for more adventure, head out into the sea to sail, kayak, paddleboard, and fish. Nearby attractions include the Bioluminescent Bay and Gilligan’s Island for an afternoon of picnicking and snorkeling. Doubles from $139/night.

Birthday: Historic Key West Inns, Florida Keys

Need a fun, warm-weather spot for a celebratory getaway? Key West is just a three-hour drive from Miami on the scenic overseas highway. Stay at one of the six Historic Key West Inns within easy access of Duval Street and other attractions. Each of the inns has a pool, and all serve complimentary breakfast. Before you head home enjoy a big, festive Sunday brunch at 2 Cents (which runs until 3 pm if you’d like to sleep in). Go snorkeling to see thousands of species of marine life or charter a sailboat or catamaran for an afternoon out at sea. Doubles from $169/night.

Retirement: Los Poblanos Historic Inn and Organic Farm, Albuquerque, NM

The two historic buildings of Los Poblanos, designed by renowned New Mexico architect John Gaw Meem, sit under cottonwood trees along the Rio Grande. Relaxation comes easy here since the 20 guestrooms all come with wood-burning fireplaces and original art. Develop a new hobby thanks to offerings that include Field Sketching Academy, cooking classes, and Meet the Farmer classes at the on-site organic farm. The complimentary breakfast uses fresh ingredients from the farm such as honey from their own bees and fruits and vegetables from their fields. Doubles from $165/night.

Babymoon: Westin Hilton Head Island Resort & Spa, South Carolina

This relaxing seaside resort is a great off-season destination. With fewer crowds around to compete with, you can enjoy golf, tennis, spa, and a covered heated pool depending on how active you’d like to be. A special babymoon package includes an ocean view guestroom, one Pea-in-a-Pod massage, beach yoga, and mocktails for two at View32. If you’re eager to start nesting, shop for baby at the island’s many factory outlet shops. Babymoon package from $249/night.

 
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